Italy: Tuscany, Chianti & Marina di Castagneto

Your vacation is about to begin! Spend your first night aloft and arrive ready for an unforgettable trip.

Start off your first day in Florence right by having a VBT representative greet you at the airport. A complimentary car service will whisk you to your centrally located hotel. From here, you are perfectly positioned to explore this charming city at your leisure, using VBT’s city information as your guide.

To visit the Uffizi Gallery, advance reservations are required. Visit florence-museum.com to reserve tickets. For information about all Italian museums, go to italy-museum.com.

After an included breakfast, meet your VBT representative in the hotel lobby at 10:30 a.m. After brief introductions, you’ll travel approximately one hour to Radda in Chianti—a stunning hilltop town in the heart of Chianti, encircled by medieval walls and defensive towers.

Your VBT trip leaders will greet you in Radda and conduct a safety session before your cycling activities begin. They’ll also offer suggestions for lunch on your own. There are plenty of cafés along the town’s ancient decumano—the east–west thoroughfare now known as Via Roma. Your rooms may not be ready until 2:00 p.m., but the hotel reception will store your luggage.

After lunch, your rooms will be available, and you’ll have time to settle in and change into your cycling clothes. Later, attend a bike-fitting session in preparation for your warm-up ride. This first ride leads you over gentle hills through a quintessential Tuscan landscape—past farmhouses, vineyards, and olive groves—en route to Castellina in Chianti.

Back in Radda, you may wish to relax in the hotel’s stone-vaulted spa and indoor swimming pool, set in ancient cellars, or unwind in the outdoor Jacuzzi pools.

This evening, gather for a welcome cocktail and dinner at the hotel.

Today's Ride Choices

Afternoon: Chianti Warm-Up Ride — 13 km (8 miles)

What to Expect:

A scenic out-and-back ride from Radda to Castellina features rolling hills and a single short ascent as you approach Castellina. The route follows a paved, winding road shared with local traffic.

Cumulative Distance Range: 13 km (8 miles)

Included Meals: Breakfast, Dinner

After breakfast, set out to explore Chianti along the “castle way,” a scenic route that winds through dense forests and charming villages like Lecchi on your way to Gaiole. The castles and watchtowers you’ll pass played strategic roles in the historic conflicts between Siena and Florence. Soon, one of these ancient fortifications comes into view—Castello di Meleto. From its hillside perch, enjoy splendid views of the valley and neighboring castles.

Castello di Meleto, founded in the 11th century by the Benedictine monks of Badia a Coltibuono, has served as a military post and a noble country residence. Despite its varied history, much of its original structure remains intact. Today, it is a wine resort where vineyards, olive groves, and gardens are cultivated using sustainable methods that preserve both the land and the spirit of Tuscany. The estate produces fine wines, organic extra virgin olive oil, Cinta Senese pigs, honey, and herbs.

During your visit, your host Gabriella—an expert in agricultural sciences—introduces you to this remarkable place. You’ll walk the grounds, visit the organic beehives, and learn how Gabriella and her team protect pollinators vital to Tuscan agriculture. VBT sponsors four of these hives through the Sustainable Travel Foundation. You’ll also explore the organic vineyards and herb gardens, tour the 17th-century noble residence, and visit a rare, unrestored theater—one of the last of its kind in Europe. In the ancient cellars, sample local wines, including Chianti Classico, Riserva, and Gran Selezione.

By lunchtime, you’ll arrive in Gaiole, a charming village that hosts the week-long L’Eroica each October—a beloved celebration of vintage cycling and the famed Strade Bianche race, held every March on Siena’s iconic white gravel roads. After exploring the village, choose a café for lunch on your own, then continue riding along Chianti’s legendary roads.

Back in Radda, take time to stroll the medieval alleyways and admire the Palazzo del Podestà, adorned with the town’s historic coat of arms. Radda is also a favorite stop for cyclists looking to purchase a jersey from the renowned—and tiny—local shop, where you’re sure to find one that suits you, perhaps bearing the iconic Black Rooster of Chianti.

Dinner is on your own this evening.

Today's Ride Choices

Morning: Radda to Meleto and Gaiole — 21 km (13 miles)

Afternoon: Gaiole to Castagnoli and Radda — 22 km (14 miles)

What to Expect:

This morning’s ride features a long, scenic descent through a shady green valley, with views opening to vineyards as you pass the picturesque hamlet of Lecchi. The route gently rolls into Gaiole, followed by a short paved climb to the base of Castello di Meleto. After lunch, choose between two return options: a shorter route with a steady two-mile uphill into Radda, which is manageable with an E-bike or can be skipped with a short van shuttle; or a longer option through Castagnoli that includes additional hills and sweeping views you won’t want to miss. Experienced cyclists may also have the opportunity for an independent ride along the unpaved L’Eroica roads—ask your trip leaders for details.

Cumulative Distance Range: 21 — 43 km (13 — 27 miles)

Included Meals: Breakfast

Your day begins with a thrilling descent along a scenic route that brings you to the medieval town of Monteriggioni. Before arriving, enjoy a short stop in Castellina, a classic Chianti hill town where you can explore cobblestone lanes, patrician palaces, and the partially covered Via delle Volte, a walkway ingeniously designed by Filippo Brunelleschi to shield the city from enemy firearms.

Continue your ride toward Monteriggioni, a stunning walled town that appears frozen in time. Its well-preserved fortifications follow the natural contours of the hillside, and 14 towers once stood as a defense against the attacks of Florence. The approach offers wide, breathtaking views along a long descent with sweeping bends. You’ll pass wheat fields, vineyards, iconic cypress-lined roads, and artistic treasures such as the Santa Cristina Church in Lilliano. Upon arrival, explore Monteriggioni on your own and take in the historic charm of this remarkable fortress town.

Later in the morning, you’ll shuttle to the hilltop town of Guardistallo and enjoy lunch at a typical locanda toscana. Here, you’ll meet Alessio and Riccardo and immerse yourself in the authentic Tuscan countryside, where a shared respect for tradition and the environment is reflected in your delicious, locally sourced meal. From this point, begin your afternoon ride along one of Italy’s most scenic wine roads, where the combination of climate, soil, and skilled winemaking yields some of Tuscany’s most elegant wines. Your route passes the renowned Ornellaia vineyards and continues along gently rolling hills through Bibbona. Along the way, stop at the popular bike shop owned by Daniela, a long-time friend of VBT, to browse the latest cycling gear or pick up a local jersey.

The day’s ride ends at Tombolo Talasso Resort, your deluxe hotel set directly on the Tyrrhenian Sea. Unwind on the hotel’s private beach or indulge in the Wellness Center, where five thermal swimming pools are filled with filtered seawater pumped directly from the sea.

This evening, after an aperitivo with your trip leaders, you’ll head to the home of longtime VBT friend Chicca (pronounced “Key-ka”) for an unforgettable home-cooked dinner. Through her organization, Cooking in Tuscany, Chicca shares the warmth and tradition of Tuscan cuisine, researching and preparing seasonal, regional dishes. You’ll take part in a hands-on cooking class before sitting down to enjoy your creations under her pergola at sunset.

