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
Tuscany cycling tour from Pienza to Siena biking

Italy - Tuscany Wine & History Bike Tour

from €1,189

When people think about vacationing in Italy, they often bring the image of Tuscany to mind. A place that focuses its lifestyle on world-renown wine, culture, and romantic getaways, it’s a perfect vacation spot for anyone, especially for those looking for a moderate intensity cycling vacation. Pure Adventures Tours takes ... 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 will meet you in 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 to enjoy with a bottle of Chianti wine during your travels. Or maybe you'd rather reward yourself with some ice cream at our favorite gelateria? Back in Pienza, we highly recommend a local restaurant where you can enjoy homemade 'pici' - special Tuscan pasta. Your welcome orientation begins at 5:00 PM at the hotel.

Some foods to try in Italy. Have questions? Send us your questions here!

Meals: on own
Highlights: explore Pienza, welcome orientation
Overnight: Pienza
 

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.

Air Conditioning '; Open Parking '; Non-Smoking Rooms '; Cable TV '; Hair Dryer '; Safe in Room ';

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: 33 or 51 km

Enjoy breakfast at the hotel on your own, as you like. You have a choice of two rides today:
The first is an easier ride to the charming village of Bagno Vignoni. Here you will find the famous Roman baths but also modern spa facilities. You may like to spend some time here, enjoying 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, hydro-massage pool, Roman sauna, spa kit with robe, slippers) or, you can 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 for its wine and because it is one of the most charming villages in 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 of the Tuscany countryside. Be sure to enjoy a glass of this delicious and famous Montepulciano wine. Salute! Optional private transfer back to Pienza is available on request for this option as well, to best enjoy the wine in Montepulciano and skip the hills on return - 30 euros/person.

Another fun option is a cooking class near Pienza:
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 / 21 miles +476 m elev gain; Option 2: 51 km / 32 miles +1160 m
Highlights: so many choices! Bagno Vignoni, Montepulciano, cooking class
Overnight: Pienza
 

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.

Air Conditioning '; Open Parking '; Non-Smoking Rooms '; Cable TV '; Hair Dryer '; Safe in Room ';
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: 31 km

Ride from Pienza to the darling, peaceful town of Montalcino, with an option again to visit 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.

Meals: breakfast
Distance: 31 km / 19 miles, +628m
Highlights: Castiglione d'Orcia, monastery of Sant'Antim, Montalcino & Brunello
Overnight: Montalcino  

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).

Swimming Pool '; Air Conditioning '; Open Parking '; Pets Allowed '; Non-Smoking Rooms '; Internet Access '; Cable TV '; Hair Dryer ';
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: 56 km

Ride from Montalcino to Siena. Enjoy the beautiful ride along the UNESCO countryside, 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. Level today is moderate to strenuous.

Meals: breakfast
Distance: 56 km / 35 miles, +895 m
Highlights: UNESCO countryside, Piazza del Campo, Mangia Tower, Siena Cathedral
Overnight: Siena
 

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.

Air Conditioning '; Open Parking '; Pets Allowed '; Non-Smoking Rooms '; Internet Access '; Cable TV '; Hair Dryer '; Safe in Room '; Restaurant ';
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 a rest day to enjoy the man sites of Siena.

Optional Walking Tour:
As a great walking town, you will learn much from our local expert & city guide, Elena, who will take you on a thorough visit of the town (please inquire in advance for the cost of a guided walking tour.) Later, you can go back and visit the many sites you just learned about on your tour!

Meals: breakfast
Highlights: explore Siena
Overnight: Siena
 

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.

Air Conditioning '; Open Parking '; Pets Allowed '; Non-Smoking Rooms '; Internet Access '; Cable TV '; Hair Dryer '; Safe in Room '; Restaurant ';
Tuscany cycling tour from Pienza to Siena biking

Tuscany cycling tour from Pienza to Siena biking

Overview Map

Day 6 | Ride to San Gimignano: 46 km

Today you will 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 Gothic and Romanesque architectures clearly recognizable in churches and palaces.

Meals: breakfast
Distance: 46 km / 29 miles, +838 m elev gain
Highlights: UNESCO site - San Gimignano, Gothic & Romanesque architecture
Overnight: San Gimignano

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.

Air Conditioning '; Non-Smoking Rooms '; Internet Access '; Cable TV '; Hair Dryer '; Safe in Room ';
Tuscany cycling tour from Pienza to Siena biking

Tuscany cycling tour from Pienza to Siena biking

Overview Map

Day 7 | Ride to Volterra: 31 km

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 the end of the 8th century BC, if not earlier. It became a municipality in the Roman Age. In the 5th century, the city was a bishop's residence and its Episcopal power was affirmed during the 12th century. Nowadays, it is part of the charming, rolling Tuscany landscape.

Meals: breakfast
Distance: 31 km / 19 miles, +721 m Highlights: explore Volterra & its history
Overnight: Volterra

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.

Swimming Pool '; Air Conditioning '; Closed Parking '; Non-Smoking Rooms '; Handicap Accessible '; Internet Access '; Cable TV '; Hair Dryer '; Mini-Bar '; Hotel Lounge/Bar '; Safe in Room '; Restaurant ';
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 and enjoy breakfast at your leisure. Transportation to Florence is available, just ask us for assistance in making arrangements. Added hotel nights in Florence are also possible, as well as other onward travel services. Please inquire and one of our experts will be happy to assist you in what you would like to do next!

Meals: breakfast

Have questions? Send us your questions here!

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 195 euros
- Bike rentals - see tab

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: - La Bandita - Pienza
- Veloona Castle - Montalcino
- Palazzetto Rosso - Siena
- Villa San Paola - near San Gimignano including dinner
- Hotel San Lino - Volterra
Extra hotel nights in Florence before or after are available at our contracted rates; please book in advance.

