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. Routes 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, offering the most scenic routes from Florence to Montalcino Sample fresh cheeses at an agriturismo before biking serene roads past olive orchards, farmhouses and wheat fields Pedal to medieval Greve and stroll through nearby Montefioralle, the home of Amerigo Vespucci, the Tuscan explorer who discovered New York Harbor.
Days 2-3 Ascend quiet roads into the heart of the Chianti region The hidden nooks of Via delle Volte, Castellina's unique arcaded passageway, are a delight to explore Cruise the ridge to the ancient hilltop town of Radda, long the center of Chianti wine production Visit Badia a Coltibuono ("Abbey of the Good Harvest"), where you're treated to a private tour and olive oil tasting Wine and dine in exclusive style - for one special evening, San Felice's renowned restaurant is open just for us.
Day 4 The narrow streets of Montalcino, known for harboring 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 extraordinary Renaissance architecture and sample splendid pecorino cheese.
- Ride, relax and savor every drop of this vintage Backroads experience
- Pedal our favorite Tuscan roads with ample shuttle support
- Luxuriate at handpicked hotels that represent Tuscany's finest
- Taste critically acclaimed wines with a local sommelier
- Discover idyllic hilltop towns brimming with medieval and Renaissance architecture
Castello del Nero (1 night): 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 San Felice (2 nights): Praised by the Hideaway Report as an "enchanting resort enclave set within a restored medieval hamlet fringed by olive groves and vineyards in the Chianti Classico region." A Relais & Châteaux member. (pool, spa, tennis)
Castello di Velona (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)
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.
Routes For All Abilities
|Daily Route Options|
|Level 1||Level 2||Level 3||Level 4||Level 5|
|miles||feet gain||miles||feet gain||miles||feet gain||miles||feet gain||miles||feet gain|
* Includes a shuttle
2014 Dates & Pricing*
- 5/11-16 Price: $4698 pp dbl. occ., (+ $1860 for sgl. occ.)
- 5/25-30 Price: $4798 pp dbl. occ., (+ $1860 for sgl. occ.)
- 6/1-6 Price: $4598 pp dbl. occ., (+ $1860 for sgl. occ.)
- 6/8-13 Price: $4698 pp dbl. occ., (+ $1860 for sgl. occ.)
- 6/15-20 Price: $4798 pp dbl. occ., (+ $1860 for sgl. occ.)
- 6/22-27 Price: $4698 pp dbl. occ., (+ $1860 for sgl. occ.)
- 6/29-7/4 Price: $4698 pp dbl. occ., (+ $1860 for sgl. occ.)
- 7/6-11 Price: $4798 pp dbl. occ., (+ $1860 for sgl. occ.)
- 8/3-8 Price: $4698 pp dbl. occ., (+ $1860 for sgl. occ.)
- 9/7-12 Price: $4898 pp dbl. occ., (+ $1860 for sgl. occ.)
- 9/9-14 Price: $4398 pp dbl. occ., (+ $1860 for sgl. occ.)
- 9/14-19 Price: $4698 pp dbl. occ., (+ $1860 for sgl. occ.)
- 9/16-21 Price: $4398 pp dbl. occ., (+ $1860 for sgl. occ.)
- 9/21-26 Price: $4898 pp dbl. occ., (+ $1860 for sgl. occ.)
- 9/23-28 Price: $4398 pp dbl. occ., (+ $1860 for sgl. occ.)
- 9/28-10/3 Price: $4798 pp dbl. occ., (+ $1860 for sgl. occ.)
- 9/30-10/5 Price: $4398 pp dbl. occ., (+ $1860 for sgl. occ.)
- 10/5-10 Price: $4598 pp dbl. occ., (+ $1860 for sgl. occ.)
- 10/12-17 Price: $4698 pp dbl. occ., (+ $1860 for sgl. occ.)
- 10/19-24 Price: $4398 pp dbl. occ., (+ $1860 for sgl. occ.)
*Prices may change. Once you book your trip, your price is guaranteed.
Private Trips Options & Pricing
Gather your favorite people to share a Backroads adventure on a ready-to-book Private Trip - featuring all the legendary Backroads hallmarks from expert leaders to unforgettable activities.
You can pick from a large selection of dates for your group of 8 or more. Call us for date availability.
If your party has fewer than 8 guests, or if your preferred date is not available, we'll create a departure just for you.
Pricing for Private Trips
- 2 - 3 guests $6,698 pp dbl. occ.
- 4 - 5 guests $6,098 pp dbl. occ.
- 6 - 7 guests $5,598 pp dbl. occ.
- 8 - 9 guests $5,298 pp dbl. occ.
- 10 - 11 guests $4,698 pp dbl. occ.
- 12 or more guests $4,398 pp dbl. occ.
Guest Trip Reviews
Beyond special...the indulgence of a consistent 5-star experience in locations only experienced in the movies.- Aspen, CO
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! Thanks, Backroads, for the trip of a lifetime!- Allen, TX
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 the best trip I have taken in my entire life! Everything was perfect. Our trip leaders were the greatest, our fellow travelers were great people and Tuscany is amazing. I cannot wait to go on another Backroads trip.- Toronto, ON
Once again Backroads delivered! This trip was totally enjoyable thanks to the attention to detail and quality of the leaders. Tuscany is beautiful and the intimate experience of seeing it by bike was intoxicating! Tagliatelle with funghi porcini and a nice Chianti Classico may have added to the experience.
Our first Backroads trip far exceeded our expectations! The weather was gorgeous every day. How did you arrange that? The guides adapted amazingly to the needs of the group. They were knowledgeable, thorough, fun, and around when you needed them. The hotels were quite lovely... The biking was phenomenal! We did it all! How you got together such a perfect traveling group of people was quite a feat! We thoroughly enjoyed everyone and everyone was very gracious, warm and friendly. Can't wait for our next Backroads trip.- Montreal, QC
We had a wonderful time, as usual! Everything ran smoothly (due to our stellar leaders), the biking was so scenic it seemed unreal, the food and wine were superb, and the companionship interesting and fun. Can't wait for our next trip with y'all.- Winter Haven, FL
Incredible! Still thinking and dreaming about it... Even though the trip was only 6 days, I feel like we packed in a few weeks' worth of experiences.- Snoqualmie, WA
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
The trip was very special from all standpoints. Good group of guests, excellent leaders and super locations. The area and route chosen were truly remarkable. Every turn in the road revealed a stunning vista that took your breath away. Probably the only cycling trip with the physical demands we experienced on which I could gain weight. Thanks, we will be back and are already putting the next trip together.- Greensboro, NC
Excellent trip and assistance throughout the tour. Backroads was my first 'active' vacation and I'm never going back to a relaxing day at the beach... I feel more refreshed after doing, seeing and learning interesting things while making new friends within our group.- Tracy, CA
It was awesome! This trip was a graduation present for my daughter. We had an amazing experience and sharing this experience with her was a gift to me! Thank you and I am looking forward to another Backroads adventure!- Kingwood, TX
You have brought us such joy over the years and 12 Backroads trips. Thank you for all the research and hard work in making our trips joyful memories that we will always treasure.- Excelsior, MN
I chose this trip because I wanted challenging biking in addition to beautiful scenery. I got it! I feel that I really accomplished something. The first part of the trip - through the Chianti region - was spectacular. I honestly feel sorry for anyone that doesn't get to experience the region on a bike. Every view was a postcard.- San Mateo, CA