Tuscany Getaway: 4 Nights in Siena, Montalcino & Pienza

    5/5 (4)
    4 nights | 26 miles/day
    Self guided from EUR € 1090
    Bike tour in Italy
    Rider Level: Active Electric bike tours
    5/5 (4)

    Rider Level: Active Electric bike tours

    4 nights | 26 miles/day
    Self guided from EUR € 1090
    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, besides 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, savor meals created from the finest local ingredients and relax in charming Tuscan retreats.

      • Montalcino, Tuscany, Italy. John Cameron@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 (34 miles/55km)
      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 (29 miles/46km)
      Today bike trip 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 (32 miles/50 km)
      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.

      The accommodations are 3-star hotels.

      Hotel Il Chiostro di Pienza, Pienza
      www.anghelhotels.it

      Hotel Giglio, Montalcino
      www.gigliohotel.com

      La Villa STR, Siena
      www.lavilladistr.it

      Luxury hotel upgrade pricing upon request.

      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, 2023

      Prices

      Tour package

      Per person, double occupancy €1090
      Single use room (1 person/1 room) €1390

      Bike Rentals

      Hybrid touring bike €105
      Road bike €130
      Gravel bike €130
      Electrically assisted bike €130

      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
      • Pick-up of bikes and gear in Siena

      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.


      Bike rentals

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

        • Hybrid 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 

      • Andrew Cochran 2 months ago

        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 3 months ago

        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

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