Tuscany Getaway: 4 Nights in Siena, Montalcino & Pienza
★★★★★★4.9/5 (11)
Tuscany Getaway: 4 Nights in Siena, Montalcino & Pienza
Self guided from EUR € 1150
Bike tour in Italy
Tap above to jump to different sections of this tour
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Cycle through the hillside and to vineyards in the world's most well-known wine region.
We put together this short bike tour for those who do not feel like taking a vacation entirely on a saddle. Each day there will be a choice for short easier bike rides and more challenging ones.
Whether crowned by timeless villages, covered by vineyards and olive groves, or strewn with wildflowers, the hills of Tuscany have one thing in common: they’re perfect for exploring on two wheels. Pedal to lofty hill towns, spin through broad valleys, and follow sinuous country roads past cypress-lined lanes and quiet woodland.
Off your bike, discover unforgettable Renaissance art and architecture, visit winery and cellars: you will be in the heart of Brunello wine land, so savor meals created from the finest local ingredients and relax in charming Tuscan retreats.
Highlights
- Pienza
- Montepulicano and Monticchiello
- Bagno Vignoni, a thermal spa town
- Catiglione d'Orcia
- Siena
- Etruscan Museum
- Renaissance-era architecture
- Vineyard landscapes
Learn More
Learn more about our self-guided tours or see more bike tours in Italy.
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![Siena, Tuscany, Italy. Antonio Ristallo@Unsplash]()
![Cathedral of Siena, Tuscany, Italy. Agatha Depine@Unsplash]()
![Vineyards throughout Siena, Italy. rich martello@Unsplash]()
![Palazzo Pubblico, Siena, Tuscany, Italy. CC:Wpopp]()
![Montalcino Tuscany wines! Didriks@Flickr]()
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![Gelato in Italy! Alexander E Rust@Flickr]()
![Siena Cathedral in Siena, Tuscany, Italy. CC:Nikolai Karaneschev]()
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![Great Italian feasts! Liubo Vilchu@Unsplash]()
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![Tuscany countryside in Italy. Fabrizio Lunardi@Unsplash]()
![Gorgeous Churches in Tuscany! CC:Peter K Burian]()
![Bruschetta origins in Italy! Calum Lewis@Unsplash]()
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![Siena, Tuscany, Italy. Patrick Schneider@Unsplash]()
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![Siena, Tuscany, Italy. CC:Raymondlafourchette]()
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![Piazza Pio II in Pienza, Tuscany, Italy. CC:Oschirmer]()
![Tuscany, Italy. Flo P@Unsplash]()
![Siena, Tuscany, Italy. CC:Guido Haeger]()
![Delicious Italian pastas! Nerfee Mirandilla@Unsplash]()
![Montepulciano, Tuscany, Italy. Valerio Gentile@Unsplash]()
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![Italy's verdant greens! rich martello@Unsplash]()
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![Pienza, Tuscany, Italy. CC:sherseydc]()
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![Siena, Tuscany, Italy. Massimiliano Morosinotto@Unsplash]()
![Pienza, Tuscany, Italy. Kristof Van Rentergem@Unsplash]()
![Great sunsets in Italy! rich martello@Unsplash]()
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![Siena, Tuscany, Italy. Patrick Schneider@Unsplash]()
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![Sunflower fields in Italy! todd kent@Unsplash]()
![Montepulciano in region Tuscany & province Siena, Italy. Łukasz Czechowicz@Unsplash]()
![Cycling the Tuscany Italy Bike Tour]()
![Cathedral of Siena interior, Siena, Tuscany, Italy. CC:Peter K Burian]()
