Italy: Puglia, Alberobello & Lecce

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

Upon arrival at Bari International Airport, make your own independent travel arrangements to your centrally located hotel in Alberobello. For details, refer to your Vacation Preparation Handbook.

When you arrive in Alberobello, you might feel as if you’ve stepped into a fairytale, thanks to the city’s many trulli. These round, whitewashed, dry-stone huts capped with conical limestone roofs were originally built without mortar so they could be quickly dismantled when the tax collector was approaching. Though they were once used to store agricultural tools, many later became dwellings. Today, they are a carefully preserved symbol of Puglia and a UNESCO World Heritage site. Many trulli have been beautifully restored for modern living, including those that make up Trulli e Puglia, your unique hotel for the night.

This charming boutique property is composed of individual trulli homes, allowing guests to experience the magic of sleeping in one of these historic structures while enjoying modern comforts. Make yourself at home in your own private trullo, relax after your journey, and stroll through this enchanting village of 500-year-old dwellings—some with chalk-white symbols on their roofs meant to bless the people who live within. VBT provides city information to help you make the most of your time in Alberobello.

After breakfast at Trulli e Puglia, meet your Local Host in the lobby at 10:30 a.m. for your Welcome Orientation, along with any other VBT guests arriving 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’ll enter the rolling Itria Valley. Take your time on today’s route, pausing to savor the rustic landscape of ancient olive trees, small vineyards, and vegetable gardens nestled among farmhouses and trulli. These buildings are so distinctive that UNESCO has listed them as a World Heritage site.

Your ride brings you through Locorotondo, where a photo stop is recommended to admire the typical cummerse houses. A final panoramic stretch leads you to the white-washed city of Ostuni. As beautiful as it is unique, the historic center—where your hotel is located—is a maze of narrow, winding alleyways. Colorful flower pots add a cheerful contrast to the white façades, traditionally painted to reflect intense sunlight and keep interiors cool.

Tonight, settle into Hotel La Terra, a charming historic property set in a 13th-century stone building in the heart of the Old Town. With its vaulted ceilings, exposed stone walls, and warm hospitality, the hotel offers a memorable blend of medieval atmosphere and modern comfort. Later, walk up into the white Cittadella, where some homes are carved directly into the limestone, and choose a restaurant for dinner on your own—you may even opt for one located in a former cave.

Today's Ride Choices

Alberobello to Ostuni — 39 km (24 miles)

Locorotondo Walk — 1 km (0.5 miles)

What to Expect:

The ride begins by leaving the narrow town streets and following paved rural roads through ancient olive groves, passing traditional farmhouses and trulli huts. After about 7 miles, you’ll arrive in Locorotondo—a must-see village well worth a short visit. A few miles beyond town, you’ll cross the scenic Figazzano Bridge and continue on a well-beaten, unpaved bike path for approximately 2 miles. Gentle ascents and descents lead you into Ostuni, where you’ll need to be alert for some car traffic as you approach the city center. The hotel is nearby, located in the heart of town. You’ll ride a short stretch over cobblestones, then briefly walk your bike up a section of large stone paving, which may be slippery when wet. Upon arrival, ask the hotel reception to open the garage so you can park and lock your bike. Please do not leave your bike unattended outside the hotel entrance.

Included Meals: Breakfast

After breakfast, walk your bike to the hotel parking area, where your private coach will be ready to depart at 9:00 a.m. A 60-minute drive brings you to the Salento Peninsula on the magnificent Ionian Coast, where sandy beaches and cobalt-blue waters invite a refreshing dip. Your destination is the seaside town of Porto Cesareo, known for its charming harbor and the imposing 16th-century watchtower that overlooks the bay.

From here, set out on a spectacular coastal ride through the heart of Salento. Your route winds past rural villages and seaside vistas that showcase the authentic character of Puglia. Take your time—pause for photos, browse local shops, or chat with friendly residents in this lesser-traveled region of Italy.

Later, glide into the Old Town of Gallipoli, the “Gem of Salento.” This fortified medieval city, situated on an island and linked to the mainland by a 16th-century bridge, was once part of Magna Graecia. Gallipoli blends ancient Greek and Roman roots with vibrant modern life. The daily fishing port still delivers the catch of the day, and the city walls—once defensive—now serve as a scenic promenade. Join locals for the traditional passeggiata and soak in views of Sant’Andrea’s lighthouse as the sun begins to set.

