now offered in Tuscany
on trips after 9/1/13.
Call for availability
- The quintessential Tuscan journey - great for cyclists of all levels
- Pedal our favorite Tuscan roads with ample shuttle support
- Handpicked hotels that represent Tuscany's finest
- Taste the region's most acclaimed wines with a local sommelier
- Picturesque hilltop towns brimming with medieval architecture
Chianti to Montalcino, the Land of Brunello
Few things in this world live up to the hype. But everything you've ever heard about Tuscany is true. It's not a destination. It's an experience. Rides lined with cypress trees overlooking the patchwork vineyards below will stop you on your bike. And no view will compare to that view. Until you round the next bend and see another. It's a wonder anyone ever finishes the rides. And that's only what you'll see; imagine the wines and flavors you'll discover.
Day 1 The quintessential Tuscan journey - great for cyclists of all levels Sample fresh cheeses at an agriturismo before biking quiet roads past olive orchards, farmhouses and wheat fields Pedal to medieval Greve and explore nearby Montefioralle, the home of Amerigo Vespucci, the Tuscan explorer who discovered New York Harbor.
Days 2-3 Pedal rolling hills in the heart of Chianti to Badia a Coltibuono (“Abbey of the Good Harvest”) where you’re treated to a private tour and olive oil tasting The hidden nooks of Via delle Volte, Castellina's unique arcaded passageway are a delight to explore Ascend to the ancient hilltop town of Radda, the center of Chianti wine production.
Day 4 The narrow streets of Montalcino, known for having the region's finest wines, are yours to discover Point your wheels toward southern Tuscany, where stately cypresses crisscross open rolling hills Our route leads through the chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Florentine paintings.
Days 5-6 Taste world-famous Brunello Pedal through the undulating wheat fields and hilltop towns of the Val d'Orcia In Pienza, marvel at the famed Renaissance architecture and sample splendid pecorino cheese.
Guests Reviews About This Trip
We had a fabulous time - our leaders were fantastic!! We loved the fact that support was always available and that we periodically saw the other group members on the road but for much of the time it was just the two of us enjoying the scenery and the ride. We can't wait to come back and do another Backroads trip. Meals were fantastic and we totally enjoyed the flexibility to ride as much or as little as we wanted. All in all it was definitely the best vacation ever--can't wait to download my 500+ pictures--everywhere was "una bella vista"- Atlanta, GA
This was a dream trip! It was definitely challenging (in a good way!) as well as extremely rewarding and enjoyable. I'd do it again in a heartbeat!- Allen, TX
We had a spectacular trip. I made the comment to my wife after the very first day of biking that I could go home today and feel like all my expectations had been fulfilled - and that was just the first day! We had been dreaming of and planning this trip for so long, that I was afraid I would be expecting too much. But it was so much better than we had even hoped for. Thanks, Backroads, for the trip of a lifetime! Now my only thought is how could the next Backroads trip possibly compare with this one--but I bet it will be exciting to find out!- Allen, Texas
Castello del Nero
Tavarnelle Val di Pesa (2 nights) Situated on a hilltop overlooking rolling vineyards and olive orchards in the Colle Fiorentini, this former castle is steeped in Tuscan charm. (pool, spa)
Relais Borgo Scopeto
Vagliagli (1 night) Once owned by the Sienese cathedral in the 1200s, this elegant estate offers commanding views of Siena and the Mangia Tower. (pool, spa)
Castello di Velona
Castelnuovo dell'Abate (2 nights) This 11th-century fortress features terra-cotta floors, individually decorated rooms and stunning views of the Val d'Orcia. A Small Luxury Hotels of the World member. (pool, spa)
Dolomites Biking New!
Epic Alpine Passes in Northern Italy
Piedmont Biking New!
A Food & Wine Lover's Paradise
Ancient Civilizations & Mediterranean Sensations
Tuscany & Umbria Biking New!
Undiscovered Umbria to Cortona, Land of the Tuscan Sun
This Trip Is Rated Level 2-5
Routes For All Abilities
Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. We know your pace may vary from one day to the next-and your traveling companion's may differ somewhat from yours. So we present a range of mileage options, and each day you decide exactly what and how much you want to do.
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There is less than 5% of riding on hard-packed dirt on this trip. Since the overwhelming majority of the trip is paved, we've elected to use standard road bike tires on our titanium road bikes. Most guests find this to be the right answer. If you prefer to skip the dirt, a shuttle is always a possibility.
* Includes a shuttle