Southern Tuscany Biking
This trip is currently only available as a Private Trip. Looking for a similar trip? See Tuscany Biking, Tuscany Easy Biking, Piedmont Biking, Puglia Biking, and Italy/Slovenia Biking. Or call 800-462-2848 to speak with a Trip Consultant.
The extraordinary beauty of everyday life in southern Tuscany never fails to delight visitors. Pedal between villages so intimate you experience the sounds and aromas of pranzo (the midday meal) as it's being prepared inside ancient stone cottages. Spin through rolling vineyards, past undulating wheat fields and over chalky white hills. Discover Renaissance architecture in the hill towns of Pienza and Cortona. Savor pecorino cheese, homemade pasta, fruity olive oils and celebrated Brunello di Montalcino wines. And throughout, delight in the friendliness of locals, who enthusiastically share their culture and heritage.
Days 1-2 rocca d'orcia
Meet in Siena 
Visit Montalcino's Sant'Antimo Abbey, a notable example of Romanesque architecture Warm up with a ride into the Val d'Orcia and the Brunello wine region Pedal to the southern Tuscan town of Pienza, one of the area's architectural centerpieces Discover hidden squares, Renaissance palaces and churches in Montepulciano, the highest Tuscan hill town Sample Brunello vintages with a local expert Spin past exposed chalk hills known as biancane, a distinctive part of the southern Tuscan landscape.
Day 3 Citta della Pieve
Enjoy a picnic lunch in the medieval hamlet of Celle sul Rigo Dip into the neighboring region of Umbria and explore the small town of Città della Pieve, renowned for its art and architecture.
Days 4-6 cortona
Head across the rolling hills of the Chiana Valley to Cortona, a postcard-perfect hilltop village Sample one of Tuscany's most famous dishes, bistecca alla Fiorentina (steak grilled rare over charcoal, lightly salted with olive oil drizzled over the top) Ride through the pastoral landscape of the hills and valleys east of Cortona or enjoy a guided walking tour of town.
TUSCAN TASTE: Casual Inns
Hotel San Simeone (2 nights): A beautifully restored hotel offering stunning views of the Val d'Orcia and an inviting swimming pool.
Logge del Perugino (1 night): A restored 18th-century mansion featuring elegantly furnished guest rooms and an outdoor heated swimming pool.
Hotel San Michele (2 nights): A stately Renaissance manor house situated in the heart of town.
Daily Mileage Options & Cumulative Elevation Gain
Day 1
- Level 1 2 Route Options Available
- 10, 20 miles
- 1000 - 3000 feet elevation gain
Day 2
- Levels 3 to 4 3 Route Options Available
- 37, 40, 50 miles
- 1500 - 3000 feet elevation gain
Day 3
- Levels 2 to 4 2 Route Options Available
- 30, 41 miles
- 2000 - 3000 feet elevation gain
Day 4
- Levels 1 to 4 3 Route Options Available
- 19, 35, 48 miles
- 500 - 1500 feet elevation gain
Day 5
- Levels 3 to 5 3 Route Options Available
- 35, 49, 64 miles
- 2000 - 3500 feet elevation gain
Day 6
- Level 1 2 Route Option Available
- 17 miles
- 0 - 500 feet elevation gain
- Walking Tour 1.5 hours
- 0 - 500 feet elevation gain
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 | Average Distance | |
|---|---|---|---|
| Biking | Walking & Hiking | ||
| 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 |
Reserve early for the best available price. Prices may change during the course of the year--if they do change, the best prices are available earlier. Once you book your trip, your price is guaranteed.
Guest Trip Reviews
The combination of activity and culture made it the best trip of my life! With Backroads' itinerary and support, I was able to completely enjoy the experience without one hassle.- Truckee, CA
The cycling was terrific. The scenery was beautiful. It felt like we were in a Tuscan landscape painting. We traveled as a family of 4 and created wonderful lifetime family memories.- Ann Arbor, MI
Wonderful area, well thought out route, fantastic cycling. Very authentic accommodations and great places to eat.- Aspen, CO
This was my 3rd biking adventure through Tuscany and I must say that this particular trip was outstanding. I had traveled with other premiere groups but had heard so much about Backroads that I wanted to experience Backroads for myself! (I'm already surfing your site for my next adventure!) I selected this particular trip because it took me back to some of my favorite places like Pienza & Montepulciano, as well as into new terrain, such as Cortona & parts of Umbria. Having travled through Tuscany a bit, I felt that this trip gave the best portrayal of the varying landscapes. The food offered a good taste of what the region has to offer. The picnics by our guides were especially a treat! Anna & Olivia were super guides - off the charts! The hotels - quite charming. The guest speakers - entertaining & knowledgeable. I had a few teary-eyed moments at the end of each day as I reflected on how lucky I was to be in beautiful Tuscany, sharing fabulous food & spectacular views with such a great group of people!- Atlanta, GA
Cycling was an excellent way to experience the Tuscany region. Exercise heightened my sensory experience with the scenery, culture, flavors and wonderfully gracious tour leaders. It was a truly decadent week. The leaders did an outstanding job of providing that individual touch that made everyone feel special and left no one out. This was group travel at its best.- Portland, OR
Amazing, incredible and spectacular. These are the adjectives to describe my Southern Tuscany experience. Our guides were flawless---organized, fun, informed, spirited, and simply outstanding. They made the trip flow with ease. I can't imagine how much behind the scenes work and coordination they put in but it was phenomenal. The integration of culture and cuisine into the trip was excellent.- Milwaukee, WI
After visiting Southern Tuscany in Iris Origo's novel, "War in the Val d'Orcia", you'll certainly feel compelled to discover the beauty of this area in person. The tranquil landscape combined with the rich history makes for a very enlightening journey and our local guide Giovanni shares information about his hometown, Cortona, that is certain to bring a deeper appreciation and understanding of that bustling, art-filled town.- Regional Manager, Italian Trip Operations
I will say that my husband and I were so happy to arrive at Hotel San Simeone on Day One -the view is the perfect ending to the first day of biking, and the pool is gorgeous.- Maplewood, NJ
Once again Backroads exceeded my expectations. I don't think we'll ever take another trip that's NOT Backroads. Summit, NJ
Funny thing is that I didn't want to go on the trip because I travel every single week for work and my wife set it up as a surprise. This was the best vacation I have ever had and it was nearly all due to the staff and organization of the bike portion of our trip. What more can I say?- Midlothian, VA