This evening, continue to your accommodations at Masseria Relais Santa Teresa, a beautifully restored 17th-century farmhouse nestled in the countryside near Gallipoli. This elegant property offers rustic charm, modern comfort, and a peaceful atmosphere—an ideal place to unwind after a rewarding day of cycling.

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 from Porto Cesareo, your ride follows a mix of roads and dedicated bike lanes along the coast, passing through populated areas, farmland, and open fields with sea views on your right. Around kilometer 13 (mile 8), you’ll encounter the day’s steepest climb—rewarded with spectacular views—before veering inland for about 5 km (3 miles). The route then returns to the coast, winding past charming small ports and beaches before rolling into the center of Gallipoli. You may ride as far as the old cittadella and make a full loop around it, then park and lock your bike to explore on foot. The ride continues out of town toward your masseria–hotel. Please be attentive to car traffic when riding in and out of Gallipoli.

Nardò Loop (Optional):
Enjoy an optional 9 km (6 mile) countryside loop into the historic town of Nardò. Rich in heritage, its monuments offer a glimpse into the region’s storied past. Experience the authentic atmosphere of this Salentine village by visiting the historic winery Schola Sarmenti, grabbing a pastry from a local shop, or enjoying lunch at a historic café in the main square. You’ll rejoin the main route from Porto Cesareo to Gallipoli at kilometer 27 (mile 16.7).

Included Meals: Breakfast

Relish another day of cycling along the Ionian Sea, where each crystalline beach seems more inviting than the last. You may want to start early today to allow time for refreshing swim breaks. Along the way, you’ll find opportunities to stop for a proper Italian coffee and enjoy lunch at a seaside restaurant in Marina di Torre San Giovanni. And of course, no Italian cycling adventure would be complete without a daily stop for gelato. While the culinary and swim breaks are a highlight, it’s the breathtaking coastal views and picturesque marinas that truly inspire in this beautiful corner of Puglia.

You’ll end your ride in Santa Maria di Leuca, a coastal town perched on a low promontory steeped in history and legend. Named for the region’s striking white cliffs (leukos is Greek for “white”), Leuca has long been thought of as the place where the Ionian and Adriatic seas meet—though officially that point lies farther east. Be sure to pause at Punta Ristola for sweeping views of the coastline, lighthouse (Italy’s second most important), and the Basilica Sanctuary of Saint Mary, also known as De Finibus Terrae or “The End of the Land”—a name from when it was believed the earth was flat. Built atop a Roman temple dedicated to Minerva, the basilica marks where Saint Peter is said to have begun his walk to Rome, a journey now retraced by modern pilgrims along the Via Francigena.

Tonight, settle into your comfortable accommodations at Hotel Approdo, a well-located property just steps from the sea promenade. Enjoy modern amenities, coastal views, and easy access to the town’s cafés and waterfront. Your included dinner tonight will be served in the hotel’s restaurant.

Today's Ride Choices

Sannicola to Santa Maria di Leuca — 65 km (40 miles)

Optional 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:
Today’s ride is mostly easy and follows the coast almost entirely, using roads and shared-use bike lanes (marked percorso cicloturistico in Italian, indicating reduced speed limits for vehicles). Portions of the route are on unpaved surfaces. Along the way, you’ll pass sandy beaches, marinas, and seaside resorts, with plenty of opportunities to stop for a swim, lunch, coffee, or gelato. The ride is rich with scenic viewpoints and historic watchtowers. As you round the southern tip of the peninsula, look for the Devil’s Cave, a dramatic natural limestone formation.

Santa Maria di Leuca Loop (Optional):
Enjoy a scenic loop from the hotel that heads inland on quiet countryside roads with gentle ascents and descents. The route leads back through Santa Maria di Leuca before rejoining rural roads, offering delightful sea views as you descend toward the coast.

Santa Maria di Leuca Walk (Optional):
A 5 km roundtrip walk from your hotel brings you to the key highlights of Santa Maria di Leuca, including the basilica, lighthouse, and scenic overlook. For those interested in seeing the coastline from the water, inquire locally at the embarcadero about optional boat excursions.