Today's Ride Choices

Morning: Radda to Monteriggioni — 26 km (16 miles)

Afternoon: Le Giunche to Tombolo — 30 km (19 miles)

What to Expect:

The first 7 miles of your morning ride are gently rolling until you reach Castellina in Chianti. From there, enjoy an exhilarating and scenic 5-mile descent to Castellina Scalo. A bike path and a short half-mile stretch along the busier Cassia Road bring you to Monteriggioni, where you’ll park your bike at the base of the walled village and walk up to explore. After your visit, relax during a 70-minute shuttle ride to your lunch stop. In the afternoon, you’ll ride from there to your hotel, starting with a short uphill followed by a long, panoramic descent into the wine village of Bibbona. The route continues along moderately rolling terrain through vineyards and past wineries on the renowned Via Bolgherese—named after the medieval village of Bolgheri and popular with local cyclists. The final miles are flat as you approach Donoratico and ride on to your seaside hotel.

Cumulative Distance Range: 26 — 56 km (16 — 35 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, cycle the historic Strada del Vino Bolgherese, one of the most prestigious wine routes in Italy. These lush vineyards produce some of the country’s most celebrated DOC wines, regulated by the Denominazione di Origine Controllata (Denomination of Controlled Origin). Be sure to sample the Super Tuscans today—revolutionary red wines that transformed Italian viticulture. The area is also renowned for the elegant Viale dei Cipressi, a cypress-lined avenue immortalized in Giosuè Carducci’s poem San Guido.

Midday, stop at the family-owned Fonte di Foiano olive oil mill for a farm-fresh lunch. Enjoy a private tour of the press and workshop with your host. As you sample the oils on the terrace during a degustazione (tasting), Simone Di Gaetano will guide you through the flavors and characteristics of Italy’s diverse olive-growing regions. Then, sit down to a delicious vegetarian lunch featuring organic vegetables, thoughtfully prepared by chef siblings Beatrice and Paolo.

After lunch, continue your ride along peaceful countryside roads back to your beachside hotel.

This evening, your trip leaders will be happy to recommend a restaurant for dinner on your own in the charming seaside village of Marina di Castagneto.

Today's Ride Choices

Morning: La Strada del Vino — 32 km (20 miles)

Afternoon : Oil Mill to Tombolo — 12 km (7 miles)

What to Expect:

This morning’s ride sets a relaxed pace as you follow the Strada del Vino, mostly along narrow country roads en route to the lunch stop. Before arriving in the wine village of Bolgheri, you’ll ride the iconic cypress-lined avenue, flanked by towering trees. As you approach the Fonte di Foiano olive oil mill, the landscape transitions to gently rolling roads bordered by hundreds of olive trees. After lunch, return to the hotel via a different route that includes a 1.6 km (1 mile) stretch on an unpaved bike path through a pine forest. Experienced cyclists may have the opportunity for an additional independent ride—ask your trip leader for details.

Cumulative Distance Range: 12 — 44 km (7 — 27 miles)

Included Meals: Breakfast, Lunch

Today, you ride one of the most picturesque routes in Europe, pedaling past chestnut, cork, and pine trees, medieval estates, and fields of sunflowers. Your destination is Suvereto, an ancient village with roots stretching back over a millennium. Set in a stunning location overlooking the Costa degli Etruschi in the green valley of the Cornia River, Suvereto is celebrated throughout Tuscany for its architectural harmony. Its ancient walls enclose cobbled streets, stone houses, historic buildings, elegant churches, and serene cloisters. Lunch is included in this charming town, at a typical local taverna discovered by your trip leaders.

After lunch, enjoy a rolling and mostly downhill ride through the peaceful Cornia Valley, free of traffic and full of natural beauty. Your unforgettable ride ends at Hotel Calidario, which pays tribute to the region’s Etruscan legacy with a natural, open-air thermal pool covering 3,000 square meters. Fed by mineral-rich springs that rise from a granite basin below, the water has been enjoyed for centuries. The surrounding area is also home to several natural parks with fascinating Roman and Etruscan archaeological sites.

Settle in and relax, taking full advantage of the springs and hotel spa. This evening, enjoy dinner in a traditional Tuscan restaurant in the picturesque town of Campiglia Marittima, where you’ll have the option to sample local fish specialties.

Today's Ride Choices

Morning: Tombolo to Suvereto — 31 km (19 miles) | Sassetta to Suvereto with Shuttle — 15 km (9 miles)

Afternoon : Suvereto to Calidarium — 23 km (14 miles)

What to Expect:

This morning’s ride begins with either a shuttle or an uphill climb to Castagneto Carducci—easily manageable with an e-bike. From there, the route continues along a scenic and gently rolling stretch of road to Suvereto. If you prefer a shorter ride, you may choose to shuttle to Sassetta and begin cycling from there, trimming 16.1 km (10 miles) off the morning route before lunch. In the afternoon, enjoy an easy, mostly downhill ride to Cafaggio, followed by a 3-km climb to a panoramic viewpoint overlooking the Tuscan coast. From there, a long descent leads you directly to Hotel Calidario.

Cumulative Distance Range: 15 — 54 km (9 — 33 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, cycle or take a shuttle to Campiglia Marittima. While this authentic hillside village is best known for its medieval buildings, its roots stretch back to Etruscan and Roman times. The ancient Etruscans once forged and smelted metal here, evidence of which can still be seen as you pass the Archeological Mines Park of San Silvestro—a protected natural area now home to a museum. From there, your winding, panoramic route descends through a broad plain and dense pine forest, eventually reaching the edge of the Tyrrhenian Sea.

At Baratti—a tiny seaside enclave with a population in the double digits—you may use the support vehicle or opt to ride uphill to Populonia, where splendid views of the sea await. Once one of the most active ports of the Etruscan and Roman eras, Populonia imported copper ore from the nearby hills and the Isle of Elba, smelted it, and traded the finished goods across the Mediterranean. The remnants of this once-thriving city are preserved within its historic walls, and you can explore its fascinating past at the small but engaging museum housed in the Tower of Populonia.

Back in the bay of Baratti, enjoy lunch in a spectacular setting—a former watchtower now transformed into a fine restaurant with sweeping sea views. Afterward, you may choose to swim or explore Baratti’s Etruscan archaeological sites, including legendary burial mounds, before riding back to the hotel.

You might choose to end your final cycling day with a relaxing massage at the hotel spa (available at your own expense). Your Tuscany bike tour concludes here, and this evening you’ll gather for a memorable farewell dinner with your fellow cyclists.

Today's Ride Choices

Morning: Calidarium to Campiglia and Baratti — 32 km (20 miles)

Afternoon : Baratti to Hotel Calidarium — 15 km (9 miles)

What to Expect:

This morning, you may shuttle to the hilltop town of Campiglia Marittima to begin an easy valley ride, or opt for a workout by cycling the initial 4-mile uphill stretch from the hotel to Campiglia. The route features gentle hills, giving you plenty of time to explore Baratti’s scenic seaside bay before retracing your path back to the hotel. Experienced cyclists may have the option of a short but challenging independent ride—ask your trip leader for details.

