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Italy – Tuscany Escape Short Bike Tour

(4 Reviews)

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.

Arrival & Departure Locations

Fly to Rome or Florence (closer) and train to Pienza, for start of tour. Depart from Siena and train to airport of choice.

Price Includes

  • Deluxe lodging in 3 and 4 star hotels; all excellent locations
  • Arrival orientation and bike set up in Pienza
  • Route maps, route cue sheets with GPS notes for navigation
  • Buffet breakfast daily
  • GPS with pre-programmed routes (1 per 2 participants)
  • Daily luggage transfers from hotel to hotel
  • Local emergency support throughout your tour during daylight riding hours
  • Suggestions for visitations, sites, restaurants, monuments
  • All pre and post travel planning services
  • Pre-travel documents sent electronically to help you prepare for your trip
  • Customer incentives & post trip offers

Not Included: Choice of Hybrid, Road or E-bike Rental


Included Standard Hotels: 

  • Pienza: Hotel Piccolo La Valle ***
  • Montalcino: Hotel Dei Capitani ***
  • Siena: Hotel Chiusarelli ***

Upgraded Hotels:

  • Pienza: La Bandita ****
  • Montalcino: Velona Castle ****
  • Siena: Palazzetto Rosso ****

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. 

Optional Add-Ons

  • Private Arrival Transfer Chiusi-Pienza: 85 euros/person
  • Bagno Vignoni Spa: 210 euro/person with massage & return transfer
  • Cooking Class near Pienza: 160 euros/person with min 2; includes meal
  • Siena Guided Walking Tour
  • Florence/Rome add on - special hotel contract rates available for our guests
  • VIP Museum Visits
  • Leather Workshop in Florence: 60 or 80 euros per person
  • Travel Insurance

Guides & Local Support

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.  

Tour Highlights
  • Cycle through Tuscan vineyards & UNESCO rated hills & countryside
  • Enjoy icon, historic towns of Pienza, Montalcino and Siena
  • Ride quiet roads for peaceful riding and amazing vistas 
  • Stop at Bagno Vignoni, where you find the Roman thermal baths and modern spa 
  • Visit Castiglione d’Orcia and the Sant’Antimo monastery
  • Culinary delights along the way: wines and olive oils in every town, traditional dishes throughout
  • GPS driven navigation makes route finding easy; new Garmin Touring devices 

Need to Know: 

  • Road or hybrid bikes available; distances relatively short, all routes paved.
  • Some busier connector roads are used between the small back country roads.
  • Be prepared to ride some Tuscan hills throughout each day.
  • Groups of more than 2 have a bike delivery supplement.
  • Not available July 16-August 31; BEST time to visit is May/June or October/November



Day 1Arrival Day - Pienza

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.

Day 2Loop tour around Pienza: 33 or 51 km / 21 or 32 mi

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.

Meals: breakfast
Distance: Option 1: 33 km +476 m elev gain; Option 2: 51 km +1160 m
Highlights: Bagno Vignoni & baths, Montepulciano & wine, cooking class
Overnight: Pienza

Day 3Ride from Pienza to Montalcino: 31 km / 19 mi

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!

Meals: breakfast
Distance: 31 km +628 m
Highlights: Montalcino, Castiglione d’Orcia, Sant’Antimo monastery, Brunello
Overnight: Montalcino

Day 4Ride from Montalcino to Siena: 56 km / 35 mi

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!

Meals: breakfast
Distance: 56 km +895 m
Highlights: UNESCO countryside, Siena sightseeing
Overnight: Siena

Day 5Departure day

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.

Meals: breakfast


Tour Rates: (based on double occupancy)

Superior Three & Four Star Hotels:

  • 2 persons:  965 euros/person
  • 4 persons:  935 euros/person
  • 6 persons:  895 euros/person
  • Single Supplement:  163 Euros/person (applies when 2 or more traveling but in separate single use rooms)
  • Solo Supplement:  ask us for rates

Upgraded Four+ Star Hotels:

  • 2 persons:  1720 euros/person 
  • 4 persons:  1678 euros/person
  • 6 persons:  1620 euros/person
  • Single Supplement:  TBD (applies when 2 or more traveling but in separate single use rooms)
  • Solo Supplement:  ask us for rates

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!

How do our tours compare to similar trips? You Get MoreIf you compare price, we are much less than guided trips with similar experiences. In our private, independent format, you get much more than what most traditional self guided tours offer, plus it’s a better experience! Our team has gone to great lengths to build and create exceptional tours all over the world, vacations that will give you lifelong memories. From the accommodations to the bikes, to the routes themselves, we hold each component of our tours to a very high standard. We are dedicated to empowering people through travel!
Ready to book? Our well-traveled, knowledgeable and dedicated team is standing by and eager to make your travel dreams come true. Call now at 800-960-2221 (USA/Canada 8 am-5 pm MST) +1.480.905.1235; or email us.   
4 Reviews
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Jim Tomassetti

Couple Traveller

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.

October 10, 2018

Emily Roach

Couple Traveller

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.

October 3, 2018

Rob Campbell

Couple Traveller

Enrico was our local Pure Adventures guide, and was early, and very thorough on all facets of the Tuscany Wine & History tour.

October 7, 2017

Julieta Patricia Lyall

Group Traveller

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.

May 26, 2017