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Every corner of Tuscany is postcard-worthy, and you’ll witness this firsthand during a week-long exploration of the Italian countryside. Spring and fall transform the birthplace of Renaissance into a truly magical destination, making it the ideal season for a bike-food-wine tour. Travel back in time by pedaling through its rolling hills, medieval towns, and vineyards, and learn something new about its history and culture each and every day. To get the full picture, take a cooking class or go for a wine, cheese, or olive oil tasting. The accommodation you’ll be staying at is absolutely divine—in a wonderful farmhouse, seamlessly blended with the unique landscape surrounding it. It’s time to finally book your vacanze italiane, taste la cucina toscana, and experience la dolce vita.

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Adventure highlights

  • Return home with new skills

    After making your own meals and Italian specialties, pair them with delicious wine and enjoy

  • Dreamy Tuscan landscapes

    Spend a week cruising through the bucolic setting and medieval towns of Val d’Orcia, a UNESCO site

  • Charming accommodation

    Stay at peaceful and comfy farmhouses, stroll around its lush gardens


Hop onto a bike and explore gorgeous loop rides of the spectacular Val d’Orcia UNESCO site! This 7-day adventure is much more than just a bike tour—you’ll also do cooking classes and go for wine, cheese, and olive oil tastings. Your guides designed this trip with the Tuscan culture and history in mind, as this week-long trip is a total immersion into all-things Italian. There will be a support vehicle by your side, all breakfasts and dinners are included, and you’ll be based at gorgeous, historic farmhouses. Let your next holidays be Italian!

  • Meet your guides at the Chiusi train station at around 1 pm. Begin your journey with a private van transfer to Palazzo Massaini, your charming Tuscan accommodation. The villa is surrounded by vineyards, olive groves, and medicinal plants, providing the ideal setting for your adventure! This is in the Val d’Orcia region—so it’s exactly what you picture when you think of quintessential Italian countryside!

    After all participants are set up with bikes and equipment, you’ll do a short bike ride test. And after that, your first cooking class! Paolo will help you prepare fresh pasta as primo piatto, which you’ll pair with an Italian Spumante sparkling wine. Get some rest for tomorrow as that’s when you’ll start cycling!

    Meals: Lunch and dinner
    Activity: Cooking class
    Accommodation: Palazzo Massaini

    Driveway to Palazzo Massaini
  • Saddle up for a 40-km (25-mile) cycling journey that takes you through landscapes reminiscent of a Renaissance painting. First stop is the ancient Roman spa of Bagno Vignoni, where you’ll find the Square of Sources, a tank containing water coming from the underground aquifer. Pedal through the sea of San Giovese grapes, the heart of Brunello di Montalcino, and visit the city bearing its name. Montalcino’s medieval history is intriguing, with battles between Florentine and Sienese city-states, and a towering fortress built by the Sienese in the 14th century.

    Now the climb to Castiglione d’Orcia is the challenging part of the day! Once at the top, enjoy a long downhill until you reach the Romanesque abbey of Sant’Antimo that dates back to the time of Charlemagne. For your last effort of the trip, climb a gentle uphill to Montalcino, a hilltown famous for the Brunello wine. Enjoy a wine tour at Solaria winery (where you’ll taste the Brunello wine, the rosso and the supertuscan) and a light lunch at Tenuta Fanti Estate before returning to La Pieve for your second cooking lesson. The day concludes with a cheese and olive oil tasting, followed by dinner at Ristorante di Daria.

    Meals: Breakfast and dinner
    Activity: Wine tour, cooking class, cheese and olive oil tasting
    Cycling: 40 km / 25 miles
    Elevation gain/loss: +698 m (+2,290 ft) / -817 m (-2,680 ft)
    Accommodation: Palazzo Massaini

    Montalcino town in Tuscany
  • Venture out for a bike ride that leads you to Pienza, a 1458 town transformed into the epitome of Renaissance perfection by Pope Pius II. Explore the meticulously designed Piazza Pio II, adorned with a loggia, Palazzo Piccolomini, and the impressive Duomo. After tasting delicious cheese from sheep milk, continue to the next village Montepulciano (known as the Pearl of the Sixteenth Century), and enjoy lunch at a small farm specializing in cinta senese pig.

