Italy: Puglia, Alberobello & Lecce

Depart for Italy. The particulars of your arrival overseas are detailed with your flight itinerary.

Upon arrival at the Bari airport, make your own travel arrangements to Alberobello. For details, refer to your VBT Vacation Preparation Handbook.

When you arrive in Alberobello at the start of your Puglia Self-Guided Biking Vacation, you might feel as if you’ve stepped into a fairytale, thanks to the city’s many trulli. These round, white-washed, dry-stone huts capped with conical limestone roofs were constructed without mortar so they could be quickly disassembled when word got around that the taxman was on his way. Their original purpose was to store agricultural tools but they later became dwellings. Today, they are a carefully preserved symbol of Puglia and a UNESCO World Heritage site. Many have been beautifully restored for modern living, including the ones clustered within the hotel village that welcomes you today. Make yourself at home in your very own charming trullo house, relax after your journey, and stroll among these 500-year-old dwellings, some of their roofs marked with chalk-white symbols meant to bless their inhabitants.

Please make sure you check in before 6:00 p.m. as the reception closes earlier on weekends.

After breakfast at Trulli & Puglia, meet your Local host in the lobby at 12:30 p.m. for your Welcome Orientation, along with any other VBT guests arriving on the same day. Please be dressed and ready for cycling. Your Local host will be carrying a VBT sign.

Get to know your bicycle and ease into the rhythm of biking in Italy during today’s ride. From the center of Alberobello, you will enter the rolling Itria Valley. Take your time on today’s ride, stopping to savor the rustic landscape of ancient olive trees, small vineyards, and vegetable gardens interspersed among farmhouses and trulli. These buildings are so unique and special that UNESCO has listed them among the World Heritage Sites. Your route brings you though Locorotondo, where a picture stop is recommended to the typical cummerse houses. A last panoramic stretch takes you to the white-washed city of Ostuni. As unique as beautiful, the heart of the city where your hotel is located, is a maze of narrow and winding alleyways, where colorful pots of flowers make a delightful and picturesque contrast with the white houses. Traditionally painted white, the buildings reflect the intense sunlight and keep the interiors cool. Tonight, walk up the white ‘Cittadella’ where the houses were excavated into the limestone and pick a restaurant for dinner on own – you may try one that was a former cave.

Today's Ride Choices

Alberobello to Ostuni — 38 km (24 miles)

What to Expect:

Alberobello to Ostuni:
The ride departs narrow town streets and follows paved rural roads into ancient olive groves and past farmhouses and typical trulli huts. After 7 miles you enter Locorotondo, a must-do visit. A few miles out of this small town, you cross the scenic bridge of Figazzano and start a 2 mile unpaved well-beaten bike path.  Some easy ascents and descents take you finally into Ostuni, where you need to pay attention to some car traffic. The hotel is at short distance and located in the city enter. You ride a short stretch on cobblestone and then walk your bike shortly up on large stones, that could be slippery in the rain.  Ask the reception to open the garage for you, park and lock your bike there. Do not leave it unattended out of the hotel door.

Included Meals: Breakfast

After breakfast, at 9:00 a.m. a 60-minute drive takes you to the Salento Peninsula on the magnificent Ionian Coast, where sandy beaches and the cobalt-blue waters of inviting inlets are sure to lure you in for a refreshing dip. Your initial destination is the seaside resort town of Porto Cesareo, overseen by a handsome 16th-century watchtower. From here, your Puglia Self-Guided Biking Vacation takes you for a spectacular coastal ride, passing through villages that showcase the real Puglia. Get out of the saddle as the spirit moves you, for photos, or to poke into a shop. You’ll find that conversations with locals come easily in this corner of Italy that sees few visitors!

Later, you’ll glide into the Old Town of Gallipoli, the “Gem of Salento,” a medieval fortified island city linked to the mainland by a 16th-century bridge. Gallipoli was part of Magna Graecia, or Greater Greece, which included vast swathes of southern Italy and Sicily in ancient times. Once a center for olive oil, today Gallipoli is a lively city, full of boutiques, cafés, and vestiges from its Greek and Roman days. The fishing port still brings in the catch of the day and the surrounding walls, once a defense against centuries of invasions, is the perfect place to join locals in their passeggiata, or afternoon stroll, before a well-earned aperitivo overlooking Sant’ Andrea’s lighthouse. Resume cycling to get to your cozy masseria for an authentic Salento experience.

Today's Ride Choices

Porto Cesareo to Gallipoli and Sannicola — 47 km (29 miles)

Nardò loop — 9 km (6 miles)

What to Expect:

Porto Cesareo to Gallipoli and Sannicola:
Departing Porto Cesareo, your ride stays mainly along the coast on a mixture of roads and dedicated bike lanes through populated areas, farmland, and open fields with the sea in the distance on your right. Rising after 13 km (eight miles), the day’s steepest ascent is more than made up for by stunning sea views, after which you will veer inland for about five km (three miles). The route returns to the coast through some charming small ports and beaches before rolling into the center of Gallipoli. There you can get as far as the old ‘cittadella’ and make a loop all around it, then park and lock your bike to explore on foot. The ride continues out of town to your masseria-hotel. Pay attention to car traffic as you ride in and out of Gallipoli.

Nardò loop:
Enjoy an optional visit of Nardò, on an almost 9 km (6 miles) ride in the countryside, into the heart of Nardò and returning to the coast. Nardò is rich in history and the monuments will offer you a cultural insight into its past. Breath the authentic life of a back-country Salentine village by stopping at the historical vinery, Schola Sarmenti. Grab a snack from a pastry shop or enjoy lunch in a historical café in the main square. You rejoin the Porto Cesareo to Gallipoli route at the 16.7 km (27 mile) point.

Included Meals: Breakfast

Relish another day cycling as your Puglia self-guided biking tour takes you along the Ionian Sea, where each crystalline beach seems more inviting than the last. You might want to plan on an early start so you can take as many swim breaks as you wish. There will also be opportunities to stop for true Italian coffee and to grab lunch at a seaside restaurant in Marina di Torre San Giovanni. And of course, an Italian cycling adventure cannot live up to its reputation if it doesn’t include at least a daily stop for gelato. As much as you’ll enjoy the culinary and swim breaks, it’s the vistas and picturesque marinas that are truly inspiring in this breathtaking corner of Puglia. You will end the day in Santa Maria di Leuca—a beautiful destination perched on a low seaside promontory and steeped in ancient history and legend. This historic town was named for the white cliffs that have been providing the scenic backdrop to your ride (leukos is Greek for “white”).

The locals claim that this is where the Ionian meets the Adriatic, although officially it is further east. Pause at Punta Ristola for sweeping views of the lighthouse, Italy’s second most important, and the adjacent Basilica Sanctuary of Saint Mary—also known as De Finibus Terrae, or “The End of the Land,” named when it was commonly believed that the earth was flat. The Basilica, built over a Roman temple and dedicated to the goddess Minerva, marks where Saint Peter is said to have started his long walk to Rome after crossing the Mediterranean from Jerusalem. Today, the devout follow in his footsteps along the Via Francigena pilgrimage route.

After a rewarding day, settle into your exclusive enclave and enjoy an included dinner at your hotel.

