To D.H. Lawrence, Tuscany was "the perfect centre of man's universe." Poet Shelley called the region a "paradise for exiles." Dante, a Tuscan native, more than likely called it "divine." You'll undoubtedly conjure up a few superlatives of your own as you pedal from one unbelievable view to the next, gaze in awe at incredible Renaissance art and architecture, and savor delicious pecorino cheese, homemade pasta, fruity olive oils and celebrated Chianti and Brunello di Montalcino wines. Few things in this world live up to the hype. We're delighted to report that everything you've ever heard about Tuscany is true.
Days 1-2 Explore some of the region's most celebrated towns, including Pienza, famous for pecorino cheese, exquisite ceramics and Renaissance architecture After savoring Tuscan treats, pedal cypress-lined roads through southern Tuscany's open undulating terrain into the Val d'Orcia Montepulciano, with its winding streets and hidden squares, invites a stroll.
Day 3 Climb through a sea of vineyards to the wine village of Montalcino, where enoteche pour samples and remarkable views reach as far as Siena on a clear day Check out Abbazia di Monte Oliveto Maggiore, the region's most notable monastery, where monks still pray in Gregorian chant.
Day 4 Engaging Q&A session with Dario Castagno, author of Too Much Tuscan Sun Bike past the exposed chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Florentine and Sienese paintings Sun-baked pastures dotted with sheep and crumbling stone farmhouses make way for oak woodland and olive groves Explore Siena on your own.
Days 5-6 Pedal rolling hills alongside Chianti Classico and Sangiovese vineyards Get to know ridgetop Radda, the center of Chianti wine production, and Castellina, a medieval village with a unique arcaded passageway Looking for a gift? Family-owned Ceramiche Rampini offers ceramics hand-painted in the Renaissance tradition.
- A quintessential Tuscan experience from south to north
- Sample fine wines before dining on local specialties
- Relax at day's end in cozy historic hotels, all with swimming pools
- Explore some of the region's most celebrated towns, including Pienza, Montalcino, Siena and Radda in Chianti
- Pedal rolling hills past Brunello, Chianti Classico and Sangiovese vineyards
Albergo le Terme (2 nights): This charming family-owned hotel overlooks the town's central piazza, whose ancient pool is fed by underground thermal springs. (pool, spa)
Borgo Casabianca (1 night): An agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (pool, tennis)
Villa Curina Resort (2 nights): A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool, tennis)
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
2015 Dates & Pricing*
- 5/3-8 Price: $3698 pp dbl. occ., (+ $720 for sgl. occ.)
- 5/17-22 Price: $3798 pp dbl. occ., (+ $720 for sgl. occ.)
- 5/31-6/5 Price: $3798 pp dbl. occ., (+ $720 for sgl. occ.)
- 6/7-12 Price: $3698 pp dbl. occ., (+ $720 for sgl. occ.)
- 6/14-19 Price: $3698 pp dbl. occ., (+ $720 for sgl. occ.)
- 6/28-7/3 Price: $3798 pp dbl. occ., (+ $720 for sgl. occ.)
- 7/5-10 Price: $3598 pp dbl. occ., (+ $720 for sgl. occ.)
- 7/12-17 Price: $3598 pp dbl. occ., (+ $720 for sgl. occ.)
- 7/19-24 Price: $3698 pp dbl. occ., (+ $720 for sgl. occ.)
- 8/2-7 Price: $3598 pp dbl. occ., (+ $720 for sgl. occ.)
- 8/30-9/4 Price: $3598 pp dbl. occ., (+ $720 for sgl. occ.)
- 9/1-6 Price: $3598 pp dbl. occ., (+ $720 for sgl. occ.)
- 9/6-11 Price: $3598 pp dbl. occ., (+ $720 for sgl. occ.)
- 9/8-13 Price: $3598 pp dbl. occ., (+ $720 for sgl. occ.)
- 9/13-18 Price: $3698 pp dbl. occ., (+ $720 for sgl. occ.)
- 9/20-25 Price: $3398 pp dbl. occ., (+ $720 for sgl. occ.)