Cumulative Distance Range: 15 — 47 km (9 — 29 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, transportation is provided to Lucca. You’ll arrive around 10:00 a.m. at Porta Sant’Anna, one of the city’s historic gates. From here, you’ll meet our expert local guide for a two-hour walking tour of this historic city. Because Lucca’s Old Town is enclosed by Renaissance-era walls, large coaches cannot enter; your luggage will be transferred from the bus to our post-tour hotel, Hotel Ilaria Residenza dell’Alba, located in the city center. The walking tour concludes at the hotel around 12:30 p.m.

Please note that your hotel room may not be available until 2:30 p.m., but you may store your luggage at the front desk. The remainder of the day is yours to explore at your leisure—use the included city information to help you discover Lucca’s charming piazzas, Renaissance walls, and hidden gems.

Included Meals: Breakfast

After an included breakfast this morning, complimentary transportation to the Florence Airport will be provided (an approximately 50- to 60-minute drive) for your departing flight.

Included Meals: Breakfast

Your vacation is about to begin! Spend your first night aloft and arrive ready for an unforgettable trip.

Start off your first day in Florence right by having a VBT representative greet you at the airport. A complimentary car service will whisk you to your centrally located hotel. From here, you are perfectly positioned to explore this charming city at your leisure.

After an included breakfast, meet your VBT representative in the hotel lobby at 10:30 a.m. After brief introductions you travel approximately one hour to Radda in Chianti, a stunning Chianti hilltop town surrounded by city walls and defensive towers.

Your VBT trip leaders welcome you to this medieval town and hold a safety session. They also offer suggestions for lunch on your own. There are ample cafes along the ancient decumano – the east-west road that is today called via Roma. Your rooms may not be ready until 2:00 p.m. but the reception desk will store your luggage.

By lunch end, your rooms will be ready and you will have time to settle in and change into your biking clothes. Later, attend a bike-fitting session in preparation for a warm-up ride. Your first thrilling spin leads you over gentle hills through a countryside dotted with farmhouses and blanketed with vineyards and olive groves through Castellina in Chianti.

Back in Radda, perhaps you’ll relax in the hotel’s stone-vaulted spa and indoor swimming pool, built in the ancient cellars, or lounge at the outdoor Jacuzzi-pools.

This evening, gather for a welcome cocktail and dinner at the hotel.

Today's Ride Choices

Afternoon: Warm-up ride Chianti — 13 km (8 miles)

What to Expect:

A back-and-forth ride from Radda to Castellina on rolling hills, with just one short ascent entering Castellina. The road is paved and winding, shared with cars.

Cumulative Distance Range: 13 km (8 miles)

Included Meals: Breakfast, Dinner

After breakfast, set out to explore Chianti along the “castle way,” traversing dense forests that embrace picturesque villages like Lecchi, on your way to Gaiole. The castles and watchtowers you’ll see as you ride played a strategic role in the frequent battles between Siena and Florence. Soon, you spy one of these old fortifications on a hillside: Castello di Meleto. From its heights, take in splendid vistas of the valley and other distant castles.

The 11th-century Castello di Meleto was founded by the Benedictine monks of Badia Coltibuono. Since then, it has played many roles, including a military post and a noble country house, but its original structure and appearance have largely been preserved. Today, it is a wine resort where vineyards, olive groves, and other gardens are cultivated with sustainable methods that support the environment and the authenticity of Tuscany. Great wines, organic extra virgin olive oil, quality Cinta Senese pigs, honey, and herbs are all produced and raised here.

During your visit, your host Gabriella, an expert in agricultural sciences, immerses you in this very special place. You walk through the property to the organic beehives, and learn how she and her team protect these pollinators that are so important to farmers throughout Tuscany. VBT sponsors four beehives through the Sustainable Travel Foundation. You also visit the organic vineyards and the herb garden, see the noble living quarters of the 17th-century house and only theatre of this kind left in Europe and never restored. During the visit of the ancient cellars, you are introduced to local wines and have a taste of Chianti Classico, Riserva and Gran Selezione.

By lunch time, you are in Gaiole. This idyllic village hosts the annual, week-long L’Eroica, an event for vintage bicycle enthusiasts. The October event celebrates biking culture and the Strade Bianche, a race held every March along Siena’s famous white gravel roads.  After exploring the village, pick a cafe for lunch on your own. Then continue riding the iconic Chianti roads.

Back in Radda, stroll medieval alleyways and admire the Palazzo del Podesta, studded with the town’s coat of arms. Radda is also a popular stop for cyclists who want to get their own bicycle jersey in the renowned – and tiny – shop here. You’re sure to find one that suits you, perhaps emblazoned with the Black Rooster of Chianti!

Dinner is on your own tonight.

Today's Ride Choices

Morning: Radda to Meleto and Gaiole — 21 km (13 miles)

Afternoon: Gaiole to Castagnoli and Radda — 22 km (14 miles)

What to Expect:

The morning route is a long descent through a shady green valley, with vistas opening up to vineyards as you pass the picturesque hamlet of Lecchi. The route is a gentle roll as you continue into Gaiole where a short paved uphill leads to the bottom of the castle of Meleto. After lunch choose between two options. The short option includes a final steady uphill of approximately two miles into Radda, that is manageable with an E-bike, or can be skipped with a short van shuttle. The longer option through Castagnoli offers some hills and vistas that you will regret missing.

Today may offer an additional independent ride for experienced cyclists on the unpaved L’Eroica roads. Ask your trip leaders for details.

Cumulative Distance Range: 21 — 43 km (13 — 27 miles)

Included Meals: Breakfast

Your day begins with a thrilling coast down a scenic route that delivers you to Monteriggioni. Before it, do not miss a short stop in Castellina, a classic Chianti town, to explore cobblestone lanes, patrician palaces, and the partially covered walkway – the Via delle Volte – running through the center, ingeniously designed by Filippo Brunelleschi to protect the city from the firearms of enemies.  Later continue to Monteriggioni. This magnificent medieval-era city seems frozen in time, surrounded by walls that follow the natural contours of the hill on which it rests. Wide breathtaking views accompany your ride of long downhill stretches and lovely bends. You sweep past wheat fields, vineyards, the region’s iconic cypress trees, and small artistic treasures like the Santa Cristina church in Lilliano. Arrive in the walled city of Monteriggioni and explore on your own. Be sure to take the time to stroll among its 14 towers that once protected the city from the attacks of Florence.

Later in the morning, get a lift to the hilltop town of Guardistallo to a typical locanda toscana, your lunch stop. Meet Alessio and Riccardo, immerse in the beautiful Tuscan countryside where authenticity and respect for the environment are shared values that are reflected in your delicious meal. This is your starting point for a ride along one of Italy’s most beautiful wine roads, where the climate, soil, and winemaking techniques help to produce some of the region’s most elegant wines. Your route skirts the lush Ornellaia vineyards, traversing gently rolling hills through Bibbona. On the way stop at the popular bike shop of Daniela, a long-time friend, to check out the latest bicycle models on display and maybe buy a local jersey. End your afternoon ride at the Tombolo Talasso Resort, your deluxe hotel right on the Tyrrhenian Sea.

Stretch out in the sand at the hotel’s private beach, or relax in one of the five thermal swimming pools at the Wellness Center. Filtered water is pumped directly from the sea into the pools. Tonight, after an aperitivo with your trip leaders, you head to the typical Tuscan home of longtime VBT friend Chicca (pronounced “Key-ka”) for an incredible home-cooked dinner that you can help prepare. Through her organization called Cooking in Tuscany, Chicca promotes the culture and warmth of Italian and Tuscan cuisine, researching and experimenting with traditional recipes and seasonal local ingredients. After a hands-on cooking class, you savor your creations at sunset under her pergola.

