Trip
Overview
Lodging
Detailed Itinerary
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All meals included except 2 lunches and 1 dinner.
Siena, Italy/Arezzo, Italy
Culture & History, Fine Wine & Cuisine, Natural Beauty &/or Wildlife, Romance &/or Honeymoon
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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 cottages of ancient stone. 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 and Montalcino wines. And throughout, delight in the friendliness of the locals, who enthusiastically share their culture and heritage.
You are viewing the Classic Casual Inns version of this trip.
View the Classic Premiere Inns Itineraries.
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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.
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.
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.
Route Rating What's this? Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. Each offers options for more or less activity, so you can decide exactly how much you want to do day by day.
Lodging What's
this? Our lodgings are divided into three different categories.
Premiere Inns:These lodgings possess both elegance and authentic
regional flair.
Casual Inns:These lodgings are comfortable and appropriate to the
areawith such characteristics as authenticity, scenic settings and
proximity to our activities.
Deluxe Camping:We set up the tents (and take them down), handle every
camp chore and perform culinary magic.
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
For more than 29 years, Backroads has been perfecting the art of active travel. We are the Tuscany tour experts. For biking tours in Europe Italy, trust our in-depth connections. To see all our Europe Italy biking tours click here. For our selection of award-winning Europe Italy walking and hiking tours click here. For our selection of award-winning Europe Italy multisport tours click here.
Rocca d'Orcia (2 nights): A beautifully restored hotel offering stunning views of the Val d'Orcia and an inviting swimming pool.
Città della Pieve (1 night): A restored 18th-century mansion featuring elegantly furnished guest rooms and an outdoor heated swimming pool.
Cortona (2 nights): A stately Renaissance manor house situated in the heart of town.
You are viewing the Classic Casual Inns version of this trip.
View the Classic Premiere Inns Itineraries.
1 Route Option Available
3 Route Options Available
2 Route Options Available
3 Route Options Available
3 Route Options Available
 2 Route Option Available
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 |
||
| 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 |
