Tuscany Getaway: 4 Nights in Siena, Montalcino & Pienza

5/5 (5)
4 nights
26 miles/day
Self guided from EUR € 1150
Bike tour in Italy
Rider Level: Active Electric bike tours

Tuscany Getaway: 4 Nights in Siena, Montalcino & Pienza

5/5 (5)

Rider Level: Active Electric bike tours

4 nights
26 miles/day

Self guided from EUR € 1150
Bike tour in Italy

Tap above to jump to different sections of this tour

  • Tuscany Getaway

    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

    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.

  • Traveler photos

    • A nice lunch break at Montepulciano (photo by VICTOR GONZALEZ)
    • Rest stop (photo by Elizabeth)
  • 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.

    Surface and terrain

    Tuscany is a hilly region, but each day you will have a choice for more challenging or shorter, easier bike rides.


    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 il Giglio

    Siena: La Villa STR


    Luxury hotels - available on request

    Pienza: La Bandita

    Montalcino: Relais Mastrojanni

    Siena: Campo Regio Relais


    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.


    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

     Tour Photos Dates & Prices 

  • Dates

    Daily: Mar 15-Oct 31, 2024

    Prices

    Tour package

    Per person, double occupancy €1150
    Single use room (1 person/1 room) €1700
    Solo traveler (1 person in party with single use room) €1765

    Bike Rentals

    Standard touring bike €120
    Road bike €150
    Gravel bike €150
    Electrically assisted bike €150

    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.


    Bike rentals

    Bikes available for rent (in advance at the time of booking) on this tour are:

    • Standard touring bike, 27 or 30 speed, equipped with:
      • Aluminum frame
      • Full Carbon
      • Shimano Deore components 
      • Gel saddle
      • Upright handle bar
      • Wheelset: Shimano RS30
    • Road bike, 20 speed, equipped with:
      • Full Carbon fiber 
      • Carbon forks
      •  Shimano Ultegra  or 105  – 11/32 –  11 speed
      • Drop handle bar
      • Wheel set: Shimano R561
    • Gravel bike
      • Addict Gravel Disc Hmf / Imp Carbon
      • Shifters: Shimano St-R8020 Disc  Dual Control  22 Speed
      • Seat: Syncros Tofino T-Cutout 2.0
      • Wheel set:Syncros Rp2.0 Disc  Syncros Rws
    • Electrically assisted bike with 250w Sunstar motor
      • Frame E-Sub 6061 Alloy
      • Bosch Performance 250w System W/ 500wh Power Tube Battery
      • Brakes: Shimano Br-M365 Disc

    *More about electrically-assisted bikes >

    Equipment included with bike rental:

    • Handlebar bag or map holder
    • 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 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.


    Tour Company


    Tuscany Getaway

     Daily program Route Map 

  • Route Map

    Maps are for information purposes only and reflect typical routes between overnight locations. They may not reflect your actual route.


    Tuscany Getaway

     Dates & Prices Tour Reviews 

    • Juan Pablo Beca 10 months ago

      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

     Route Map Book This Tour 

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