Today's Ride Choices

Sannicola to Santa Maria di Leuca — 64 km (40 miles)

Santa Maria di Leuca loop — 14 km (9 miles)

Optional Santa Maria di Leuca walk — 6 km (3 miles)

What to Expect:

Sannicola to Santa Maria di Leuca:
An easy ride that stays almost entirely along the coast on roads or shared-use bike lanes (in Italian, signs for percorso cicloturistico indicate a slower speed limit for cars). You will pass many sandy beaches, marinas, and beach resorts with ample options for swimming, lunch, coffee, and ice cream, as well as many scenic viewpoints and ancient watchtowers. As you round the tip of the peninsula, you will pass the Devil’s Cave, a natural limestone cave.

Santa Maria di Leuca loop:
Enjoy a loop from the hotel heading inland on peaceful countryside routes with gentle ascents and descents. The route takes you into Santa Maria di Leuca before returning to rural roads leading to delightful views of the sea on your way down to the coast!

Optional Santa Maria di Leuca walk:
The walk, roundtrip from your hotel, is about 5 km and takes you to the most important highlights of the village. You can find information about the embarcadero if you wish to enjoy the boat excursion along the coast from a sea perspective.

Included Meals: Breakfast, Dinner

Today’s ride continues along the dramatic Adriatic Coast with the sea on your right for the entire day, as your Puglia self-guided biking tour takes you descending into enticing crystalline coves. Later, some invigorating climbs lead to high bluffs with breathtaking views followed by exhilarating descents bringing you to quaint harbor villages. At today’s highest elevations, you’ll pass a series of ancient watchtowers where guards once kept an eye out for intruders approaching from the southern Mediterranean. As you ride, you’ll find plenty of options for lunch and snacks; perhaps you’ll sample freshly prepared seafood or provola e mortadella. One final long and steady downhill brings you into Otranto, Italy’s easternmost point. Surrounded by great ramparts, it is one of Italy’s most scenic coastal towns, situated on the Strait of Otranto, which separates Italy from Albania by just 45 miles.

Otranto’s Old Town is a rich amalgam of the history of past invaders: Greeks, Romans, and Turks among them. Exploring it on your Puglia self-guided biking tour is a must, and stopping in its 11th-century cathedral is absolutely required. Behind the altar, the bones of 813 martyrs who fell in a 15th-century siege are encased in a glass cabinet. But the medieval mosaic floor, the largest in Europe, is the real draw: Created in 1163 by a resident monk, the “Tree of Life” spans 8,611 square feet. Back outside, you might find your own mosaics—and other crafts—among the bustling stalls that line the narrow lanes. Otranto’s 15th-century castle is also worth a visit for its history and the exhibit devoted to the now-closed Neolithic caves in Porto Badisco that you passed on your way into town.

At dinnertime, you can stroll to the city’s inviting waterfront with its wide terrace and lovely vistas.

Today's Ride Choices

Santa Maria di Leuca to Otranto — 52 km (32 miles)

What to Expect:

You will ride along the Adriatic Coast, with the week’s highest elevation gains and losses. The route is high above the sea on bluffs and also dips down to charming harbor villages with stops for swimming, food, and drinks. The second climb of the day takes you to Torre Nasparo, with its spectacular views east and north. On a clear day, after the last big climb to Torre Minervino, before reaching Italy’s most easterly lighthouse of Punta Palascia, you may spot Albania’s Acroceurani mountain range and some Greek islands on the other side of the Adriatic Sea. A sustained descent brings you to Porto Badisco, Approdo di Enea and then into Otranto.

Included Meals: Breakfast

Enjoy a Stay Put Day to do as you please. If you just can’t stay off the saddle, take a loop ride into the interior away from the sea, following quiet country roads. An initial slight ascent lifts you above Otranto and then flattens out as it winds through olive groves framed by stone walls. You may stop to ponder ancient dolmens and menhirs, the region’s mysterious prehistoric standing stones. Take your time on this scenic route, perhaps pausing to toast your good fortune at a local winery or stopping to observe a traditional weaving workshop. Back at Otranto’s beach, reward yourself with a swim and a delicious seafood lunch along the port.

Alternately, you can join a boat excursion along the dramatic coastal cliffs and past spectacular grottos, stopping for swims along the way. You may prefer to spend the day on land, browsing Otranto’s inviting shops, and the halls and grounds of its seaside castle. Your Puglia Self-Guided Biking Vacation offers plenty of choices.

Today's Ride Choices

Otranto to Uggiano la Chiesa loop — 26 km (16 miles) | Otranto Walk — 3 km (2 miles)

What to Expect:

A narrow road exits the center of Otranto. After an initial, gradual ascent, the route flattens out on quiet country roads, rolling through olive groves and past stone walls, farms and hamlets. You may stop for lunch and a tasting at a winery or visit a traditional weaving workshop along the way. Scattered throughout the landscape are prehistoric standing stones.

Included Meals: Breakfast

Leaving Otranto today, you’ll savor the last ride of your Puglia Self-Guided Biking Vacation along the dramatic Adriatic coast. Ride along the Strait of Otranto before turning into a countryside of enormous olive and oak trees. This scenic route leads to the small Renaissance village of Acaya, one of Puglia’s last remaining fortified cities. Its notable 16th-century grid of streets divides the town into rectangular “islands.” After exploring, you’ll join a bike path that leads into the center of Lecce. This beautiful city is constructed from a pink-tinged local stone called pietra dorata. There is so much Baroque-period architecture with chiseled cherubs, angels, and saints, that Lecce has been called the “Florence of the South.” As you explore, your week of cycling will no doubt bring a new sense of urgency to your gelato cravings; you’ll have plenty of options to satisfy them here!

An intimate boutique hotel in the heart of the pedestrian Old City welcomes you to Lecce, a fine finale for your trip. Settle in and then take a short stroll to historic sites, including the Piazza Sant’Oronzo, the city’s main square with its centerpiece Roman amphitheater. Pick any of the narrow streets that fan out from the square to discover charming neighborhoods—and duck into any number of rustic eateries serving the hearty cuisine for which the city is known, including pureed fava beans and broccolini and a robust primitivo wine. It’s the perfect way to celebrate your ride around Italy’s heel!

Today's Ride Choices

Otranto to Lecce — 50 km (31 miles)

Optional Lecce walk — 3 km (2 miles)

What to Expect:

Otranto to Lecce:
After an initial ascent departing Otranto from sea level, the ride is mainly flat along the coast, then at around the 30 km (18 miles) after San Foca, you will turn inland through olive groves and begin a slight sustained ascent to Acaya, one of the best examples of a Renaissance fortified town in Italy. From there, you’ll join a bike path that leads into the center of Lecce. Although Lecce is a bike-friendly city, please be aware that urban riding will be very busy compared to the low-traffic riding you have enjoyed this week. Please exercise caution and, although not required, we recommend walking your bike the last few kilometers to your hotel.

Optional Lecce walk:
A suggested walk from your hotel to discover the major monuments of the capital of Baroque style and gastronomic insights of the traditional food of the county.

Included Meals: Breakfast

After an included breakfast, you have the day to explore the city of Lecce. Visit the Piazza Duomo, enclosed on three sides by the cathedral and other church buildings. Despite being one of Europe’s largest squares, its surrounding buildings and many cafés create an intimate ambiance. You can visit up to six of Lecce’s intricate Baroque churches on one entry ticket.

Your VBT city information provides useful recommendations for exploring on your own for the rest of the day. Dinner is on your own tonight.

See Day 6 of Road Book.