![Montepulciano, Tuscany, Italy. Valerio Gentile@Unsplash]()
![Italian dining! Marie DeHayes@Unsplash]()
![Italian wines! Anna & Michal@Flickr]()
![Montepulciano in region Tuscany & province Siena, Italy. Tolga Kilinc@Unsplash]()
![Siena, Tuscany, Italy. Alessandro Rossi@Unsplash]()
![Vineyards galore in Italy! Amit Janco@Unsplash]()
![Piazza Pio II in Pienza, Tuscany, Italy. CC:Oschirmer]()
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![Pienza, Tuscany, Italy. Arianna Baldi@Unsplash]()
![Cycling the Tuscany Italy Bike Tour]()
Traveler photos
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Daily program
Day 1: Welcome! Benvenuti in Toscana
Pienza the "perfect town" is a remarkable example of Renaissance-era town planning. If you have even the least appreciation for beautiful architecture, it is a treat to stroll about its cobblestone streets. Meet and Greet, we'll fit your bikes and introduce you to each day ride. First loop to San Quirico (14 miles/22 km) to test the bicycle and the equipment!Day 2: Vino Nobile di Montepulciano (distance: 33 miles/54 km; elevation: +1068 m / -1070 m)
Loop bike tour to Montepulciano and Monticchiello. Start your day with a pleasant downhill, you’ll follow a route checkered with vineyards and cypresses. Highlight of the day is Montepulciano, which is famous for the production of Vino Nobile. Back to Pienza through Monticchiello, another hilltop village.Day 3: Montalcino and Brunello wine (distance: 28 miles/45 km; elevation: +920 m / -876 m)
Today cycle to Bagno Vignoni, a thermal spa town right before reaching the beautiful Castiglione d'Orcia. Enjoy a long downhill to the monastery of Sant'Antimo. On your way to the Etruscan village and wine town of Montalcino, where you will stay you’ll pedal through magnificent vineyards.Montalcino is a fortified town which was used as a shelter by Siena nobles during the 16th Century, but today it is even more famous thanks to the production of one of Italian’s premier fine red wines, Brunello di Montalcino.
Day 4: Siena and Palio race (distance: 34 miles/55 km; elevation: +880 m / -1076 m)
Ride from Montalcino to Siena. Start with 10 km descent and pass through Buonconvento. Heading northbound to Siena, you’ll be treated to more gorgeous cycling along secondary roads. In the village of Murlo, you can visit the fascinating Etruscan Museum. Continue to Ville di Corsano always on a breathtaking scenery and end up in Siena arch gate Porta San Marco. You'll have time to take a leisurely stroll around this medieval art city in the afternoon and to visit Piazza del Campo, Torre del Mangia and the famous Duomo. Piazza del Campo is famous because here it is held twice a year the disputed “Palio” horse race, which opposes the 17 “contrade” of this fascinating city.Day 5: End of tour
End of bike tour after breakfast. -
Accommodation
Hotels
These are sample hotels and may vary by availability.
Standard hotels
The accommodations are 3-star superior + 4-star hotels.Pienza: Relais Il Chiostro
Montalcino: Hotel Vecchia Oliviera
Siena: La Villa STR
Luxury hotels - available on request
Pienza: La Bandita
Montalcino: Relais Mastrojanni
Siena: La Certosa di Maggiano
Please note any visitor's taxes are not included in the tour price. These taxes range from €1-5 per person daily, payable to each hotel.
Interested in visiting other areas before or after your tour? Visit our hotels page to learn more about lodging options.
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Dates & Prices
Questions about pricing or options? Call +1-215-613-0874 to talk to a Tour Advisor now.