- 9/27-10/2 Price: $3698 pp dbl. occ., (+ $720 for sgl. occ.)
- 9/29-10/4 Price: $3398 pp dbl. occ., (+ $720 for sgl. occ.)
- 10/4-9 Price: $3798 pp dbl. occ., (+ $720 for sgl. occ.)
- 10/6-11 Price: $3698 pp dbl. occ., (+ $720 for sgl. occ.)
- 10/18-23 Price: $3398 pp dbl. occ., (+ $720 for sgl. occ.)
- 5/12-17 Price: $3798 pp dbl. occ., (+ $620 for sgl. occ.)
- 6/9-14 Price: $3798 pp dbl. occ., (+ $620 for sgl. occ.)
- 7/26-31 Price: $3598 pp dbl. occ., (+ $620 for sgl. occ.)
- 10/13-18 Price: $3398 pp dbl. occ., (+ $620 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 $5,598 pp dbl. occ.||8 - 9 guests from $4,198 pp dbl. occ.|
|4 - 5 guests from $4,798 pp dbl. occ.||10 - 11 guests from $3,698 pp dbl. occ.|
|6 - 7 guests from $4,398 pp dbl. occ.||12 or more guests from $3,398 pp dbl. occ.|
All Private Singles-Solos trips require a minimum of 16 guests.
Guest Trip Reviews
I can see how these trips can become addicting. This was the BEST way to experience Tuscany. You are encouraged to be in the moment, focusing only on the road in front of you, the beauty that surrounds you and the food you will indulge in when you reach your destination.- Westport, CT
Magnifico! I can't think of a better way to immerse myself in the Italian culture in the Tuscany region than with Backroads. The scenery, wonderful local towns/bastions, the food (off the charts), gracious people, the great leaders and people on the trip exceeded my expectations once again. We ate like kings (peasants technically), stayed in wonderful accommodations complete with their own great views, sampled the wine like royalty, the pizza and sorbet we gorged on were out of this world, and we biked some of the most beautiful countryside I have traveled. Time will tell where Backroads will lead me next...- Annapolis, MD
This trip changed my life. I am a passionate biker, and this was the best week of my life. I will be a Backroads junky.- Potsdam, NY
This was the best vacation I think I've ever had - it was absolutely wonderful. Our leaders were great. And the setting... Wow. There were times when I wished I had more downtime to relax, but then I remembered that, of course, I had all the time I wanted. I had merely to say the word and I could be whisked off my bike and be back at the hotel pool. The fact is, the scenery was so spectacular and the riding so much fun that I never WANTED to get whisked off my bike. It was a trip of a lifetime. Thank you for everything. I'll never forget it.- Bethlehem, PA
I was worried about the biking as I am not experienced or in shape, but this was PERFETTO! Enough interaction to be fun, but plenty of blissful solitude on the bike as well and no pressure, everyone hopped in the van whenever they wanted.- Skokie, IL
Exceeded my expectations by focusing on the smallest details. Did not go unnoticed. I was 100% satisfied with my experience and would do it again in a heartbeat.- Wellesley, ON
This was my third consecutive Backroads trip and my wife's first Backroads trip and I could not have imagined a better introduction to Backroads. All hotels had great character, were in good locations, comfortable and well decorated. The restaurants and menus chosen by Backroads was the best of three trips I have taken. The menus offered a variety of cuisine with superb quality.- Burlington, ON
This was the best vacation we ever had. We had been to Italy before, and thought we knew it fairly well, but the experience of seeing it on a bike opened an entirely new window... We looked at people touring around in cars and on buses and shook our heads in wonder as to all they were missing. Would absolutely do another one almost anywhere with Backroads. You give new meaning to excellence in customer service and satisfaction!- New York, NY
Even though I was the weakest biker on the trip I felt very positive about my biking because of the support and positive attitude of the trip leaders as well as the group. The Tuscany trip is demanding yet I would do it again and hopefully conquer more of those hills because of the support. I was concerned that this 60+ couple might be making their last trip; not so. I can't wait for the next one... Thank you!- Chevy Chase, MD
We had a wonderful time. Our leaders were knowledgeable and very helpful no matter what the need. It was great to have so many options for cycling routes, and having a pool at every hotel was a huge bonus. Opportunities to shop and sightsee were very welcome and fully utilized.- Calgary, AB