Today's Ride Choices

Morning: Radda to Monteriggioni — 26 km (16 miles)

Afternoon: Le Giunche to Tombolo — 30 km (19 miles)

What to Expect:

The first 7 miles of your morning ride are slightly rolling until Castellina in Chainti. From there an exhilarating and scenic descent of 5 miles takes you to Castellina Scalo. There, a biking path and a half mile stretch on the busier Cassia Road, delivers you to  Monteriggioni. You will park your bike at the foothills of the walled village of Monteriggioni, then walk up to enjoy the visit. After that, relax on a 70-minute shuttle to your lunch stop. From there you will bike all the way to your hotel, with an initial short uphill followed by a long panoramic descent into the wine village of Bibbona. The ride meanders past vineyards and wineries on moderately rolling terrain along the famous ‘bolgherese’ road, named after the medieval village of Bolgheri and very popular with local cyclists. The last few miles are flat as you approach the village of Donoratico and then the sea, continuing on to the hotel.

Cumulative Distance Range: 26 — 56 km (16 — 35 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, cycle the historic bolgherese Strada del Vino, one of the most prestigious wine regions in Italy. These lush vineyards produce some of Italy’s most celebrated DOC wines, regulated by the Denominazione di Origine Controllata or Denomination of Controlled Origin. Be sure to sample the Super Tuscans today – red wines that revolutionized Italian viticulture. The area is also known for the elegant Viale dei Cipressi, a cypress-lined avenue immortalized in the poem “San Guido” by Giosuè Carducci.

The family-owned and operated Fonte di Foiano olive oil mill is your stop for a farm-fresh lunch. Enjoy a private tour of the press and workshop with your host. As you taste the oil during a degustazione (sampling) on the terrace, Simone Di Gaetano will explain the different flavors of Italy’s olive-growing regions. Afterward, savor a delicious vegetarian lunch of organic vegetables prepared by chef brothers Beatrice and Paolo.

Once lunch is finished, continue cycling easy countryside roads back to your beach hotel.

Tonight your trip leaders can suggest a restaurant for dinner on your own in the lovely seaside village of Marina di Castagneto.

Today's Ride Choices

Morning: La Strada del Vino — 32 km (20 miles)

Afternoon : Oil Mill to Tombolo — 12 km (7 miles)

What to Expect:

The morning ride sets a relaxed pace for the day along the Strada del Vino, mostly on narrow country roads to our lunch stop. Before we stop in the wine village of Bolgheri you will ride the famous cypress road, flanked by big cypress trees.  As you approch Fonte di Foiano oil mill, you will ride on country roads lined with hundreds of olive trees. After lunch, follow a different route that includes 1.6 km (1 mile) on an unpaved bike path in a pine forest, back to our hotel.

Today may offer an additional independent ride for experienced cyclists. Ask your trip leader for details.

Cumulative Distance Range: 12 — 44 km (7 — 27 miles)

Included Meals: Breakfast, Lunch

Today, you ride one of the most picturesque routes in Europe, spinning past chestnut, cork, and pine trees, medieval estates, and sunflower fields. Your destination is Suvereto, an ancient village dating back a millennium. Its setting is truly magnificent, overlooking the Costa degli Etruschi in the green valley beside the Cornia River. Throughout Tuscany, it is renowned for its architectural harmony: Its ancient walls surround paved streets, stone houses, historic buildings, impressive churches, and shadowy cloisters. Lunch is included in this ancient small town, in one of the typical local taverna discovered by your trip leaders.

After lunch, cycle a rolling and mostly downhill route through the peaceful Cornia Valley, free from car traffic. You end your unforgettable ride at the Hotel Calidario, which pays homage to the region’s Etruscan hot springs with a natural open-air 3,000 square meter pool that is fed by mineral-rich springs that flow from a cavernous granite basin below. Several of the nearby natural parks house fascinating Roman and Etruscan relics.

Settle in, relax and enjoy the springs and hotel spa. Tonight, enjoy dinner in a Tuscan restaurant in the picturesque town of Campiglia Marittima, where you have the choice to taste fish specialties.

Today's Ride Choices

Morning: Tombolo to Suvereto — 31 km (19 miles) | Sassetta to Suvereto with Shuttle — 15 km (9 miles)

Afternoon : Suvereto to Calidarium — 23 km (14 miles)

What to Expect:

Today’s morning ride can begin with a shuttle or an uphill climb to Castagneto Carducci, very manageable with an e-bike. From there, it follows a scenic and undulating stretch of road to Suvereto. If you wish, you may shuttle to Sassetta to begin your ride to Suvereto, trimming 16.1 km (10 miles) off your morning route before our lunch stop. The afternoon ride follows an easy and downhill route until Cafaggio. There a 3 km uphill takes you up a panoramic view point of the Tuscan coast, before a long descent all the way to Hotel Calidario.

Cumulative Distance Range: 15 — 54 km (9 — 33 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, cycle or get a lift to Campiglia Marittima. Though this authentic hillside village has medieval buildings, it dates to Etruscan and Roman times. The ancient Etruscans forged and melted metal here, as you can see as you cycle by the Archeological Mines Park of San Silvestro, a protected natural park. Today, the historic site is home to a museum. Your winding panoramic route descends through a wide plain and thick pine forest, culminating at the edge of the Tyrrhenian Sea.

At Baratti, a charming seaside enclave with a population in the double digits, you may use the support vehicle or ride up the hill to Populonia for splendid views across the water. One of the most active ports during the Etruscan and Roman eras, Populonia imported and smelted copper ore from the nearby hills and the Isle of Elba and traded finished metal goods. The remains of this once-thriving city are preserved within the walled city. You can trace the history of the place at the small but very interesting museum organized in the Tower of Populonia.

Back at the bay of Baratti, pause for lunch at a unique setting with amazing sea views: a former watch tower turned into a fine restaurant. After, you might want to swim or explore Barattti’s Etruscan archeological sites, including its legendary burial mounds, before riding back to the hotel.

You might close your final cycling day with a massage in the hotel spa. Your Tuscany bike tour concludes here, and tonight you’ll enjoy a memorable farewell dinner with your fellow cyclists.

Today's Ride Choices

Morning: Calidarium to Campiglia and Baratti — 32 km (20 miles)

Afternoon : Baratti to Hotel Calidarium — 15 km (9 miles)

What to Expect:

This morning you can shuttle to start an easy valley ride from the hilltop town of Campiglia Marittima or opt for a workout by riding from the hotel to Campiglia on the initial 4 miles uphill. Today’s gentle hills leave you ample time to explore Baratti’s seaside bay and then retrace your route back to the hotel.

Today may offer an additional short but tough independent ride for experienced cyclists. Ask your trip leader for details.

Cumulative Distance Range: 15 — 47 km (9 — 29 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, transportation is provided to your Lucca hotel for your final overnight stay. You will arrive at approximately 10:30 a.m. to meet our expert local guide, who will lead an interesting city walking tour.  Your hotel room may not be available until 2:30 p.m., but you may store your luggage at the reception desk.