Included Meals: Breakfast, Dinner

Today’s ride continues along the dramatic Adriatic Coast, with the sea on your right for most of the day. Descend into enticing crystalline coves, then take on invigorating climbs that reward you with breathtaking views from high coastal bluffs. Exhilarating descents lead into quiet harbor villages. At the day’s highest points, you’ll pass a series of ancient watchtowers where guards once kept watch for invaders arriving from the southern Mediterranean. Along the way, there are plenty of options for lunch or a snack—perhaps you’ll sample freshly prepared seafood or a provola e mortadella sandwich.

A final long, steady downhill brings you into Otranto, Italy’s easternmost point. Perched on the Strait of Otranto—just 45 miles from Albania—this walled seaside town is among the most scenic on Italy’s coast.

Otranto’s Old Town is a vibrant blend of the many civilizations that once passed through: Greek, Roman, Turkish, and more. A visit to its 11th-century cathedral is a must. Behind the altar are the remains of 813 martyrs who died in a 15th-century siege. But the true highlight is the cathedral’s magnificent mosaic floor—Europe’s largest—spanning over 8,600 square feet. Created in 1163 by a local monk, it depicts the “Tree of Life” in remarkable medieval detail. Outside, browse local mosaics and other artisan crafts in the narrow streets. The town’s 15th-century castle is also worth exploring, especially its exhibit on the Neolithic caves of nearby Porto Badisco, which you passed on your way into town.

You’ll be staying for the next two nights at Hotel Albania, ideally located near the waterfront and a short stroll from Otranto’s Old Town. The hotel offers modern comforts and a rooftop terrace with sweeping views of the Adriatic.

This evening, you may wish to stroll along the town’s inviting promenade, with its wide seafront terrace and open-air cafés.

Today's Ride Choices

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

What to Expect:

You’ll ride along the Adriatic Coast today, encountering the week’s highest elevation gains and losses. The route alternates between soaring coastal bluffs and dips into charming harbor villages, with opportunities to stop for swimming, food, and drinks. The second major climb leads to Torre Nasparo, where spectacular views stretch to the east and north. Later, after the final big ascent to Torre Minervino—just before reaching Italy’s easternmost lighthouse at Punta Palascia—you may even spot Albania’s Acroceraunian mountain range and a few distant Greek islands across the Adriatic Sea. A long, rewarding descent brings you through Porto Badisco, past the Approdo di Enea, and into the historic town of 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 inland, away from the sea, following quiet country roads. A gentle ascent lifts you above Otranto before the route levels out, winding through olive groves bordered by dry stone walls. You may choose to stop and reflect at ancient dolmens and menhirs, the region’s mysterious prehistoric standing stones. Take your time on this scenic route—perhaps pausing for a tasting at a local winery or visiting a traditional weaving workshop.

Back in Otranto, reward yourself with a refreshing swim and a delicious seafood lunch along the port.

Alternatively, you may opt for a boat excursion along the dramatic cliffs and sea grottos, with opportunities to swim in hidden coves. Or stay on land to explore Otranto’s inviting shops and stroll the halls and grounds of its seaside castle.

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 leads out of the center of Otranto. After a gradual initial ascent, the route flattens out along quiet country roads, winding through olive groves, past stone walls, farms, and small hamlets. Along the way, you may stop for lunch and a tasting at a local winery or visit a traditional weaving workshop. Scattered throughout the landscape are prehistoric standing stones, offering a glimpse into the region’s ancient past.

Included Meals: Breakfast

Leaving Otranto today, you’ll savor the final ride of your vacation along the dramatic Adriatic coast. Begin along the Strait of Otranto, then turn inland into a landscape of majestic olive and oak trees. This scenic route leads to the small Renaissance village of Acaya, one of Puglia’s last remaining fortified towns. Its distinctive 16th-century grid layout divides the village into rectangular “islands.” After a bit of exploration, continue on a bike path that brings you directly into the heart of Lecce.

Constructed largely from the warm, pink-hued local stone known as pietra dorata, Lecce is famed for its Baroque architecture—lavishly adorned with carved cherubs, angels, and saints—earning it the nickname “Florence of the South.” As you explore its winding streets, you may find your week of cycling has given you a well-earned craving for gelato—luckily, Lecce offers no shortage of delicious options.

