Up to $600
late-fall savings
on added departure 10/17.
Roll over date
for details.
more info
Tuscany Easy Biking
South of Siena
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.
- Spin on Tuscany’s most gentle byways in the Val di Chiana (the van is always close by for a lift)
- 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
- Iconic hill towns of Pienza and Montepulciano
The Day-to-Day Itinerary
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.
- Premiere Inns: These lodgings possess both elegance and authentic regional flair.
- Casual Inns: These lodgings are comfortable and appropriate to the area with such characteristics as authenticity, scenic settings and proximity to our activities.
- Deluxe Family Camping: We set up the tents (and take them down), handle every camp chore and perform culinary magic.
Other Trips You Might Like:
Loire Valley Biking Turkey Biking Tuscany WalkingOther Italy Trips
Look at what other guests are saying about this trip!
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.More about this Trip All Guest Reviews
For 30 years, Backroads has been perfecting the art of active travel. We are the tour experts. For biking tours in , trust our in-depth connections. To see all our biking tours click here. For our selection of award-winning walking and hiking tours click here. For our selection of award-winning multisport tours click here.
Tuscany Easy Biking
TIMELESS BEAUTY: Premiere Inns*
Villa Marsili
Cortona (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
Petrignano del Lago (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
Montefollonico (2 nights) An old stone farmhouse and olive oil mill converted into a charming country inn with an acclaimed restaurant featuring fresh homemade cuisine.
* Casual Inn
Tuscany Easy Biking
Daily Mileage Options & Cumulative 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 |
|---|---|---|---|
| 1 | 2-3 hours | 10-20 miles | 2-5 miles |
| 2 | 2-4 hours | 21-30 miles | 5-7 miles |
| 3 | 3-5 hours | 31-40 miles | 7-9 miles |
| 4 | 4-6 hours | 41-55 miles | 9-11 miles |
| 5 | 5-7+ hours | 56-75+ miles | 11-13+ miles |
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