Included Meals: Breakfast

After an included breakfast this morning, if traveling by public transportation, allow yourself a minimum of four hours’ transportation time prior to your flight from Brindisi airport; for details, refer to your VBT Vacation Preparation Handbook. This timeframe includes approximately 1.5 hours of travel and around two hours of recommended pre-flight check-in time.

Included Meals: Breakfast

Depart for Italy. The particulars of your arrival overseas are detailed with your flight itinerary.

Upon arrival at the Bari airport, make your own travel arrangements to Alberobello. For details, refer to your VBT Vacation Preparation Handbook.

When you arrive in Alberobello at the start of your Puglia Self-Guided Biking Vacation, you might feel as if you’ve stepped into a fairytale, thanks to the city’s many trulli. These round, white-washed, dry-stone huts capped with conical limestone roofs were constructed without mortar so they could be quickly disassembled when word got around that the taxman was on his way. Their original purpose was to store agricultural tools but they later became dwellings. Today, they are a carefully preserved symbol of Puglia and a UNESCO World Heritage site. Many have been beautifully restored for modern living, including the ones clustered within the hotel village that welcomes you today. Make yourself at home in your very own charming trullo house, relax after your journey, and stroll among these 500-year-old dwellings, some of their roofs marked with chalk-white symbols meant to bless their inhabitants.

Please make sure you check in before 6:00 p.m. as the reception closes earlier on weekends.

After breakfast at Trulli & Puglia, meet your Local host in the lobby at 12:30 p.m. for your Welcome Orientation, along with any other VBT guests arriving on the same day. Please be dressed and ready for cycling. Your Local host will be carrying a VBT sign.

Get to know your bicycle and ease into the rhythm of biking in Italy during today’s ride. From the center of Alberobello, you will enter the rolling Itria Valley. Take your time on today’s ride, stopping to savor the rustic landscape of ancient olive trees, small vineyards, and vegetable gardens interspersed among farmhouses and trulli. These buildings are so unique and special that UNESCO has listed them among the World Heritage Sites. Your route brings you though Locorotondo, where a picture stop is recommended to the typical cummerse houses. A last panoramic stretch takes you to the white-washed city of Ostuni. As unique as beautiful, the heart of the city where your hotel is located, is a maze of narrow and winding alleyways, where colorful pots of flowers make a delightful and picturesque contrast with the white houses. Traditionally painted white, the buildings reflect the intense sunlight and keep the interiors cool. Tonight, walk up the white ‘Cittadella’ where the houses were excavated into the limestone and pick a restaurant for dinner on own – you may try one that was a former cave.

Today's Ride Choices

Alberobello to Ostuni — 38 km (24 miles)

What to Expect:

Alberobello to Ostuni:
The ride departs narrow town streets and follows paved rural roads into ancient olive groves and past farmhouses and typical trulli huts. After 7 miles you enter Locorotondo, a must-do visit. A few miles out of this small town, you cross the scenic bridge of Figazzano and start a 2 mile unpaved well-beaten bike path.  Some easy ascents and descents take you finally into Ostuni, where you need to pay attention to some car traffic. The hotel is at short distance and located in the city enter. You ride a short stretch on cobblestone and then walk your bike shortly up on large stones, that could be slippery in the rain.  Ask the reception to open the garage for you, park and lock your bike there. Do not leave it unattended out of the hotel door.

Included Meals: Breakfast

After breakfast, at 9:00 a.m. a 60-minute drive takes you to the Salento Peninsula on the magnificent Ionian Coast, where sandy beaches and the cobalt-blue waters of inviting inlets are sure to lure you in for a refreshing dip. Your initial destination is the seaside resort town of Porto Cesareo, overseen by a handsome 16th-century watchtower. From here, your Puglia Self-Guided Biking Vacation takes you for a spectacular coastal ride, passing through villages that showcase the real Puglia. Get out of the saddle as the spirit moves you, for photos, or to poke into a shop. You’ll find that conversations with locals come easily in this corner of Italy that sees few visitors!

Later, you’ll glide into the Old Town of Gallipoli, the “Gem of Salento,” a medieval fortified island city linked to the mainland by a 16th-century bridge. Gallipoli was part of Magna Graecia, or Greater Greece, which included vast swathes of southern Italy and Sicily in ancient times. Once a center for olive oil, today Gallipoli is a lively city, full of boutiques, cafés, and vestiges from its Greek and Roman days. The fishing port still brings in the catch of the day and the surrounding walls, once a defense against centuries of invasions, is the perfect place to join locals in their passeggiata, or afternoon stroll, before a well-earned aperitivo overlooking Sant’ Andrea’s lighthouse. Resume cycling to get to your cozy masseria for an authentic Salento experience.

Today's Ride Choices

Porto Cesareo to Gallipoli and Sannicola — 47 km (29 miles)

Nardò loop — 9 km (6 miles)

What to Expect:

Porto Cesareo to Gallipoli and Sannicola:
Departing Porto Cesareo, your ride stays mainly along the coast on a mixture of roads and dedicated bike lanes through populated areas, farmland, and open fields with the sea in the distance on your right. Rising after 13 km (eight miles), the day’s steepest ascent is more than made up for by stunning sea views, after which you will veer inland for about five km (three miles). The route returns to the coast through some charming small ports and beaches before rolling into the center of Gallipoli. There you can get as far as the old ‘cittadella’ and make a loop all around it, then park and lock your bike to explore on foot. The ride continues out of town to your masseria-hotel. Pay attention to car traffic as you ride in and out of Gallipoli.

Nardò loop:
Enjoy an optional visit of Nardò, on an almost 9 km (6 miles) ride in the countryside, into the heart of Nardò and returning to the coast. Nardò is rich in history and the monuments will offer you a cultural insight into its past. Breath the authentic life of a back-country Salentine village by stopping at the historical vinery, Schola Sarmenti. Grab a snack from a pastry shop or enjoy lunch in a historical café in the main square. You rejoin the Porto Cesareo to Gallipoli route at the 16.7 km (27 mile) point.

Included Meals: Breakfast

Relish another day cycling as your Puglia self-guided biking tour takes you along the Ionian Sea, where each crystalline beach seems more inviting than the last. You might want to plan on an early start so you can take as many swim breaks as you wish. There will also be opportunities to stop for true Italian coffee and to grab lunch at a seaside restaurant in Marina di Torre San Giovanni. And of course, an Italian cycling adventure cannot live up to its reputation if it doesn’t include at least a daily stop for gelato. As much as you’ll enjoy the culinary and swim breaks, it’s the vistas and picturesque marinas that are truly inspiring in this breathtaking corner of Puglia. You will end the day in Santa Maria di Leuca—a beautiful destination perched on a low seaside promontory and steeped in ancient history and legend. This historic town was named for the white cliffs that have been providing the scenic backdrop to your ride (leukos is Greek for “white”).

The locals claim that this is where the Ionian meets the Adriatic, although officially it is further east. Pause at Punta Ristola for sweeping views of the lighthouse, Italy’s second most important, and the adjacent Basilica Sanctuary of Saint Mary—also known as De Finibus Terrae, or “The End of the Land,” named when it was commonly believed that the earth was flat. The Basilica, built over a Roman temple and dedicated to the goddess Minerva, marks where Saint Peter is said to have started his long walk to Rome after crossing the Mediterranean from Jerusalem. Today, the devout follow in his footsteps along the Via Francigena pilgrimage route.

After a rewarding day, settle into your exclusive enclave and enjoy an included dinner at your hotel.

