Tuscany Wine Country Bike Tour
Tuscany Wine Country Bike Tour
6 days
5 nights
Activity Levels 2-4
Premiere Hotels
2025: Sep-Oct2026: May-Jun, Sep-Oct
Cuisine, Culture & Chianti in the Heart of Italy
Tuscany is not only a destination, it's a sublime experience. Pause on the cypress-lined roads that overlook the vineyards and take it all in. You'll think that no view will compare to that view, until you round the next bend and see another. It's a wonder anyone ever finishes the bike rides. And this is only a preview of what you'll see. Imagine the wines, flavors and luxuries you'll discover.
Highlights
- Bike our favorite Tuscan roads—with ample van support, of course—as we wind our way from breathtaking Chianti to remarkable Crete Senesi and beyond
- Luxuriate at handpicked hotels that represent Tuscany's finest, from elegance in Chianti to unforgettable COMO Castello del Nero
- Taste Chianti Classico and Vernaccia, among other critically acclaimed regional wines that have been cultivated in the region for hundreds of years
- Discover idyllic hilltop towns like San Gimignano and Siena, brimming with character and stunning examples of medieval and Renaissance architecture
StartArezzo
EndFlorence
* Start/End locations may vary. Do not book flights until your trip details are confirmed.
Itinerary
Days 1-3
Embark on a quintessential Tuscan adventure, riding scenic routes in the Chianti Classico wine region • Spin through the rolling countryside and take in the sweeping vistas—you’ll soon realize why this is one of the most famous regions in the world • Sample local specialties at an organic agriturismo before biking past olive orchards and vineyards • Ride toward the heart of the Chianti, passing through legendary wine villages like Gaiole in Chianti and Castelnuovo Berardenga • Cycle into the Crete Senesi, an area known for its lunar landscape • Explore Siena’s medieval back streets and grand Piazza del Campo, home to Italy’s most important horse race, Il Palio • Learn the nuances of Tuscany’s renowned red wines at an exclusive sommelier-led tasting.
Nights 1-3
Experience the essence of Chianti at this award-winning hilltop retreat encircled by the quiet Tuscan countryside. (pool, spa)
Days 4-6
Ride the ridge to ancient hilltop Radda, former capital of the Antica Lega del Chianti (Old Chianti League) • Visit the picturesque neighboring village of Castellina in Chianti • Celebrate in Tuscan style over dinner • Bike to Colli Fiorentini, northern Tuscany's slice of Chianti wine production • Follow cycling routes in the verdant Elsa River Valley to the spectacular World Heritage town of San Gimignano, crowned by 13 towers • Toast la dolce vita with a glass of refreshing Vernaccia, Tuscany's most famous white wine, before heading to Florence.
Nights 4-5
Relax at a castle that has been converted into a Renaissance villa, steeped in Tuscan charm and situated on a hilltop overlooking rolling vineyards and olive orchards in the Colli Fiorentini. (pool, spa)
What's Included
See moreHotels
World-Class Hotels
Our hand-selected Premiere hotels offer exceptional hospitality and experiences as special as the regions we explore.
Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.
Nights 1-3
Premiere Hotel
Experience the essence of Chianti at this award-winning hilltop retreat encircled by the quiet Tuscan countryside. (pool, spa)
Nights 4-5
Premiere Hotel
Relax at a castle that has been converted into a Renaissance villa, steeped in Tuscan charm and situated on a hilltop overlooking rolling vineyards and olive orchards in the Colli Fiorentini. (pool, spa)
Gallery
Bikes
Choose Your Perfect Bike
Our bikes are designed and built with specific cyclists and riding styles in mind, so we can always offer you a perfect ride. Please note that bike requests are subject to availability and prioritized based on the date they're submitted.
