Tuscany Bike Tours

 Tuscany Cycling Tours

Discover the enchanting landscapes of Tuscany with Hirides, offering unforgettable bike tours that combine scenic routes, rich culture, and unparalleled adventure. Pedal through rolling vineyards, olive groves, and mediaeval hilltop towns while soaking in the timeless beauty of Italy’s most iconic region.
Whether you’re an experienced cyclist or prefer a more relaxed pace, our Tuscany cycling tours are designed to suit all skill levels and interests. With thoughtfully planned itineraries, top-of-the-range E-Bikes, and expert local guides, Hirides ensures every mile of your journey is as memorable as the stunning scenery that surrounds you.
This is more than just a bike ride—it’s an opportunity to delve into Tuscany’s rich history, savour its world-renowned cuisine, and experience the magic of its rolling hills and charming villages. Book a Tuscany bike tour vacation today!

 Why Choose a Cycling Holiday in Tuscany

A cycling holiday in Tuscany is the perfect way to explore one of Italy’s most stunning regions. With breathtaking landscapes, rich history, and exceptional food and wine, Tuscany offers an unforgettable experience on two wheels.
Cycle through rolling hills, picturesque vineyards, and iconic cypress-lined roads, each route showcasing Tuscany’s natural beauty. Explore historic towns like Siena and San Gimignano, uncover hidden villages, and immerse yourself in the region’s timeless charm. You can also savour every moment off the bike with freshly prepared Italian dishes, local cheeses, and world-renowned wines like Chianti and Brunello di Montalcino.
Whether you prefer leisurely rides through Chianti or the thrill of tackling the famous Strade Bianche gravel roads, Tuscany has trails for every skill level. Its mild climate makes it ideal for cycling nearly year-round, with spring, summer, and autumn offering stunning views and perfect conditions.

Bike Tours in Tuscany Overview

At a glance

  • 6 Days | 5 Nights | 5 Rides

  • Roads type: 60% Gravel – 40% Tarmac

  • Bike: e-Gravel provided

Daily itineraries

2 different itineraries to chose from every day.
You are free to mix them to create your personal vacation.

Experience Level
Regular itinerary: Suitable for RECREATIONAL LEVEL cyclists

Total distance: 129 miles (211 km)
Total climb:  13,170 feet (4,015 m)

Extended itinerary: Suitable for ENTHUSIAST LEVEL cyclists

Total distance: 181 miles (290 km)
Total climb:  18,700 feet (5,700 m)

Daily itineraries

Upon your arrival at Florence Airport (FLR), we’ll be there to greet you. A comfortable three-hour van transfer will take you to the heart of Val d’Orcia, where your Tuscan adventure begins. After checking into your hotel and enjoying a light lunch, you’ll have two options:

  • Relax and unwind at the hotel.
  • Get your bike set up and head out for a ride to explore the stunning surroundings.

Cycling Through a Biker’s Paradise

From the moment you start pedalling, you’ll be immersed in the beauty of Val d’Orcia. Ride through rolling slopes to Pienza, a UNESCO World Heritage Site and a Renaissance gem known as the city of the Pope. From there, descend to the iconic Cappella della Vitaleta, one of Tuscany’s most photographed landmarks.

Evening Charm and Culinary Delight

As the sun sets, enjoy an aperitivo at Bagno Vignoni, a charming 16th-century village. Here, you’ll be warmly welcomed to Osteria del Leone, where your culinary journey through Tuscan cuisine begins. Relish exceptional dishes, modern yet rooted in tradition, paired with the finest regional wines. After dinner, return to your well-appointed hotel in Val d’Orcia for a restful night.

Cycling Itineraries:

  • Regular Itinerary (Recreational Level Cyclists):
    • Distance: 15 miles (24 km)
    • Total Climb: 1,480 feet (450 m)
  • Extended Itinerary (Enthusiast Level Cyclists):
    • Distance: 19 miles (30 km)
    • Total Climb: 1,840 feet (560 m)

Today’s ride takes you deep into the breathtaking vineyards of Brunello di Montalcino, a region renowned for its world-class wines and picturesque landscapes. The route winds through historic dirt roads of the Val d’Arbia, Crete Senesi, and Val d’Orcia, offering stunning views and unique cycling experiences. Highlights include the Castello di Argiano, San Angelo in Colle, the serene Abbazia di Sant’Antimo, and some of the most beautiful Brunello vineyards. This is also the setting for the Eroica Montalcino, where historic bicycle enthusiasts gather to challenge themselves in late May.

A Toast to Tuscany and a Night in Siena

As the day winds down, enjoy an aperitivo at Osteria Le Logge, a delightful prelude to the evening ahead.

In Siena, you’ll experience the charm of one of Italy’s most iconic cities. Stroll through the historical centre, visit a cellar in the Jewish ghetto, and marvel at the beauty of Piazza del Campo, the city’s heart. Dinner is served in one of Siena’s finest trattorias, offering a warm, elegant atmosphere and exceptional regional cuisine. Pair your meal with Tuscany’s celebrated Chianti “Gallo Nero”, the King of Tuscan red wines. After this unforgettable evening, return to Val d’Orcia for a restful overnight stay.