Today's Ride Choices

Sannicola to Santa Maria di Leuca — 64 km (40 miles)

Santa Maria di Leuca loop — 14 km (9 miles)

Optional Santa Maria di Leuca walk — 6 km (3 miles)

What to Expect:

Sannicola to Santa Maria di Leuca:
An easy ride that stays almost entirely along the coast on roads or shared-use bike lanes (in Italian, signs for percorso cicloturistico indicate a slower speed limit for cars). You will pass many sandy beaches, marinas, and beach resorts with ample options for swimming, lunch, coffee, and ice cream, as well as many scenic viewpoints and ancient watchtowers. As you round the tip of the peninsula, you will pass the Devil’s Cave, a natural limestone cave.

Santa Maria di Leuca loop:
Enjoy a loop from the hotel heading inland on peaceful countryside routes with gentle ascents and descents. The route takes you into Santa Maria di Leuca before returning to rural roads leading to delightful views of the sea on your way down to the coast!

Optional Santa Maria di Leuca walk:
The walk, roundtrip from your hotel, is about 5 km and takes you to the most important highlights of the village. You can find information about the embarcadero if you wish to enjoy the boat excursion along the coast from a sea perspective.

Included Meals: Breakfast, Dinner

Today’s ride continues along the dramatic Adriatic Coast with the sea on your right for the entire day, as your Puglia self-guided biking tour takes you descending into enticing crystalline coves. Later, some invigorating climbs lead to high bluffs with breathtaking views followed by exhilarating descents bringing you to quaint harbor villages. At today’s highest elevations, you’ll pass a series of ancient watchtowers where guards once kept an eye out for intruders approaching from the southern Mediterranean. As you ride, you’ll find plenty of options for lunch and snacks; perhaps you’ll sample freshly prepared seafood or provola e mortadella. One final long and steady downhill brings you into Otranto, Italy’s easternmost point. Surrounded by great ramparts, it is one of Italy’s most scenic coastal towns, situated on the Strait of Otranto, which separates Italy from Albania by just 45 miles.

Otranto’s Old Town is a rich amalgam of the history of past invaders: Greeks, Romans, and Turks among them. Exploring it on your Puglia self-guided biking tour is a must, and stopping in its 11th-century cathedral is absolutely required. Behind the altar, the bones of 813 martyrs who fell in a 15th-century siege are encased in a glass cabinet. But the medieval mosaic floor, the largest in Europe, is the real draw: Created in 1163 by a resident monk, the “Tree of Life” spans 8,611 square feet. Back outside, you might find your own mosaics—and other crafts—among the bustling stalls that line the narrow lanes. Otranto’s 15th-century castle is also worth a visit for its history and the exhibit devoted to the now-closed Neolithic caves in Porto Badisco that you passed on your way into town.

At dinnertime, you can stroll to the city’s inviting waterfront with its wide terrace and lovely vistas.

Today's Ride Choices

Santa Maria di Leuca to Otranto — 52 km (32 miles)

What to Expect:

You will ride along the Adriatic Coast, with the week’s highest elevation gains and losses. The route is high above the sea on bluffs and also dips down to charming harbor villages with stops for swimming, food, and drinks. The second climb of the day takes you to Torre Nasparo, with its spectacular views east and north. On a clear day, after the last big climb to Torre Minervino, before reaching Italy’s most easterly lighthouse of Punta Palascia, you may spot Albania’s Acroceurani mountain range and some Greek islands on the other side of the Adriatic Sea. A sustained descent brings you to Porto Badisco, Approdo di Enea and then into Otranto.

Included Meals: Breakfast

Enjoy a Stay Put Day to do as you please. If you just can’t stay off the saddle, take a loop ride into the interior away from the sea, following quiet country roads. An initial slight ascent lifts you above Otranto and then flattens out as it winds through olive groves framed by stone walls. You may stop to ponder ancient dolmens and menhirs, the region’s mysterious prehistoric standing stones. Take your time on this scenic route, perhaps pausing to toast your good fortune at a local winery or stopping to observe a traditional weaving workshop. Back at Otranto’s beach, reward yourself with a swim and a delicious seafood lunch along the port.

Alternately, you can join a boat excursion along the dramatic coastal cliffs and past spectacular grottos, stopping for swims along the way. You may prefer to spend the day on land, browsing Otranto’s inviting shops, and the halls and grounds of its seaside castle. Your Puglia Self-Guided Biking Vacation offers plenty of choices.

Today's Ride Choices

Otranto to Uggiano la Chiesa loop — 26 km (16 miles) | Otranto Walk — 3 km (2 miles)

What to Expect:

A narrow road exits the center of Otranto. After an initial, gradual ascent, the route flattens out on quiet country roads, rolling through olive groves and past stone walls, farms and hamlets. You may stop for lunch and a tasting at a winery or visit a traditional weaving workshop along the way. Scattered throughout the landscape are prehistoric standing stones.

Included Meals: Breakfast

Leaving Otranto today, you’ll savor the last ride of your Puglia Self-Guided Biking Vacation along the dramatic Adriatic coast. Ride along the Strait of Otranto before turning into a countryside of enormous olive and oak trees. This scenic route leads to the small Renaissance village of Acaya, one of Puglia’s last remaining fortified cities. Its notable 16th-century grid of streets divides the town into rectangular “islands.” After exploring, you’ll join a bike path that leads into the center of Lecce. This beautiful city is constructed from a pink-tinged local stone called pietra dorata. There is so much Baroque-period architecture with chiseled cherubs, angels, and saints, that Lecce has been called the “Florence of the South.” As you explore, your week of cycling will no doubt bring a new sense of urgency to your gelato cravings; you’ll have plenty of options to satisfy them here!

A stunning five-star hotel in the heart of the pedestrian Old City welcomes you to Lecce, a fine finale for your trip. Settle in and then take a short stroll to historic sites, including the Piazza Sant’Oronzo, the city’s main square with its centerpiece Roman amphitheater. Pick any of the narrow streets that fan out from the square to discover charming neighborhoods—and duck into any number of rustic eateries serving the hearty cuisine for which the city is known, including pureed fava beans and broccolini and a robust primitivo wine. It’s the perfect way to celebrate your ride around Italy’s heel!

Today's Ride Choices

Otranto to Lecce — 50 km (31 miles)

Optional Lecce walk — 3 km (2 miles)

What to Expect:

Otranto to Lecce:
After an initial ascent departing Otranto from sea level, the ride is mainly flat along the coast, then at around the 30 km (18 miles) after San Foca, you will turn inland through olive groves and begin a slight sustained ascent to Acaya, one of the best examples of a Renaissance fortified town in Italy. From there, you’ll join a bike path that leads into the center of Lecce. Although Lecce is a bike-friendly city, please be aware that urban riding will be very busy compared to the low-traffic riding you have enjoyed this week. Please exercise caution and, although not required, we recommend walking your bike the last few kilometers to your hotel.

Optional Lecce walk:
A suggested walk from your hotel to discover the major monuments of the capital of Baroque style and gastronomic insights of the traditional food of the county.

Included Meals: Breakfast

After an included breakfast, you have the day to explore the city of Lecce. Visit the Piazza Duomo, enclosed on three sides by the cathedral and other church buildings. Despite being one of Europe’s largest squares, its surrounding buildings and many cafés create an intimate ambiance. You can visit up to six of Lecce’s intricate Baroque churches on one entry ticket.