You’ll stay tonight at Suite Hotel Santa Chiara, an intimate boutique property located in the pedestrianized Old City. This elegant hotel offers stylish comfort in a prime location just steps from Lecce’s main sights. After settling in, take a stroll to nearby landmarks like Piazza Sant’Oronzo, home to the impressive Roman amphitheater. Let the evening unfold as you wander the charming streets and discover cozy trattorias serving the hearty cuisine of Salento—think pureed fava beans with broccolini and a glass of robust primitivo wine. It’s a fitting celebration to conclude your ride through Italy’s heel.

Today's Ride Choices

Otranto to Lecce — 49 km (30 miles)

Optional Lecce Walk — 3 km (2 miles)

What to Expect:

Otranto to Lecce:
After a brief initial ascent departing Otranto from sea level, the ride is mostly flat as it follows the coastline. Around kilometer 30 (mile 18), after passing San Foca, the route turns inland through olive groves and begins a gentle, sustained climb to Acaya, one of Italy’s finest examples of a Renaissance fortified town. From there, you’ll join a bike path that leads into the center of Lecce. Although Lecce is a bike-friendly city, please note that urban riding will be significantly busier than the quiet, low-traffic roads you’ve enjoyed throughout the week. Exercise caution and, while not required, we recommend walking your bike for the final few kilometers to your hotel.

Optional Lecce Walk:
Enjoy a self-guided walk from your hotel to discover the major landmarks of this Baroque capital, along with insights into the region’s culinary traditions.

Included Meals: Breakfast

After an included breakfast, you have the day free to explore the city of Lecce. Be sure to visit Piazza Duomo, one of Europe’s largest squares, enclosed on three sides by the cathedral and other historic buildings. Despite its size, the surrounding architecture and nearby cafés create an intimate, welcoming atmosphere. With a single entry ticket, you can visit up to six of Lecce’s intricately detailed Baroque churches.

Your VBT city information includes helpful recommendations for making the most of your time in Lecce. Dinner is on your own tonight.

Included Meals: Breakfast

After an included breakfast this morning, if you are traveling by public transportation, allow a minimum of four hours before your flight from Brindisi Airport. For details, refer to your Vacation Preparation Handbook. This recommended timeframe accounts for approximately 1.5 hours of travel and at least two hours for pre-flight check-in.

Included Meals: Breakfast

We recommend arriving in Italy at least one day before your tour begins, as the tour starts promptly at 10:30 a.m. on Day 1. Please make your own independent travel arrangements to your tour meeting point hotel in Alberobello. For details, refer to your Vacation Preparation Handbook.

If you are delayed and unable to meet your VBT Local Host at the scheduled time, please contact the first hotel on your itinerary as soon as possible with your expected arrival time. You may also call our 24/7 third-party travel assistance provider (contact information is included in this document) and they will notify the hotel on your behalf.

When you arrive in Alberobello, you’ll feel as if you’ve stepped into a fairytale. The town’s iconic trulli—round, whitewashed stone huts with conical limestone roofs—were originally built without mortar to allow for quick dismantling to evade taxation. Once used to store agricultural tools, these unique structures later became homes. Today, trulli are a symbol of Puglia and a UNESCO World Heritage site. Many have been beautifully restored for modern living, including those that make up Trulli e Puglia, your tour’s meeting point hotel.

Please meet your VBT Local Host at 10:30 a.m. in the lobby of Trulli e Puglia, along with any other VBT guests arriving that day. Be dressed and ready for cycling. Your Local Host will be holding 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’ll enter the rolling Itria Valley. Take your time on today’s route, pausing to savor the rustic landscape of ancient olive trees, small vineyards, and vegetable gardens nestled among farmhouses and trulli. These buildings are so distinctive that UNESCO has listed them as a World Heritage site.

Your ride brings you through Locorotondo, where a photo stop is recommended to admire the typical cummerse houses. A final panoramic stretch leads you to the white-washed city of Ostuni. As beautiful as it is unique, the historic center—where your hotel is located—is a maze of narrow, winding alleyways. Colorful flower pots add a cheerful contrast to the white façades, traditionally painted to reflect intense sunlight and keep interiors cool.

