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Tuscany Biking

Tuscany Biking

Tuscany's vibrant, colorful landscape is a magical place for bicycling. In spring, fields are aflame with red poppies, and come fall, the air is rich with scents of thyme, rosemary and fennel. Tomatoes hang heavy in gardens and vineyards burst with purple grapes. Join Backroads and bike the same hills that draw local cyclists, explore medieval villages that have seen their share of war and peace, and enjoy the cultural and culinary wealth that northern and southern Tuscany have to offer. Savor pecorino cheese, homemade pasta, fruity olive oils and celebrated Chianti and Brunello di Montalcino wines. Discover the region’s irresistible combination of natural beauty, Renaissance art and architecture, and friendly people.

Days 1-2 Castiglione d'Orcia

Meet in Florence Enjoy a picnic of Tuscan treats at an organic farm that produces olive oil, butter, salami and prosciutto  From the flanks of Mount Amiata, warm up your legs on a rolling route through the countryside Get to know southern Tuscany en route to the Roman thermal baths in Bagno Vignoni  Wander around Montepulciano, chock-full of hidden squares, Renaissance palaces and ornate churches  Stop at an enoteca to experience the region's claim to fame, Vino Nobile di Montepulciano  In Pienza, sample delicious pecorino (sheep’s milk) cheese.

Day 3 Castelnuovo Berardenga

Today’s route takes you from the open, undulating hills of southern Tuscany to the wooded, olive tree-lined roads of the north  In Montalcino, climb the tower of San Martino for panoramic views of the Val d’Orcia including, on a clear day, Siena  Indulge in a picnic feast beneath the arches of the Monte Oliveto Maggiore abbey.

Days 4-6 San Leonino

Pedal through some of Chianti’s most beloved towns, such as Gaiole, Radda and Castellina Author Dario Castagno joins us for an engaging Q & A session  Explore Siena on your own  Spin past Sangiovese vineyards to Greve, where you can sample local wines or sip a cappuccino in the lively piazza  Shuttle to Florence.

big map

MEDIEVAL MODERNITY: Casual Inns

Osteria dell'Orcia (2 nights): Set in the Tuscan countryside, this post station from the 1600s has been lovingly restored into a beautiful four-star hotel.

Villa Curina Resort (1 night): A restored 16th-century villa, this resort features traditional and modern furnishings, a large swimming pool, a solarium and tennis court.

Belvedere di San Leonino (2 nights): Surrounded by vineyards and cypress trees, this hotel offers rustic Tuscan-style furnishings, a beautiful garden and panoramic views of Siena.

Daily Mileage Options & Cumulative Elevation Gain

Day 1
Day 2
Day 3
Day 4
Day 5
Day 6
Trips 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.

Activity Level Average Time Biking Average Walking Average
Insider Trips
Explore at a leisurely pace—on village walks, market strolls, art history excursions, hands-on cooking classes and more.
Level 1 2-3 hours 10-20 mile 2-5 miles
Level 2 2-4 hours 21-30 miles 5-7 miles
Level 3 3-5 hours 31-40 miles 7-9 miles
Level 4 4-6 hours 41-55 miles 9-11 miles
Level 5 5-7+ hours 56-75+ miles 11-13+ miles
2010 DATES
CLASSIC TRIPS

Guest Trip Reviews

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...
Jeff Dalton - Annapolis, MD

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.
Jim Gerlacki - Bethlehem, PA

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.
Glenn Cockfield - Burlington, ON

This is my second Backroads trip and I absolutely loved it. It’s such a wonderful experience in multiple regards. I love the idea of meeting new people who become your best friends and I’m already quite sad having left them. It was a completely carefree trip - the very definition of a vacation. I’ll definitely be back for a third trip sometime soon.
Joey Bortfeld - New York NY

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. The experience is physically challenging but intimate in terms of really imbibing the culture. 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!
Jeffrey Gracer - New York, NY

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.
Terry Reed - Potsdam, NY

Even though I was the weakest biker on the trip I felt very positive about my biking because of the support and posiitve 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, which is a tribute to Kat and Krista and to the group in general. Thank you!
French McConnaughey - 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 sight see were very welcome and fully utilized.
Susan Buchanan - Calgary, AB

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.
Janene Gull - Salt Lake City, UT

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.
Stephanie Marks - 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.
Joni Andrioff - Chicago, IL

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.
Kate Morris - Wilmington, DE

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.
Heather Craig - 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, eat, drank and experienced Tuscany like a local . . .
Lisa Lanzkowsky - Post Washington, NY

We took this as a family of four (adult children) and had an outstanding vacation! We loved the region, the biking terrain, the inns we stayed in, the group mix, and especially the leaders! We couldn't have asked for anything better—just sorry it's over! LOVED the Casual Inn trip option.
Pauline Jeffers—Milwaukee, WI

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!
Linda Shiraiwa—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.
Cindy Nelson - Austin, TX

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.
Connally Penley - Nashville, TN