Your VBT city information provides useful recommendations for exploring on your own for the rest of the day. Dinner is on your own tonight.

See Day 6 of Road Book.

Included Meals: Breakfast

After an included breakfast this morning, if traveling by public transportation, allow yourself a minimum of four hours’ transportation time prior to your flight from Brindisi airport; for details, refer to your VBT Vacation Preparation Handbook. This timeframe includes approximately 1.5 hours of travel and around two hours of recommended pre-flight check-in time.

Included Meals: Breakfast

We suggest arriving in Italy at least one day prior to the start date as your Puglia Self-Guided Biking Vacation begins at 12:30 p.m. Make your own way to Alberobello, where you will begin your self-guided adventure. For details, refer to your VBT Vacation Preparation Handbook.

When you arrive in Alberobello, you might feel as if you’ve stepped into a fairytale, thanks to the many trulli. These round, white-washed, dry-stone huts capped with conical limestone roofs were constructed without mortar to be quickly disassembled when word got around that the taxman was on his way. Their original purpose was to store agricultural tools and they later became dwellings. Today, they are a carefully preserved symbol of Puglia and a UNESCO World Heritage site. Many have been beautifully restored for modern living, including the ones clustered within the hotel village that welcomes you today.

Meet your VBT Local host at 12:30 p.m. for your Welcome Orientation in the lobby of the Trulli & Puglia, along with any other VBT guests arriving on the same day. Please be dressed and ready for cycling. Your Local host will be carrying a VBT sign.

Get to know your bicycle and ease into the rhythm of your Puglia Self-Guided Biking Vacation during today’s ride. From the center of Alberobello, you will enter the rolling Itria Valley. Take your time on today’s ride, stopping to savor the rustic landscape of ancient olive trees, small vineyards, and vegetable gardens interspersed among farmhouses and trulli. These buildings are so unique and special that UNESCO has listed them among the World Heritage Sites. Your route brings you though Locorotondo, where a picture stop is recommended to the typical cummerse houses. A last panoramic stretch takes you to the white-washed city of Ostuni. As unique as beautiful, the heart of the city where your hotel is located, is a maze of narrow and winding alleyways, where colorful pots of flowers make a delightful and picturesque contrast with the white houses. Traditionally painted white, the buildings reflect the intense sunlight and keep the interiors cool. Tonight, walk up the white ‘Cittadella’ where the houses were excavated into the limestone and pick a restaurant for dinner on own – you may try one that was a former cave.

Today's Ride Choices

Alberobello to Ostuni — 38 km (24 miles)

What to Expect:

Alberobello to Ostuni:
The ride departs narrow town streets and follows paved rural roads into ancient olive groves and past farmhouses and typical trulli huts. After 7 miles you enter Locorotondo, a must-do visit. A few miles out of this small town, you cross the scenic bridge of Figazzano and start a 2 mile unpaved well-beaten bike path.  Some easy ascents and descents take you finally into Ostuni, where you need to pay attention to some car traffic. The hotel is at short distance and located in the city enter. You ride a short stretch on cobblestone and then walk your bike shortly up on large stones, that could be slippery in the rain.  Ask the reception where to park your bike, then park and lock your bike there. Do not leave it unattended out of the hotel door.

After breakfast, at 9:00 a.m. a 60-minute drive takes you to the Salento Peninsula on the magnificent Ionian Coast, where sandy beaches and the cobalt-blue waters of inviting inlets are sure to lure you in for a refreshing dip. Your initial destination is the seaside resort town of Porto Cesareo, overseen by a handsome 16th-century watchtower. From here, your Puglia Self-Guided Biking Vacation takes you for a spectacular coastal ride, passing through villages that showcase the real Puglia. Get out of the saddle as the spirit moves you, for photos, or to poke into a shop. You’ll find that conversations with locals come easily in this corner of Italy that sees few visitors!

Later, you’ll glide into the Old Town of Gallipoli, the “Gem of Salento,” a medieval fortified island city linked to the mainland by a 16th-century bridge. Gallipoli was part of Magna Graecia, or Greater Greece, which included vast swathes of southern Italy and Sicily in ancient times. Once a center for olive oil, today Gallipoli is a lively city, full of boutiques, cafés, and vestiges from its Greek and Roman days. The fishing port still brings in the catch of the day and the surrounding walls, once a defense against centuries of invasions, is the perfect place to join locals in their passeggiata, or afternoon stroll, before a well-earned aperitivo overlooking Sant’ Andrea’s lighthouse. Resume cycling to get to your cozy masseria for an authentic Salento experience.

Today's Ride Choices

Porto Cesareo to Gallipoli and Sannicola — 47 km (29 miles)

Nardò loop — 9 km (6 miles)

What to Expect:

Porto Cesareo to Gallipoli and Sannicola:
Departing Porto Cesareo, your ride stays mainly along the coast on a mixture of roads and dedicated bike lanes through populated areas, farmland, and open fields with the sea in the distance on your right. Rising after 13 km (eight miles), the day’s steepest ascent is more than made up for by stunning sea views, after which you will veer inland for about five km (three miles). The route returns to the coast through some charming small ports and beaches before rolling into the center of Gallipoli. There you can get as far as the old ‘cittadella’ and make a loop all around it, then park and lock your bike to explore on foot. The ride continues out of town to your masseria-hotel. Pay attention to car traffic as you ride in and out of Gallipoli.

Nardò loop:
Enjoy an optional visit of Nardò, on an almost 9 km (6 miles) ride in the countryside, into the heart of Nardò and returning to the coast. Nardò is rich in history and the monuments will offer you a cultural insight into its past. Breath the authentic life of a back-country Salentine village by stopping at the historical vinery, Schola Sarmenti. Grab a snack from a pastry shop or enjoy lunch in a historical café in the main square. You rejoin the Porto Cesareo to Gallipoli route at the 16.7 km (27 mile) point.

Included Meals: Breakfast

Relish another day cycling as your Puglia self-guided biking tour takes you along the Ionian Sea, where each crystalline beach seems more inviting than the last. You might want to plan on an early start so you can take as many swim breaks as you wish. There will also be opportunities to stop for true Italian coffee and to grab lunch at a seaside restaurant in Marina di Torre San Giovanni. And of course, an Italian cycling adventure cannot live up to its reputation if it doesn’t include at least a daily stop for gelato. As much as you’ll enjoy the culinary and swim breaks, it’s the vistas and picturesque marinas that are truly inspiring in this breathtaking corner of Puglia. You will end the day in Santa Maria di Leuca—a beautiful destination perched on a low seaside promontory and steeped in ancient history and legend. This historic town was named for the white cliffs that have been providing the scenic backdrop to your ride (leukos is Greek for “white”).

The locals claim that this is where the Ionian meets the Adriatic, although officially it is further east. Pause at Punta Ristola for sweeping views of the lighthouse, Italy’s second most important, and the adjacent Basilica Sanctuary of Saint Mary—also known as De Finibus Terrae, or “The End of the Land,” named when it was commonly believed that the earth was flat. The Basilica, built over a Roman temple and dedicated to the goddess Minerva, marks where Saint Peter is said to have started his long walk to Rome after crossing the Mediterranean from Jerusalem. Today, the devout follow in his footsteps along the Via Francigena pilgrimage route.

After a rewarding day, settle into your exclusive enclave and enjoy an included dinner at your hotel.