    After learning about the traditional black pig, what they eat, and how they live, you’ll enjoy a special meal ending with Cantucci and Vin Santo wine. Back in the saddle, the last stop is Montepulciano. Bold cypress trees line the route to the Orcia Valley where you will bike through fields which have inspired Renaissance painters. Dinner is at La Porta di Bacco.

    Meals: Breakfast, lunch and dinner
    Cycling: 38 km / 24 miles
    Elevation gain/loss: +763 m (+2,503 ft) / -764 m (-2,507 ft)
    Accommodation: Palazzo Massaini

    Pienza in Tuscany
  • Today you’re crossing the Orcia Valley! you’ll first ride to the village of Monticchiello and afterward to the hot springs village of Bagno Vignoni. The spa here is very old and there’s also an impressive town hall from the Renaissance to visit.

    The historic centre is well worth the visit with its characteristic hilltown-plan of alleys and small piazzas. You’ll enjoy the thermal pool, feeling the healing power of the hot springs. The therapeutic pool promises a journey of revitalization unlike any other! Head back to your villa for a cooking lesson followed by dinner.

    Meals: Breakfast, lunch, and dinner
    Activity: Hot springs and cooking class
    Cycling: 28 km / 17 miles
    Elevation gain/loss: +387 m (+1,270 ft) / -529 m (-1,735 ft)
    Accommodation: Palazzo Massaini

    Landscapes of Tuscany
  • Start from the villa and reach Radicofani, a medieval and enchanting village with the Rocca fortress from the dark ages before the year 1,000—one of the most impressive fortresses in Tuscany. Radicofani is included in the Park of Val d’Orcia and Via Francigena (which was the main route followed by pilgrims in antiquity who went to Rome). Still, it’s quite off the beaten path so this will mostly be a quiet day.

    From Radicofani, reach another secluded road called Le Conie and reach Bagni San Filippo. Enjoy the flowy downhill back to the valley. It rises along Francigena Road near the old Spedaletto Castle, shelter for wayfarers, who—back in the Middle Ages—wanted to get to Rome. The castle has been adapted into a granary, a fortified farm. On the way back, stop at the cheese farm to taste the delicious Pecorino di Pienza, 100% sheep milk with a variety of aging. Then you’ll have another incredible dinner, in Abbadia Sicille at the Fondo restaurant.

    Meals: Breakfast and dinner
    Cycling: 70 km / 45 miles
    Elevation gain/loss: +1,147 m (+3,763 ft) / -1,179 m (-3,868 ft)
    Accommodation: Palazzo Massaini

    Pici pasta in Italy
  • Begin your day by pedaling to San Quirico, an Etruscan origin village with a superb example of an Italian garden: the Horti Leonini. Pass through the Asciano and Le Crete area, where you’ll notice strange rock formations, lone farmhouses, and cypress trees.

    Keep pedaling through the vineyards and forests until you reach Siena, a medieval city with beautifully preserved Gothic architecture. The entire city was built around the Piazza del Campo. Here you’ll have time to stop while exploring the many hidden medieval walkways. Visit the shell-shaped square where the Palio horse race is held. Before returning back to your villa for one final night, have a farewell dinner at a restaurant La Bandita in Pienza.

    Meals: Breakfast and dinner
    Cycling: 47 km / 30 miles
    Elevation gain/loss: +672 m (+2,204 ft) / -900 m (-2,952 ft)
    Accommodation: Palazzo Massaini

    Piazza del Campo in Siena
  • Have one final breakfast together with your group. Pack up and say your goodbyes—your guides will transfer you to the Chiusi train station around 10-11 am. If you’d like to stay longer and explore the area, just ask your guides for some recommendations!

