Tuscan Wine Classic: Pienza to Castellina via Siena

    5/5 (4)
    6 nights | 32 miles/day
    Self guided from EUR € 1290
    Rider Level: Enthusiast Electric bike tours
    5/5 (4)

    6 nights | 32 miles/day
    Self guided from EUR € 1290

    Rider Level: Enthusiast Electric bike tours

    Tap above to jump to different sections of this tour

    • Tuscan Wine Classic

      6 night self guided bike tour in Italy

      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 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, to 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).

      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

      Learn More

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

    • Daily program

      Day 1: Pienza
      Meet and greet in Pienza, the purest reniassance town in the world, for welcome and bike fitting. Pienza is a remarkable example of reniassance-era town planning. If you have even the least appreciation for beautiful architechture, it's a real treat to stroll around it's 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 (34 miles/55 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.
      Overnight in Pienza

      Day 3: Pienza – Montalcino brunello land (29 miles/46 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.
      Overnight in Montalcino

      Day 4: Montalcino – Siena and Monte Oliveto Abbey (36 miles/58 km)
      Today will take you through typical postcard scenery of Tuscany, Italy’s most photographed region—for good reasons. 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. Afterwards, 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.
      Overnight in Siena

      Day 5: Siena – Chianti hills (31 miles/50 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 hamlet. 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.
      Overnight in Castellina in Chianti

      Day 6: Castellina – Greve in Chianti and Panzano (34 miles/56 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 honeys and rich olive oil. Have a stop at Greve's main piazza, characterized by an original formation of irregular triangular shape, 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 poolspilling into the countryside of endless vineyards.
      Overnight in Castellina

      Day 7: Monteriggioni (optional 20 mile/32 km loop ride)
      The short bike ride allow you to visit Monteriggioni, literally a town-in-a-castle. Barely two hundred yards across, its eighty residents all reside within the picture-perfect round turreted walls that crown the hilltop visible for miles around.

      Surface and terrain

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


      Hotels

      These are sample hotels and may vary based on availability.

      The accommodations are 3- and 4-star hotels.

      Relais il Chiostro, Pienza
      www.relaisilchiostrodipienza.com

      or luxury upgrade:

      La Bandita, Pienza
      www.la-bandita.com

      Si Montalcino, Montalcino
      www.hotelsinmontalcino.com

      or

      Giglio Hotel, Montalcino
      www.gigliohotel.com

      La Villa STR, Siena
      www.lavilladistr.it

      or luxury upgrade:

      Villa del Sole, Siena
      www.villadelsolesiena.com

      Hotel Palazzo Squarcialupi, Castellina
      www.palazzosquarcialupi.com

      or

      Hotel Colle Etrusco, Castellina
      www.hotelsalivolpi.com

      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
      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 in 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

    • Dates

      Daily: Mar 15-Oct 31, 2022

      Prices

      Tour package

      Per person, double occupancy € 1290
      Single room surcharge (1 person/1 room) € 350

      Bike Rentals

      Hybrid touring bike € 180
      Road bike € 210
      Electrically assisted bike € 210

      Included services

      • 6 nights in excellent 3- and 4-star superior hotels
      • 6 breakfasts
      • All baggage transfers
      • Route maps and itineraries, elevation gain
      • Sightseeing, restaurant, and shopping suggestions
      • Pick-up of bikes and gear in Castellina
      • 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.


      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
        • Carbon forks
        • Shimano Deore components 27/30 speed
        • Gel saddle
        • Upright handlebar
        • 28 road wheels
      • Road bike, 20 speed, equipped with:
        • Carbon fiber or Scandium frame
        • Carbon forks
        • Shimano Ultegra compact gear 20 speed
        • Drop handlebar
        • 28 race wheels
      • Electrically assisted bike with 500w Bosch Internal battery

      *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)

      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

    • Route Map

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

      • Amanda De Wet 1 month ago

        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)