Today's Ride Choices

Sannicola to Santa Maria di Leuca — 64 km (40 miles)

Santa Maria di Leuca loop — 14 km (9 miles)

Optional Santa Maria di Leuca walk — 6 km (3 miles)

What to Expect:

Sannicola to Santa Maria di Leuca:
An easy ride that stays almost entirely along the coast on roads or shared-use bike lanes (in Italian, signs for percorso cicloturistico indicate a slower speed limit for cars). You will pass many sandy beaches, marinas, and beach resorts with ample options for swimming, lunch, coffee, and ice cream, as well as many scenic viewpoints and ancient watchtowers. As you round the tip of the peninsula, you will pass the Devil’s Cave, a natural limestone cave.

Santa Maria di Leuca loop:
Enjoy a loop from the hotel heading inland on peaceful countryside routes with gentle ascents and descents. The route takes you into Santa Maria di Leuca before returning to rural roads leading to delightful views of the sea on your way down to the coast!

Optional Santa Maria di Leuca walk:
The walk, roundtrip from your hotel, is about 5 km and takes you to the most important highlights of the village. You can find information about the embarcadero if you wish to enjoy the boat excursion along the coast from a sea perspective.

Included Meals: Breakfast, Dinner

Today’s ride continues along the dramatic Adriatic Coast with the sea on your right for the entire day, as your Puglia self-guided biking tour takes you descending into enticing crystalline coves. Later, some invigorating climbs lead to high bluffs with breathtaking views followed by exhilarating descents bringing you to quaint harbor villages. At today’s highest elevations, you’ll pass a series of ancient watchtowers where guards once kept an eye out for intruders approaching from the southern Mediterranean. As you ride, you’ll find plenty of options for lunch and snacks; perhaps you’ll sample freshly prepared seafood or provola e mortadella. One final long and steady downhill brings you into Otranto, Italy’s easternmost point. Surrounded by great ramparts, it is one of Italy’s most scenic coastal towns, situated on the Strait of Otranto, which separates Italy from Albania by just 45 miles.

Otranto’s Old Town is a rich amalgam of the history of past invaders: Greeks, Romans, and Turks among them. Exploring it on your Puglia self-guided biking tour is a must, and stopping in its 11th-century cathedral is absolutely required. Behind the altar, the bones of 813 martyrs who fell in a 15th-century siege are encased in a glass cabinet. But the medieval mosaic floor, the largest in Europe, is the real draw: Created in 1163 by a resident monk, the “Tree of Life” spans 8,611 square feet. Back outside, you might find your own mosaics—and other crafts—among the bustling stalls that line the narrow lanes. Otranto’s 15th-century castle is also worth a visit for its history and the exhibit devoted to the now-closed Neolithic caves in Porto Badisco that you passed on your way into town.

At dinnertime, you can stroll to the city’s inviting waterfront with its wide terrace and lovely vistas.

Today's Ride Choices

Santa Maria di Leuca to Otranto — 52 km (32 miles)

What to Expect:

You will ride along the Adriatic Coast, with the week’s highest elevation gains and losses. The route is high above the sea on bluffs and also dips down to charming harbor villages with stops for swimming, food, and drinks. The second climb of the day takes you to Torre Nasparo, with its spectacular views east and north. On a clear day, after the last big climb to Torre Minervino, before reaching Italy’s most easterly lighthouse of Punta Palascia, you may spot Albania’s Acroceurani mountain range and some Greek islands on the other side of the Adriatic Sea. A sustained descent brings you to Porto Badisco, Approdo di Enea and then into Otranto.

Included Meals: Breakfast

Enjoy a Stay Put Day to do as you please. If you just can’t stay off the saddle, take a loop ride into the interior away from the sea, following quiet country roads. An initial slight ascent lifts you above Otranto and then flattens out as it winds through olive groves framed by stone walls. You may stop to ponder ancient dolmens and menhirs, the region’s mysterious prehistoric standing stones. Take your time on this scenic route, perhaps pausing to toast your good fortune at a local winery or stopping to observe a traditional weaving workshop. Back at Otranto’s beach, reward yourself with a swim and a delicious seafood lunch along the port.

Alternately, you can join a boat excursion along the dramatic coastal cliffs and past spectacular grottos, stopping for swims along the way. You may prefer to spend the day on land, browsing Otranto’s inviting shops, and the halls and grounds of its seaside castle. Your Puglia Self-Guided Biking Vacation offers plenty of choices.

Today's Ride Choices

Otranto to Uggiano la Chiesa loop — 26 km (16 miles) | Otranto Walk — 3 km (2 miles)

What to Expect:

A narrow road exits the center of Otranto. After an initial, gradual ascent, the route flattens out on quiet country roads, rolling through olive groves and past stone walls, farms and hamlets. You may stop for lunch and a tasting at a winery or visit a traditional weaving workshop along the way. Scattered throughout the landscape are prehistoric standing stones.

Included Meals: Breakfast

Leaving Otranto today, you’ll savor the last ride of your Puglia Self-Guided Biking Vacation along the dramatic Adriatic coast. Ride along the Strait of Otranto before turning into a countryside of enormous olive and oak trees. This scenic route leads to the small Renaissance village of Acaya, one of Puglia’s last remaining fortified cities. Its notable 16th-century grid of streets divides the town into rectangular “islands.” After exploring, you’ll join a bike path that leads into the center of Lecce. This beautiful city is constructed from a pink-tinged local stone called pietra dorata. There is so much Baroque-period architecture with chiseled cherubs, angels, and saints, that Lecce has been called the “Florence of the South.” As you explore, your week of cycling will no doubt bring a new sense of urgency to your gelato cravings; you’ll have plenty of options to satisfy them here!

An intimate boutique hotel in the heart of the pedestrian Old City welcomes you to Lecce, a fine finale for your trip. Settle in and then take a short stroll to historic sites, including the Piazza Sant’Oronzo, the city’s main square with its centerpiece Roman amphitheater. Pick any of the narrow streets that fan out from the square to discover charming neighborhoods—and duck into any number of rustic eateries serving the hearty cuisine for which the city is known, including pureed fava beans and broccolini and a robust primitivo wine. It’s the perfect way to celebrate your ride around Italy’s heel!

Today's Ride Choices

Otranto to Lecce — 50 km (31 miles)

Optional Lecce walk — 3 km (2 miles)

What to Expect:

Otranto to Lecce:
After an initial ascent departing Otranto from sea level, the ride is mainly flat along the coast, then at around the 30 km (18 miles) after San Foca, you will turn inland through olive groves and begin a slight sustained ascent to Acaya, one of the best examples of a Renaissance fortified town in Italy. From there, you’ll join a bike path that leads into the center of Lecce. Although Lecce is a bike-friendly city, please be aware that urban riding will be very busy compared to the low-traffic riding you have enjoyed this week. Please exercise caution and, although not required, we recommend walking your bike the last few kilometers to your hotel.

Optional Lecce walk:
A suggested walk from your hotel to discover the major monuments of the capital of Baroque style and gastronomic insights of the traditional food of the county.

Included Meals: Breakfast

Enjoy breakfast at your hotel in Lecce and depart on your own. For details, refer to your VBT Vacation Preparation Handbook. Depending upon your destination, it may not be possible to depart for the U.S. on the last day of your Puglia Self-Guided Biking Vacation. Please check airline schedules carefully. If you plan to schedule a return flight immediately following the tour’s conclusion, please call your airline directly for specific check-in requirements.