Tonight, settle into Hotel La Terra, a charming historic property set in a 13th-century stone building in the heart of the Old Town. With its vaulted ceilings, exposed stone walls, and warm hospitality, the hotel offers a memorable blend of medieval atmosphere and modern comfort. Later, walk up into the white Cittadella, where some homes are carved directly into the limestone, and choose a restaurant for dinner on your own—you may even opt for one located in a former cave.

Today's Ride Choices

Alberobello to Ostuni — 39 km (24 miles)

Locorotondo Walk — 1 km (0.5 miles)

What to Expect:

The ride begins by leaving the narrow town streets and following paved rural roads through ancient olive groves, passing traditional farmhouses and trulli huts. After about 7 miles, you’ll arrive in Locorotondo—a must-see village well worth a short visit. A few miles beyond town, you’ll cross the scenic Figazzano Bridge and continue on a well-beaten, unpaved bike path for approximately 2 miles. Gentle ascents and descents lead you into Ostuni, where you’ll need to be alert for some car traffic as you approach the city center. The hotel is nearby, located in the heart of town. You’ll ride a short stretch over cobblestones, then briefly walk your bike up a section of large stone paving, which may be slippery when wet. Upon arrival, ask the hotel reception to open the garage so you can park and lock your bike. Please do not leave your bike unattended outside the hotel entrance.

After breakfast, walk your bike to the hotel parking area, where your private coach will be ready to depart at 9:00 a.m. A 60-minute drive brings you to the Salento Peninsula on the magnificent Ionian Coast, where sandy beaches and cobalt-blue waters invite a refreshing dip. Your destination is the seaside town of Porto Cesareo, known for its charming harbor and the imposing 16th-century watchtower that overlooks the bay.

From here, set out on a spectacular coastal ride through the heart of Salento. Your route winds past rural villages and seaside vistas that showcase the authentic character of Puglia. Take your time—pause for photos, browse local shops, or chat with friendly residents in this lesser-traveled region of Italy.

Later, glide into the Old Town of Gallipoli, the “Gem of Salento.” This fortified medieval city, situated on an island and linked to the mainland by a 16th-century bridge, was once part of Magna Graecia. Gallipoli blends ancient Greek and Roman roots with vibrant modern life. The daily fishing port still delivers the catch of the day, and the city walls—once defensive—now serve as a scenic promenade. Join locals for the traditional passeggiata and soak in views of Sant’Andrea’s lighthouse as the sun begins to set.

This evening, continue to your accommodations at Masseria Relais Santa Teresa, a beautifully restored 17th-century farmhouse nestled in the countryside near Gallipoli. This elegant property offers rustic charm, modern comfort, and a peaceful atmosphere—an ideal place to unwind after a rewarding day of cycling.

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 from Porto Cesareo, your ride follows a mix of roads and dedicated bike lanes along the coast, passing through populated areas, farmland, and open fields with sea views on your right. Around kilometer 13 (mile 8), you’ll encounter the day’s steepest climb—rewarded with spectacular views—before veering inland for about 5 km (3 miles). The route then returns to the coast, winding past charming small ports and beaches before rolling into the center of Gallipoli. You may ride as far as the old cittadella and make a full loop around it, then park and lock your bike to explore on foot. The ride continues out of town toward your masseria–hotel. Please be attentive to car traffic when riding in and out of Gallipoli.

Nardò Loop (Optional):
Enjoy an optional 9 km (6 mile) countryside loop into the historic town of Nardò. Rich in heritage, its monuments offer a glimpse into the region’s storied past. Experience the authentic atmosphere of this Salentine village by visiting the historic winery Schola Sarmenti, grabbing a pastry from a local shop, or enjoying lunch at a historic café in the main square. You’ll rejoin the main route from Porto Cesareo to Gallipoli at kilometer 27 (mile 16.7).

Included Meals: Breakfast

Relish another day of cycling along the Ionian Sea, where each crystalline beach seems more inviting than the last. You may want to start early today to allow time for refreshing swim breaks. Along the way, you’ll find opportunities to stop for a proper Italian coffee and enjoy lunch at a seaside restaurant in Marina di Torre San Giovanni. And of course, no Italian cycling adventure would be complete without a daily stop for gelato. While the culinary and swim breaks are a highlight, it’s the breathtaking coastal views and picturesque marinas that truly inspire in this beautiful corner of Puglia.

