Italy: Tuscany, Chianti & Marina di Castagneto

7 days
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4.9/5 Excellent
100+ reviews  
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Group Tour
For a sublime bike tour in Tuscany’s wine regions, we’ve found the perfect pairing – the lush vineyards of Chianti and the sun-soaked coast of the Tyrrhenian Sea. This unique bicycling vacation showcases dreamy landscapes, mouthwatering cuisine, and a rich culture that welcomes you with open arms. Cycle the scenic Strada del Vino, rolling hills, and gentle va...
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Trip type
Group Tour
Lodging level
Premium - 4 star
Physical level
Trip pace
Full schedule


    • 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 a 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.

What's this trip about?

    For a sublime bike tour in Tuscany’s wine regions, we’ve found the perfect pairing – the lush vineyards of Chianti and the sun-soaked coast of the Tyrrhenian Sea. This unique bicycling vacation showcases dreamy landscapes, mouthwatering cuisine, and a rich culture that welcomes you with open arms. Cycle the scenic Strada del Vino, rolling hills, and gentle valleys lined with cypress trees. Visit a 13th-century castle-turned-winery and haven for bees. Learn the ancient crafts of spinning pottery and pressing olive oil. Along the way, step into medieval days in remarkably preserved villages, including stunning Monteriggioni. Immerse yourself in Italy’s rich culinary traditions in the kitchen of a longtime VBT friend. And at day’s end, indulge in thermal pool soaks, dine on incredible meals, and sip world-renowned wines.


Itinerary focusActive
Group sizeSmall Group - max of 22 people
Age range13 to 80 years
Flights and transportAll internal ground transport included
Start CityFlorence
End CityLucca

Travel Themes

  • Culinary & Wine
  • Cultural
  • Cycling & Biking
  • Nature & Wildlife


  • Europe
  • Italy


  • Florence
  • Lucca
  • Tuscany


  • Adventure & Adrenaline
  • Cooking
  • Cycling
  • Mountain Biking
  • Nature
  • Photography
  • Guided Group

Trip includes

    • 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


Travel Map
DAY 1: VBT Bicycle Vacation begins / Travel to Radda in Chianti / Warm-up ride

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 defe...

DAY 2: Ride to Castello di Meleto / Gaiole in Chianti / Visit a pottery workshop

After breakfast, set out to explore Chianti along the “castle way,” traversing dense forests that embrace picturesque villages like Tornano and Lecchi. The castles and watchtowers you’ll see as you ride played a strategic role in the frequent battles between Siena and...

DAY 3: Monteriggioni / Montescudaio / Spa and beach time

Your day begins with a thrilling coast down a scenic route that delivers you 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 accompan...

DAY 4: Bolgheri / Visit an oil mill / Cooking class

After breakfast, cycle the historic Strada del Vino into Bolgheri, 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 Contr...

DAY 5: Cycle Castagneto, Sassetta, and Suvereto / Enjoy natural hot springs

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 ...

DAY 6: Explore Campiglia Marittima, Baratti Bay and the ancient city of Populonia

After breakfast, cycle or get a lift to Campiglia Marittima. Though this authentic hillside village has medieval origins, 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 P...

DAY 7: Travel to Lucca / VBT Bicycle Vacation ends

After breakfast, transportation is provided to Lucca with your fellow travelers. From there 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

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Dates & Availability

Price From $4,045
Price per day$578
Last Updated: 3/1/2024
Start Date
End Date
Shared Room
Single Supplement
20 Apr 2024
27 Apr 2024
25 Apr 2024
02 May 2024
Limited Spaces Left
27 Apr 2024
04 May 2024
Call Required
02 May 2024
09 May 2024
04 May 2024
11 May 2024
Limited Spaces Left
09 May 2024
16 May 2024
11 May 2024
18 May 2024
16 May 2024
23 May 2024
Limited Spaces Left
18 May 2024
25 May 2024
23 May 2024
30 May 2024

Check Current Availability, prices, specials with VBT Bicycling Vacations.

