Pure Adventures - vacations and travel

Italy - Tuscany Bicycling Tour 4 nights

Italy, Europe

from €995* per person 5 Days March-November
Boutique accommodations Exertion level: 4
Operator: Pure Adventures 24 people max
  • Pienza, italy
  • Active & Adventure trips
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!

Locations visited/nearby

Italy, Europe

0 testimonials about this trip.

3 testimonials about the provider, Pure Adventures:

  • Reviewer:
    'The trip was great! I lived in France for 5 years and took many great trips around Europe, but this may well have been the most memorable!'
  • Reviewer:
    The trip exceeded my expectations in just about every way. It was awesome and challenging to be alone on a bike in a foreign country. I would recommend it to anyone with a sense of adventure who is in good health.
  • Reviewer: located in CO USA
    Costa Brava Explorer - This is a WONDERFUL tour.  Bo was amazing and helpful, as were his directions and additional information in the hand-outs of things to see and recommended stops and restaurants.  I will recommend Pure Adventures to my bicyclist friends, and will certainly return to you for our next European bicycle adventure!

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Special information

  • This is a custom departure, meaning this trip is offered on dates that you arrange privately with the provider. Additionally, you need to form your own private group for this trip. The itinerary and price here is just a sample. Contact the provider for detailed pricing, minimum group size, and scheduling information. For most providers, the larger the group you are traveling with, the lower the per-person cost will be.
  • Self-guided (includes hotels, maps, luggage transfer, etc but no guide).


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.

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)

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)

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 four-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)

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)

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