Included Meals: Breakfast

After an included breakfast this morning, complimentary transportation to the Florence airport will be provided (an approximately 50 to 60 minute drive for your departing flight).

Included Meals: Breakfast

Your tour begins at 10:30 a.m. at our Pre-Tour hotel in Florence: 25hours Hotel Florence Piazza San Paolino. Your VBT representative will meet you in the lobby holding a VBT sign.

After brief introductions, you’ll travel approximately one hour to Radda in Chianti—a stunning hilltop town in the heart of Chianti, encircled by medieval walls and defensive towers.

Your VBT trip leaders will greet you in Radda and conduct a safety session before your cycling activities begin. They’ll also offer suggestions for lunch on your own. There are plenty of cafés along the town’s ancient decumano—the east–west thoroughfare now known as Via Roma. Your rooms may not be ready until 2:00 p.m., but the hotel reception will store your luggage.

After lunch, your rooms will be available, and you’ll have time to settle in and change into your cycling clothes. Later, attend a bike-fitting session in preparation for your warm-up ride. This first ride leads you over gentle hills through a quintessential Tuscan landscape—past farmhouses, vineyards, and olive groves—en route to Castellina in Chianti.

Back in Radda, you may wish to relax in the hotel’s stone-vaulted spa and indoor swimming pool, set in ancient cellars, or unwind in the outdoor Jacuzzi pools.

This evening, gather for a welcome cocktail and dinner at the hotel.

Today's Ride Choices

Afternoon: Chianti Warm-Up Ride — 13 km (8 miles)

What to Expect:

A scenic out-and-back ride from Radda to Castellina features rolling hills and a single short ascent as you approach Castellina. The route follows a paved, winding road shared with local traffic.

Cumulative Distance Range: 13 km (8 miles)

Included Meals: Dinner

After breakfast, set out to explore Chianti along the “castle way,” a scenic route that winds through dense forests and charming villages like Lecchi on your way to Gaiole. The castles and watchtowers you’ll pass played strategic roles in the historic conflicts between Siena and Florence. Soon, one of these ancient fortifications comes into view—Castello di Meleto. From its hillside perch, enjoy splendid views of the valley and neighboring castles.

Castello di Meleto, founded in the 11th century by the Benedictine monks of Badia a Coltibuono, has served as a military post and a noble country residence. Despite its varied history, much of its original structure remains intact. Today, it is a wine resort where vineyards, olive groves, and gardens are cultivated using sustainable methods that preserve both the land and the spirit of Tuscany. The estate produces fine wines, organic extra virgin olive oil, Cinta Senese pigs, honey, and herbs.

During your visit, your host Gabriella—an expert in agricultural sciences—introduces you to this remarkable place. You’ll walk the grounds, visit the organic beehives, and learn how Gabriella and her team protect pollinators vital to Tuscan agriculture. VBT sponsors four of these hives through the Sustainable Travel Foundation. You’ll also explore the organic vineyards and herb gardens, tour the 17th-century noble residence, and visit a rare, unrestored theater—one of the last of its kind in Europe. In the ancient cellars, sample local wines, including Chianti Classico, Riserva, and Gran Selezione.

By lunchtime, you’ll arrive in Gaiole, a charming village that hosts the week-long L’Eroica each October—a beloved celebration of vintage cycling and the famed Strade Bianche race, held every March on Siena’s iconic white gravel roads. After exploring the village, choose a café for lunch on your own, then continue riding along Chianti’s legendary roads.

Back in Radda, take time to stroll the medieval alleyways and admire the Palazzo del Podestà, adorned with the town’s historic coat of arms. Radda is also a favorite stop for cyclists looking to purchase a jersey from the renowned—and tiny—local shop, where you’re sure to find one that suits you, perhaps bearing the iconic Black Rooster of Chianti.

Dinner is on your own this evening.

Today's Ride Choices

Morning: Radda to Meleto and Gaiole — 21 km (13 miles)

Afternoon: Gaiole to Castagnoli and Radda — 22 km (14 miles)

What to Expect:

This morning’s ride features a long, scenic descent through a shady green valley, with views opening to vineyards as you pass the picturesque hamlet of Lecchi. The route gently rolls into Gaiole, followed by a short paved climb to the base of Castello di Meleto. After lunch, choose between two return options: a shorter route with a steady two-mile uphill into Radda, which is manageable with an E-bike or can be skipped with a short van shuttle; or a longer option through Castagnoli that includes additional hills and sweeping views you won’t want to miss. Experienced cyclists may also have the opportunity for an independent ride along the unpaved L’Eroica roads—ask your trip leaders for details.

Cumulative Distance Range: 21 — 43 km (13 — 27 miles)

Included Meals: Breakfast

Your day begins with a thrilling descent along a scenic route that brings you to the medieval town of Monteriggioni. Before arriving, enjoy a short stop in Castellina, a classic Chianti hill town where you can explore cobblestone lanes, patrician palaces, and the partially covered Via delle Volte, a walkway ingeniously designed by Filippo Brunelleschi to shield the city from enemy firearms.

Continue your ride toward Monteriggioni, a stunning walled town that appears frozen in time. Its well-preserved fortifications follow the natural contours of the hillside, and 14 towers once stood as a defense against the attacks of Florence. The approach offers wide, breathtaking views along a long descent with sweeping bends. You’ll pass wheat fields, vineyards, iconic cypress-lined roads, and artistic treasures such as the Santa Cristina Church in Lilliano. Upon arrival, explore Monteriggioni on your own and take in the historic charm of this remarkable fortress town.

Later in the morning, you’ll shuttle to the hilltop town of Guardistallo and enjoy lunch at a typical locanda toscana. Here, you’ll meet Alessio and Riccardo and immerse yourself in the authentic Tuscan countryside, where a shared respect for tradition and the environment is reflected in your delicious, locally sourced meal. From this point, begin your afternoon ride along one of Italy’s most scenic wine roads, where the combination of climate, soil, and skilled winemaking yields some of Tuscany’s most elegant wines. Your route passes the renowned Ornellaia vineyards and continues along gently rolling hills through Bibbona. Along the way, stop at the popular bike shop owned by Daniela, a long-time friend of VBT, to browse the latest cycling gear or pick up a local jersey.

The day’s ride ends at Tombolo Talasso Resort, your deluxe hotel set directly on the Tyrrhenian Sea. Unwind on the hotel’s private beach or indulge in the Wellness Center, where five thermal swimming pools are filled with filtered seawater pumped directly from the sea.

This evening, after an aperitivo with your trip leaders, you’ll head to the home of longtime VBT friend Chicca (pronounced “Key-ka”) for an unforgettable home-cooked dinner. Through her organization, Cooking in Tuscany, Chicca shares the warmth and tradition of Tuscan cuisine, researching and preparing seasonal, regional dishes. You’ll take part in a hands-on cooking class before sitting down to enjoy your creations under her pergola at sunset.

