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  • Tuscany
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International calls:

(001) 970-230-5896

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Italy – Tuscany Escape Short Bike Tour

(13 Reviews)

Deluxe Tuscany self-guided bike tour: Discover one of the most iconic regions in Europe: Tuscany! An area rife with wine, art, and culture, the adventurous bicyclist can explore the place that truly symbolizes “the good life” in Italy! Start in sunny Pienza, and admire the many cathedrals and rustic charm of the town. Then, the bicycle tour moves to Sienna – the surrounding area which is what made Tuscany famous for its villages. Pure Adventures Tours takes care of you with deluxe, boutique lodging, local intel, and carefully selected bicycling routes, providing our bicyclists with a relaxing cycling vacation. On this deluxe self-guided tour through Tuscany, the only thing you have to do is explore the hilly, Mediterranean countryside from the back of your bike. E-bikes available! Have more time? Ask about extending with our gorgeous rides from Siena to Greve in Chianti and/or San Gimignano! 

Pro-tip: Book early! Lodging in Tuscany is in high demand, and the boutique hotels along our tour route book up many months in advance. June and September are especially popular. We recommend booking 4-6+ months before your desired travel date.

Get your adventure!   
1. Call or email with questions: +1-970-230-5896 or email us. 
2. Book the trip, pay a deposit, and get excited about your adventure!
Book This Tour

Arrival & Departure Locations

Fly to Rome or Florence (closer). Train to Chiusi-Chianciano and taxi to Pienza for the start of your tour. Departure is from Siena, where you can easily take the train to any airport or other towns.

Price Includes

  • Travel on a date that fits your schedule; no fixed departure dates!
  • Deluxe lodging in 3 or 4-star hotels; all authentic feeling and in excellent locations
  • Private, personalized welcome orientation and bike set up in Pienza
  • Delicous & nourishing buffet breakfast daily
  • Daily luggage transfers from hotel to hotel
  • Local emergency support throughout your tour during daylight riding hours
  • GPX tour files and maps provided in Ride With GPS
  • Digital tour packet with maps, suggestions for visitation, and site information

Not Included: 

Lodging

Deluxe Hotels – Standard Offer: 

  • Pienza: Hotel Corsignano **** (2 nights)
  • Montalcino: Hotel Dei Capitani *** (1 night)
  • Siena: Hotel Santa Caterina *** (1 night)

Deluxe Hotels – Upgraded Offer:

  • Pienza: La Bandita Townhouse Hotel, Superior Room (2 nights)
  • Montalcino: Castello di Velona *****, Deluxe Room (1 night)
  • Siena: Palazetto Rosso ****, Jr. Suite (1 night)

About: All lodging includes a private bathroom and a variety of other amenities. Most hotels collect a small city tax at checkout of 1-3 euros/person/day, not included in the rate. Those staying at Castello di Velona have the option to visit Abbey of Sant’Antimo, due to its proximity to the hotel.  All lodging is subject to availability.

Optional Add-Ons

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
  • Experience Tuscany in a unique way: with a private, self-guided bike tour!
  • Travel on a date that fits your schedule; no fixed departure dates!
  • Cycle through Tuscan vineyards & UNESCO rated hills & countryside
  • Enjoy the iconic, historic towns of Pienza, Montalcino, and Siena
  • Option to visit Bagno Vignoni, where you find the Roman baths and modern spa facilities
  • Ride quiet roads for peaceful riding and amazing vistas 
  • Culinary delights along the way: wines and olive oils in every town, traditional dishes throughout
  • GPS-driven navigation makes route finding easy; Ride With GPS event included.

Need to Know: 

  • All routes are paved and safe; some busier connector roads are used between the small backcountry roads.
  • Be prepared to ride some Tuscan hills throughout each day.
  • The best time to visit is May/June or October/November.
  • Not recommended July 16-August 31 due to heat and higher hotel rates.
  • Your tour’s Welcome Orientation is on Day 1 of your tour at 5:00 PM at your hotel.
  • Travel Insurance is required on all Pure Adventures tours.