Mar 15–31 (Daily)Mar 15–31 (Daily) € 1320 Book Mar 15–31 (Daily)Mar 15–31 (Daily) € 1870 Book Apr 1–30 (Daily)Apr 1–30 (Daily) € 1320 Book Apr 1–30 (Daily)Apr 1–30 (Daily) € 1870 Book May 1–31 (Daily)May 1–31 (Daily) € 1320 Book May 1–31 (Daily)May 1–31 (Daily) € 1870 Book Jun 1–30 (Daily)Jun 1–30 (Daily) € 1320 Book Jun 1–30 (Daily)Jun 1–30 (Daily) € 1870 Book Jul 1–31 (Daily)Jul 1–31 (Daily) € 1320 Book Jul 1–31 (Daily)Jul 1–31 (Daily) € 1870 Book Aug 1–31 (Daily)Aug 1–31 (Daily) € 1320 Book Aug 1–31 (Daily)Aug 1–31 (Daily) € 1870 Book Sep 1–30 (Daily)Sep 1–30 (Daily) € 1320 Book Sep 1–30 (Daily)Sep 1–30 (Daily) € 1870 Book Oct 1–31 (Daily)Oct 1–31 (Daily) € 1320 Book Oct 1–31 (Daily)Oct 1–31 (Daily) € 1870 Book Show pricing details and extra options →
Pricing details and extra options
Daily Mar 15–Oct 31
- Tour Package 2025 Daily Mar 15–Oct 31 from € 13202025 departures: Daily Mar 15–Oct 31
2025 March Sun Mon Tue Wed Thu Fri Sat 2025 April Sun Mon Tue Wed Thu Fri Sat 2025 May Sun Mon Tue Wed Thu Fri Sat 2025 June Sun Mon Tue Wed Thu Fri Sat 2025 July Sun Mon Tue Wed Thu Fri Sat 2025 August Sun Mon Tue Wed Thu Fri Sat 2025 September Sun Mon Tue Wed Thu Fri Sat 2025 October Sun Mon Tue Wed Thu Fri Sat Tour package Double occupancy € 1320 Single occupancy € 1870 Bike rental Price Standard touring bike Included Road bike € 30 Gravel bike € 30 Electric bike € 30
Included services
- 4 nights accommodation in excellent 3-star hotels
- 4 breakfasts
- Route notes, maps, elevation gain and city maps
- Sightseeing, restaurant and shopping suggestions
- Luggage transfers
- RideWithGPS App: tracks & off-line navigation
- Deliver and pick-up of bikes
- Waterbottle
- Sales tax
Please note any city/visitor's taxes are not included in the tour price. These taxes range from €1-5 per person daily, payable to each hotel.
- Tour Package 2025 Daily Mar 15–Oct 31 from € 1320
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Map
Maps are for information purposes only and reflect typical routes between overnight locations. They may not reflect your actual route.
Surface and terrain
Tuscany is a hilly region, but each day you will have a choice for more challenging or shorter, easier bike rides.
How to get there
Tour start and end
Nearest airport: Rome Fiumicino or Florence Peretola airportsFrom Fiumicino airport, take the Leonardo Express train (about 30 minutes) to Termini train station.
From Florence Peretola, take a bus or taxi to Florence station.
To get in Chiusi by train (www.fsitaliane.it) and once in Chiusi, take a bus or taxi to Pienza.
Bus: from Chiusi to Montepulciano, there is a bus every 30 minutes. The bus ride is 40-50 minutes, and the fare is approximately €4 per person. From the bus terminal in Montepulciano, take the bus to Pienza, about a 15 minute ride (this connection is not available on Sundays).
Taxi: from the small train station, the cost is €60-65 per person.
At the tour end, you can easily take a bus or train from Siena to Rome or Florence.
Tips on getting to and from your tour
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Reviews
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★★★★★ Marc Lieber 2 months ago
Great tour
Despite two days of intermittent fog/clouds/rain, we loved this tour. The bikes and equipment were perfect. The tour operator, Cicloposse, was efficient, responsive, flexible. The hotels were quite good including lovely breakfasts. The routes were wonderful, so many interesting and beautiful places to see, and even though we were on roads, we felt safe.
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★★★★★ Daniel Dupont 2 months ago
Amazing trip through Tuscany
What a great trip we had! Biking through Tuscany was truly the experience of a lifetime. Although the weather wasn’t great, the accommodations that were provided, along with the bikes and equipment were 5-stars.
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★★★★★ Daniel Dupont 2 months ago
Amazing trip through Tuscany
What a great trip we had! Biking through Tuscany was truly the experience of a lifetime. Although the weather wasn’t great, the accommodations that were provided, along with the bikes and equipment were 5-stars.