You’ll end your ride in Santa Maria di Leuca, a coastal town perched on a low promontory steeped in history and legend. Named for the region’s striking white cliffs (leukos is Greek for “white”), Leuca has long been thought of as the place where the Ionian and Adriatic seas meet—though officially that point lies farther east. Be sure to pause at Punta Ristola for sweeping views of the coastline, lighthouse (Italy’s second most important), and the Basilica Sanctuary of Saint Mary, also known as De Finibus Terrae or “The End of the Land”—a name from when it was believed the earth was flat. Built atop a Roman temple dedicated to Minerva, the basilica marks where Saint Peter is said to have begun his walk to Rome, a journey now retraced by modern pilgrims along the Via Francigena.

Tonight, settle into your comfortable accommodations at Hotel Approdo, a well-located property just steps from the sea promenade. Enjoy modern amenities, coastal views, and easy access to the town’s cafés and waterfront. Your included dinner tonight will be served in the hotel’s restaurant.

Today's Ride Choices

Sannicola to Santa Maria di Leuca — 65 km (40 miles)

Optional 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:
Today’s ride is mostly easy and follows the coast almost entirely, using roads and shared-use bike lanes (marked percorso cicloturistico in Italian, indicating reduced speed limits for vehicles). Portions of the route are on unpaved surfaces. Along the way, you’ll pass sandy beaches, marinas, and seaside resorts, with plenty of opportunities to stop for a swim, lunch, coffee, or gelato. The ride is rich with scenic viewpoints and historic watchtowers. As you round the southern tip of the peninsula, look for the Devil’s Cave, a dramatic natural limestone formation.

Santa Maria di Leuca Loop (Optional):
Enjoy a scenic loop from the hotel that heads inland on quiet countryside roads with gentle ascents and descents. The route leads back through Santa Maria di Leuca before rejoining rural roads, offering delightful sea views as you descend toward the coast.

Santa Maria di Leuca Walk (Optional):
A 5 km roundtrip walk from your hotel brings you to the key highlights of Santa Maria di Leuca, including the basilica, lighthouse, and scenic overlook. For those interested in seeing the coastline from the water, inquire locally at the embarcadero about optional boat excursions.

Included Meals: Breakfast, Dinner

Today’s ride continues along the dramatic Adriatic Coast, with the sea on your right for most of the day. Descend into enticing crystalline coves, then take on invigorating climbs that reward you with breathtaking views from high coastal bluffs. Exhilarating descents lead into quiet harbor villages. At the day’s highest points, you’ll pass a series of ancient watchtowers where guards once kept watch for invaders arriving from the southern Mediterranean. Along the way, there are plenty of options for lunch or a snack—perhaps you’ll sample freshly prepared seafood or a provola e mortadella sandwich.

A final long, steady downhill brings you into Otranto, Italy’s easternmost point. Perched on the Strait of Otranto—just 45 miles from Albania—this walled seaside town is among the most scenic on Italy’s coast.

Otranto’s Old Town is a vibrant blend of the many civilizations that once passed through: Greek, Roman, Turkish, and more. A visit to its 11th-century cathedral is a must. Behind the altar are the remains of 813 martyrs who died in a 15th-century siege. But the true highlight is the cathedral’s magnificent mosaic floor—Europe’s largest—spanning over 8,600 square feet. Created in 1163 by a local monk, it depicts the “Tree of Life” in remarkable medieval detail. Outside, browse local mosaics and other artisan crafts in the narrow streets. The town’s 15th-century castle is also worth exploring, especially its exhibit on the Neolithic caves of nearby Porto Badisco, which you passed on your way into town.

You’ll be staying for the next two nights at Hotel Albania, ideally located near the waterfront and a short stroll from Otranto’s Old Town. The hotel offers modern comforts and a rooftop terrace with sweeping views of the Adriatic.

This evening, you may wish to stroll along the town’s inviting promenade, with its wide seafront terrace and open-air cafés.