Today's Ride Choices

Morning: Radda to Monteriggioni — 26 km (16 miles)

Afternoon: Le Giunche to Tombolo — 30 km (19 miles)

What to Expect:

The first 7 miles of your morning ride are gently rolling until you reach Castellina in Chianti. From there, enjoy an exhilarating and scenic 5-mile descent to Castellina Scalo. A bike path and a short half-mile stretch along the busier Cassia Road bring you to Monteriggioni, where you’ll park your bike at the base of the walled village and walk up to explore. After your visit, relax during a 70-minute shuttle ride to your lunch stop. In the afternoon, you’ll ride from there to your hotel, starting with a short uphill followed by a long, panoramic descent into the wine village of Bibbona. The route continues along moderately rolling terrain through vineyards and past wineries on the renowned Via Bolgherese—named after the medieval village of Bolgheri and popular with local cyclists. The final miles are flat as you approach Donoratico and ride on to your seaside hotel.

Cumulative Distance Range: 26 — 56 km (16 — 35 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, cycle the historic Strada del Vino Bolgherese, one of the most prestigious wine routes in Italy. These lush vineyards produce some of the country’s most celebrated DOC wines, regulated by the Denominazione di Origine Controllata (Denomination of Controlled Origin). Be sure to sample the Super Tuscans today—revolutionary red wines that transformed Italian viticulture. The area is also renowned for the elegant Viale dei Cipressi, a cypress-lined avenue immortalized in Giosuè Carducci’s poem San Guido.

Midday, stop at the family-owned Fonte di Foiano olive oil mill for a farm-fresh lunch. Enjoy a private tour of the press and workshop with your host. As you sample the oils on the terrace during a degustazione (tasting), Simone Di Gaetano will guide you through the flavors and characteristics of Italy’s diverse olive-growing regions. Then, sit down to a delicious vegetarian lunch featuring organic vegetables, thoughtfully prepared by chef siblings Beatrice and Paolo.

After lunch, continue your ride along peaceful countryside roads back to your beachside hotel.

This evening, your trip leaders will be happy to recommend a restaurant for dinner on your own in the charming seaside village of Marina di Castagneto.

Today's Ride Choices

Morning: La Strada del Vino — 32 km (20 miles)

Afternoon : Oil Mill to Tombolo — 12 km (7 miles)

What to Expect:

This morning’s ride sets a relaxed pace as you follow the Strada del Vino, mostly along narrow country roads en route to the lunch stop. Before arriving in the wine village of Bolgheri, you’ll ride the iconic cypress-lined avenue, flanked by towering trees. As you approach the Fonte di Foiano olive oil mill, the landscape transitions to gently rolling roads bordered by hundreds of olive trees. After lunch, return to the hotel via a different route that includes a 1.6 km (1 mile) stretch on an unpaved bike path through a pine forest. Experienced cyclists may have the opportunity for an additional independent ride—ask your trip leader for details.

Cumulative Distance Range: 12 — 44 km (7 — 27 miles)

Included Meals: Breakfast, Lunch

Today, you ride one of the most picturesque routes in Europe, pedaling past chestnut, cork, and pine trees, medieval estates, and fields of sunflowers. Your destination is Suvereto, an ancient village with roots stretching back over a millennium. Set in a stunning location overlooking the Costa degli Etruschi in the green valley of the Cornia River, Suvereto is celebrated throughout Tuscany for its architectural harmony. Its ancient walls enclose cobbled streets, stone houses, historic buildings, elegant churches, and serene cloisters. Lunch is included in this charming town, at a typical local taverna discovered by your trip leaders.

After lunch, enjoy a rolling and mostly downhill ride through the peaceful Cornia Valley, free of traffic and full of natural beauty. Your unforgettable ride ends at Hotel Calidario, which pays tribute to the region’s Etruscan legacy with a natural, open-air thermal pool covering 3,000 square meters. Fed by mineral-rich springs that rise from a granite basin below, the water has been enjoyed for centuries. The surrounding area is also home to several natural parks with fascinating Roman and Etruscan archaeological sites.

Settle in and relax, taking full advantage of the springs and hotel spa. This evening, enjoy dinner in a traditional Tuscan restaurant in the picturesque town of Campiglia Marittima, where you’ll have the option to sample local fish specialties.

Today's Ride Choices

Morning: Tombolo to Suvereto — 31 km (19 miles) | Sassetta to Suvereto with Shuttle — 15 km (9 miles)

Afternoon : Suvereto to Calidarium — 23 km (14 miles)

What to Expect:

This morning’s ride begins with either a shuttle or an uphill climb to Castagneto Carducci—easily manageable with an e-bike. From there, the route continues along a scenic and gently rolling stretch of road to Suvereto. If you prefer a shorter ride, you may choose to shuttle to Sassetta and begin cycling from there, trimming 16.1 km (10 miles) off the morning route before lunch. In the afternoon, enjoy an easy, mostly downhill ride to Cafaggio, followed by a 3-km climb to a panoramic viewpoint overlooking the Tuscan coast. From there, a long descent leads you directly to Hotel Calidario.

Cumulative Distance Range: 15 — 54 km (9 — 33 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, cycle or take a shuttle to Campiglia Marittima. While this authentic hillside village is best known for its medieval buildings, its roots stretch back to Etruscan and Roman times. The ancient Etruscans once forged and smelted metal here, evidence of which can still be seen as you pass the Archeological Mines Park of San Silvestro—a protected natural area now home to a museum. From there, your winding, panoramic route descends through a broad plain and dense pine forest, eventually reaching the edge of the Tyrrhenian Sea.

At Baratti—a tiny seaside enclave with a population in the double digits—you may use the support vehicle or opt to ride uphill to Populonia, where splendid views of the sea await. Once one of the most active ports of the Etruscan and Roman eras, Populonia imported copper ore from the nearby hills and the Isle of Elba, smelted it, and traded the finished goods across the Mediterranean. The remnants of this once-thriving city are preserved within its historic walls, and you can explore its fascinating past at the small but engaging museum housed in the Tower of Populonia.

Back in the bay of Baratti, enjoy lunch in a spectacular setting—a former watchtower now transformed into a fine restaurant with sweeping sea views. Afterward, you may choose to swim or explore Baratti’s Etruscan archaeological sites, including legendary burial mounds, before riding back to the hotel.

You might choose to end your final cycling day with a relaxing massage at the hotel spa (available at your own expense). Your Tuscany bike tour concludes here, and this evening you’ll gather for a memorable farewell dinner with your fellow cyclists.

Today's Ride Choices

Morning: Calidarium to Campiglia and Baratti — 32 km (20 miles)

Afternoon : Baratti to Hotel Calidarium — 15 km (9 miles)

What to Expect:

This morning, you may shuttle to the hilltop town of Campiglia Marittima to begin an easy valley ride, or opt for a workout by cycling the initial 4-mile uphill stretch from the hotel to Campiglia. The route features gentle hills, giving you plenty of time to explore Baratti’s scenic seaside bay before retracing your path back to the hotel. Experienced cyclists may have the option of a short but challenging independent ride—ask your trip leader for details.

Cumulative Distance Range: 15 — 47 km (9 — 29 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, transportation is provided to Lucca with your fellow travelers, arriving around 10:00 a.m. at Porta Sant’Anna, one of the city’s historic gates. This marks the official conclusion of your tour. From here, it’s a short walk to the nearby taxi stands at Piazzale Verdi. You are responsible for your own transportation to the airport for your flight home—travel time is approximately 25 minutes to Pisa Airport and 60 minutes to Florence Airport.

