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.
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!
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
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
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
After breakfast, we depart by bike from the villa, heading towards San Quirico, an Etruscan-origin village known for its stunning Italian garden, the Horti Leonini. We’ll ride through Asciano and the Crete area, where we’ll be captivated by strange rock formations and lone farmhouses flanked by twin cypress trees. Pedaling through vineyards and forests, we’ll arrive in Siena, a medieval city famous for its beautifully preserved Gothic architecture. We’ll have time to explore the hidden medieval walkways, shop, and visit the iconic Piazza del Campo, where the Palio horse race takes place, before enjoying a free lunch on our own.
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: 47 km / 29 miles
Elevation gain/loss: +672 m (+2,204 ft) / -900 m (-2,952 ft)
Accommodation: Palazzo Massaini
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
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
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
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Add-ons:
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For a truly authentic experience of the Tuscan countryside, there’s no better base for your trip than Palazzo Massaini. Nestled in the heart of the Val d’Orcia, a UNESCO World Heritage Site, this estate is surrounded by vineyards, olive groves, and medicinal plants. The price of the trip is based on double occupancy, but a single supplement is available.
This place guarantees 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.
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 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. Prices are per person and for the entire week if cycling:
This is a list of clothing & footwear we recommend you bring:
Miscellaneous
First aid kit
Group sizes and pricing
Tuscany bike, wine, and food tours can be arranged for larger groups. Contact us to make arrangements.
Min. age requirements
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 medical and travel protection. To make your booking and traveling experience as carefree as possible, simply choose Redpoint—the official 57hours insurance partner!
Redpoint tailors their 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.
Once your booking is confirmed and your trip is paid in full, you will be offered to purchase Redpoint’s protection. If you need any help or require more information, 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.
Cancellations
Booking fees are non-refundable in all cases. During checkout, however, you can choose one of 57hours’ flexibility options:
Basic
Flexible
Super Flexible