    Meals: Breakfast

    Group of people in Tuscany
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Meet your guides

Tommaso Tornaghi
Tommaso Tornaghi
Tommaso is a passionate tour leader with a great passion for cycling, swimming, tennis, and basketball. Currently pursuing studies in sports science and physical education at Rome University, he harmonizes his academic pursuits with a deep love for physical activity. Tommaso’s favorite tours combine cycling and the art of cooking, and no wonder—he also went through special training for pastry making and he’s very passionate about the culinary arts and history.
Cicloposse is a bike tour operator based in Tuscany, dedicated to delivering unforgettable cycling experiences and active vacations throughout Italy. With their passion for biking and love for travel, they are committed to providing excellent services while being socially responsible and creating low-impact trips that respect the environment. They pride themselves in working with local people and small businesses, enabling their guests not only to experience the authentic essence of Italy, but also to positively impact communities they visit. Cicloposse offers seamless organization, meticulous attention to detail, and fostering genuine connection with their guests.


5.00 (4 reviews)
Carolyn Hayes (source: Google Reviews)

This was a fabulous experience in every sense – majestic 13th century towns, incredible vistas, wonderful caring guides, amazing farmhouse accomodation, a world class chef, a genuine family with local knowledge and a generous spirit wanting you to feel and live the Tuscan way.
We felt like we had the privilege to be brought into their world and didn’t want to leave. The cycling was outstanding and cooking lessons encouraging and informative – I highly recommend you do this!

Glenn Massey (source: Google Reviews)

Cycling & Cooking in Tuscany Guided Tour–my wife and I had a great experience with Cicloposse on this tour. Cicloposse is a LOCAL, FAMILY-OWNED business based in Pienza. They are avid cyclists, know all the routes, and they hand select the other people involved in the tour experience–Sabrina, our gracious host at the villa, the farmers, wineries, chefs, etc to ensure the highest levels of hospitality. Each day we rode to a different destination (25-35 mi) and then returned home to our lovely villa in time to clean up for dinner. We had a diverse set of cycling skills within our group, but our guides, Thomasso and Panos, kept us all organized. All of our needs were met and not a single thing was left to chance. Breakfast, lunch and dinner were all included every day, so no need to find them on our own. One or more of the family members joined us at every meal, making us feel like part of their family. They made sure that my wife’s dietary and food allergy needs were met at each meal. The cooking classes were fun, informative and, above all, the food we made was great! And of course, there was beautiful Tuscan scenery, luscious olive oil and delicious wine! It was very emotional for us to say goodbye to all of our new friends when the tour ended. Grazie mille, Guiliana and the Cicloposse family!

Sean-Julia McEligot (source: Google Reviews)

This was the best trip EVER (went in June 2023). This is run by Italian locals, NOT a large US tour company. All spoke English well. Great accommodations, cooking experiences were to die for, and the biking was well managed and fun. The bikes were well maintained, in working order and they were very accommodating. I’m just afraid that they will become TOO popular as they are soooo excellent.

Leigh Gorman (source: Google Reviews)

This is the ONLY way to truly experience Tuscany! It was up there with one of our best experiences ever! The only thing we regret is not bringing our kids…..but I guess we’ll have to come back!

Things to know

  • What you get on this adventure:

      • An experienced, local cycling guide with extensive knowledge of the area
      • 7-day Tuscany bike, wine, and food tour
      • Accommodation in Palazzo Massaini for 6 nights (luxury farmhouse)
      • Bike rental — hybrid, road bike, gravel, or e-bike (available to rent upon checkout)
      • Six breakfasts, six dinners, and two lunches
      • Two cooking classes
      • One wine tour
      • One cheese tasting
      • All maps, trip notes, and detailed route directions
      • All shuttles and technical assistance
      • Support van
      • Luggage transfers
      • Services of experienced guides
      • Cicloposse water bottle
      • Transfer on Day 1 from the Chiesi station to the accommodation
      • Transfer on Day 7 to the Chiesi station
      • Sales taxes

    What’s not included:

      • Airfare to Italy
      • Train to Chiusi
      • Five lunches
      • Beverages
      • Laundry expenses
      • Guide gratuities — optional
      • Travel and medical insurance — optional
  • For a truly authentic experience of the Tuscan countryside, there’s no better base for your trip than Palazzi del Papa or Palazzo Massaini. Nestled in the heart of the Val d’Orcia, a UNESCO World Heritage Site, these estates are surrounded by vineyards, olive groves, and medicinal plants. The price of the trip is based on double occupancy, but a single supplement is available.

