Tuscan Wine Classic: Pienza to Castellina via Siena

★★★★★★4.8/5 (5)
6 nights
32 miles/day
Self guided from EUR € 1720
Bike tour in Italy
Rider Level: Enthusiast Electric bike tours
Book this tour
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Tuscan Wine Classic: Pienza to Castellina via Siena

★★★★★★4.8/5 (5)

Rider Level: Enthusiast Electric bike tours

6 nights
32 miles/day
Self guided from EUR € 1720
Bike tour in Italy

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

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  • Cycle to Renaissance Gems, Vineyards, and Historic Abbeys in Italy's Rolling Hills of Tuscany

    Yes, there are hills, but your efforts on this tour will be rewarded with sunny Mediterranean ambiance and a spirited flair for hospitality. Tuscany nourishes the soul and leads you to rejoice in the earthly pleasures of daily life.

    The route takes you along tranquil country lanes tracing the expanses between farmland crowned with walled villages, ancient monasteries in secluded valleys, and medieval forts. Staying in Pienza, Montalcino, Siena, and the heart of Chianti, you are sure to experience the true essence of Tuscany, where history and beauty fill the heart as water fills a well.

    We suggest, after spinning through rolling vineyards, golden wheat fields, and chalky white hills by day, that you spend your evenings savoring pecorino cheese, homemade pasta pici, fruity olive oils, and sipping the Tuscan wines Brunello and Nobile.

    This tour immerses you in Tuscany!

    Upon request longer routes can be provided as well (55-63 miles per day).

    • Cycling the Tuscan Wine Classic: Pienza to Castellina via Siena Bike Tour
    • Cathedral of Siena, Tuscany, Italy. Agatha Depine@Unsplash
    • Wine tasting in Montepulciano, Italy. PictureSeeker@Unsplash
    • Sunflower fields in Italy! rehan shaik@Unsplash
    • Tuscany countryside in Italy. Fabrizio Lunardi@Unsplash
    • Piazza Pio II in Pienza, Tuscany, Italy. CC:Oschirmer
    • Great prosciutto hams in Italy! Daniel Uvegard@Unsplash
    • Vineyards galore in Italy! Amit Janco@Unsplash
    • Cycling the Tuscan Wine Classic: Pienza to Castellina via Siena Bike Tour
    • Siena, Tuscany, Italy. Alessandro Rossi@Unsplash

    View more photos

    Highlights

    • Pienza, a Renaissance town
    • Castelmuzio
    • Montepulciano, the jewel of southern Tuscany
    • Monticchiello, the quintessential Tuscan hill town.
    • Bagno Vignoni, a miniature spa
    • Monastery of Sant'Antimo
    • Wine town Montalcino
    • Monte Oliveto Maggiore monastery
    • Castello di Brolio
    • Siena - famous for the Palio run

    Learn More

    Learn more about our self-guided tours or see more bike tours in Italy.

    Tuscan Wine Classic

    Photos 

  • Tour Photos

    Tuscan Wine Classic

     Tour Description Daily Program 

  • Daily program

    Day 1: Pienza
    Meet and greet in Pienza, the purest renaissance town in the world, for welcome and bike fitting. Pienza is a remarkable example of renaissance-era town planning. If you have even the least appreciation for beautiful architecture, it's a real treat to stroll around its cobblestone streets. Take an optional test ride to San Quirico d'Orcia (13 miles/20 km).

    Overnight in Pienza

    Day 2: Pienza – Montepulciano and vino nobile (33 miles/54 km)
    Your tour starts with a circular ride from Pienza. Be sure to stop along the way to visit the remote convent where parts of The English Patient were filmed and in the enchanting little hamlet of Castelmuzio. By lunchtime, you'll come to Montepulciano, the jewel of southern Tuscany. After relaxing a while, return to Pienza with a stop in the village of Monticchiello, the quintessential Tuscan hill town.
    Elev. + 1068 m / - 1070 m
    Overnight in Pienza

    Day 3: Pienza – Montalcino brunello land (28 miles/45 km)
    Ride from Pienza to Montalcino, with a pause in fairy-tale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe. You can have lunch in Castiglione d'Orcia, then push on to the monastery of Sant'Antimo, where you might catch one of several vesper services performed each day by the monks. The famed wine town of Montalcino is your destination. Visit the fortress to see a breathtaking view of the entire valley you've just biked.
    Elev. + 920 m / -876 m
    Overnight in Montalcino

