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 (or cruising on an e-bike!) 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.
Adventure Highlights
Cook up Italian classics:
After making your own meals and Italian specialties, pair them with delicious local 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 a peaceful, typically Tuscan & comfy farmhouse, stroll around its lush gardens and relax by the pool
Duration
7 days
Season
May through June, September through October
Group size
Up to 14 people
Accommodation
Palazzo Massaini is a place where nature, tradition, Tuscan food, and wine seamlessly blend. Palazzo Massaini produces quality wines, oil, and spirits with typical Tuscan aromas. This estate is located far away from the noisy city life, and every corner of it offers wonderful panoramic views and an enchanting atmosphere. Palazzo Massaini guarantees maximum privacy and an unforgettable stay. You’ll be based at one of its two beautiful farmhouses that combine elegance and modern comforts with the rustic Tuscan traditions. There’s even an infinity pool overlooking the countryside!
Accommodation
Comfort: Charming farmhouses in the Tuscan countryside
Difficulty
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 gaining up to 1,338 m (4,389 ft) in elevation— 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 you 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.
Difficulty
Easy: Good fitness required, riding 40-70 km (25-45 mi) per day (e-bike optional, possible to skip a riding day or two)
What's included
Included:
An experienced, local cycling guide with extensive knowledge of the area
7-day Tuscany bike, wine, and food tour
Accommodation for 6 nights in Palazzo Massaini (luxury farmhouse)
Six breakfasts, six gourmet dinners, and two lunches
Two cooking classes
Two wine tastings
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 Chiusi station to the accommodation
Transfer on Day 7 to the Chiusi station
Sales taxes
Add-ons (pricing shown at checkout):
Single occupancy room
Hybrid, road, gravel, or gravel e-bike rental
Not included:
Airfare to Italy
Train to Chiusi
Five lunches
Beverages
Laundry expenses
Guide gratuities — optional
Insurance — recommended, available to add at checkout
What's included
Guide, palazzo accommodation, most meals, 2 cooking classes, 2 wine tastings, 1 cheese tasting, transfers, support van
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!
Day 1: Welcome to the Val d’Orcia region
We begin our journey with a private van transfer to La Pieve di Massaini, our charming Tuscan accommodation. Surrounded by vineyards, olive groves, and medicinal plants, the villa offers the perfect setting for our adventure.
Once we’re all set with bikes and equipment, we’ll take a short test ride. At 6pm, we’ll gather for an introduction to the week ahead, and Chef Paolo will present the cooking lesson, starting with a cheese and olive oil tasting, followed by a delicious dinner at the villa.
Meals: Dinner Accommodation: Palazzo Massaini
Day 2: Montalcino & the art of Brunello wine
We saddle up for a 40 km (24.8 mi) cycling journey through landscapes that feel straight out of a Renaissance painting. The first half of the ride to Montalcino is 80% gravel, as we pedal through Sangiovese vineyards and head toward the city bearing its name. Montalcino’s medieval history is fascinating, with battles between the Florentine and Sienese city-states and a towering fortress built by the Sienese in the 14th century. We take time to explore Montalcino’s charming piazzas and the fortress.
A gentle downhill ride leads us to Castelnuovo dell’Abate to visit the Abbey of Sant’Antimo. We’ll enjoy a wine tour and a light lunch at Tenuta Fanti winery before returning to La Pieve. There are two options: we can ride back for a total of 48 miles (77.2 km), which is a challenging but rewarding way to end the day. The ball’s in your court. We finish with dinner at 13Gobbi in Montefollonico, where the specialty is cacio e pepe with pici pasta.
Meals: Breakfast, lunch, and dinner Cycling: 40 km / 25 miles Elevation gain/loss: +698 m (+2,290 ft) / -817 m (-2,680 ft) Accommodation: Palazzo Massaini
Day 3: Charming Pienza
We venture out on a 38 km (23.6 mi) bike ride that takes us to Pienza, the perfect example of Renaissance architecture, created by Pope Pius II. We’ll explore the meticulously designed Piazza Pio II, complete with a loggia, Palazzo Piccolomini, and the impressive Duomo. Along the way, we cycle through picturesque villages like Castelmuzio, Montisi, and Trequanda, enjoying the charm of secondary paved roads. We’ll stop to visit Pienza and enjoy lunch on our own before completing the last 4 km (2.4 mi) on gravel roads as we return to La Pieve.
Back at La Pieve, we’ll be ready for our first cooking session with Paolo at 4:30pm. In this hands-on lesson, we’ll prepare fresh pasta as a primo piatto. After a short rest with Italian spumante metodo classico sparkling wine as an aperitif, we’ll gather around the table with all the guests and savor the delicious dinner we’ve made together.
