Tuscany cycling tour from Pienza to Siena biking
Tuscany cycling tour from Pienza to Siena biking
Tuscany cycling tour from Pienza to Siena biking
Tuscany cycling tour from Pienza to Siena biking
Tuscany cycling tour from Pienza to Siena biking
Tuscany cycling tour from Pienza to Siena biking
Tuscany cycling tour from Pienza to Siena biking
Tuscany cycling tour from Pienza to Siena biking
Tuscany cycling tour from Pienza to Siena biking

Italy - Tuscany Wine & History Bike Tour

from €1,189

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 ... Read More

  • Reviews
  • Difficulty
    Fit: 3/5
  • Tour Type
    Self Guided Cycling Hybrid or Road (Level 3)
  • Availability
    March 15 - November 15
  • Duration
    7 Nights / 8 Days
  • Distance
    km/day

Day 1 | Arrival Day - Pienza

We'll meet you in 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-flavored 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. 5PM orientation at the hotel. Some foods to try in Italy.
 

Hotel Piccolo La Valle


Pienza Tuscany

Hotel Piccolo La Valle

The Piccolo Hotel “La Valle” is situated a few steps away from the historical center of Pienza, one of the city which in 1996 became a member of the UNESCO’s global heritage.. The new building, made of bricks and stones, opens into the marvelous countryside of Pienza and the Orcia Valley.

Profile

Tuscany cycling tour from Pienza to Siena biking

Tuscany cycling tour from Pienza to Siena biking

Overview Map

Day 2 | Loop tour around Pienza (33km or 51km)

Enjoy breakfast at the hotel on your own, when you want. Then, for your rides, you have a choice of two rides today: 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. Dinner on your own back in Pienza; we do recommend a local restaurant where you can enjoy home made 'pici' - special Tuscan pasta. In fact, for 30 euros/person, you can have a Pici Making Class - learn to make your own Tuscany pasta! (book in advance). (B) Rides: Option 1: 33km +476m elev gain; Option 2: 51km +1160m.  

Hotel Piccolo La Valle


Pienza Tuscany

Hotel Piccolo La Valle

The Piccolo Hotel “La Valle” is situated a few steps away from the historical center of Pienza, one of the city which in 1996 became a member of the UNESCO’s global heritage.. The new building, made of bricks and stones, opens into the marvelous countryside of Pienza and the Orcia Valley.

Tuscany cycling tour from Pienza to Siena biking

Tuscany cycling tour from Pienza to Siena biking

Overview Map

Day 3 l Ride from Pienza to Montalcino (31km)

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 dinner at one of the local recommendations we provide. Dinner on your own. Distance: 31 km; +628m. (B)  

Hotel Dei Capitani


Montalcino Tuscany

Hotel Dei Capitani

The hotel is situated in part of the 18th C. "Catasto Leopoldino" in the historic center of Montalcino. The building may have been used since the Middle Ages (because of its location close to Porta Burelli) as a shelter for the Sienese people fleeing from the Florentine army. The rooms at the back offer a splendid view of the Val d'Orcia and the Val d'Arbia. Enjoy the large, panoramic garden, and the swimming pool (created to look like a medieval fountain).

Tuscany cycling tour from Pienza to Siena biking

Tuscany cycling tour from Pienza to Siena biking

Overview Map

Day 4 l Ride from Montalcino to Siena (56km)

Ride from Montalcino to Siena. Enjoy the beautiful ride along the Unesco country side, included into the list just because the beauty of the valleys and hills of the province. Siena is well known for its lovely oval shaped central square – the Piazza del Campo 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 small neighborhood guest houses in central Siena. Dinner on your own. Level: Moderate to strenuous Distance: 56 km and 895m elev gain. (B)  

Hotel Chiusarelli


Siena Tuscany

Hotel Chiusarelli

Hotel Chiusarelli is a 3* hotel located in the center of Siena, one of the most beautiful art cities in Italy. The building is a Neoclassical villa which was built around the 1860s and became one of the first hotels in Siena. In 2010, it was completely renovated, keeping its original style. Hotel Chiusarelli adds a gastronomic note to your stay in Siena with its Restaurant "Gli Orti di San Domenico", where you can dine in a charming atmosphere, tasting typical recipes and dishes from traditional Tuscan cuisine. The rooms are all equipped with comforts such as bathroom with shower or bathtub, hairdryer, telephone, TV with SKY-Satellite, safe, air conditioning/heating and Wi-Fi Internet upon request. Some rooms also have a small balcony which overlooks a green area on the back side of the building.

