Tuscany Getaway: 4 Nights in Siena, Montalcino & Pienza

★★★★★★4.9/5 (11)
4 nights
26 miles/day
Self guided from EUR € 1320
Bike tour in Italy
Rider Level: Active Electric bike tours
Book this tour
Ask a tour advisor

Tuscany Getaway: 4 Nights in Siena, Montalcino & Pienza

★★★★★★4.9/5 (11)

Rider Level: Active Electric bike tours

4 nights
26 miles/day
Self guided from EUR € 1320
Bike tour in Italy

Book this tour
Ask a tour advisor
Why book with us?

Tap above to jump to different sections of this tour

  • 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.

    • Montalcino Tuscany wines! Didriks@Flickr
    • Gelato in Italy! Alexander E Rust@Flickr
    • Siena Cathedral in Siena, Tuscany, Italy. CC:Nikolai Karaneschev
    • Great Italian feasts! Liubo Vilchu@Unsplash
    • Tuscany countryside in Italy. Fabrizio Lunardi@Unsplash
    • Gorgeous Churches in Tuscany! CC:Peter K Burian
    • Bruschetta origins in Italy! Calum Lewis@Unsplash

    View more photos

    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.

    Tuscany Getaway

    Photos 

  • Tour Photos

    Traveler photos

    • Day 4 in Montelciano (photo by Tera Hurst)
    • Heading to Siena (photo by Tera Hurst)
    • A nice lunch break at Montepulciano (photo by VICTOR GONZALEZ)
    • Rest stop (photo by Elizabeth)

    Tuscany Getaway

     Tour Description Daily Program 

  • 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!
    Overnight in Pienza

    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.
    Overnight in Pienza

    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.
    Overnight in Montepulciano

    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.
    Overnight in Siena

    Day 5: End of tour
    End of bike tour after breakfast.

    Photos

    • Montalcino Tuscany wines! Didriks@Flickr
    • Gelato in Italy! Alexander E Rust@Flickr
    • Siena Cathedral in Siena, Tuscany, Italy. CC:Nikolai Karaneschev
    • Great Italian feasts! Liubo Vilchu@Unsplash
    • Tuscany countryside in Italy. Fabrizio Lunardi@Unsplash
    • Gorgeous Churches in Tuscany! CC:Peter K Burian

    View more photos

    Tuscany Getaway

     Photos Accommodation 

  • 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.

    Tuscany Getaway

     Daily program Bikes 

  • Bikes

    Standard touring bike

    Frame: Aluminum frame
    Fork: Full carbon
    Chain ring: Shimano Deore – triple or compact
    Cassette: Shimano Deore – 11/34 or 11/36
    Brakes: Shimano Deore
    Saddle: Selle Italia XO & lady gel
    Wheel set: Shimano RS30
    Tires: Panaracer close
    Weight: 9,5 kg
    Size: We can fit riders from 5.0 to 6.4 ft / 1,50 to 1,95 m
    Size frame from 46cm to 62cm

    Road bike

    Frame: Full carbon frame
    Fork: Full carbon
    Chain ring: Shimano Ultegra compact 50/34
    Crank: 172.5 / 175.00 mm
    Cassette: Shimano Ultegra or 105 – 11/32 – 11 speed
    Brakes: Shimano Ultegra rear and front
    Saddle: Selle Italia
    Wheel set: Shimano R561
    Tires: Panaracer Extreme
    Weight: 7,6 kg
    Size: We can fit riders from 5.0 to 6.3 ft / 1,50 to 1,92 m
    Size frame from 46cm to 59cm

    Gravel bike

    SCOTT Addict Gravel 20

    The SCOTT Addict Gravel has been set up to allow you to ride any road, anywhere and in any weather conditions.

    A lightweight Carbon fiber frame, Equipped compact Ultegra, rugged Schwalbe G-One tires and Shimano Hydraulic disc brakes give you a rig that will let you get your adventure on, no matter what.

    A cyclocross touring oriented to enjoy the classic strade bianche in Tuscany: Eroica itinerary and Francigena path.

    Our gravel bikes are all brand-new, reliable, and well maintained for your ideal cycling light off-road experience of Tuscany.

    Size: S, M, L , XL

    Gravel bike

    CANNONDALE Topstone1 Gravel

    Straightforward, reliable and a whole hell of a lotta fun, the Topstone Alloy is a gravel bike crafted for those with a taste for adventure – and value.

    Roll light and free, or load it up for a long haul, Topstone’s comfortable ride, confident handling and up-for-anything capability make it the perfect partner on any road, anywhere.

    A Lightweight frame and full carbon fork equipped with Shimano GRX 800/600 11-speed shifting

    Size: XS, S, M, L, XL

    Electric bike

    Scott E-SUB Cross 10

    E-sub cross 10 as the best for our tours: The SCOTT E-SUB Cross 10’s newly developed frame ePowered by a new 500wh Bosch Internal battery, will get you where you are going faster and more comfortably than ever before.