The total tour cost includes the tour price (regular or promotional) and the compulsory local payment. The promotional price is subject to change. Check directly with the operator for the latest price offer. The tour operator requires you to pay only the tour price to purchase your travel. The compulsory local payment will be paid when you join the trip. All prices are based on double, twin or triple share occupancy. Solo passengers will be accommodated in a double, twin or triple room according to availability with a passenger(s) of the same gender. Single supplement only needs to be paid if the passenger does not want to share and requests their own room. Discounts can only be applied at the time of booking and cannot be added at a later date, regardless of any changes made to the original booking.

Prices may vary due to local taxes and trip seasonality. Click "Request Info" to inquire directly with the tour operator for the final trip price.

VBT Bicycling Vacations Reviews & Ratings

4.9/5  Excellent
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Other VBT Bicycling Vacations Reviews



Nov 2023

Written on

Absolutely stunning scenery with relatively easy cycling.

This tour was one of our favorites. The tour leaders (Claudio and Tiziana) were great. The Dolomites and Italian Alps were breathtaking and the bike paths and towns ...



Nov 2023

Written on

Fantastic intro to a bike vacation!

VBT came highly recommended by several friends and family so we took the plunge and did our first guided bike trip. We were never disappointed. Guides, hotels, bikes...



Nov 2023

Written on

life at its fullest

Unlike tours where you gaze at world class natural and historic wonders in another culture, this tour put us in intimate touch with them through cycling, eating, dri...

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Tour Operator

VBT Bicycling Vacations

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Since 1971, VBT has crafted immersive and authentic biking vacations for active travelers. When you travel with VBT, you’re not just another tourist—you’re a traveler. With us, you’ll experience your destination with the help of a local, bilingual trip leader with a passion for sharing their home with you. You’ll eat in local restaurants, stay in accommodations that have been family-owned for generations and cycle through vineyards, olive groves, and medieval villages. 

With VBT, you won’t just visit a place—you’ll immerse yourself in it. You might follow a centuries-old pasta recipe while taking a cooking class in Rome—or learn a folk dance in Croatia, followed by sharing a bottle of locally-produced Grk wine with your new friends. Exploring the world on two wheels lets you experience your surroundings on a deeper level.


VBT offers exceptional value without compromising on quality. Simply put, no other US-based active travel company offers an experience this rich for such a reasonable price. On our tours, you can see more sights, have more local experiences, and enjoy more delicious, authentic meals—all while staying in high-quality, boutique hotels and charming, family-run inns.


All you have to do is show up at the airport—we’ll handle the rest! From tour consultants who help you find the perfect vacation to expert local trip leaders who show you the best place for gelato, we take care of all the little details that make your trip memorable. We book your flights, arrange all your transportation and accommodations, and move your luggage between hotels. Our support vans are available to give you a lift up a hill or quickly fix a flat tire. VBT takes care of your travel details and creates unique itineraries so you can relax and enjoy your small-group vacation from start to finish.


Friendly camaraderie, cultural immersion, and casual comforts are the hallmarks of our vacations. Discover delightful people, beautiful hotels, foreign cultures, and fascinating lifestyles that will enrich your life and provide memories for years to come.

Why we love this operator
Their unique emphasis on immersive cultural experiences combined with active exploration with personalized cycling experiences.
What they’re known for
VBT Cycling are renowned for offering exceptional guided and self-guided bicycle tours worldwide.


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,6 nights in country estates and one 5-star hotel
Travel Insurance
We strongly recommend purchasing travel insurance alongside your travel package to safeguard against unforeseen circumstances such as medical expenses, trip cancellations, and other contingencies. It offers you peace of mind and ensures you are prepared for unexpected events that may occur before or during your journey
Visa requirements
Visa requirements vary depending on your country of origin and your country of destination. It is your responsibility to familiarize yourself with the relevant requirements. For a handy tool that can help you quickly find the requirements, please visit this link .
Meals Included

13 meals: 6 breakfasts, 3 lunches, 4 dinners

Age Requirements
13 to 80 years
Additional Information
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
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