Italy - Tuscany


Tuscany is an iconic name, symbolizing the good life - a vacation to enjoy all that is good: food, sun, lifestyle, wine, amusement, and relaxation. The culture of the region adds charm, and you can indulge yourself in this opulent way because you will cycle the famous undulating countryside. This Tuscany cycling tour starts in Pienza, and makes its way to Florence, where along the way you will visit the villages that have made Tuscany famous. You can enjoy very charming 3/4 star accommodations and devour your choice of divine mediterranean cuisine. The hilly terrain makes this tour somewhat challenging!

Itinerary

Click on a day to see that days itinerary.

DAY 1 DAY 2 DAY 3 DAY 4 DAY 5

Day 1 | Arrival Day

We'll meet you at Pienza, the purest Renaissance town in the world (you will arrive by the train to Chiusi-Chianciano station, a major stop on all the Rome-Florence lines). Your charming hotel overlooks the val d'orcia. Pienza is a rare masterpiece: entirely rebuilt between 1459 and 1462, it was the brainstorm of Pope Pius II and today is memorable not only for its architectural purity but also for its exquisite food shops. As you stroll through the pristine streets, you might decide to stock up on truffle-flavoured cheese, wild herbs or other delicacies to take home or to use for an informal dinner with a bottle of Chianti wine. Or maybe you'd rather reward yourself with some ice cream at our favorite gelateria. Dinner on your own.

Relais Il Chiostro

4

Corso Rossellino, 26

Relais Chiostro di Pienza is situated in the heart of Pienza, a Renaissance city planned by Rosselli...

Day 2 | Ride Day

Your tour starts with a circular ride from Pienza. Be sure to stop along the way to visit the remote convent where parts of The English Patient were filmed, and in the enchanting little hamlet of Castelmuzio. By lunchtime you'll come to Montepulciano, the jewel of southern Tuscany. After relaxing a while, return to Pienza with a stop in the village of Monticchiello, the quintessential Tuscan hill town. Overnight at the same hotel; dinner on your own again. Level: Moderate to easy Distance: 50 km. (Breakfast included)

Relais Il Chiostro

4

Corso Rossellino, 26

Relais Chiostro di Pienza is situated in the heart of Pienza, a Renaissance city planned by Rosselli...

Day 3 | Ride Day

Ride from Pienza to Montalcino, with a pause in fairy-tale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe. You can have lunch in Castiglione d'Orcia, then push on to the monastery of Sant'Antimo, where you might catch one of several vesper services performed each day by the monks. The famed wine town of Montalcino is your destination. Visit the fortress to see a breathtaking view of the entire valley you've just biked, then reward yourself with dinner at our favourite wine cellar. Accommodations are at a panoramic three-star hotel. Dinner on your own. Level: Moderate to strenuous. Distance: 46 km. (B)

Hotel Il Giglio

3

Montalcino

A charming retreat in the heart of Montalcino, a family-run Hotel in a warm and quiet building, faci...

Day 4 | Ride Day

Ride from Montalcino to Siena. On the way you'll coast along the forested crest of a ridge, home to the famed Monte Oliveto Maggiore monastery. Stop here to visit the beautiful buildings and perhaps have lunch at the restaurant. Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands. Late afternoon arrival in Siena. You will stay in a historic three-star hotel right in the center of town, or at a garden hotel Santa Caterina. Dinner on your own. Level: Moderate to strenuous Distance: 60 km. (B)

Hotel Il Chiostro del Carmine

4

Siena, Toscana, Italia

Il Chiostro del Carmine is a restored 14th-century monastery, with great views of the countryside. I...

Day 5 | Departure Day

Departure after breakfast, at your leisure. If you want to go on to Florence, we can arrange transportation and hotels. Trains, car rentals can be arranged as well additional stays throughout Italy. (B)



Virtual Tour

See more of this region by clicking below for the virtual tour

Lodging

Lodging on this tour is the same as that found in guided group tours costing $3000 and more!

Cycling in Tuscany is one of the best ways to experience this famously romantic countryside. Traveling from one famous village to another along small country roads, this bicycle tour can be adapted to your needs.

Accommodation: [Virtual Hotel Tour] 4 nights in deluxe hotels: Pienza - Piccolo hotel La valle, Montalcino-Hotel dei capitani, Siena-Hotel Duomo. These properties are all excellent hotels offering views, and charming typical Tuscan ambiance. They are also in demand, so last minute requests can be difficult. In case of no availability; we will check equivalent alternative hotels that may require a change in price.

Bike: [Click for image] Included; Custom hybrid; aluminum frame with carbon fork, Shimano Ultegra or Deore; 3x9. Bikes come equipped with handlebar bag, lock, water bottle, gel saddle, tire repair kit, cycle computer. Hybrids are fitted with thin tires for better road performance. Racing models also available. Hilly terrain, rated as intermediate to advanced. All towns where lodging is located are perched hilltop villages. A Cannondale tandem is also available for experienced tandem riders. Persons from 5 ft to 6-5 can be accommodated. Bike quality is top; averaging $1500 each retail. A reduction is not available for customers who bring their own bikes.

Images from this Tour

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