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Italy: Tuscany, Chianti & Marina di Castagneto

On this unique cycling vacation, we’ve paired the sun-soaked Tuscan seacoast with the lush vineyards of Chianti. Along the way, you’ll pedal rolling hills and gentle valleys lined with cypress tress—stopping to discover a 13th century castle, observe artists crafting traditional pottery, visit a local olive oil mill, and explore the walled medieval village of Monteriggioni. As you discover the azure coast of Tuscany, your trip leaders will bring you to a quintessential Tuscan farmhouse to introduce a local friend who teaches you how to prepare authentic Italian dishes in her kitchen. In the evenings, there’s so much to look forward to—including a restorative soak in your hotel’s thermal pool, incredible cuisine, world-renowned wines, and the envy of all your friends. 

Tour Highlights

  • Indulge in luxurious accommodations where you can relax on a private sandy beach, soak in natural Etruscan hot springs, dine on elegant meals, and more.
  • Visit the home of longtime VBT friend and founder of Cooking in Tuscany, then cook a traditional Tuscan meal with her.
  • Learn about bee life and preservation as you tour a 13th-century castle in Chianti.
  • Cycle past Bolgheri’s Super Tuscan vineyards and along its famous cypress-lined avenue, a prelude to the stunning medieval towns of Castagneto Carducci, Sassetta, and Suvereto.
  • Explore the fascinating Etruscan city of Populonia, a bustling port in ancient times, and take in breathtaking views of the turquoise waters of Baratti Bay.

Positive Impact

VBT is proud to support In the Name of the Bee with a donation on behalf of each guest on this tour. The beehives that guests visit at Castello di Meleto protect pollinators that are vital to farmers in Tuscany. In the Name of the Bee is Castello’s initiative to triple the number of bees in the region, along with creating premium organic honey.

What to Expect

This tour offers a combination of easy terrain and moderate hills, ideal for both beginner and experienced cyclists. Our VBT support vehicle is always available for those who would like assistance with the hills. The rides are almost entirely on paved roads or bike paths with a few short stretches in pine forests on unpaved, but even, terrain.

  • Daily Mileage: 8-39 miles|
  • Biking: 1-5 hours|
  • Max Group Size: 22
Activity Easy/Moderate Easy/Moderate
Bar Graph Beginner - Experienced
Cyclists
Vehicle Support Vehicle
Support
Activity Easy/Moderate
Easy/Moderate

Ideal for active beginners to more experienced riders.

  • Average Daily Mileage: 18-32 mi.
  • Average Daily Cycling Time: Up to 4 hrs.
  • Average Daily Elevation gain: Up to 2200 feet.

Average High /
Low Temperature (°F):

Apr68º/40º

May75º/53º

Jun84º/58º

Sep81º/58º

Oct69º/51º

Average
Precipitation:

Apr2.9 in

May3.0 in

Jun2.7 in

Sep3.3 in

Oct4.0 in

Air Package

Tour Only

Roundtrip international airfare

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Airport car service for arrival and departure

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One night in Florence and one night in Lucca in conveniently located hotels with daily breakfast

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6 nights in one country estate, one 4-star and one 5-star hotel

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13 meals: 6 breakfasts, 3 lunches, 4 dinners

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2025 2026

Step-Through Electric Assisted Bicycle V Frame (E-Bike)

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Electric-Assisted Bicycle (E-bike)

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Road Bicycle (Carbon frame)

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2025 2026

Step-Through Electric Assisted Bicycle V Frame (E-Bike)

See More >

Electric-Assisted Bicycle (E-bike)

See More >

Road Bicycle (Carbon frame)

See More >

Biking Packages Include:

Custom VBT Bike and Helmet

Two Local, Bilingual Trip Leaders

Support Vehicle

Luggage Transportation

Ride with GPS and Daily Route Notes

Welcome Reception

Facilitated Cultural Experiences

Your Choice of VBT Branded Gear for Your Adventure

Itinerary

Tue, Apr 14 to Thu, Apr 23, 2026

Show Itinerary:

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.