    Day 4: Montalcino – Siena and Monte Oliveto Abbey (36 miles/58 km)
    Today will take you through the typical postcard scenery of Tuscany, Italy’s most photographed region. Following a picturesque crest road, you’ll ride by Monte Oliveto Maggiore Abbey, a Benedictine abbey built in the 13th century and famous for its frescoed cloister and stunning setting. Afterward, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands. Here the verdant hills give way to little domes of clay and Tuscany reveals another face of its identity, an unusual, almost lunar landscape of chalk cliffs and gullies soaked in a primeval atmosphere.
    Elev. +1035 m / -1217 m
    Overnight in Siena

    Day 5: Siena – Chianti hills (35 miles/56 km)
    Ride from Siena to Castellina in Chianti, following the "Chiantigiana" road. Along the way, you can visit Castelnuovo Berardenga, a medieval town that marks the gateway to Chianti country. From here you will ride inside the vineyard of famous chianti classico wine passing through many little hamlets. Not far away is Castello di Brolio, a castle and winery that you can visit. There's also the chance to shop at a first-class ceramics workshop. Arrive in time in Radda for a light lunch and enjoy the last 10 km of gentle rolling hills to get to Castellina.

    Castellina's medieval street, the Via delle Volte, was originally open to the sky, but over the years houses and shops have encroached on the ancient city walls, covering the street and providing an intriguing underground home for shops and restaurants.
    Elev. + 1019 m / -787 m
    Overnight in Castellina in Chianti

    Day 6: Castellina – Greve in Chianti and Panzano (34 miles/55 km)
    Circular bike ride to Florence Chianti: bike along quiet roads to the three villages that formed the Chianti Alliance centuries ago. Visit Tuscany's forgotten abbeys and hamlets then enjoy a winery tour and taste their supple reds, fresh honey, and rich olive oil. Have a stop at Greve's main piazza, which is characterized by an original formation of irregular triangular shape and defined by beautiful long porticos. Back via Panzano with preserved the old walls, gate, and the keep of the medieval castle, relax by the vanishing edge pool spilling into the countryside of endless vineyards.
    Elev. +1019 m / -1019 m
    Overnight in Castellina

    Day 7: Castellina
    Individual departure

    Photos

    • Cycling the Tuscan Wine Classic: Pienza to Castellina via Siena Bike Tour
    • Cathedral of Siena, Tuscany, Italy. Agatha Depine@Unsplash
    • Wine tasting in Montepulciano, Italy. PictureSeeker@Unsplash
    • Sunflower fields in Italy! rehan shaik@Unsplash
    • Tuscany countryside in Italy. Fabrizio Lunardi@Unsplash
    • Piazza Pio II in Pienza, Tuscany, Italy. CC:Oschirmer
    • Great prosciutto hams in Italy! Daniel Uvegard@Unsplash
    • Vineyards galore in Italy! Amit Janco@Unsplash
    • Cycling the Tuscan Wine Classic: Pienza to Castellina via Siena Bike Tour

    View more photos

    Tuscan Wine Classic

     Photos Accommodation 

  • Accommodation

    Hotels

    These are sample hotels and may vary based on availability.

    Standard hotels
    The accommodations are 3- and 4-star hotels.

    Pienza: Relais il Chiostro

    Montalcino: Hotel Vecchia Oliviera

    Siena: La Villa STR

    Castellina: Hotel Palazzo Squarcialupi

    Luxury hotels - available on request

    Pienza: La Bandita

    Montalcino: Relais Mastrojanni

    Siena: La Certosa di Maggiano

    Gaiole: Castello Di Spaltenna

    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.

    Tuscan Wine Classic

     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

    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

    Equipment included with bike rental:

    • Helmet
    • 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.

    Tuscan Wine Classic

     Accommodation Dates & Prices 

  • Dates & Prices

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



    Jun 14–30 (Daily)Jun 14–30 (Daily) from € 1720Book
    Jul 1–31 (Daily)Jul 1–31 (Daily) from € 1720Book
    Aug 1–31 (Daily)Aug 1–31 (Daily) from € 1720Book
    Sep 1–30 (Daily)Sep 1–30 (Daily) from € 1720Book
    Oct 1–30 (Daily)Oct 1–30 (Daily) from € 1720Book

    Pricing details and extra options

    Included services

    • 6 nights in excellent 3- and 4-star superior hotels
    • 6 breakfasts
    • Luggage transfer
    • Route maps and itineraries, elevation gain
    • Sightseeing, restaurant, and shopping suggestions
    • RideWithGPS App: tracks & off-line navigation
    • Delivery and pick-up of bikes
    • Water bottle
    • Sales tax

    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.

    Tour Company

    Tuscan Wine Classic

     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

    There are lots of ups and downs on rolling hills and some climbs and challenging hills. The terrain is rarely flat.

    Roads:
    90 % are on small country roads( no cycle path). You will encounter a little more traffic when entering the villages and towns, you will see this especially going in and out of Siena.

