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When referring to “Old-World” Italy, people are most likely referring to Tuscany, an area rife with wine, art, and culture. With Pure Adventures Tours, the adventurous bicyclist can enjoy the iconic name that has come to symbolize the good life in Italy. Start in sunny Pienza, admiring the many cathedrals and rustic charm of the town. Then, the bicycle tour moves to Sienna — the surrounding area of which is what made Tuscany famous for its villages. Pure Adventures Tours takes care of your food, lodging, and bicycling routes, providing our bicyclists with a relaxing cycling vacation. On this self-guided tour through Tuscany, the only thing you have to do is explore the hilly, Mediterranean countryside from the back of your bike.
Fly to Rome or Florence (closer) and train to Pienza, for start of tour. Depart from Siena and train to airport of choice.
Not Included: Choice of Hybrid, Road or E-bike Rental
Included Standard Hotels:
Note: Most hotels collect a small city tax at checkout of 1-3 euros/person/day, not included in rate.
About: Hotels are deluxe 3 & 4-star hotels in convenient locations. All lodging includes private bathroom and a variety of other amenities.
Local Experts: When you arrive in Pienza at your hotel you will shortly after have an orientation with one of our local support staff. You will get your bicycles and cover the details of the roadbook and day by day navigation during the orientation. Our local colleagues are experts on the sites and will offer ‘local’ expertise to enhance your trip experience. During your tour you will have telephone assistance available to you in English as well to our main office in Italy. Daniele is a good companion of adventure, he lives in Trevi and knows very well Umbria and Tuscany region.
Need to Know:
Welcome to Pienza, widely considered 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 indeed, a rare masterpiece: entirely rebuilt between 1459 and 1462, it was the creation 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-flavored cheese, wild herbs or other delicacies to take home. Or, you may wish to enjoy with a bottle of Chianti wine during your travels! Or perhaps you’d rather reward yourself with some ice cream at our favorite gelateria? Back in Pienza, we highly recommend our favorite local restaurant, where you can enjoy homemade ‘pici’ – a special Tuscan pasta. Delicious! 5PM orientation at the hotel.
Enjoy breakfast at the hotel on your own, when you want. For your rides today, you have a choice of two: the first is an easier ride to the small village of Bagno Vignoni, where you find the Roman baths and modern spa facilities. You may like to just enjoy the relaxing bath at the spa and come back by a private shuttle (not included, supplement 215 euros for 6 hours access, 50 min massage, thermal pools, hydromassage pool, Roman sauna, spa kit with robe, slippers) or just ride back to Pienza. The second option will take you to one of the most famous places of Italy: Montepulciano. This town is recognized worldwide because its wine and because is just one of the nicest villages of the region. The rolling road to Montepulciano and back is an enjoyable one, with some steep climbs that will allow you to have larger views on the Tuscany countryside. Don’t miss a glass of the good Montepulciano wine. Salute! Optional private transfer back to Pienza is available on request for this option as well to enjoy wine in Montepulciano and skip the hills on return – 30 euros/person.
Another option today is a cooking class: Traditional Italian Farm to Table Cooking class: You will tour the local farm with our chef/guide and learn how produce and dairy are produced in the region. Using farm raised produce and ingredients, you will learn how to make traditional wood fired pizza and breads. Be sure to come hungry. Once your creation is complete, you will be able to eat the delicious food you have prepared.
Distance: Option 1: 33 km +476 m elev gain; Option 2: 51 km +1160 m
Highlights: Bagno Vignoni & baths, Montepulciano & wine, cooking class
Ride from Pienza to Montalcino, with an option to visit again Bagno Vignoni. Continue on to Castiglione d’Orcia, then pass the monastery of Sant’Antimo, where you will want to stop and enjoy a short visit and some shade. The famed wine town of Montalcino is not far now and you can begin to think about Brunello, one of the famous wines from Montalcino! Visit the fortress to see a breathtaking view of the entire valley you’ve just biked, then reward yourself with a delicious dinner of local delicacies!
Distance: 31 km +628 m
Highlights: Montalcino, Castiglione d’Orcia, Sant’Antimo monastery, Brunello
Today you ride from Montalcino to Siena. Enjoy the breathtakingly scenic ride along the UNESCO countryside, included on the list just because of the province’s beautiful valleys and hills. Siena is well known for its lovely central square – the Piazza del Campo, which is crowned with the Mangia Tower. This is the gathering place for Siena and is the site for the Palio horse race that takes place twice a year; once in July and once in August. Siena has several beautiful churches including the Siena Cathedral, a Romanesque-Gothic duomo built in the 12th and 13th Centuries. Lodging is in a small neighborhood guest house, perfectly located in central Siena. Today is moderate to strenuous; you will earn your wine and a delicious dinner tonight!
Distance: 56 km +895 m
Highlights: UNESCO countryside, Siena sightseeing
Today is your departure day. Take your time in the morning if you wish and enjoy breakfast at your leisure. Transportation to Florence is available, ask for assistance. Added hotel nights in Florence are possible or other onward travel services, please inquire.
Tour Rates: (based on double occupancy)
Superior Three & Four Star Hotels:
Upgraded Four+ Star Hotels:
Hybrid Bike Rental: 108 euros
Road Bike Rental: 162 euros; recommended
E-bike Rental: 174 euros
Bike Rental Details Page
Make it Custom: Do you like this tour but want to make it different? Tell us your wishes & we will quote it!
The tour was really good. We enjoyed it and had a great time. The instruction and set up of the bikes was excellent. The bikes Trek Emonda S5 bikes were good. The compact gearing was good for the terrain (50/34 & 11/28). The bikes should be outfitted with 2 water cages. One bike had 1 water cage and one bike had 2 water cages in our case. The accommodations were outstanding throughout the tour. All the hotels were in really great locations in the towns with excellent views. The towns we visited were outstanding (Pienza, Montepulciano, Montalcino, Siena, San Gimignano, Voltera). The luggage pick-up and delivery was good. Only 2 days did we arrive before the luggage. One of these days was a short riding day and one day the car with the luggage had broke down. Still the luggage arrived in a timely manor. The only suggestion would be to have options of longer rides on the short days. Perhaps on the 19 mile (31 km) and 17 mile (27 km) days should have an option to lengthen the rides to 30 miles (48 km). The optional route on the day off should have a shorter option than 40 miles (65 Km). I enjoyed the self guided tour. With the use of the Garmins we had turn by turn instructions and navigation was easy. Only in Siena did we have problems finding the hotel. And this was only after we arrived in town. With the self guided tour we could start when we wanted and set our own pace which was quite nice.I would highly recommend this tour and tour style (self guided) to other people.
My husband and I knew we wanted to bike in Italy, but it was hard to choose which company to use. We chose Pure adventures based on the destinations and cost and were extremely satisfied. Communication leading up to the trip was thorough and prompt. The bikes were perfectly sized to our needs and in near new condition. We had an amazing time biking through the Tuscany countryside while winding up and down roads leading into each town. Each afternoon we were welcomed at nice hotels and enjoyed an afternoon or evening of wandering throughout each city. Overall it was a highlight of our trip to Italy we will always remember.
Enrico was our local Pure Adventures guide, and was early, and very thorough on all facets of the Tuscany Wine & History tour.
The transportation was great we had some really fun nice men. They always loaded our bags safely and made sure that our fragile items were well taken care of. The men took great care of my computor and wine. Some things were too hard for us to manage, as a group of 60 year old woman, like learning the GPS and managing glare on the screen. I’d like to say thank you to Melanie who put the trip together she was such a great glue to us having the good times we did have. I would perhaps take another Pure Adventures trip in the future. Maybe in the states.