If you wish, you may join our expert local guide for an optional two-hour walking tour of Lucca. If you choose this option, your luggage will be transferred from Porta Sant’Anna to our post-tour hotel, Hotel Ilaria Residenza dell’Alba, located in the city center. The walking tour ends at the hotel, where your luggage will be available for pickup at reception around 12:30 p.m.

Included Meals: Breakfast

Your tour starts at 10:30 a.m. at our Florence hotel. Your VBT representative will meet you in the lobby holding a VBT sign.

After brief introductions you travel approximately one hour to Radda, a stunning Chianti hilltop town surrounded by city walls and defensive towers.

Your VBT trip leaders welcome you to this medieval town and hold a safety session. They also offer suggestions for lunch on your own. There are ample cafes along the ancient decumano – the east-west road that is today called via Roma. Your rooms may not be ready until 2:00 p.m. but the reception desk will store your luggage.

By lunch end, your rooms will be ready and you will have time to settle in and change into your biking clothes. Later, attend a bike-fitting session in preparation for a warm-up ride. Your first thrilling spin leads you over gentle hills through a countryside dotted with farmhouses and blanketed with vineyards and olive groves through Castellina in Chianti.

Back in Radda, perhaps you’ll relax in the hotel’s stone-vaulted spa and indoor swimming pool, built in the ancient cellars, or lounge at the outdoor Jacuzzi-pools.

This evening, gather for a welcome cocktail and dinner at the hotel.

Today's Ride Choices

Afternoon: Warm-up Chianti — 13 km (8 miles)

What to Expect:

A back-and-forth ride from Radda to Castellina on rolling hills, with just one short ascent entering Castellina. The road is paved and winding, shared with cars.

Cumulative Distance Range: 13 km (8 miles)

Included Meals: Dinner

After breakfast, set out to explore Chianti along the “castle way,” traversing dense forests that embrace picturesque villages like Lecchi, on your way to Gaiole. The castles and watchtowers you’ll see as you ride played a strategic role in the frequent battles between Siena and Florence. Soon, you spy one of these old fortifications on a hillside: Castello di Meleto. From its heights, take in splendid vistas of the valley and other distant castles.

The 11th-century Castello di Meleto was founded by the Benedictine monks of Badia Coltibuono. Since then, it has played many roles, including a military post and a noble country house, but its original structure and appearance have largely been preserved. Today, it is a wine resort where vineyards, olive groves, and other gardens are cultivated with sustainable methods that support the environment and the authenticity of Tuscany. Great wines, organic extra virgin olive oil, quality Cinta Senese pigs, honey, and herbs are all produced and raised here.

During your visit, your host Gabriella, an expert in agricultural sciences, immerses you in this very special place. You walk through the property to the organic beehives, and learn how she and her team protect these pollinators that are so important to farmers throughout Tuscany. VBT sponsors four beehives through the Sustainable Travel Foundation. You also visit the organic vineyards and the herb garden, see the noble living quarters of the 17th-century house and only theatre of this kind left in Europe and never restored. During the visit of the ancient cellars, you are introduced to local wines and have a taste of Chianti Classico, Riserva and Gran Selezione.

By lunch time, you are in Gaiole. This idyllic village hosts the annual, week-long L’Eroica, an event for vintage bicycle enthusiasts. The October event celebrates biking culture and the Strade Bianche, a race held every March along Siena’s famous white gravel roads.  After exploring the village, pick a cafe for lunch on your own. Then continue riding the iconic Chianti roads.

Back in Radda, stroll medieval alleyways and admire the Palazzo del Podesta, studded with the town’s coat of arms. Radda is also a popular stop for cyclists who want to get their own bicycle jersey in the renowned – and tiny – shop here. You’re sure to find one that suits you, perhaps emblazoned with the Black Rooster of Chianti!

Dinner is on your own tonight.

Today's Ride Choices

Morning: Radda to Meleto and Gaiole — 21 km (13 miles)

Afternoon: Gaiole to Castagnoli and Radda — 22 km (14 miles)

What to Expect:

The morning route is a long descent through a shady green valley, with vistas opening up to vineyards as you pass the picturesque hamlet of Lecchi. The route is a gentle roll as you continue into Gaiole where a short paved uphill leads to the bottom of the castle of Meleto. After lunch choose between two options. The short option includes a final steady uphill of approximately two miles into Radda, that is manageable with an E-bike, or can be skipped with a short van shuttle. The longer option through Castagnoli offers some hills and vistas that you will regret missing.

Today may offer an additional independent ride for experienced cyclists on the unpaved L’Eroica roads. Ask your trip leaders for details.

Cumulative Distance Range: 21 — 43 km (13 — 27 miles)

Included Meals: Breakfast

Your day begins with a thrilling coast down a scenic route that delivers you to Monteriggioni. Before it, do not miss a short stop in Castellina, a classic Chianti town, to explore cobblestone lanes, patrician palaces, and the partially covered walkway – the Via delle Volte – running through the center, ingeniously designed by Filippo Brunelleschi to protect the city from the firearms of enemies.  Later continue to Monteriggioni. This magnificent medieval-era city seems frozen in time, surrounded by walls that follow the natural contours of the hill on which it rests. Wide breathtaking views accompany your ride of long downhill stretches and lovely bends. You sweep past wheat fields, vineyards, the region’s iconic cypress trees, and small artistic treasures like the Santa Cristina church in Lilliano. Arrive in the walled city of Monteriggioni and explore on your own. Be sure to take the time to stroll among its 14 towers that once protected the city from the attacks of Florence.

Later in the morning, get a lift to the hilltop town of Guardistallo to a typical locanda toscana, your lunch stop. Meet Alessio and Riccardo, immerse in the beautiful Tuscan countryside where authenticity and respect for the environment are shared values that are reflected in your delicious meal. This is your starting point for a ride along one of Italy’s most beautiful wine roads, where the climate, soil, and winemaking techniques help to produce some of the region’s most elegant wines. Your route skirts the lush Ornellaia vineyards, traversing gently rolling hills through Bibbona. On the way stop at the popular bike shop of Daniela, a long-time friend, to check out the latest bicycle models on display and maybe buy a local jersey. End your afternoon ride at the Tombolo Talasso Resort, your deluxe hotel right on the Tyrrhenian Sea.

Stretch out in the sand at the hotel’s private beach, or relax in one of the five thermal swimming pools at the Wellness Center. Filtered water is pumped directly from the sea into the pools. Tonight, after an aperitivo with your trip leaders, you head to the typical Tuscan home of longtime VBT friend Chicca (pronounced “Key-ka”) for an incredible home-cooked dinner that you can help prepare. Through her organization called Cooking in Tuscany, Chicca promotes the culture and warmth of Italian and Tuscan cuisine, researching and experimenting with traditional recipes and seasonal local ingredients. After a hands-on cooking class, you savor your creations at sunset under her pergola.