    How to get there

    Tour start
    Nearest airport: Rome Fiumicino (FCO) and Florence Peretola, Italy (FLR)
    Nearest train station: Chiusi-Chianciano, Italy

    From either airport, take a train to Chiusi (www.trenitalia.com/tcom-en). Once in Chiusi, you can take a bus or taxi to get to Pienza. Take the bus from Chiusi to Montepulciano. The bus fare is approximately €4 per person, and the bus leaves every 30 minutes (40-50 minute ride). From Montepulciano, take the bus to Pienza (15-minute ride). Please note the bus from Montepulciano to Pienza is not available on Sundays.

    Tour end
    Nearest airport: Florence, Italy (FLR)
    Nearest train station: Castellina, Italy

    At tour end, buses and trains are available. By bus, go to Siena station where you can take a direct bus or train to Rome or other destination.

    Tips on getting to and from your tour

    Tuscan Wine Classic

     Dates & Prices Tour Reviews 

  • Reviews

      Write a review

    • ★★★★★ Michael Burkardt September 16, 2023

      Beautiful Countryside

      Our Bike Tour Company Cicloposse was exceptional, the best we ever had. There was not a single detail they missed, providing a booklet covering highlights for a given day of each town we'd pass through and as well as where to eat. We had a minor issue that was no fault of their own and the customer service was top notch. They're professional and knowledgeable. The only hiccup was a closed bridge that added a hour to our ride that day. Warning: unless you are a very strong rider get an E bike. Some climbs are miles long with a 14% grade.

    • ★★★★★ Amanda De Wet August 10, 2022

      Best holiday ever!

      Tuscany is beautiful, and it was amazing exploring by bike. We had the best time! Organization was excellent, local company was amazing and helpful, hotel accommodation was perfect - really cannot fault anything. Highly recommended!

      What was the date of your tour?
      July 2022
      How many tours have you completed?
      This was our first.
      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
    • ★★★★★ Rasp November 24, 2017

      BEST honeymoon ever!

      Well planned itinerary. Italian Guides were very friendly and knowledgeable and Set us up quickly and efficiently. Accompanying materials had great suggestions and option to do long or short ride every day was terrific.

      What was the date of your tour?
      October-nov
      How many tours have you completed?
      Several
      Difficulty (actual vs. expected)?
      As expected
      Who is this tour suitable for?
      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
      • 4/5 Ease of navigation
      • 5/5 Tour documents
      • 5/5 Local tour company services
      • 5/5 Route selection
    • ★★★★★ Snowball September 27, 2016

      Best local bike company ever!

      The local bike company were responsive to our needs and provided really excellent bikes. Accommodation was inspired.

      What was the date of your tour?
      July
      How many tours have you completed?
      15
      Difficulty (actual vs. expected)?
      As expected
      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 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
    • ★★★★★ Rotsen June 21, 2016

      A great way to embark on the endless search for a bad Tuscan wine.

      The only thing that wasn't absolutely perfect on this trip was the weather. The bikes provided were new and light, 25c tires, Shimano 105 11sp compact group w/32T cog for easy climbing.

      The route selection was wonderful, with a loop the first day to get acclimated and a loop the last day to provide options. The route cue sheets and maps included profiles and were spot-on so we hardly even bothered using the GPS routes they gave us to upload. We didn't have as much freedom to actually "tour" and stop at all of the sites as we usually do on tours due to the nearly constant threat of rain. Still we mostly avoided the rain until it arrived within last 5 or 6 kilometers on three of the days.

      The upside was that we had more time in the towns we spent the nights, for wine and cheese tastings, and of course Gelato (If you ever come across Pear-Pecorino-Honey gelato don't be shy.) The hotel accommodations were terrific! Our luggage always made it there before we did. The breakfasts, the only meals included, were above par Continental with great coffee and, at the least, hard boiled eggs.. A number of times we ate dinner at the Hotel Restaurant. Following our arduous afternoon and evening searches for bad wine we kind of liked being close to our beds.

      I am happy to admit that we failed utterly in our quest for a less-than-great Tuscan wine. We didn't bring any of the terrific Brunello's or Rosso's or Chianti's that we drank back, but did return home with 22kg of Pecorino Cheese most notably the Formaggio di Fosse. (My apologies to those who shuttled our baggage.) Someday soon we will return to continue our search, perhaps during a more dependably dry part of the year.

      What was the date of your tour?
      June 1
      How many tours have you completed?
      8
      Difficulty (actual vs. expected)?
      As expected
      Who is this tour suitable for?
      First-time bike tourists, 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
      • 5/5 Guides (if applicable)

    Tuscan Wine Classic

     Other Details Book this tour 

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