Lecce has good train connections with all main lines connecting to destinations throughout Italy (e.g., Naples, five hours; Rome, 5.5 hours). The train and bus stations are just under 1.4 km (0.9 miles) from your hotel; a 20-minute walk across the pedestrian city center.

Included Meals: Breakfast

We suggest arriving in Italy at least one day prior to the start date as your Puglia Self-Guided Biking Vacation begins at 12:30 p.m. Make your own way to Alberobello, where you will begin your self-guided adventure. For details, refer to your VBT Handbook.

When you arrive in Alberobello, you might feel as if you’ve stepped into a fairytale, thanks to the many trulli. These round, white-washed, dry-stone huts capped with conical limestone roofs were constructed without mortar to be quickly disassembled when word got around that the taxman was on his way. Their original purpose was to store agricultural tools and they later became dwellings. Today, they are a carefully preserved symbol of Puglia and a UNESCO World Heritage site. Many have been beautifully restored for modern living, including the ones clustered within the hotel village that welcomes you today.

Meet your VBT Local host at 12:30 p.m. for your Welcome Orientation in the lobby of the Trulli & Puglia, along with any other VBT guests arriving on the same day. Please be dressed and ready for cycling. Your Local host will be carrying a VBT sign.

Get to know your bicycle and ease into the rhythm of your Puglia Self-Guided Biking Vacation during today’s ride. From the center of Alberobello, you will enter the rolling Itria Valley. Take your time on today’s ride, stopping to savor the rustic landscape of ancient olive trees, small vineyards, and vegetable gardens interspersed among farmhouses and trulli. These buildings are so unique and special that UNESCO has listed them among the World Heritage Sites. Your route brings you though Locorotondo, where a picture stop is recommended to the typical cummerse houses. A last panoramic stretch takes you to the white-washed city of Ostuni. As unique as beautiful, the heart of the city where your hotel is located, is a maze of narrow and winding alleyways, where colorful pots of flowers make a delightful and picturesque contrast with the white houses. Traditionally painted white, the buildings reflect the intense sunlight and keep the interiors cool. Tonight, walk up the white ‘Cittadella’ where the houses were excavated into the limestone and pick a restaurant for dinner on own – you may try one that was a former cave.

Today's Ride Choices

Alberobello to Ostuni — 38 km (24 miles)

What to Expect:

Alberobello to Ostuni:
The ride departs narrow town streets and follows paved rural roads into ancient olive groves and past farmhouses and typical trulli huts. After 7 miles you enter Locorotondo, a must-do visit. A few miles out of this small town, you cross the scenic bridge of Figazzano and start a 2 mile unpaved well-beaten bike path.  Some easy ascents and descents take you finally into Ostuni, where you need to pay attention to some car traffic. The hotel is at short distance and located in the city enter. You ride a short stretch on cobblestone and then walk your bike shortly up on large stones, that could be slippery in the rain.  Ask the reception where to park your bike, then park and lock your bike there. Do not leave it unattended out of the hotel door.

After breakfast, at 9:00 a.m. a 60-minute drive takes you to the Salento Peninsula on the magnificent Ionian Coast, where sandy beaches and the cobalt-blue waters of inviting inlets are sure to lure you in for a refreshing dip. Your initial destination is the seaside resort town of Porto Cesareo, overseen by a handsome 16th-century watchtower. From here, your Puglia Self-Guided Biking Vacation takes you for a spectacular coastal ride, passing through villages that showcase the real Puglia. Get out of the saddle as the spirit moves you, for photos, or to poke into a shop. You’ll find that conversations with locals come easily in this corner of Italy that sees few visitors!

Later, you’ll glide into the Old Town of Gallipoli, the “Gem of Salento,” a medieval fortified island city linked to the mainland by a 16th-century bridge. Gallipoli was part of Magna Graecia, or Greater Greece, which included vast swathes of southern Italy and Sicily in ancient times. Once a center for olive oil, today Gallipoli is a lively city, full of boutiques, cafés, and vestiges from its Greek and Roman days. The fishing port still brings in the catch of the day and the surrounding walls, once a defense against centuries of invasions, is the perfect place to join locals in their passeggiata, or afternoon stroll, before a well-earned aperitivo overlooking Sant’ Andrea’s lighthouse. Resume cycling to get to your cozy masseria for an authentic Salento experience.

Today's Ride Choices

Porto Cesareo to Gallipoli and Sannicola — 47 km (29 miles)

Nardò loop — 9 km (6 miles)

What to Expect:

Porto Cesareo to Gallipoli and Sannicola:
Departing Porto Cesareo, your ride stays mainly along the coast on a mixture of roads and dedicated bike lanes through populated areas, farmland, and open fields with the sea in the distance on your right. Rising after 13 km (eight miles), the day’s steepest ascent is more than made up for by stunning sea views, after which you will veer inland for about five km (three miles). The route returns to the coast through some charming small ports and beaches before rolling into the center of Gallipoli. There you can get as far as the old ‘cittadella’ and make a loop all around it, then park and lock your bike to explore on foot. The ride continues out of town to your masseria-hotel. Pay attention to car traffic as you ride in and out of Gallipoli.

Nardò loop:
Enjoy an optional visit of Nardò, on an almost 9 km (6 miles) ride in the countryside, into the heart of Nardò and returning to the coast. Nardò is rich in history and the monuments will offer you a cultural insight into its past. Breath the authentic life of a back-country Salentine village by stopping at the historical vinery, Schola Sarmenti. Grab a snack from a pastry shop or enjoy lunch in a historical café in the main square. You rejoin the Porto Cesareo to Gallipoli route at the 16.7 km (27 mile) point.

Included Meals: Breakfast

Relish another day cycling as your Puglia self-guided biking tour takes you along the Ionian Sea, where each crystalline beach seems more inviting than the last. You might want to plan on an early start so you can take as many swim breaks as you wish. There will also be opportunities to stop for true Italian coffee and to grab lunch at a seaside restaurant in Marina di Torre San Giovanni. And of course, an Italian cycling adventure cannot live up to its reputation if it doesn’t include at least a daily stop for gelato. As much as you’ll enjoy the culinary and swim breaks, it’s the vistas and picturesque marinas that are truly inspiring in this breathtaking corner of Puglia. You will end the day in Santa Maria di Leuca—a beautiful destination perched on a low seaside promontory and steeped in ancient history and legend. This historic town was named for the white cliffs that have been providing the scenic backdrop to your ride (leukos is Greek for “white”).

The locals claim that this is where the Ionian meets the Adriatic, although officially it is further east. Pause at Punta Ristola for sweeping views of the lighthouse, Italy’s second most important, and the adjacent Basilica Sanctuary of Saint Mary—also known as De Finibus Terrae, or “The End of the Land,” named when it was commonly believed that the earth was flat. The Basilica, built over a Roman temple and dedicated to the goddess Minerva, marks where Saint Peter is said to have started his long walk to Rome after crossing the Mediterranean from Jerusalem. Today, the devout follow in his footsteps along the Via Francigena pilgrimage route.

After a rewarding day, settle into your exclusive enclave and enjoy an included dinner at your hotel.