Tuscany cycling tour from Pienza to Siena biking

Tuscany cycling tour from Pienza to Siena biking

Overview Map

Day 5 l Day off Siena

Today is rest day to enjoy all the sites of Siena. Optional walking tour: As a great walking town, you will learn much from our city guide Elena who will take you on a thorough visit of the town (please inquire for cost of guided walking tour). Later you can go back and visit more any of the sites you heard about. (B)  

Hotel Chiusarelli


Siena Tuscany

Hotel Chiusarelli

Hotel Chiusarelli is a 3* hotel located in the center of Siena, one of the most beautiful art cities in Italy. The building is a Neoclassical villa which was built around the 1860s and became one of the first hotels in Siena. In 2010, it was completely renovated, keeping its original style. Hotel Chiusarelli adds a gastronomic note to your stay in Siena with its Restaurant "Gli Orti di San Domenico", where you can dine in a charming atmosphere, tasting typical recipes and dishes from traditional Tuscan cuisine. The rooms are all equipped with comforts such as bathroom with shower or bathtub, hairdryer, telephone, TV with SKY-Satellite, safe, air conditioning/heating and Wi-Fi Internet upon request. Some rooms also have a small balcony which overlooks a green area on the back side of the building.

Tuscany cycling tour from Pienza to Siena biking

Tuscany cycling tour from Pienza to Siena biking

Overview Map

Day 6 | Ride to San Gimignano (46km)

Today you'll ride to the Unesco heritage site of San Gimignano. This lovely medieval town still preserves dozen of tower houses which, with its hilltop setting and encircling walls, form an unforgettable skyline. The town includes notable examples of both Gotic and Romanesque architectures clearly recognizable in churches and palaces. Dinner on your own. (B) 46km and 838m elev gain. 

Hotel Antico Pozzo


San Gimignano Tuscany

Hotel Antico Pozzo

Hotel L'Antico Pozzo, the style hotel in San Gimignano, is not only a fine period residence but also a place where the stories, legends and magic of San Gimignano come alive. This medieval town is unanimously acknowledged among Italy's most fascinating, and you can discover the secrets held within the walls of this ancient palace and experience the beauty of our land here in the heart of Tuscany.

Tuscany cycling tour from Pienza to Siena biking

Tuscany cycling tour from Pienza to Siena biking

Overview Map

Day 7 | Ride to Volterra (31km)

Your last ride in Tuscany is to Volterra, another jewel of the Tuscany heritage, less known than some of the others. This town was inhabited as a city since at least the end of the 8th century BC. It became a municipality in the Roman Age. The city was a bishop's residence in the 5th century, and its episcopal power was affirmed during the 12th century. Nowadays it is part of the charming Tuscany landscape. 31km and +721m. (B) 

Hotel San Lino


Volterra

Hotel San Lino

Hotel San Lino is a renovated 15th century convent rich in charm and fascinating history situated in the city of Volterra. The hotel offers two different standards of accommodation: standard rooms and superior rooms. The standard rooms are located on the first floor of the hotel and are furnished in Tuscan "arte povera" style. This linear and unfussy style of furniture, typical to the area, corresponds with the wish to retain the simplicity of the original monastic atmosphere. All rooms however, are equipped with free Wi-Fi access, mini-bar, direct dial telephone line, colour television with satellite channels, air conditioning, en-suite bathroom with shower and hairdryer. The superior rooms are situated on the 2nd and 3rd floor of the hotel and are in a classic-continental style. Refined and elegant, the rooms have been furnished with care and attention being paid to the smallest detail: cherry wood furniture, wall to wall carpet, curtain drapes. The high standard of these rooms is complimented by the numerous comforts which can be found within: free Wi-Fi access, mini-bar, direct dial telephone line, colour television with satellite channels, air conditioning, en-suite bathroom with shower and hairdryer.

Tuscany cycling tour from Pienza to Siena biking

Tuscany cycling tour from Pienza to Siena biking

Overview Map

Day 8 | Departure Day

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.  

Tuscany cycling tour from Pienza to Siena biking

Tuscany cycling tour from Pienza to Siena biking

Overview Map
The tour package inclusions and exclusions at a glance.