    These places guarantee maximum privacy and an unforgettable stay. The feeling of peace and serenity here is like nowhere else in the world. It’s exactly what you imagine when you think of the Tuscan countryside—and soon you’ll be strolling through picture-perfect bucolic landscapes.

    More info on these lodgings is found above.

  • Your guides will take you out to dine every evening, and you’ll get to discover simple osterias, family trattorias, and elegant restaurants. Tuscan cooks take advantage of the freshest seasonal products and tamper with their natural state as little as possible. In Italy, a meal can tell a lot about the local culture, so pay attention! A variety of bike tours get you deep into some of the world’s most awe-inspiring landscapes, while the sampling of food and beverages let you dig into the Tuscan way of life. Each meal will be paired with a Tuscan wine: besides the must Brunello, Nobile and Chianti classico you will learn about and sip Morellino di Scansano, Super Tuscan & Bolgheri, Orcia doc, Vin Santo, Syrah di Cortona.

    Actually tasting all that delicious food won’t be the only thing you’ll be doing—you’ll also get to make it by yourself! Most days include a hands-on cooking class or a visit to local artisan shops to taste local food, wine, and cheese. You can check out the itinerary to learn more about what your days will look like.

    You’ll leave this Tuscany food, wine, and bike tour feeling inspired and eager to make delicious Italian meals! Anyone becomes enamored with the Italian way of life and cuisine, so the enthusiasm to cultivate these lessons into your daily life won’t linger soon.

    Vegetarian, vegan, and gluten-free diets can be accommodated, as well as certain intolerances or allergies!Cooking class in Tuscany

  • The itinerary of this Tuscany bike, wine, and food tour is designed to make it a true vacation, not a race! The pace is leisurely in order to enjoy the scenery along the way. You will be covering an average of 25-45 miles (40-70 km) per day and you can find day-by-day distance breakdowns in the itinerary. You can choose between a hybrid bike, race bike, e-bike, and gravel bike. The pace is about 9-12 miles/hour (15-20 km/hour) – but this is just an average. Covering shorter distances is also possible. If you want to skip riding on a particular day and do something else (or just stay at the villa), just join your group in the late afternoon or in the evening.

    Advanced cyclists who’d like to kick it up a notch can be accommodated as well—you’ll just have to follow the route on an app in case want to go faster, while the guide stays with the group. Keep in mind that back-up transportation and support will be available throughout the adventure.

    Note that it’s possible to have non-riding participants! There will be optional activities available. Contact us for more information.

  • Yes! If you’d like to skip the hassle of bringing a bike with you to Tuscany, your guides offer bike rental. Prices are per person and for the entire week if cycling:

      • Hybrid bike — $195
      • Race bike, e-bike, or gravel bike — $270
  • This is a list of clothing & footwear we recommend you bring:

      • Cycling shorts (padded shorts recommended, try them out before the tour)
      • Riding jerseys
      • T-shirts and/or casual shirts (quick-dry)
      • Bathing suit
      • Bike socks and/or sports socks (quick-dry)
      • Dress or casual socks
      • Windbreaker or cool-weather jacket (rainproof and breathable)
      • Light rain jacket or poncho (cheap version is fine—insurance on sunny days!)
      • Bike shoes
      • Riding gloves
      • Underwear (quick-dry)
      • Sweater or fleece
      • Slacks or light jeans (quick-dry, wrinkle resistant)
      • Belt
      • Comfortable walking shoes
      • Sandals