Meals: Breakfast and dinner Cycling: 38 km / 24 miles Elevation gain/loss: +763 m (+2,503 ft) / -764 m (-2,507 ft) Accommodation: Palazzo Massaini
Day 4: Monte Olivato Abbey & Le Crete Senesi region
After breakfast, we’ll hop on our bikes and depart from the villa. Following a picturesque crest road, we’ll ride by Monte Oliveto Maggiore Abbey, a Benedictine abbey built in the 13th century, famous for its frescoed cloister and stunning setting. Afterwards, we’ll travel through the fascinating area called Le Crete, Tuscany’s answer to the Badlands. Here, lush hills give way to clay domes and chalk cliffs, revealing a different side of Tuscany—an otherworldly, almost lunar landscape steeped in ancient, untouched beauty.
Tonight, we’ll gather at the villa for a pizza party! No Italian food & wine vacation is complete without a gourmet pizza evening, so we’ll sample a variety of delicious pizzas paired with carefully selected wines that will surprise and delight our taste buds.
Meals: Breakfast and dinner Cycling: 62 km / 38 miles Elevation gain/loss: +1,338 m (+4,389 ft) / -1,338 m (-4,389 ft) Accommodation: Palazzo Massaini
Day 5: Monticchiello & Bagno Vignoni spa day
We’ll embark on a bike ride to Monticchiello, a charming village that has preserved its medieval charm through the ages. From there, we’ll make our way to Bagno Vignoni, famous for its ancient healing pool. Today, we’ll enjoy a picnic lunch before relaxing in the thermal waters that have drawn travelers along the Via Francigena pilgrimage route for centuries. As we wander the streets of this remarkable village, we’ll explore its rich history of healing and renewal. Dinner tonight will be at either Bandita Townhouse or Podere il Casale.
Meals: Breakfast, lunch, and dinner Cycling: 28 km / 18 miles Elevation gain/loss: +387 m (+1,269 ft) / -529 m (-1,735 ft) Accommodation: Palazzo Massaini
Day 6: Radicofani area & Pici pasta
Today, we’ll cycle through gentle uphills and rolling hills, taking us to the medieval village of Radicofani. Here, we’ll explore the impressive fortress with its extraordinary panoramic views of the Val d’Orcia, Amiata, the Apennines, and Lakes Trasimeno and Bolsena. We’ll also uncover the tale of Ghino di Tacco, the charismatic gentleman bandit celebrated in Dante’s *Divine Comedy*, and stroll through Radicofani’s stately old town.
In the evening, we’ll join Chef Paolo for another hands-on cooking lesson, followed by our farewell dinner. All you need is an appetite and an apron!
Meals: Breakfast and dinner Cycling: 54 km / 34 miles Elevation gain/loss: +877 m (+2,877 ft) / -1,007 m (-3,303 ft) Longer cycling option: 71 km / 44 miles Longer option elevation gain/loss: +1,147 m (+3,763 ft) / -1,147 m (-3,763) Accommodation: Palazzo Massaini
Day 7: Departure
Have one final breakfast together with your group. Pack up and say your goodbyes—we will transfer you to the Chiusi train station around 10-11am. If you’d like to stay longer and explore the area, just ask your guides for some recommendations!
Meals: Breakfast
Adventure Architect
Let’s build something unique. Design your own adventure from the ground up and let us handle the rest.
Palazzo Massaini is a place where nature, tradition, Tuscan food, and wine seamlessly blend. Palazzo Massaini produces quality wines, oil, and spirits with typical Tuscan aromas. This estate is located far away from the noisy city life, and every corner of it offers wonderful panoramic views and an enchanting atmosphere. Palazzo Massaini guarantees maximum privacy and an unforgettable stay. You’ll be based at one of its two beautiful farmhouses that combine elegance and modern comforts with the rustic Tuscan traditions. There’s even an infinity pool overlooking the countryside!
Adventure, packed to go
A Journey Through Tuscany: Bike, Food, and Wine Tour
Adventure Brochure
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A Journey Through Tuscany: Bike, Food, and Wine Tour
Adventure Brochure
Adventure brochure
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Seasoned pros, local legends, and passionate adventurers—your trip is in the best hands.
5.00
Tommaso
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.
What others say about this adventure
5.00(15reviews)
N
Nevada L.
|October 2025
Far exceeded our expectations! The cycling routes were beautiful, the bikes were perfectly maintained, the accommodations were gorgeous and the food! So delicious. We loved every minute.
K
Kara L.
|July 2025
Our trip was amazing. We enjoyed every single day. The accommodations, the food, the guides, the bikes and the ride were all fantastic. I wouldn’t change one detail.
M
Miles W.
|June 2025
Breathtaking views, amazing food and wine, luxurious accommodations at the "farmhouse", warm and welcoming people.
Far exceeded our expectations! The cycling routes were beautiful, the bikes were perfectly maintained, the accommodations were gorgeous and the food! So delicious. We loved every minute.
K
Kara L.
|July 2025
Our trip was amazing. We enjoyed every single day. The accommodations, the food, the guides, the bikes and the ride were all fantastic. I wouldn’t change one detail.
M
Miles W.
|June 2025
Breathtaking views, amazing food and wine, luxurious accommodations at the "farmhouse", warm and welcoming people.
m
michael c.
|May 2025
Views, food and routes were amazing. The best.