Have Questions? Check out our FAQ tip sheet and for Other Frequently Asked Questions see our general FAQs for booking a tour

Contact us with your questions!
Tuscany Wine & History - 7 nights (based on double occupancy)
 
Standard
Upgraded
Based on 2 participants1348 euros/person 2385 euros/person
Based on 4 participants1339 euros/person 2366 euros/person
Based on 6 participants 1304 euros/person 2335 euros/person
Single supplement287 Euros/single TBD Euros/single
Road Bike rental 210 Euros 210 Euros
Hybrid Bike rental 155 Euros 155 Euros
Transfer Chiusi-Pienza (2 passengers) 134 Euros 134 Euros
Cooking Class Near Pienza161 Euros/person 161 Euros/person
Transfer Bagno Vignoni-Pienza 54 Euros/person 54 Euros/person
Spa Day at Bagno Vignoni 252 Euros/person 252 Euros/person
Custom Trip RequestInquire Here

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

*All add on experiences must be booked and confirmed in advance of travel. Bagno Vignoni (minimum 2 persons) - optional visit and spa facilities; this rate includes 50 minute massage, 6 hours access to the site, thermal pools and waterfalls, hydro-massage pool, Roman sauna with immersion pool, spa kit with bathrobe, transfer back to hotel after extra.
Triples available in some locations; Upgrades possible, please inquire. City tax must be paid where applicable in each hotel at checkout; approx 1.5 euros/person/day.
Road Bike Rentals are recommended; rental rate of 210 euros, please see the bike info below for details.

BOOK NOW


The Pure Adventures Difference

Pure Adventures is a premier, boutique biking and hiking tour operator that offers private, custom, independent and guided travel in Europe, Asia, South and North America. We specialize in hand crafted travel for couples, families and groups who want active, immersive and meaningful experiences with their family and friends. Our travel experiences are customized around outdoor activities including: cycling, hiking, water sports, trail running, mountain biking and more.

How do our tours compare to similar trips? You Get More! Because our passion is taking care of and empowering people, our team has gone to great lengths to build and create exceptional biking and hiking experiences, all over the world, for you. From the accommodations, to the bikes, to the routes themselves, we hold each component of our tours to a very high standard, ensuring that your tour will create amazing memories to last a lifetime. If you compare price, we are much less than high quality guided trips with similar experiences and you obviously get much more in our private, self guided, independent format than most traditional self guided trips. See our why: Why Pure Adventures is Better. 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 8am-5pm MST) +1.480.905.1235; or eMail Us.  

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
- Groups of more than 2 have a bike delivery supplement
- Most hotels collect a small city tax at checkout of 1-3 euros/person/day

Options:
- Private transfer from rail station at start
- Bagno Vignoni Spa package
- Siena Guided Walking Tour
- Cooking Class near Pienza
- Florence/Rome add on - special hotel contract rates available for our guests.

- Groups of 4 or more save on tour price but bike delivery has a supplement

*All add on experiences must be booked and confirmed in advance of travel. Bagno Vignoni (minimum 2 persons) - optional visit and spa facilities; this rate includes 50 minute massage, 6 hours access to the site, thermal pools and waterfalls, hydro-massage pool, Roman sauna with immersion pool, spa kit with bathrobe, transfer back to hotel after.

BOOK NOW
Why Pure Adventures
As a premier boutique biking and hiking tour operator that offers private, custom, independent and guided travel in Europe, Asia, South and North America, we specialize in hand crafted travel for couples, families and groups who want active, immersive and meaningful experiences with their family and friends. Our travel experiences are customized around outdoor activities including: cycling, hiking, water sports, trail running, mountain biking and more.
Dates: March 15-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; Make it Custom - Tell us your Wishes

Best Time To Go: May - June, September - October.

How is this Tour Rated in degree of difficulty? Rates Level 3 - See Why - Mid level difficulty (Fit) tour with rolling to hilly countryside with hilltop village finishes.

Travel Safe Travel Insurance - Our Preferred Vendor to Protect You In Case You Need to Cancel and Provide Added Coverage and Peace of Mind: See Rates - Get Quotes
Why Insure your Travel? See our tip sheet about why to take travel insurance

Average Tuscany temperatures:
March: 61 °F (16 °C) 43 °F (6 °C)
April: 66 °F (19 °C) 46 °F (8 °C) *Some rainy days, but not too wet*
May: 73 °F (23 °C) 54 °F (12 °C)
June: 81 °F (27 °C) 59 °F (15 °C)
July: 86 °F (30 °C) 64 °F (18 °C)
August: 86 °F (30 °C) 63 °F (17 °C)
Sept: 81 °F (27 °C) 59 °F (15 °C)
October: 72 °F (22 °C) 52 °F (11 °C) *Some rainy days, but not too wet*

See Our Italy Travel guides here
Check out our English-Italian Phrase Manual
Preparing to Ride - Our Pure Adventures Bike Tour Preparation Guide

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. Daniele is a good companion of adventure, he lives in Trevi and knows very well Umbria and Tuscany region.  

Bikes Available on This Tour:

Hybrid bike options are 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*.

Road bike option: Canondale Synapse. Compact 50/34 with 11-34. Comes with cantilevered seat post bag. Rental rate 210 euros.

Hybrid 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.
Electric Bikes Available Rental Rate: 288 euros* HaiBike Sduro


Thinking about bringing your own bike? See Our Tip Sheet - What you Need to Know

Request Additional Information

Request your Tour Summary for this tour and also get the free Destination Guide by email.

The Tour Summary is a PDF document you can share with your friends and puts all the key info shown in different tabs here into 1 short compiled document. Our Destination guide will give you general travel info about this country; best time to travel, interesting sites, airports, weather, and more.