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

Italy: Tuscany, Chianti & Marina di Castagneto

Download Sample Itinerary:

Air Package (PDF) Tour Only (PDF)

Thu, Apr 16 to Wed, Apr 22, 2026

Show Itinerary:

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

Italy: Tuscany, Chianti & Marina di Castagneto

Download Sample Itinerary:

Air Package (PDF) Tour Only (PDF)

Accommodations (Please Note: Days are based on the Air Package Itinerary. Accommodations may vary depending on departure date. )

Enjoy Your Vacation Longer With Low-Cost Trip Extensions

Airplane

Air Package Only

2025 2026

2026 Pre-Tour Extension - Florence

2 Nights From $495 per person, double occupancy
Single Supplement: From $395

  • 2 nights at 25hours Hotel Florence Piazza San Paolino
  • Airport arrival transportation
  • Orientation tour
  • Hospitality desk
  • Daily breakfast
  • City information

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.

At the hotel, a local VBT representative will be available at 5:00 p.m. to answer questions, help you plan your time in Florence, and recommend optional walking or biking tours to discover the city’s hidden gems. You’ll have the remainder of the day free to explore, using VBT’s city information as your guide.

After enjoying an included breakfast at your hotel, spend the day exploring at your own pace with the help of our provided city information.

Included Meals: Breakfast

After another included breakfast at your hotel, enjoy a full day of independent exploration, using our provided city information to uncover more of the area’s hidden gems and highlights.

Included Meals: Breakfast

25hours Hotel Piazza San Paolino

Situated in the heart of Florence’s Santa Maria Novella district, the 25hours Hotel Piazza San Paolino is inspired by Dante’s Divine Comedy. A whimsical 4-star property, the hotel has playfully designed rooms with air conditioning and complimentary WiFi, a lively restaurant, a COMPANION Dolceamaro bar, a specialty food and wine shop, and a movie lounge in its Cinema Paradiso. Guests will exclusively be assigned Paradiso Heaven rooms, not Inferno rooms.

Wi-Fi In Room
FREE WiFi Included
Air Conditioning
Air Conditioning
Airplane

Air Package Only

2025 2026

2025 Pre-Tour Extension - Florence

2 Nights From $595 per person, double occupancy
Single Supplement: From $345

  • 2 nights at 25hours Hotel Florence Piazza San Paolino
  • Airport arrival transportation
  • Orientation tour
  • Hospitality desk
  • Daily breakfast
  • City information

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. Here, a local VBT representative will be available at 5:00 p.m. to answer your questions, help you organize your time in Florence, and suggest optional walking and biking tours to discover the secret corners of the city. From here, you are perfectly positioned to explore this charming city at your leisure.

After a delicious included breakfast at your hotel, you are free to explore on your own, using our included city information packet to guide your discoveries.

Included Meals: Breakfast

After a delicious included breakfast at your hotel, you are free to explore on your own, using our included city information packet to guide your discoveries.

Included Meals: Breakfast

25hours Hotel Piazza San Paolino

Situated in the heart of Florence’s Santa Maria Novella district, the 25hours Hotel Piazza San Paolino is inspired by Dante’s Divine Comedy. A whimsical 4-star property, the hotel has playfully designed rooms with air conditioning and complimentary WiFi, a lively restaurant, a COMPANION Dolceamaro bar, a specialty food and wine shop, and a movie lounge in its Cinema Paradiso. Guests will exclusively be assigned Paradiso Heaven rooms, not Inferno rooms.

Wi-Fi In Room
FREE WiFi Included
Air Conditioning
Air Conditioning
Airplane

Air Package Only

2025 2026

2026 Post-Tour Extension - Lucca

2 Nights From $395 per person, double occupancy
Single Supplement: From $195

  • 2 nights at the Hotel Ilaria & Residenza dell’Alba
  • Airport departure transportation
  • Daily breakfast
  • City information
1 Begin Your Post-Tour Extension: Lucca

After enjoying an included breakfast at your hotel, feel free to continue exploring at your own pace, using our provided city information to guide your discoveries. It’s easy to take a short trip to nearby Pisa to visit the famous Piazza dei Miracoli (Miracle Square), home to the iconic Leaning Tower.