Today's Ride Choices

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

What to Expect:

You’ll ride along the Adriatic Coast today, encountering the week’s highest elevation gains and losses. The route alternates between soaring coastal bluffs and dips into charming harbor villages, with opportunities to stop for swimming, food, and drinks. The second major climb leads to Torre Nasparo, where spectacular views stretch to the east and north. Later, after the final big ascent to Torre Minervino—just before reaching Italy’s easternmost lighthouse at Punta Palascia—you may even spot Albania’s Acroceraunian mountain range and a few distant Greek islands across the Adriatic Sea. A long, rewarding descent brings you through Porto Badisco, past the Approdo di Enea, and into the historic town of 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 inland, away from the sea, following quiet country roads. A gentle ascent lifts you above Otranto before the route levels out, winding through olive groves bordered by dry stone walls. You may choose to stop and reflect at ancient dolmens and menhirs, the region’s mysterious prehistoric standing stones. Take your time on this scenic route—perhaps pausing for a tasting at a local winery or visiting a traditional weaving workshop.

Back in Otranto, reward yourself with a refreshing swim and a delicious seafood lunch along the port.

Alternatively, you may opt for a boat excursion along the dramatic cliffs and sea grottos, with opportunities to swim in hidden coves. Or stay on land to explore Otranto’s inviting shops and stroll the halls and grounds of its seaside castle.

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 leads out of the center of Otranto. After a gradual initial ascent, the route flattens out along quiet country roads, winding through olive groves, past stone walls, farms, and small hamlets. Along the way, you may stop for lunch and a tasting at a local winery or visit a traditional weaving workshop. Scattered throughout the landscape are prehistoric standing stones, offering a glimpse into the region’s ancient past.

Included Meals: Breakfast

Leaving Otranto today, you’ll savor the final ride of your vacation along the dramatic Adriatic coast. Begin along the Strait of Otranto, then turn inland into a landscape of majestic olive and oak trees. This scenic route leads to the small Renaissance village of Acaya, one of Puglia’s last remaining fortified towns. Its distinctive 16th-century grid layout divides the village into rectangular “islands.” After a bit of exploration, continue on a bike path that brings you directly into the heart of Lecce.

Constructed largely from the warm, pink-hued local stone known as pietra dorata, Lecce is famed for its Baroque architecture—lavishly adorned with carved cherubs, angels, and saints—earning it the nickname “Florence of the South.” As you explore its winding streets, you may find your week of cycling has given you a well-earned craving for gelato—luckily, Lecce offers no shortage of delicious options.

You’ll stay tonight at Suite Hotel Santa Chiara, an intimate boutique property located in the pedestrianized Old City. This elegant hotel offers stylish comfort in a prime location just steps from Lecce’s main sights. After settling in, take a stroll to nearby landmarks like Piazza Sant’Oronzo, home to the impressive Roman amphitheater. Let the evening unfold as you wander the charming streets and discover cozy trattorias serving the hearty cuisine of Salento—think pureed fava beans with broccolini and a glass of robust primitivo wine. It’s a fitting celebration to conclude your ride through Italy’s heel.

Today's Ride Choices

Otranto to Lecce — 49 km (30 miles)

Optional Lecce Walk — 3 km (2 miles)

What to Expect:

Otranto to Lecce:
After a brief initial ascent departing Otranto from sea level, the ride is mostly flat as it follows the coastline. Around kilometer 30 (mile 18), after passing San Foca, the route turns inland through olive groves and begins a gentle, sustained climb to Acaya, one of Italy’s finest examples of a Renaissance fortified town. From there, you’ll join a bike path that leads into the center of Lecce. Although Lecce is a bike-friendly city, please note that urban riding will be significantly busier than the quiet, low-traffic roads you’ve enjoyed throughout the week. Exercise caution and, while not required, we recommend walking your bike for the final few kilometers to your hotel.

Optional Lecce Walk:
Enjoy a self-guided walk from your hotel to discover the major landmarks of this Baroque capital, along with insights into the region’s culinary traditions.

Included Meals: Breakfast

Enjoy breakfast at your hotel in Lecce and depart on your own. For details, refer to your Vacation Preparation Handbook. Depending on your destination, it may not be possible to return to the U.S. on the final day of your Puglia Self-Guided Biking Vacation. Please check airline schedules carefully. If you plan to book a return flight immediately after the tour concludes, we recommend calling your airline directly for specific check-in requirements.

Lecce has good train connections to major destinations throughout Italy (e.g., Naples in approximately five hours; Rome in about 5.5 hours). The train and bus stations are located just under 1.4 km (0.9 miles) from your hotel—a pleasant 20-minute walk through the pedestrian-friendly city center.

Included Meals: Breakfast