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Tuscany Bike Tour
Tuscany Bike Tour

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 a sublime 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, flavors and luxuries you'll discover.

Day 1 The quintessential Tuscan journey, offering the most scenic routes from Florence to Montalcino  Sample fresh Tuscan specialties at an agriturismo before biking serene roads past olive orchards, farmhouses and wheat fields  Pedal to medieval Greve in Chianti, where you can stroll through the narrow lanes and pretty piazza of this former market town before continuing to the splendid Castello del Nero  Kick off the week with superb Michelin-starred cuisine inspired by Tuscan traditions and flavors.

Days 2-3 Ascend quiet roads into the heart of the Chianti region  Cruise the ridge to the ancient hilltop town of Radda, long the center of Chianti wine production The hidden nooks of Via delle Volte, Castellina's unique arcaded passageway, are a delight to explore  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 style at San Felice's renowned restaurant.

Day 4 Visit Monte Oliveto Maggiore, a Benedictine abbey featuring some of the best preserved frescoes in Europe  Our route leads through the chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Florentine paintings  Stroll Montalcino's medieval streets in search of the perfect trattoria for dinner.

Days 5-6 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  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  Visit the imposing abbey of Sant'Antimo, where monks celebrate mass with stirring Gregorian chants.

Trip Highlights
  • 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 regional wines
  • Discover idyllic hilltop towns brimming with medieval and Renaissance architecture
big map

Premiere Inns

Castello del Nero (1 night): A castle steeped in Tuscan charm and situated on a hilltop overlooking rolling vineyards and olive orchards in the Colli Fiorentini. (pool, spa)

Relais Borgo San Felice (2 nights): Described 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): Soak up superb hilltop views at this elegant 11th-century fortress featuring a magnificent vantage point above the Val d'Orcia. A Small Luxury Hotels of the World member. (pool, spa)

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.

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
1 19 1300
2 24* 1800 40* 2200 48 3100
3 19* 1800 29 2400 36 3100
46 3900
4 28* 1200 33* 1200 48 2700
5 22* 2000 32* 2400 45 3500 62 4400
6 14 900

* Includes a shuttle

2015 Dates & Pricing*

  • 5/10-15 Price: $4948 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 5/24-29 Price: $5048 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 6/7-12 Price: $4948 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 6/14-19 Price: $5048 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 6/21-26 Price: $5048 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 6/28-7/3 Price: $4848 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 7/5-10 Price: $4848 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 7/12-17 Price: $4848 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 7/19-24 Price: $5048 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 7/26-31 Price: $4848 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 8/2-7 Price: $4948 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 8/9-14 Price: $4948 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 8/16-21 Price: $4598 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 8/30-9/4 Price: $4598 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 9/6-11 Price: $5048 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 9/8-13 Price: $4848 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 9/13-18 Price: $5048 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 9/15-20 Price: $4848 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 9/20-25 Price: $4948 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 9/22-27 Price: $4948 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 9/27-10/2 Price: $4848 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 9/29-10/4 Price: $5048 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 10/4-9 Price: $4948 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 10/11-16 Price: $4848 pp dbl. occ., (+ $1600 for sgl. occ.)
  • 10/18-23 Price: $4598 pp dbl. occ., (+ $1600 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 (prices may vary based on departure date)


2 - 3 guests from $6,998 pp dbl. occ. 8 - 9 guests from $5,498 pp dbl. occ.
4 - 5 guests from $6,198 pp dbl. occ. 10 - 11 guests from $4,898 pp dbl. occ.
6 - 7 guests from $5,698 pp dbl. occ. 12 or more guests from $4,598 pp dbl. occ.

All Private Singles-Solos trips require a minimum of 16 guests.

Guest Trip Reviews

Beyond special...the indulgence of a consistent 5-star experience in locations only experienced in the movies.
Fredric Levin- 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!
Michael Kellum- 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."
Michelle Ross- 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.
Michele Cummings- 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.
Bob Tanz- Chicago, IL

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.
Lynn Waxman- 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.
Amy Thornhill- 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.
Melanie Majerech- 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!
Gaynell Kellum- 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.
Tom Cason- 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.
Ken Schmidt- 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!
Kimberly Hott- 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.
Candice Nadler- 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.
Peter Heller- San Mateo, CA

Our biking trip exceeded our expectations! We had so much fun and the accommodations were spectacular! The food was incredible! We will definitely take a Backroads trip again - maybe with our kids!
Kristin Edwards- Darien, CT