      • Passport, wallet and ID
      • Waterproof, zip-lock type plastic bag for your valuables
      • Health insurance card
      • Travel insurance card
      • Cash, credit cards and/or travel cheques
      • Electronic chargers (for camera, MP3 player, e-reader, cell phone)
      • Adaptors or convertors

    First aid kit

      • Insect repellent
      • Antiseptic cream or antibiotic ointment
      • Antihistamine tablets for hay fever
      • Sunscreen and total bloc
      • Throat lozenges or hard sweets
      • Painkillers
      • Band-aids and ‘Second Skin’ for blisters
      • Rehydration salts
      • Multi-vitamins
  • Group sizes and pricing

      • For this Tuscany bike, wine, and food tour, the usual client-to-guide ratio is 6:1.
      • It takes a minimum of 6 people for this tour to operate. The maximum group size is set at 14 participants.
      • Single supplement is available at an additional cost of $535.
      • Participants need to book the Tuscany bike, wine, and food tour at least 45 days in advance.
      • Participants will receive tour confirmation at the latest 60 days prior to the start of the tour. If the minimum number is not reached, there’s the option of moving the tour to another scheduled week or getting a full refund.

    Tuscany bike, wine, and food tours can be arranged for larger groups. Contact us to make arrangements.

    Min. age requirements

      • If you are older than 18, you’re good to go.
      • Minors older than 16 may be permitted to join the hike on a case-by-case basis, but must be in the presence of a parent or legal guardian.

    If your group has hikers under the age of 18, contact us prior to booking to make arrangements.

  • Your Tuscany bike, wine, and food tour begins at Chiusi train station. Chiusi is a charming little town very well connected by rail. If you’re flying in, the nearest airports are Florence Airport (FLR), Pisa Airport (PSA), and Rome Fiumicino Airport (FCO). From there, you can reach Chiusi by bus, train, or car—Chiusi is a major stop on all Rome-Florence lines.

    You’ll meet your guide at 1 pm on Day 1 of the tour at Chiusi train station. Make sure to be fresh and ready for Day 1, so flying in a day earlier and booking your accommodation for the night might be a good idea.

  • We highly recommend that you cover all your bases with both emergency medical and travel insurance.

    With medical insurance, if you have an accident or medical emergency on or off the mountain, you’ll avoid paying out of pocket for costly expenses. This covers everything from hospital treatments to emergency air transportation and more. Travel insurance covers canceled flights, natural disasters and other scenarios that may interrupt your travel plans.

    We also expect you to respect local regulations and take measures to protect yourselves, your guides, and the communities you’re traveling to. If you need assistance selecting the right insurance for your group, let us know and we will be happy to help!

  • Deposits

    You can secure one of the set dates with a 30% deposit upon booking. The remaining 70% of the trip price is to be paid 90 days prior to departure, at the latest.

    Secure your early bird spot with a 10% deposit! This tour gets sold out very quickly, but with early-bird booking, you will be the first one to know about any new upcoming dates. Pick your preferred dates without the risk of your bucket list adventure selling out!

      • Only 10% of the total amount should be paid as a deposit upon booking. This deposit is non-refundable, but can be transferred to another 57hours adventure anytime in case the dates don’t suit you.
      • Once the dates are set, you can confirm your booking by paying another 20% of the total amount.
      • The final balance is due 3 months (90 days) prior to departure.


    Booking fees are non-refundable in all cases. During checkout, however, you can choose one of 57hours’ flexibility options:


      • In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
      • For cancellations 60 or more days before the trip, you are eligible for a 70% refund of the trip price.
      • For cancellations 0-59 days before the trip, there is no refund.


      • In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
      • For cancellations 60 or more days before the trip, you are eligible for a full refund of the trip price.
      • For cancellations 30-59 days before the trip, you are eligible for a 50% refund of the trip price.
      • For cancellations 0-29 days before the trip, there is no refund.

    Super Flexible

      • In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
      • For cancellations 30 or more days before the trip, you are eligible for a full refund of the trip price.
      • For cancellations 0-29 days before the trip, you are eligible for a 50% refund of the trip price.
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