Who’s to say which is right? Riding off into the Tuscan sunset after an amazing daylong ride, or sipping a Brunello into the sunset in a Cortona café. That’s Tuscany. Mile after mile of vistas, villages, scenery and flavors. How you experience it should be your choice. Less mileage, more time to explore. Bike to your heart’s content, then leave time to smell the sunflowers, marvel at the Renaissance towns, savor the cappuccinos, and sample the region’s delicacies. Take your cues from the pace of countryside life - Tuscany is best enjoyed slowly.
Days 1-2 Well-planned shorter routes on easier terrain
(and a lift always handy) 
An 18th-century villa sets the scene for a picnic lunch of typical Tuscan fare Soak up postcard-perfect views of Val di Chiana In the historic hill town of Cortona, immortalized by Frances Mayes’ Under the Tuscan Sun, behold majestic architecture during a guided walk.
Days 3-4 The iconic hill town of Montepulciano,
with glorious Renaissance buildings Bike past quaint farmhouses en route to the atmospheric fortified village of Castiglione del Lago, set on a promontory on Lake Trasimeno in Umbria A fourth-generation vintner invites us to his family’s cantina for a tasting of the local lifeblood, a wine esteemed through the centuries by the likes of Voltaire and Thomas Jefferson Spin leisurely through a classic southern Tuscan landscape of rolling fields, cypress-lined roads and quiet hamlets.
Days 5-6 Celebrate the relaxed Tuscan way of life
Pedal past vineyards to adored Pienza, one of the region’s architectural gems Sample locally made pecorino cheese, admire exquisite ceramics, wander down medieval streets and gaze over the Val d’Orcia Feel like shifting gears? Opt to hike through forests of oak, broom and cypress above Montefollonico.
Trip Highlights
- Spin on Tuscany’s most gentle byways in the Val di Chiana (the van is always close by for a lift)
- Iconic hill towns of Pienza and Montepulciano
- Savor the relaxed Tuscan way of life thanks to well-planned shorter routes on easier terrain
- A culinary lesson with longtime Backroads friend Viviana
- Sample prized Vino Nobile di Montepulciano
Premiere Inns
Hotel Villa Marsili (1 night): This elegant 14th-century palazzo rests within Cortona’s Etruscan walls and offers outstanding views of the Val di Chiana.
Villa Petrischio (2 nights): Set on a quiet hill, this 18th-century villa is surrounded by hundred-year-old cypress and pine trees and overlooks the Val di Chiana. (pool)
Relais La Chiusa (2 nights): A charming country inn described by Hideaway Report as a "family-run stone manor that looks across to the medieval hill town of Montepulciano."
Daily Mileage Options & Cumulative Elevation Gain
Day 1
- Level 1 2 Route Options Available
- 16, 18 miles
- 90 - 680 feet elevation gain
Day 2
- Levels 1 to 2 2 Route Options Available
- 18, 26 miles
- 500 - 780 feet elevation gain
- Guided Walk 2 hours
Day 3
- Levels 1 to 3 4 Route Options Available
- 14, 17, 27, 37 miles
- 140 - 920 feet elevation gain
Day 4
- Levels 1 to 3 4 Route Options Available
- 11, 15, 23, 35 miles
- 200 - 2460 feet elevation gain
Day 5
- Levels 1 to 4 4 Route Options Available
- 11, 21, 33, 42 miles
- 450 - 2430 feet elevation gain
Day 6
- Level 1 2 Route Options Available
- 7, 13 miles
- 210 - 1100 feet elevation gain
- or Walking 2.4 miles
- 420 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 |
2012 Dates & Pricing*
CLASSIC TRIPS
- 4/29-5/4Price: $4198 pp dbl. occ., (+ $1200 for sgl. occ.)
The trip you have selected is different from the one displayed. Here's how:
Hotel rotation: On Days 2 and 3 we stay at Relais alla Corte del Sole in Petrignano del Lago. - 5/6-11Price: $4198 pp dbl. occ., (+ $1200 for sgl. occ.)
The trip you have selected is different from the one displayed. Here's how:
Hotel rotation: On Days 2 and 3 we stay at Relais alla Corte del Sole in Petrignano del Lago. - 5/13-18Price: $4198 pp dbl. occ., (+ $1200 for sgl. occ.)
The trip you have selected is different from the one displayed. Here's how:
Hotel rotation: On Days 2 and 3 we stay at Relais alla Corte del Sole in Petrignano del Lago. - 5/27-6/1Price: $4198 pp dbl. occ., (+ $1200 for sgl. occ.)
- 6/10-15Price: $3998 pp dbl. occ., (+ $1200 for sgl. occ.)
- 6/24-29Price: $4398 pp dbl. occ., (+ $1200 for sgl. occ.)
- 7/1-6Price: $3998 pp dbl. occ., (+ $1200 for sgl. occ.)
- 7/8-13Price: $3998 pp dbl. occ., (+ $1200 for sgl. occ.)
- 7/22-27Price: $3998 pp dbl. occ., (+ $1200 for sgl. occ.)
- 8/5-10Price: $3998 pp dbl. occ., (+ $1200 for sgl. occ.)
- 8/19-24Price: $3998 pp dbl. occ., (+ $1200 for sgl. occ.)
- 9/2-7Price: $3998 pp dbl. occ., (+ $1200 for sgl. occ.)
- 9/9-14Price: $4198 pp dbl. occ., (+ $1200 for sgl. occ.)
- 9/16-21Price: $3998 pp dbl. occ., (+ $1200 for sgl. occ.)
- 9/23-28Price: $3998 pp dbl. occ., (+ $1200 for sgl. occ.)
- 9/30-10/5Price: $3998 pp dbl. occ., (+ $1200 for sgl. occ.)
- 10/7-12Price: $3998 pp dbl. occ., (+ $1200 for sgl. occ.)
- 10/14-19Price: $4198 pp dbl. occ., (+ $1200 for sgl. occ.)
- 10/21-26Price: $3998 pp dbl. occ., (+ $1200 for sgl. occ.)
SINGLES+SOLOS TRIPS
*Prices may change. Once you book your trip, your price is guaranteed.
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.
Where to begin??? The trip provided a good balance of comfort vs. adventure, organized vs. free time and active group vs. individual down time. The local staff, guides and hosts were all superb. The leaders were each warm, cheerful and highly professional; infinitely capable, flexible and dedicated to the needs of participants; and always demonstrated a positive and encouraging attitude no matter the situation or challenge. I felt like I was in a delightful movie the whole time; I loved every minute and looked forward to each new day/scene.- Raleigh, NC
As for the value relative to the price, what would you pay for a trip of a lifetime and lifelong blissful memories, made possible by the local relationships, trip design, participant preparation and services, and the excellent quality of staff you provide?