Please note: Most Italian museums are closed on Mondays.

Included Meals: Breakfast

2 Continue Your Post-Tour Extension

After another included breakfast at your hotel, enjoy a full day of independent exploration, using our provided city information to uncover more of the area’s hidden gems and highlights.

Please note: Most Italian museums are closed on Mondays.

Included Meals: Breakfast

Departure Airplane

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

Hotel Ilaria & Residenza dell'Alba

Located within the walls of historic Lucca, Hotel Ilaria & Residenza dell’Alba is an ideal starting point from which to discover the wonderful city center of Lucca. Renovated from Villa Bottini’s historic stables and a 14th-century church, Hotel Ilaria provides a plush and welcoming atmosphere. Here you can find quiet, spacious, and elegantly furnished air-conditioned rooms with modern comforts. WiFi is available throughout the hotel.

Wi-Fi In Room
FREE WiFi Included
Air Conditioning
Air Conditioning
Airplane

Air Package Only

2025 2026

2025 Post-Tour Extension - Lucca

2 Nights From $295 per person, double occupancy
Single Supplement: From $245

  • 2 nights at the Hotel Ilaria & Residenza dell’Alba
  • Airport departure transportation
  • Daily breakfast
  • City information
1 Begin your Post-Tour Extension

After a delicious included breakfast at your hotel, you are free to continue exploring on your own, using our included city information packet to guide your discoveries. See how it is easy to get to the near city of Pisa, to visit the famous Miracle square with its leaning tower.

Please note: Italian museums are closed on Mondays.

Included Meals: Breakfast

2 Continue your Post-Tour Extension

After a delicious included breakfast at your hotel, you are free to continue exploring on your own, using our included city information packet to guide your discoveries.

Please note: Italian museums are closed on Mondays.

Included Meals: Breakfast

Departure Airplane

After an included breakfast this morning, complimentary transportation to the Florence airport will be provided (an approximately 55 to 60 minute drive) for your departing flight.

Included Meals: Breakfast

Hotel Ilaria & Residenza dell'Alba

Located within the walls of historic Lucca, Hotel Ilaria & Residenza dell’Alba is an ideal starting point from which to discover the wonderful city center of Lucca. Renovated from Villa Bottini’s historic stables and a 14th-century church, Hotel Ilaria provides a plush and welcoming atmosphere. Here you can find quiet, spacious, and elegantly furnished air-conditioned rooms with modern comforts. WiFi is available throughout the hotel.

Wi-Fi In Room
FREE WiFi Included
Air Conditioning
Air Conditioning
Reviews
51 out of 51 (100%)
4.9 out of 5 stars.
Read More Reviews

This trip is beautiful. Hills (larger than I thought), castles, wine, pasta, ocean and spas. Great weather is early May, made it perfect. Guides, as usual, were friendly, knowledgeable and always so patient.

LMCH, Wisconsin

Salute to the Black Rooster

We took a wonderful bike tour from June 8 - 15, 2024 in Tuscany, Chianti and Marina Di Castagneto with Vermont Bicycle Tours. The tour was impressive and well done. All the details were planned so well - the hotels, restaurants and added activities were all excellent. Our two tour guides, Jacopo and Igor, were the best - knowledgeable, helpful, friendly, and best of all, fun! It was a great way to see a lot of the countryside in different areas, to explore many Italian villages, and to enjoy the beauty of Tuscany. We had done a bicycle tour with VBT in Vermont a long time ago and now after our recent tour, we're finding ourselves wondering why we waited so long to do another. We'd definitely like to take another tour with VBT sometime soon.

lpt travel, Boulder Colorado

Amazing Bike Tour!

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