Tuscany Easy Biking
Sweeping vistas and gently rolling hills of the Val di Chiana greet you south of Siena - the land of celebrated Sangiovese vineyards and villages rich with Renaissance architecture. On this biking trip, we’ve taken our cue from the pace of Italian country life and designed an itinerary that encourages you to stop and smell the cappuccino. Pedal past springtime poppies or autumn’s golden vineyards, then tackle the hills and be rewarded with gorgeous views. When you're ready to relax, let us shuttle you to such picture-perfect towns as Montepulciano, Pienza and Cortona for afternoons of leisurely exploration.
Day 1 cortona
Meet in Arezzo 
Savor a picnic lunch of typical Tuscan fare at an 18th-century villa Pedal the level terrain of the Val di Chiana, then climb to Cortona Enjoy postcard-perfect views of the valley from this historic hill town, immortalized by Frances Mayes in her novel Under the Tuscan Sun.
Days 2-3 petrignano del lago
Marvel at Cortona’s majestic architecture during a walking tour with a local guide Let your wheels do the work on a downhill ride to the valley floor, followed by a leisurely spin through a classic southern Tuscan landscape of rolling fields, cypress-lined roads and quiet hamlets Bike to the atmospheric fortified town of Castiglione del Lago, set on a promontory on Lake Trasimeno in Umbria Learn the secrets of Tuscan cooking from a local expert.
Days 4-6 montefollonico
No visit to southern Tuscany would be complete without seeing Montepulciano, the highest of the hill towns, filled with glorious Renaissance buildings A fourth-generation vintner invites us to his family’s cantina for a tasting of Vino Nobile Ride to historic Pienza with expansive views of the Val d’Orcia Sample locally made pecorino cheese, admire exquisite ceramics and wander down medieval streets Hike in forests of oak, broom and cypress above Montefollonico.
TIMELESS BEAUTY: Premiere Inns
Villa Marsili (1 night): This elegant 14th-century palazzo rests within Cortona’s Etruscan walls and offers outstanding views of the Val di Chiana.
Relais Alla Corte del Sole (2 nights): At this beautiful 16th-century estate, you’ll find uniquely decorated guest rooms graced with rich fabrics, antiques, wood-beam ceilings and brick floors.
Relais La Chiusa (2 nights): An old stone farmhouse and olive oil mill converted into a charming country inn with an acclaimed restaurant featuring fresh homemade cuisine.
Daily Mileage Options & Cumulative Elevation Gain
Day 1
- Level 1 2 Route Options Available
- 16, 18 miles
- 0 - 700 feet elevation gain
Day 2
- Levels 1 to 2 3 Route Options Available
- 12, 28 miles
- 0 - 800 feet elevation gain
- Walking Tour of Cortona 1.5 hours
Day 3
- Levels 1 to 3 2 Route Options Available
- 19, 34 miles
- 500 - 1000 feet elevation gain
Day 4
- Level 1 3 Route Options Available
- 9, 17, 20 miles
- 500 - 2000 feet elevation gain
Day 5
- Levels 1 to 2 2 Route Options Available
- 11, 21 miles
- 500 - 2000 feet elevation gain
Day 6
- Level 1 3 Route Options Available
- Biking 7, 13 miles
- 0 - 1000 feet elevation gain
- Walking 2.4 miles
- 500 feet elevation gain
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.
| Activity Level | Average Time | Biking Average | Walking Average |
|---|---|---|---|
| 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
- 5/16-21Price: $4298 pp dbl. occ., (+ $800 for sgl. occ.)
- 6/27-7/2Price: $4298 pp dbl. occ., (+ $800 for sgl. occ.)
- 7/25-30Price: $3998 pp dbl. occ., (+ $800 for sgl. occ.)
- 8/22-27Price: $3998 pp dbl. occ., (+ $800 for sgl. occ.)
- 9/5-10Price: $4298 pp dbl. occ., (+ $800 for sgl. occ.)
- 9/19-24Price: $4298 pp dbl. occ., (+ $800 for sgl. occ.)
- 10/10-15Price: $4198 pp dbl. occ., (+ $800 for sgl. occ.)
- 10/17-22Price: $3998 pp dbl. occ., (+ $800 for sgl. occ.)
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Late-fall savings of $600 per person; mention code PC02 when booking.
Guest Trip Reviews
For us it was a truly amazing and educational experience. Loved the physical challenge, loved the cultural interactions and loved the way that the Backroads team made it appear effortless and that we were the only riders on the road, the only customers at the hotels and restaurants. A joy, every minute of it.
This trip was wonderful! Our leaders were fabulous, the cycling was just challenging enough. The hotels were very comfortable, and the service was excellent. And the countryside was so incredibly beautiful - the food, the people - something I will remember for a very long time.- San Marcos, CA
The leaders, the varied activities, the van support, the collective personality of the group made this my most special Backroads trip.- Phoenix, AZ
Absolutely the best trip that I have ever been on and quite possibly the best week of my life. It was really a great experience.- Wayzata, MN
This was an incredible experience. The combination of cycling, food, wine and scenery made this one of our best vacations ever. The guides were all outstanding.- Matthews, NC
One of the very best trips my wife and I have ever taken. I would highly recommend it to anyone who wants to see the Tuscany region in a wonderful active way.- Fort Collins, CO
I had the most amazing vacation. Everything was perfect. The leaders were fantastic.