    • Purion Display
    • Fork: Suntour Nex-E25 Lo Ds 15mm Ta Tapered
    • E-Drive System : Bosch Performance 250w System W
    • 500wh Power Tube Battery
    • Rear Derailleur: Sram Nx 11 Speed
    • Brakes: Shimano Br-M365 Disc
    • Size: S,M,L / Man & Woman Model

    Electric bike

    Scott E-SUB Cross 10

    Meet the new Sub Cross eRIDE 10: equipped with the powerful Bosch Performance CX drive unit and a PowerTube battery intelligently integrated into the frame for a slick design.
    An adjustable stem and the ergonomic Syncros saddle result in optimal comfort

    • Intuvia 100 Display
    • Front suspension: Suntour 63mm
    • E-Drive System : Bosch Performance CX
    • 625 wh Power Tube Battery /
    • Rear Derailleur: Shimano Deore 10 speed
    • Brakes: Shimano Br-M365 Disc
    • Size: S,M,L / Man & Woman Model

    Electric bike

    E- bike Positive +

    Positive + Performance Tecnobike is the elegant and highly performing electric trekking bike.
    Equipped with a luggage rack and equipped with a powerful Shimano performance motor, the Positive e-trekking is the ideal bike for getting around for tourism by bike

    • Purion Display
    • Fork: alloy suspension fork 700C
    • E-Drive System : Bosch Active Line Plus
    • 500wh Power Tube Battery
    • Rear Derailleur: Shimano Altus
    • Brakes: hydraulic disc
    • Size: S, M / step-through frame

    More about electrically-assisted bikes >

    Equipment included with bike rental:

    • Handlebar bag or map holder
    • Helmet
    • Water bottle
    • Repair kit (mini pump, inner tube, tire levers)
    • Computer mileage counter
    • Lock (one lock with key per 2 bikes)

    Bike Protection:
    Bike protection can be purchased at the time of booking. You can read more about that HERE.

    Pedals:
    The bikes will have toe clips(upon request) or flat pedals. You can also bring your own pedals and shoes, along with the necessary equipment for installing the pedals.

    Seats:
    If you plan to bring your own seat, please don't bring the seat post. The tour company can assist you with installing.

    Helmets:
    Helmets are required on this tour. Helmets are included in the tour package; however, we recommend you bring your own helmet for safety and hygiene reasons.

    Tuscany Getaway

     Accommodation Dates & Prices 

  • Dates & Prices

    Questions about pricing or options? Call +1-215-613-0874 to talk to a Tour Advisor now.



    May 11–31 (Daily)May 11–31 (Daily) from € 1320Book
    Jun 1–30 (Daily)Jun 1–30 (Daily) from € 1320Book
    Jul 1–31 (Daily)Jul 1–31 (Daily) from € 1320Book
    Aug 1–31 (Daily)Aug 1–31 (Daily) from € 1320Book
    Sep 1–30 (Daily)Sep 1–30 (Daily) from € 1320Book
    Oct 1–30 (Daily)Oct 1–30 (Daily) from € 1320Book

    Pricing details and extra options

    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 Company

    Tuscany Getaway

     Bikes Other Details 

  • 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 airports

    From 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

    Tuscany Getaway

     Dates & Prices Tour Reviews 

  • Reviews

      Write a review

    • ★★★★★ Marc Lieber 6 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.

    • ★★★★★ Daniel Dupont 6 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.

    • ★★★★★ Daniel Dupont 6 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.

    • ★★★★★ Tera Hurst 10 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
      • Day 4 in Montelciano (photo by Tera Hurst)
      • Heading to Siena (photo by Tera Hurst)
      • 5/5 Value
      • 4/5 Included meals
      • 4/5 Bikes + equipment
      • 4/5 Hotels or boat
      • 5/5 Scenery
      • 5/5 Ease of navigation
      • 5/5 Local tour company services
      • 5/5 Route selection
    • ★★★★★ Aaron Hurst 10 months ago

      A perfect week

      The team was so friendly and helpful. The hotels were clean. The bikes worked great. Routes were incredible.

    • ★★★★★ Bruna Redinha 11 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
      • 4/5 Value
      • 5/5 Included meals
      • 5/5 Bikes + equipment
      • 5/5 Hotels or boat
      • 5/5 Scenery
      • 5/5 Ease of navigation
      • 5/5 Tour documents
      • 5/5 Local tour company services
      • 4/5 Route selection
    • ★★★★★ 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.

    • ★★★★★ 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
      • 5/5 Value
      • 5/5 Included meals
      • 5/5 Bikes + equipment
      • 5/5 Hotels or boat
      • 5/5 Scenery
      • 5/5 Ease of navigation
      • 5/5 Tour documents
      • 5/5 Local tour company services
      • 5/5 Route selection
    • ★★★★★ 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
      • A nice lunch break at Montepulciano (photo by VICTOR GONZALEZ)
      • 5/5 Value
      • 5/5 Included meals
      • 5/5 Bikes + equipment
      • 5/5 Hotels or boat
      • 5/5 Scenery
      • 5/5 Ease of navigation
      • 4/5 Tour documents
      • 5/5 Local tour company services
      • 5/5 Route selection
      • 5/5 Guides (if applicable)
    • ★★★★★ 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
      • 3/5 Value
      • 5/5 Included meals
      • 4/5 Bikes + equipment
      • 5/5 Hotels or boat
      • 5/5 Scenery
      • 5/5 Ease of navigation
      • 5/5 Tour documents
      • 5/5 Local tour company services
      • 5/5 Route selection
    • ★★★★★ 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
      • Rest stop (photo by Elizabeth)
      • 4/5 Value
      • 5/5 Included meals
      • 5/5 Bikes + equipment
      • 5/5 Hotels or boat
      • 5/5 Scenery
      • 5/5 Ease of navigation
      • 5/5 Tour documents
      • 5/5 Local tour company services
      • 5/5 Route selection

    Tuscany Getaway

     Other Details Book this tour 

Related locations