Today's Ride Choices

Morning: Radda to Monteriggioni — 26 km (16 miles)

Afternoon: Le Giunche to Tombolo — 30 km (19 miles)

What to Expect:

The first 7 miles of your morning ride are slightly rolling until Castellina in Chainti. From there an exhilarating and scenic descent of 5 miles takes you to Castellina Scalo. There, a biking path and a half mile stretch on the busier Cassia Road, delivers you to  Monteriggioni. You will park your bike at the foothills of the walled village of Monteriggioni, then walk up to enjoy the visit. After that, relax on a 70-minute shuttle to your lunch stop. From there you will bike all the way to your hotel, with an initial short uphill followed by a long panoramic descent into the wine village of Bibbona. The ride meanders past vineyards and wineries on moderately rolling terrain along the famous ‘bolgherese’ road, named after the medieval village of Bolgheri and very popular with local cyclists. The last few miles are flat as you approach the village of Donoratico and then the sea, continuing on to the hotel.

Cumulative Distance Range: 26 — 56 km (16 — 35 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, cycle the historic bolgherese Strada del Vino, one of the most prestigious wine regions in Italy. These lush vineyards produce some of Italy’s most celebrated DOC wines, regulated by the Denominazione di Origine Controllata or Denomination of Controlled Origin. Be sure to sample the Super Tuscans today – red wines that revolutionized Italian viticulture. The area is also known for the elegant Viale dei Cipressi, a cypress-lined avenue immortalized in the poem “San Guido” by Giosuè Carducci.

The family-owned and operated Fonte di Foiano olive oil mill is your stop for a farm-fresh lunch. Enjoy a private tour of the press and workshop with your host. As you taste the oil during a degustazione (sampling) on the terrace, Simone Di Gaetano will explain the different flavors of Italy’s olive-growing regions. Afterward, savor a delicious vegetarian lunch of organic vegetables prepared by chef brothers Beatrice and Paolo.

Once lunch is finished, continue cycling easy countryside roads back to your beach hotel.

Tonight your trip leaders can suggest a restaurant for dinner on your own in the lovely seaside village of Marina di Castagneto.

Today's Ride Choices

Morning: La Strada del Vino — 32 km (20 miles)

Afternoon : Oil Mill to Tombolo — 12 km (7 miles)

What to Expect:

The morning ride sets a relaxed pace for the day along the Strada del Vino, mostly on narrow country roads to our lunch stop. Before we stop in the wine village of Bolgheri you will ride the famous cypress road, flanked by big cypress trees.  As you approch Fonte di Foiano oil mill, you will ride on country roads lined with hundreds of olive trees. After lunch, follow a different route that includes 1.6 km (1 mile) on an unpaved bike path in a pine forest, back to our hotel.

Today may offer an additional independent ride for experienced cyclists. Ask your trip leader for details.

Cumulative Distance Range: 12 — 44 km (7 — 27 miles)

Included Meals: Breakfast, Lunch

Today, you ride one of the most picturesque routes in Europe, spinning past chestnut, cork, and pine trees, medieval estates, and sunflower fields. Your destination is Suvereto, an ancient village dating back a millennium. Its setting is truly magnificent, overlooking the Costa degli Etruschi in the green valley beside the Cornia River. Throughout Tuscany, it is renowned for its architectural harmony: Its ancient walls surround paved streets, stone houses, historic buildings, impressive churches, and shadowy cloisters. Lunch is included in this ancient small town, in one of the typical local taverna discovered by your trip leaders.

After lunch, cycle a rolling and mostly downhill route through the peaceful Cornia Valley, free from car traffic. You end your unforgettable ride at the Hotel Calidario, which pays homage to the region’s Etruscan hot springs with a natural open-air 3,000 square meter pool that is fed by mineral-rich springs that flow from a cavernous granite basin below. Several of the nearby natural parks house fascinating Roman and Etruscan relics.

Settle in, relax and enjoy the springs and hotel spa. Tonight, enjoy dinner in a Tuscan restaurant in the picturesque town of Campiglia Marittima, where you have the choice to taste fish specialties.

Today's Ride Choices

Morning: Tombolo to Suvereto — 31 km (19 miles) | Sassetta to Suvereto with Shuttle — 15 km (9 miles)

Afternoon : Suvereto to Calidarium — 23 km (14 miles)

What to Expect:

Today’s morning ride can begin with a shuttle or an uphill climb to Castagneto Carducci, very manageable with an e-bike. From there, it follows a scenic and undulating stretch of road to Suvereto. If you wish, you may shuttle to Sassetta to begin your ride to Suvereto, trimming 16.1 km (10 miles) off your morning route before our lunch stop. The afternoon ride follows an easy and downhill route until Cafaggio. There a 3 km uphill takes you up a panoramic view point of the Tuscan coast, before a long descent all the way to Hotel Calidario.

Cumulative Distance Range: 15 — 54 km (9 — 33 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, cycle or get a lift to Campiglia Marittima. Though this authentic hillside village has medieval buildings, it dates to Etruscan and Roman times. The ancient Etruscans forged and melted metal here, as you can see as you cycle by the Archeological Mines Park of San Silvestro, a protected natural park. Today, the historic site is home to a museum. Your winding panoramic route descends through a wide plain and thick pine forest, culminating at the edge of the Tyrrhenian Sea.

At Baratti, a charming seaside enclave with a population in the double digits, you may use the support vehicle or ride up the hill to Populonia for splendid views across the water. One of the most active ports during the Etruscan and Roman eras, Populonia imported and smelted copper ore from the nearby hills and the Isle of Elba and traded finished metal goods. The remains of this once-thriving city are preserved within the walled city. You can trace the history of the place at the small but very interesting museum organized in the Tower of Populonia.

Back at the bay of Baratti, pause for lunch at a unique setting with amazing sea views: a former watch tower turned into a fine restaurant. After, you might want to swim or explore Barattti’s Etruscan archeological sites, including its legendary burial mounds, before riding back to the hotel.

You might close your final cycling day with a massage in the hotel spa. Your Tuscany bike tour concludes here, and tonight you’ll enjoy a memorable farewell dinner with your fellow cyclists.

Today's Ride Choices

Morning: Calidarium to Campiglia and Baratti — 32 km (20 miles)

Afternoon : Baratti to Hotel Calidarium — 15 km (9 miles)

What to Expect:

This morning you can shuttle to start an easy valley ride from the hilltop town of Campiglia Marittima or opt for a workout by riding from the hotel to Campiglia on the initial 4 miles uphill. Today’s gentle hills leave you ample time to explore Baratti’s seaside bay and then retrace your route back to the hotel.

Today may offer an additional short but tough independent ride for experienced cyclists. Ask your trip leader for details.

Cumulative Distance Range: 15 — 47 km (9 — 29 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, transportation is provided to Lucca with your fellow travelers, arriving around 10:00 a.m. at Porta Sant’Anna, one of the city’s historic gates. This marks the official conclusion of your tour. From here, it’s a short walk to the nearby taxi stands at Piazzale Verdi. You are responsible for your own transportation to the airport for your flight home—travel time is approximately 25 minutes to Pisa Airport and 60 minutes to Florence Airport.

If you wish, you may join our expert local guide for an optional two-hour walking tour of Lucca. If you choose this option, your luggage will be transferred from Porta Sant’Anna to our post-tour hotel, Hotel Ilaria, located in the city center. The walking tour ends at the hotel, where your luggage will be available for pickup at reception around 12:30 p.m.

Included Meals: Breakfast