Today's Ride Choices

Sannicola to Santa Maria di Leuca — 64 km (40 miles)

Santa Maria di Leuca loop — 14 km (9 miles)

Optional Santa Maria di Leuca walk — 6 km (3 miles)

What to Expect:

Sannicola to Santa Maria di Leuca:
An easy ride that stays almost entirely along the coast on roads or shared-use bike lanes (in Italian, signs for percorso cicloturistico indicate a slower speed limit for cars). You will pass many sandy beaches, marinas, and beach resorts with ample options for swimming, lunch, coffee, and ice cream, as well as many scenic viewpoints and ancient watchtowers. As you round the tip of the peninsula, you will pass the Devil’s Cave, a natural limestone cave.

Santa Maria di Leuca loop:
Enjoy a loop from the hotel heading inland on peaceful countryside routes with gentle ascents and descents. The route takes you into Santa Maria di Leuca before returning to rural roads leading to delightful views of the sea on your way down to the coast!

Optional Santa Maria di Leuca walk:
The walk, roundtrip from your hotel, is about 5 km and takes you to the most important highlights of the village. You can find information about the embarcadero if you wish to enjoy the boat excursion along the coast from a sea perspective.

Included Meals: Breakfast, Dinner

Today’s ride continues along the dramatic Adriatic Coast with the sea on your right for the entire day, as your Puglia self-guided biking tour takes you descending into enticing crystalline coves. Later, some invigorating climbs lead to high bluffs with breathtaking views followed by exhilarating descents bringing you to quaint harbor villages. At today’s highest elevations, you’ll pass a series of ancient watchtowers where guards once kept an eye out for intruders approaching from the southern Mediterranean. As you ride, you’ll find plenty of options for lunch and snacks; perhaps you’ll sample freshly prepared seafood or provola e mortadella. One final long and steady downhill brings you into Otranto, Italy’s easternmost point. Surrounded by great ramparts, it is one of Italy’s most scenic coastal towns, situated on the Strait of Otranto, which separates Italy from Albania by just 45 miles.

Otranto’s Old Town is a rich amalgam of the history of past invaders: Greeks, Romans, and Turks among them. Exploring it on your Puglia self-guided biking tour is a must, and stopping in its 11th-century cathedral is absolutely required. Behind the altar, the bones of 813 martyrs who fell in a 15th-century siege are encased in a glass cabinet. But the medieval mosaic floor, the largest in Europe, is the real draw: Created in 1163 by a resident monk, the “Tree of Life” spans 8,611 square feet. Back outside, you might find your own mosaics—and other crafts—among the bustling stalls that line the narrow lanes. Otranto’s 15th-century castle is also worth a visit for its history and the exhibit devoted to the now-closed Neolithic caves in Porto Badisco that you passed on your way into town.

At dinnertime, you can stroll to the city’s inviting waterfront with its wide terrace and lovely vistas.

Today's Ride Choices

Santa Maria di Leuca to Otranto — 52 km (32 miles)

What to Expect:

You will ride along the Adriatic Coast, with the week’s highest elevation gains and losses. The route is high above the sea on bluffs and also dips down to charming harbor villages with stops for swimming, food, and drinks. The second climb of the day takes you to Torre Nasparo, with its spectacular views east and north. On a clear day, after the last big climb to Torre Minervino, before reaching Italy’s most easterly lighthouse of Punta Palascia, you may spot Albania’s Acroceurani mountain range and some Greek islands on the other side of the Adriatic Sea. A sustained descent brings you to Porto Badisco, Approdo di Enea and then into Otranto.

Included Meals: Breakfast

Enjoy a Stay Put Day to do as you please. If you just can’t stay off the saddle, take a loop ride into the interior away from the sea, following quiet country roads. An initial slight ascent lifts you above Otranto and then flattens out as it winds through olive groves framed by stone walls. You may stop to ponder ancient dolmens and menhirs, the region’s mysterious prehistoric standing stones. Take your time on this scenic route, perhaps pausing to toast your good fortune at a local winery or stopping to observe a traditional weaving workshop. Back at Otranto’s beach, reward yourself with a swim and a delicious seafood lunch along the port.

Alternately, you can join a boat excursion along the dramatic coastal cliffs and past spectacular grottos, stopping for swims along the way. You may prefer to spend the day on land, browsing Otranto’s inviting shops, and the halls and grounds of its seaside castle. Your Puglia Self-Guided Biking Vacation offers plenty of choices.

Today's Ride Choices

Otranto to Uggiano la Chiesa loop — 26 km (16 miles) | Otranto Walk — 3 km (2 miles)

What to Expect:

A narrow road exits the center of Otranto. After an initial, gradual ascent, the route flattens out on quiet country roads, rolling through olive groves and past stone walls, farms and hamlets. You may stop for lunch and a tasting at a winery or visit a traditional weaving workshop along the way. Scattered throughout the landscape are prehistoric standing stones.

Included Meals: Breakfast

Leaving Otranto today, you’ll savor the last ride of your Puglia Self-Guided Biking Vacation along the dramatic Adriatic coast. Ride along the Strait of Otranto before turning into a countryside of enormous olive and oak trees. This scenic route leads to the small Renaissance village of Acaya, one of Puglia’s last remaining fortified cities. Its notable 16th-century grid of streets divides the town into rectangular “islands.” After exploring, you’ll join a bike path that leads into the center of Lecce. This beautiful city is constructed from a pink-tinged local stone called pietra dorata. There is so much Baroque-period architecture with chiseled cherubs, angels, and saints, that Lecce has been called the “Florence of the South.” As you explore, your week of cycling will no doubt bring a new sense of urgency to your gelato cravings; you’ll have plenty of options to satisfy them here!

A stunning five-star hotel in the heart of the pedestrian Old City welcomes you to Lecce, a fine finale for your trip. Settle in and then take a short stroll to historic sites, including the Piazza Sant’Oronzo, the city’s main square with its centerpiece Roman amphitheater. Pick any of the narrow streets that fan out from the square to discover charming neighborhoods—and duck into any number of rustic eateries serving the hearty cuisine for which the city is known, including pureed fava beans and broccolini and a robust primitivo wine. It’s the perfect way to celebrate your ride around Italy’s heel!

Today's Ride Choices

Otranto to Lecce — 50 km (31 miles)

Optional Lecce walk — 3 km (2 miles)

What to Expect:

Otranto to Lecce:
After an initial ascent departing Otranto from sea level, the ride is mainly flat along the coast, then at around the 30 km (18 miles) after San Foca, you will turn inland through olive groves and begin a slight sustained ascent to Acaya, one of the best examples of a Renaissance fortified town in Italy. From there, you’ll join a bike path that leads into the center of Lecce. Although Lecce is a bike-friendly city, please be aware that urban riding will be very busy compared to the low-traffic riding you have enjoyed this week. Please exercise caution and, although not required, we recommend walking your bike the last few kilometers to your hotel.

Optional Lecce walk:
A suggested walk from your hotel to discover the major monuments of the capital of Baroque style and gastronomic insights of the traditional food of the county.

Included Meals: Breakfast

Enjoy breakfast at your hotel in Lecce and depart on your own. For details, refer to your VBT Handbook. Depending upon your destination, it may not be possible to depart for the U.S. on the last day of your Puglia Self-Guided Biking Vacation. Please check airline schedules carefully. If you plan to schedule a return flight immediately following the tour’s conclusion, please call your airline directly for specific check-in requirements.

Lecce has good train connections with all main lines connecting to destinations throughout Italy (e.g., Naples, five hours; Rome, 5.5 hours). The train and bus stations are just under 1.4 km (0.9 miles) from your hotel; a 20-minute walk across the pedestrian city center.

Included Meals: Breakfast