I came into this trip with very high expectations. Usually when that happens, you can only be disappointed. I was not disappointed. Everything, and I do mean everything, was absolutely fantastic. I was enthralled. Everything about this trip was so far above my expectations that I was stunned...the rooms, the biking, the leaders, all of it, just amazing. It was the best trip that I've had in 22 years.- Pleasanton, CA
I was expecting to have a good time on the trip, but I had no idea how much fun I would actually have. Kudos for organizing a trip that exceeded my expectations. The biking was challenging, but not overwhelming, and there was even enough time for a prosciutto out by the pool before dinner.- Arlington, VA
This trip was the trip of a lifetime for me, and the trip leaders made it happen. They made everything work beautifully. With their encouragement, I found that I was in good enough shape for the challenging hills. The accommodations were charming, the countryside was beautiful and the towns were interesting. What more could I ask for? Can't wait for my next Backroads trip.- Chicago, IL
Biking in the beautiful Tuscan countryside was a dream come true. I enjoyed this trip very much and would recommend it to those who are prepared for some challenging biking. As expected, Backroads had attended to all of the details to make this trip a most memorable and enjoyable experience.- Salt Lake City, UT
Going with Backroads took all the stress out of travel, while still allowing us to feel like independent (vs. tour-group) travelers. On our own, we would likely not have seen all the towns we visited, stayed in the lovely inns we stayed in, or enjoyed the wonderful meals we had on this trip. On our own with such a short amount of time, we never would have met and learned from the locals who made this trip so unique. With our first-rate guides and the itinerary, we felt like visitors, not tourists.- Wilmington, DE
I could not have anticipated the trip being as wonderful as it was - it really was a vacation of a lifetime thanks to Backroads. I feel like I made new friends for a lifetime, ate, drank and experienced Tuscany like a local...- Post Washington, NY
The whole experience was even better than I had anticipated! I didn't expect to be treated so well - I gave up all control and let myself be lead by someone else. Such a treat for someone who is always "in charge." We never wanted for anything. The routes were challenging and beautiful. The lodging was lovely. The food was amazing. Our leaders were incredible and the guests were fun. We became a quick family and we were sad when it was over.- Crownsville, MD
Beyond compare! I loved every minute of it. A wonderful experience of Italy and our leaders bent over backwards to make it a smooth one. The food, the leaders, the places we visited - Backroads has a customer for life!- Gig Harbor, WA
We had a fantastic time on our trip! Biking is such a wonderful way to see the country and I love the mix of exercise and being a tourist. I really like the way we are able to '"go behind the scenes" with your connections to meet interesting people and places.- Austin, TX
It was a wonderful trip and I enjoyed every day... The guides were outstanding and became our good friends within the short time we were together. I would do another trip of this kind in a heartbeat! The scenery was spectacular, the food amazing and the accommodations were very special. A perfect combination to make a perfect trip!- Harpswell, ME
This was hands down one of the best trips I've ever taken. I could not believe the attention to detail the leaders and trip designers take to provide the highest quality of everything - food, friendliness, accommodation, hotels, etc. I am already planning my next trip! I don't happen to think the Backroads trips are inexpensive, BUT they are worth every penny when you see where we get to eat, stay and the quality/attention to every last polished detail. Nice work, guys!- Glen Ellyn, IL
I would unhesitatingly recommend Backroads to anyone who asks. Every expectation we had was far surpassed by the actual trip. I found the cycling challenging, but the support was just right - so that I could do as much (or as little) as I wanted to on any given day.- Nashville, TN
Everything - bikes, accommodations, leaders, rides - were beyond my expectations. All wonderful, wonderful, wonderful!- Springfield, OH
It was an amazing trip. This was my first "active" vacation and I loved it. The accommodations, the food, the scenery, and the leaders couldn't have been better.- Wilmington, DE