- Deluxe lodging 3 and 4 stars - double room with private bath; all excellent locations
- Buffet breakfast daily
- GPS with pre-programmed routes (1 per 2 participants)
- All luggage transfers from hotel to hotel
- Local emergency support throughout your tour during daylight riding hours
- Arrival orientation and bike set up in Pienza
- Route maps, route cue sheets with GPS notes for navigation
- Suggestions for visitations, sites, restaurants, monuments
- All pre and post travel planning services
- A package of pre-travel documents sent electronically to help you prepare for your trip.
- Pre-travel GPX files for personal device if requested
- Customer incentives & post trip offers
OPTIONS TO ADD:
- Private transfer from rail station at start
- Bagno Vignoni Spa package
- Siena Guided Walking Tour

Lodging

Accommodations: Stay in deluxe 3 & 4-star hotels in convenient locations. All lodging includes private bathroom and a variety of other amenities. Hotels included:

- Hotel Piccolo La Valle***
- Hotel Dei Capitani***
- Hotel Chiusarelli***
- Hotel Antico Pozzo****
- Hotel San Lino****


Upgraded hotels include: - Il Chiostro - Pienza
- Castello di Valona; including dinner near Montalcino
- Palazzo Ravizza - Siena
- Villa San Paola - near San Gimignano including dinner
- Hotel San Lino - Volterra
Tuscany Wine & History - 7 nights (based on double occupancy)
 
Standard
Upgraded
Based on 2 participants1269 euros/person 1971 euros/person
Based on 4 participants1233 euros/person 1938 euros/person
Based on 6 participants TBD euros/person TBD euros/person
Single supplement247 Euros/single TBD Euros/single
Road Bike rental 210 Euros 210 Euros
Hybrid Bike rental 155 Euros 155 Euros
Transfer Chiusi-Pienza (2 passengers) 90 Euros 90 Euros
Spa Day at Bagno Vignoni 252 Euros/person 252 Euros/person

Please inquire for solo supplement if you are traveling on your own.
For a 4-night itinerary, please see our Tuscany Cycling Escape

How do our rates compare? See Why Pure Adventures is Better We include more services, respond quicker, and are there for your entire trip not just part of it. As a US based company, you can pay conveniently and securely. Call us toll free now 800-960-2221 (USA/Canada 8am-5pm MST); or eMail Us we respond same day to all emails. Our goal is to be better, respond quicker, and save you both time and money. We may not always be the least expensive, but we will be the best value for the money and time. Don't forget, we offer many destinations and will help you choose the best one for you. Let us help you and make your vacation easy!  

Tour Details

Tour Highlights:
- Wine & amazing countryside; wines and olive oils in every town, discover them all.
- Quiet roads with some busy connector routes offer peaceful riding and amazing vistas - riding is hilly
- 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 busy connector roads are used between the small back country roads.
- Be prepared to ride some Tuscan hills throughout each day

Options:
- Private transfer from rail station at start - 90 euros based on 2 persons
- Bagno Vignoni Spa package - 215 euros/person with return transfer to Pienza
- Siena Guided Walking Tour - 175 euros/2 persons
- Florence/Rome add on - special hotel contract rates available for our guests.
- Custom tours for groups
Dates: March 1-July 15; September 1-November 30.
This is self-guided touring and offers total freedom of dates - you can choose whatever dates you wish. We can accommodate small parties of 2 persons up to large groups. Custom guided groups are possible for groups of 6 or more; please inquire.
Level 3 - Mid level difficulty (Fit) tour with rolling to hilly countryside with some hilltop villages.
  • Book a Car Rental

  • Get a Travel Insurance Quote: Travel Safe (US & Canada residents only)
  • Get a Travel Insurance Quote: Australia | New Zealand
  • Local Coordinator

    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, Giuseppe, Dario, or another staff member are there to help you!

    Bikes Available on This Tour:
    Trek Emonda S5 Road Bike:
    Road bikes are recommended on this tour to make the rolling hills more easily traversed. The Trek Emonda is a great rental for these rolling and hilly routes of Piedmont. Carbon frame, compact crankset with Shimano 105, the bike is light and responsive. Rental Rate: 210 euros. See the Detailed Road Bike Spec Sheet.

    Hybrid bike options are new 2017 Trek FX 3 models : Trek Fx 3: aluminum frame; Shimano components, upright handle bar; road wheels with puncture resistant road tires. The hybrids are equipped with bags and carrying capacity. Womens frame. Hybrid Rental Rate: 155 euros.

    Either bike Includes:
    • Helmets, (one size fits all).
    • Computer (odometer): Wireless odometers.
    • Saddlebag - On Road Bikes only and contains the puncture kit
    • Rear bag or handlebar bag for hybrids - 1 per bike standard.
    • 1 GPS per 2 persons included in trip rate
    • Puncture kit: Tire levers, spare inner tube, patch kit included
    • Lock included
    • Frame pump included
    Pedals: flat or with cages. Travelers may bring their own clipless pedals to have installed. If you bring your own pedals, please bring your own wrench to remove them from the bike at the end of the tour.

    Request Additional Information

    Request your free Destination Guide and get a PDF summary of this tour by email.

    Our Destination guide will give you general travel info about this country; best time to travel, interesting sites, airports, weather, and more. We will include a PDF summary of this tour as well.