Italy: Tuscany, Chianti & Marina di Castagneto
Guided Biking
- Daily Mileage: 8-39 miles|
- Biking: 1-5 hours|
Starting From
10-day Air Package
$6,145
7-day Bike Tour Only
$4,895
Per person, double occupancy
Italy: Tuscany, Chianti & Marina di Castagneto
On this sumptuous cycling vacation, we’ve paired the sun-soaked Tuscan seacoast with the lush vineyards of Chianti. This is the beating heart of Italian wine country—and on this exhilarating adventure your local Trip Leaders introduce you to the families, vineyards, and vintages that make it world-renowned. Challenge yourself cycling Chianti’s vine-draped hills—and tour an ancient castle and vineyard where you’ll taste some of the region’s exquisite vintages with a local sommelier. Visit a family-run olive oil mill for a tasting and farm-fresh lunch, learn how to prepare authentic Italian dishes in a classic Tuscan farmhouse, and explore the walled medieval village of Monteriggioni. In the evenings, wrap yourself in luxury during stays at converted palaces and spa resorts boasting thermal pools, a private beach, and even an historic Etruscan tepidarium.
Tour Highlights
- Enjoy luxurious accommodations with sandy beaches and elegant regional cuisine.
- Visit the home of a longtime VBT friend and prepare a traditional Tuscan meal alongside her.
- Tour a 13th-century castle and vineyard in Chianti and learn about the region’s world-renown vintages.
- Cycle along Bolgheri’s iconic cypress-lined avenues, and discover the stunning medieval towns of Castagneto Carducci, Sassetta, and Suvereto.
- Explore the ancient Etruscan city of Populonia with its sweeping views 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
Cyclists
Support
Terrain includes more hills. Longer distance options can be very rewarding for those who cycle regularly.
- Average Daily Mileage: 26-42 mi.
- Average Daily Cycling Time: Up to 5 hrs.
- Average Daily Elevation gain: Up to 3400 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 |
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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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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)
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
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
Air Package Only
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.
Air Package Only
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
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
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
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.
From the beginning of talking with VBT customer support about our bike tour, through scheduling, and on the actual tour itself, the entire process could not have been better-greatly exceeded our expectations
ITALY: VBT Bike Tour-Simply the Best!
Incredible trip from e-bike to tour guides to meals to hotels to curated experiences! Every stop was beautiful and etched onto my memory. Igor and Jacopo were kind, patient, professional, fun, prepared, knowledgeable and so good at their job, especially when I got sick. They truly showed us their own Italy. Calidario was the best hotel ever, and I loved the Castello di Populonia. Tombolo Resort was beautiful but challenging. The warm up ride was a great way to get comfortable biking together. The cars and motorcycles take a bit to get used to when we only biked on bike lanes in the States. Gina the biking app was good but not great, as she can't guide lost bikers back to the route and does not allow for repeating of her instructions. Several in the group got lost. A temporary VBT sign at each turn might have helped, as the sweep guide didn't always catch everyone. I wasn't a regular biker, and loved my Fuji E-bike. The battery lasted a long time, and the 4 modes were great.
I want to see every country on an e-bike with VBT
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