Included in your trip price
- Ideal for avid cyclists
- Redesigned for 2024
- Next gen titanium frame with carbon wheels
- Responsive, efficient and comfortable
- Drop handlebars only
Included in your trip price
- Suited for a wide range of cyclists
- Comfortable ergonomic seat
- Long wheel base adds to the bike's control and stability
- Upright handlebars only
Included in your trip price
- One of the lightest e-bikes available
- Provides plenty of power and more than enough battery
- Lower top tubes for easier mounting and dismounting
- Upright handlebars only
- Limited availability on Unplugged Bike Tours; learn more
Min. age to ride e-bike: 16+
- $400 rental fee
- Hand-built frame features Co-Motion's custom-designed Cro-Moly steel tubeset, powerful Avid disc brakes, Shimano Ultegra drive train
- Custom upgraded wheelset
- Best for riders with some tandem experience.
Review Snapshot
by PowerReviews
Reviewed by 35 customers
Incredible trip. No better way to enjoy Tuscany backroads!
No better way to explore and enjoy the delights of Tuscany than with a perfectly organized BackRoads bike trip. Perfect company (we were a total of 6 travelers) in the capable hands of two fantastic tour leaders, Lucia and Abde. Very professional, highly entertaining, efficient, jovial and such fun to be with. BackRoads know how to look after you!
WOW!! surpassed expectations!
OUR GUIDES WERE EXCEPTIONAL AT THEIR JOBS- my wife and I were new to Backroads and could not have been more pleased with the enthusiasm, effort and planning provided by Corina, Lucia and Mikal The level of detail that went into the multiple side events made the trip a 10! From touring a 14th century Abby to the organic farm lunch to one of many great meals! Will do another Back Roads adventure!
Every aspect magical: the scenery on the rides, the food the
Our leaders made the trip extra special—2 were from Italy and their insight into the customs and history (and talking with your hands!) added immensely to the uniqueness of the experience. We were celebrating our anniversary and they delivered champagne and a sweet card to our suite; just an example of the genuine individual care provided
Our trip to Tuscany was one of the most romantic experience
Tuscany a land of rolling hills, cypress trees, wineries and endless landscapes. Biking through the gorgeous landscapes and the visits to quaint medieval towns, Chianti wines were one of the best red wines! Learning about the traditional way of wine making and in addition the modern technology was an amazing experience. It was my milestone birthday and none other than Backroads and their awesome leaders went over and above to make my day so special , it has left an everlasting memory in my heart. Thank you Backroads for this amazing experience Emily, Corrina and Maria - I thank you all from the bottom of my heart ♥️
Amazing Tuscany trip- A must go
Very scenic, amazing vegetarian food, excellent Chianti wines that give no headaches or hangovers. Our trip leaders were very helpful, knowledgeable and made the trip very comfortable and enjoyable. Would highly recommend this trip due to the great views and the premium hotels.
Backroads outdid themselves on this trip!
The bicycle trips and activities planned for us in this trip were spectacular. The climbs were challenging but doable, the scenery out of this world, the food amazing and last of all, the trip leaders, Lorenzo and Giulia and support staff, Giovanni, were top notch.
Our trip was amazing in every respect.
We've done 16 Backroads trips so far and our ride leaders on this trip were among the best. Very helpful, very informative, very well organized and very warm nice people. They made the whole operation seem effortless. The routes each day allowed us to experience the beauty of Tuscany on roads that, for the most part, didn't have many cars. Staying in just 2 hotels was really nice and allowed us to experience the properties, which were beautiful. Of course, the food was amazing. I especially loved the barbeque. The people on the trip were all friendly, warm and fun. A perfect trip.
Backroads continues to set the standard
We had an excellent trip to Tuscany which exceeded our expectations. The accommodations were incredible, the food and wine fantastic, the rides were challenging yet beautiful, and our leaders catered to our needs and delivered an excellent experience. I highly recommend Backroads for your next vacation.
Excellent trip
A challenging route. Scenic views. Gastronomic trip
Best vacation!!!
We can't recommend this trip highly enough!!! The biking was beautiful. The route options were varied in length and elevation to allow for all levels of fitness, and many on the trip had e-bikes. Everyday we were challenged but very physically satisfied! Both hotels were gorgeous in location and amenities- spas were excellent. The meals were wonderful. Trip leaders ensured we were cared for at every moment. We made memories to last a lifetime, and can't wait to get on another Backroads trip!
Dates & Prices
Dates & Prices
Click on dates for pricing, itinerary variations (if any) and to book your trip. Price is per person, double occupancy in USD.
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