B
Brad H.
|October 2024
The Cicloposse team covered everything - and flexed to every challenge. This was a really remarkable adventure of a great sequence of rides, fantastic food, wine, and cooking classes. Great lodging. And incredibly friendly staff of people to help at every point. Ready to do it all over again!
M
Michele G.
|September 2024
All I can say is Wow. We were treated like royalty! The accommodation was spacious and clean and I had a lovely view on Palazzo Massaini and the Olive Trees! The food was the best if the best! The Italian cooking classes were very enlightening with Chef Paulo who is a magnificent cook! The couple of hours at the SPA were also very relaxing! I must say it is really fun to cycle through the Tuscan hills and Valleys and be rewarded with lovely meals in the evenings! It is a great way also to connect and meet other people.
S
Susan K.
|September 2024
Everything was great - biking, meals, accommodation
L
Lucille R.
|September 2024
The biking tour was awesome and the food, wine and cooking classes were excellent!
K
Karin M.
|September 2024
Tuscany country side, Tuscany eating, Tuscany wines were all much more enjoyable and delicious and beautiful than expected!
C
Carolyn Hayes
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!
G
Glenn Massey
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!
S
Sean-Julia McEligot
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.
L
Leigh Gorman
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!
W
William L.
|June 2025
J
Jean S.
|October 2024
Things to know
Included:
An experienced, local cycling guide with extensive knowledge of the area
7-day Tuscany bike, wine, and food tour
Accommodation for 6 nights in Palazzo Massaini (luxury farmhouse)
Six breakfasts, six gourmet dinners, and two lunches
Two cooking classes
Two wine tastings
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 Chiusi station to the accommodation
Transfer on Day 7 to the Chiusi station
Sales taxes
Add-ons (pricing shown at checkout):
Single occupancy room
Hybrid, road, gravel, or gravel e-bike rental
Not included:
Airfare to Italy
Train to Chiusi
Five lunches
Beverages
Laundry expenses
Guide gratuities — optional
Insurance — recommended, available to add at checkout
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 fade away soon.
Vegetarian, vegan, and gluten-free diets can be accommodated, as well as certain intolerances or allergies!
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 gaining up to 1,338 m (4,389 ft) in elevation— 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 you 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—you can add it at checkout. The following bikes are available, choose the one that suits you best!
Road bike — great for those who love smooth, fast rides on pavement, this one’s built for covering long distances with ease. Ideal if you’re into performance and want to feel quick and light on the road.
Hybrid bike — a super comfy choice for relaxed rides through towns, countryside, or light trails. Perfect if you’re looking for versatility and aren’t too fussed about speed.
Gravel bike — ready for anything from paved roads to rougher paths, this bike is all about adventure and flexibility. A great pick if you’re curious to explore beyond the usual routes.
E-bike — for extra power when you need it, this bike makes hills feel flatter and long distances easier. Perfect if you want a boost but still enjoy a classic cycling experience.
Gravel e-bike (Cannondale Synapse Neo Allroad 2)— if you want to enjoy the ride without worrying about hills or long distances, this one’s for you. With its cutting-edge technology and unbeatable performance, it’s perfect for cycling through all types of terrain, ensuring a smooth and comfortable ride.
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
Miscellaneous
Passport, wallet and ID
Waterproof, zip-lock type plastic bag for your valuables
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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.
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.
The price for this Tuscany bike, wine, and food tour is based on twin-share rooms, but a single occupancy room can be arranged at an additional fee. You can add it to your booking at checkout.
Solo travelers are welcome to join, but securing a single occupancy room for themselves is mandatory—you’ll be able to add it to your booking at checkout.
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 insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.
Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.
Deposits
Secure your spot with a 30% deposit upon booking! The remaining 70% of the trip price must be paid 90 days prior to departure at the latest. If booking within 90 days of departure, the full amount is required at the time of booking.
Cancellations
Booking fees are non-refundable after a 48-hour grace period. During checkout, however, you can choose one of 57hours’ flexibility options—Basic, Flexible, or Super Flexible. Depending on which one you choose, a different cancellation policy will apply to your booking.
Basic
If cancelled within 48 hours of booking, a full refund will be issued.
If cancelled 90 or moredays before departure, a 70% refund of the total trip price will be issued.
If cancelled within 89days of departure, no refund will be issued.
Flexible
If cancelled within 48 hours of booking, a full refund will be issued.
If cancelled 90 or moredays before departure, a full refund of the total trip price will be issued.
If cancelled 60-89 days before departure, a 50% refund of the total trip price will be issued.
If cancelled within 59days of departure, no refund will be issued.
Super Flexible
If cancelled within 48 hours of booking, a full refund will be issued.
If cancelled 60 or moredays before departure, a full refund of the total trip price will be issued.
If cancelled within 59days of departure, a 50% refund of the total trip price will be issued.
Have more questions?
Our team is here to answer your questions and plan with you.
Book a fully private 57hours adventure for your group. We customize dates, group sizes, terrain, guides and accommodations — so your adventure fits your people and your goals.
