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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 different olive oils by taste with the family that owns the Fonte di Foiano olive oil mill as your guide.
  • 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|
  • Group Size: 22
Activity Easy/Moderate
Easy/Moderate
Bar Graph Beginner - Experienced
Cyclists
Vehicle Support Vehicle
Support

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 country estates and one 5-star hotel

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13 meals: 6 breakfasts, 3 lunches, 4 dinners

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2025 2024

Electric-Assisted Bicycle (E-bike)

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Road Bicycle (Carbon frame)

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Step-Through (Mixte Hybrid) Comfort Bicycle

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Step-Over (Diamond) Comfort Bicycle

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2025 2024

Electric-Assisted Bicycle (E-bike)

See More >

Road Bicycle (Carbon frame)

See More >

Step-Through (Mixte Hybrid) Comfort Bicycle

See More >

Step-Over (Diamond) Comfort Bicycle

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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

Thu, Apr 17 to Sat, Apr 26, 2025

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.

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 — 24 km (15 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: 24 km (15 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. 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 on your own, continue riding the iconic Chianti roads. 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.

By lunch time, take a seat and enjoy a delicious picnic lunch prepared by your tour leaders, where Meleto honey is matched to local cheeses and Chianti Classico wine reigns on the table.

Later, pause at Ceramiche Rampini, a small pottery workshop that honors a cherished Italian craft. See its kiln, meet some artists, and admire the pieces adorned with traditional Renaissance-era colors and designs, including some that date back to an original pattern created for the Medicis.

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 Gaiole & Meleto — 21 km (13 miles)

Afternoon: Meleto to Castagnoli & 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, your lunch stop. 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, Lunch

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 Casale Marittimo. 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 to stop in the wine village of Bolgheri where you can have lunch on your own. 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) | Casale Marittimo to Bolgheri — 11 km (7 miles)

Afternoon: Bolgheri to Tombolo — 18 km (11 miles)

What to Expect:

The first 7 miles of your morning ride are slighly rolling till Castellina in Chainti. From there an exhilarating and scenic descent of 5 miles takes you to Castellina Scalo. There, biking path and a half mile stretch on the busier Cassia road, deliver you to  Monteriggioni. You will park your bike at the foothills of the walled village of Monteriggioni, to then walk up and enjoy the visit. After that, relax on a 90 minute shuttle to Casale Marittimo, from where you can start bikingto Bolgheri. This ride starts with a long panoramic descent into the wine village of Bibbona, then meanders past vineyards and wineries on moderately rolling terrain along the famous ‘bolgherese’ road, named after the medieval village of Bolgheri. The panoramic routes you are on are also 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: 11 — 55 km (7 — 34 miles)

Included Meals: Breakfast, 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. 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 local jerseys.

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 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 on your own in this ancient small town.

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, 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

Italy: Tuscany, Chianti & Marina di Castagneto

Download PDF Itinerary:

Air Package (PDF) Tour Only (PDF)

Sat, Apr 19 to Fri, Apr 25, 2025

Show Itinerary:

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 — 24 km (15 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: 24 km (15 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. 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 on your own, continue riding the iconic Chianti roads. 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.

By lunch time, take a seat and enjoy a delicious picnic lunch prepared by your tour leaders, where Meleto honey is matched to local cheeses and Chianti Classico wine reigns on the table.

Later, pause at Ceramiche Rampini, a small pottery workshop that honors a cherished Italian craft. See its kiln, meet some artists, and admire the pieces adorned with traditional Renaissance-era colors and designs, including some that date back to an original pattern created for the Medicis.

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 Gaiole & Meleto — 21 km (13 miles)

Afternoon: Meleto to Castagnoli & 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, your lunch stop. 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, Lunch

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 Casale Marittimo. 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 to stop in the wine village of Bolgheri where you can have lunch on your own. 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) | Casale Marittimo to Bolgheri — 11 km (7 miles)

Afternoon: Bolgheri to Tombolo — 18 km (11 miles)

What to Expect:

The first 7 miles of your morning ride are slighly rolling till Castellina in Chainti. From there an exhilarating and scenic descent of 5 miles takes you to Castellina Scalo. There, biking path and a half mile stretch on the busier Cassia road, deliver you to  Monteriggioni. You will park your bike at the foothills of the walled village of Monteriggioni, to then walk up and enjoy the visit. After that, relax on a 90 minute shuttle to Casale Marittimo, from where you can start bikingto Bolgheri. This ride starts with a long panoramic descent into the wine village of Bibbona, then meanders past vineyards and wineries on moderately rolling terrain along the famous ‘bolgherese’ road, named after the medieval village of Bolgheri. The panoramic routes you are on are also 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: 11 — 55 km (7 — 34 miles)

Included Meals: Breakfast, 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. 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 local jerseys.

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 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 on your own in this ancient small town.

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, 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., you are free to follow our expert local guide on a city walking tour of approximately two hours. From Lucca you can take a taxi to the Pisa airport (approximately 25 minutes) or Florence airport (approximately 60 minutes). You are responsible for your own transportation to the airport for your flight home.

Included Meals: Breakfast

Italy: Tuscany, Chianti & Marina di Castagneto

Download PDF 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 2024

2025 Pre-Trip Extension - Florence

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

  • 2 nights at the Hotel De La Ville
  • Airport car service for arrival
  • 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

Hotel De La Ville

This hotel has been completely restored and sits in a convenient location in the heart of Florence, a few steps from the famous Duomo on the fashionable shopping street Via Tornabuoni, which is closed to car traffic and quiet. Enjoy spacious, comfortable, air-conditioned private rooms.

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

Air Package Only

2025 2024

2024 Pre-Trip Extension - Florence

2 Nights From $495 per person, double occupancy
Single Supplement: From $345

  • 2 nights at the Hotel De La Ville
  • Airport car service for arrival
  • 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

Hotel De La Ville

This hotel has been completely restored and sits in a convenient location in the heart of Florence, a few steps from the famous Duomo on the fashionable shopping street Via Tornabuoni, which is closed to car traffic and quiet. Enjoy spacious, comfortable, air-conditioned private rooms.

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

Air Package Only

2025 2024

2025 Post-Trip Extension - Lucca

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

  • 2 nights at the Hotel Ilaria & Residenza dell’Alba
  • Airport car service for arrival
  • Daily breakfast
  • City information
1 Begin your Post-Trip 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-Trip 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
Airplane

Air Package Only

2025 2024

2024 Post-Trip Extension - Lucca

2 Nights From $295 per person, double occupancy
Single Supplement: From $195

  • 2 nights at the Hotel Ilaria & Residenza dell’Alba
  • Airport car service for arrival
  • Daily breakfast
  • City information
1 Begin your Post-Trip 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-Trip 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
14 out of 14 (100%)
4.8 out of 5 stars.
Read More Reviews

Awesome scenic rides, great hotels and plenty of good food! E-bike very helpful. Took our 4 adult kids who also enjoyed the trip. Transportation between rides also well arranged.

DJK62, Missouri

VBT=Very Best Tuscany

We had the experience of a lifetime on this trip. Our guides were a huge part of that. They were funny, smart, friendly, helpful and full of wonderful stories and anecdotes to teach us about Italian culture and history. They were skilled at working with riders of all abilities and made the navigation easy.

Becki S, Medford, Oregon

Best trip ever!

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