 

Photos
Itinerary-Short Tuscany Self Guided Bike Tour

Day 1Arrival in Pienza & 5:00 PM Orientation

5PM orientation at the hotel!
Welcome to Pienza, widely considered the purest Renaissance town in the world. You can arrive by the train to Chiusi-Chianciano station, a major stop on all the Rome-Florence lines. From there, you can taxi to your hotel. 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!

Overnight: Pienza

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, a region steeped in history and wine. First make your way to Castiglione d’Orcia, a small village set in the Val d’Orcia. Castiglione d’Orcia is designated a World Heritage Site by UNESCO due to its iconic rolling hills, ravines and cypress trees. 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 or Extend!

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. Please let us know in advance if you would like to book additional nights in the area, or if you would like to add on another Pure Adventures tour!

Pro Tip: Extension options include gorgeous rides from Siena to Greve in Chianti and/or Siena to San Gimignano – please inquire!

Meals: breakfast

Map - Tuscany Self Guided Bike Tour Short
Dates & Rates - Short Tuscany Self Guided Bike Tour

Dates: Plan your trip at a time that fits your schedule best! Pure Adventures tours have flexible start dates and do not have fixed departure dates.

2024 Tour Rates: (based on double occupancy)

Standard Three & Four Star Hotels:

  • 2-4 persons:  1624 euros/person
  • 5+ persons: 1496 euros/person
  • Single Supplement:  283 euros/person (applies when 2 or more traveling but in separate single-use rooms)
  • Solo Supplement: approximately 518 euros

Upgraded Hotels: 

  • 2-4 persons:  2581 euros/person
  • 5+ persons: 2529 euros/person
  • Single Supplement:  990 euros/person (applies when 2 or more traveling but in separate single-use rooms)
  • Solo Supplement: approximately 1260 euros

Choice of Bike Rental:

  • Hybrid Bike Rental:  113 euros
  • Carbon Road Bike or Gravel Bike:  235 euros; recommended
  • E-bike Rental:  235 euros
  • Bike Rental Details Page

Need to Know:

  • July-August is not recommended due to heat and increased high-season hotel rates; a high-season supplement will apply.
  • New! Travel Insurance is now required to participate in this tour. You can book through our preferred vendors or your own. Proof of coverage may be required.

Make it Custom: Do you like this tour but want to make it different? Tell us your wishes & we will quote them!

How do our tours compare to similar trips? You Get More! We are much less than guided trips with similar experiences if you compare prices. 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 worldwide, 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! Why travel with us? Read more!
 
Next Steps:   
1. Call or email with questions:  +1-970-230-5896 or email us. 
2. Book the trip, pay a deposit, and get excited about your adventure!
Book This Tour
 
 
13 Reviews
Sort By:RatingDate

J.M.

Couple Traveller

The trip was amazing and everything worked out great. The hotel accommodations were super nice and your local man was super helpful and got us all set up on our bikes. All the rides were great as well. Thanks again!

October 3, 2023

Lars Olsen

Family Traveller

Finally got the kids on board and up to snuff to do this trip – had it on radar for years and this was the year! Pure Adventures always goes above and beyond and our quick Tuscany tour was no exception. Our family is still talking about this trip and undoubtedly will for years to come. Thanks to Mar and Loren for getting us back out in the saddle again!

June 20, 2023

Chris Reckers

Couple Traveller

A+ + + + + +

June 10, 2023

Anna Abraham

Couple Traveller

Finally took our dream trip after 3 years of covid and cancellations! It was every bit the dream trip we had hoped for. Mar and her colleagues helped us with all of the details but Tom and I still had flexibility to manage our time independently. A big thank you to the Pure Adventures team in Tuscany, as they made us feel perfectly at home and cared for!

June 8, 2023

Barbie Benson

Couple Traveller

Super fun getaway for us and especially nice to go at our own pace. Hotels, food, bikes, and daily rides were honestly just what we were hoping for. We will definitely be back to visit Tuscany and Pure Adventures!

May 30, 2023
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