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★★★★★ Tera Hurst 6 months ago
Amazing trip, highly recommend
My brother wanted to do a bike trip for his 50th birthday. After months of research I finally landed on this itinerary and I am so glad we did it! Leading up to the trip bike tours staff was very responsive. The info they sent took awhile and wasn’t tailored to our trip, but they make up for that by answering all questions promptly and without making you feel like a burden!! We had some last minute changes they were very accommodating with as well. The local tour company was wonderful! They were very patient with all of our anxieties and questions. We had never done a trip like this and in a foreign country self guided was intimidating. They broke it down for us and it was amazing. The routes they gave us were stunning and we only made a few quick wrong turns. GPS app they use was helpful and easy to use and follow. We were directed to a different hotel than the one we were staying at twice which was a bit annoying but once we found our place it was lovely and so nice to jump in a cold pool after a hot long ride. Their lunch and dinner recs were delicious! And the one time we had an issue where our bike lock wouldn’t unlock they came out to our remote spot and helped! It’s such a magical place to experience by bike! They never made us feel like a burden and were so professional, accommodating and supportive. I highly recommend this trip. It’s totally worth the price.
- What was the date of your tour?
- July 2024
- How many tours have you completed?
- 1
- Difficulty (actual vs. expected)?
- Somewhat harder
- Who is this tour suitable for?
- First-time bike tourists, Families with teens
- Do you recommend this tour?
- Yes
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★★★★★ Aaron Hurst 6 months ago
A perfect week
The team was so friendly and helpful. The hotels were clean. The bikes worked great. Routes were incredible.
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★★★★★ Bruna Redinha 7 months ago
Amazing views!
The itinerary was wonderful, the medieval cities are amazing and very well located hotels. The only thing we didn't like very much was that the way was mostly on narrow paved roads, we were expecting to ride more on dirt roads.
Apart from that, we liked everything, including the e-bikes and local support.
- What was the date of your tour?
- May 2024
- How many tours have you completed?
- 2
- Difficulty (actual vs. expected)?
- As expected
- Who is this tour suitable for?
- First-time bike tourists
- Do you recommend this tour?
- Yes
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★★★★★ Juan Pablo Beca June 7, 2023
A nice and perfect organization
Routes and the booklet given to us were very clear and helpful. We would have liked to receive details of each of our two bikes sot to ask for change. In fact we did not need so heavy bikes for the roads of our tour, and one as 27 and the other was 29" wheels for same height of the two of us.
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★★★★★ Andrew Cochran October 5, 2022
Wonderful experience
My wife and I spent 9 days in Italy, with the first three days being our bike tour and that was by far our favorite part of the trip. The tour operators were so kind and friendly and helpful and were also very flexible as our travel plans were delayed last minute. We will absolutely being doing another one of their tours!
- What was the date of your tour?
- September 2022
- How many tours have you completed?
- One
- Difficulty (actual vs. expected)?
- As expected
- Who is this tour suitable for?
- First-time bike tourists, Solo travelers, Families with teens
- Do you recommend this tour?
- Yes
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★★★★★ VICTOR GONZALEZ September 21, 2022
Very nice experience
The trip was perfect. The hotels, the bikes and the support team, the routes, everything. I will strongly recommned the trip. The hotels locations, breakfasts, the retaurants recomendetions, the APP to get the indications during the routes.
- What was the date of your tour?
- September 2022
- How many tours have you completed?
- 2
- Difficulty (actual vs. expected)?
- As expected
- Who is this tour suitable for?
- First-time bike tourists, Solo travelers, Families with teens
- Do you recommend this tour?
- Yes
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★★★★★ Gary O August 1, 2019
An excellent bike tour to include
This was our first time in Italy and the self guided trip was and excellent way to experience all the charms and challenges of this amazing place. Everything from our briefing to the charming and very comfortable hotels was excellent and exceeded our expectations. The bike ride was suitably challenging with regular touring bikes, and proved to be an excellent workout. Towns and villages along the way were all an added bonus. Our tour hosts were excellent and even provided a ride back to Sienna to gather my car on the last day. Thank YOU!
- What was the date of your tour?
- July 10 - 14
- How many tours have you completed?
- over 12
- Difficulty (actual vs. expected)?
- Somewhat harder
- Who is this tour suitable for?
- Solo travelers, First-time bike tourists, Families with teens
- Do you recommend this tour?
- Yes
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★★★★★ Elizabeth August 17, 2017
Awesome getaway!
- What was the date of your tour?
- July
- How many tours have you completed?
- Lots
- Difficulty (actual vs. expected)?
- As expected
- Who is this tour suitable for?
- Solo travelers, Families with teens
- Do you recommend this tour?
- Yes
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