Cycling Itineraries

  • Recreational Level Cyclists:
    • Distance: 22 miles (36 km)
    • Total Climb: 2,820 feet (860 m)
  • Enthusiast Level Cyclists:
    • Distance: 34 miles (54 km)
    • Total Climb: 4,180 feet (1,270 m)

Day 3 takes you to the enchanting Chianti region, offering a delightful change of scenery without sacrificing the thrill of riding Tuscany’s iconic dirt roads. This route is inspired by the famous vintage bike event, L’Eroica, held in Gaiole, and features a stunning ride along the ridge of the rolling Chiantishire hills.

You’ll pass through charming villages whose names grace the labels of the finest Chianti wines: Panzano in Chianti, Fonterutoli, Radda in Chianti, and Gaiole in Chianti, to name just a few. The landscape, steeped in history and viticulture, makes for an unforgettable ride.

An Evening in Montepulciano: Vino Nobile and Fine Dining

As the sun sets, we head to Le Logge del Vignola for an elegant dinner in Montepulciano, an ancient Etruscan city dating back to the 4th century. Known for its renowned Vino Nobile di Montepulciano, the evening will feature a tasting of this celebrated Tuscan red wine.

Your dinner will be served in an elegant restaurant located in the upper part of the city, offering a warm and inviting atmosphere, impeccable service, and a modern interpretation of regional Tuscan cuisine crafted with the highest quality ingredients.

After dinner, return to Val d’Orcia for a restful overnight stay.

Cycling Itineraries

  • Recreational Level Cyclists:
    • Distance: 32 miles (52 km)
    • Total Climb: 3,050 feet (930 m)
  • Enthusiast Level Cyclists:
    • Distance: 47 miles (75 km)
    • Total Climb: 4,790 feet (1,460 m)

On day 4, we leave the enchanting Chianti vineyards behind to embark on the southern loop of L’Eroica, a route celebrated for its scenic gravel roads winding through the Crete Senesi. This ride takes us through some of Tuscany’s most picturesque villages, including the charming Lucignano, a personal favorite.

The route features climbs through the Sante Marie hills and the famed ascent dedicated to cycling legend Fabian Cancellara, where many iconic moments of the Strade Bianche races have unfolded.

A Tuscan Feast in Trequanda

As the day concludes, we gather at Il Conte Matto, nestled in the mediaeval village of Trequanda (12th century). Begin your evening with an aperitif at sunset, enjoyed on a terrace overlooking the rolling hills of Crete Senesi.

Dinner is a celebration of Tuscany’s finest flavours, with Chianina beef and Cinta Senese pork taking center stage. Indulge in the legendary Bistecca alla Fiorentina, widely considered the pinnacle of Italian grilled meats. Pair your meal with selections from the cellar, which boasts over 300 Tuscan wines, including offerings from the boutique wineries of Montepulciano.

After dinner, return to Val d’Orcia for a peaceful overnight stay.

Cycling Itineraries

  • Recreational Level Cyclists:
    • Distance: 31 miles (50 km)
    • Total Climb: 2,770 feet (845 m)
  • Enthusiast Level Cyclists:
    • Distance: 44 miles (71 km)
    • Total Climb: 3,970 feet (1,210 m)

Today’s journey takes us through the heart of Val d’Orcia, a UNESCO World Heritage Site and the Renaissance soul of Tuscany. Ride through rolling hills to the famed vineyards of Montepulciano, home to the renowned Vino Nobile di Montepulciano, one of Tuscany’s signature red wines.

Beyond the vineyards, the route traverses the sweeping, open landscapes of the Crete Senesi, dotted with rugged beauty. Along the way, we pass through two small fortified hilltop villages, frozen in time, where the charm of Tuscany’s past comes alive.

An Evening at Boccon Divino

As the sun sets, we arrive at Boccon Divino, an iconic trattoria in Montalcino that has been a culinary institution since 1992. Set against a postcard-perfect backdrop, this gem offers timeless recipes deeply rooted in Tuscan tradition.

Nestled in the homeland of Brunello di Montalcino, Boccon Divino is the ideal place to savor niche wines crafted by small, dedicated winemakers. Pair your meal with these exceptional wines for an authentic taste of Tuscany’s finest.

After dinner, return to your accommodation in Val d’Orcia for a restful night.

Cycling Itineraries

  • Recreational Level Cyclists:
    • Distance: 29 miles (49 km)
    • Total Climb: 3,050 feet (930 m)
  • Enthusiast Level Cyclists:
    • Distance: 37 miles (60 km)
    • Total Climb: 3,950 feet (1,200 m)

After breakfast, it’s time to say goodbye and start the journey back home.

If you are returning home, we will accompany you to Florence Airport (FLR).
If you plan to continue your stay in Italy, we will be happy to assist you.

We hope to see you soon on one of our next tours on the roads of Italy !

Tours Calendar

HiRides -Tuscany - Strade Bianche Bike Tour
HiRides -Tuscany - Strade Bianche Bike Tour
HiRides -Tuscany - Strade Bianche Bike Tour

 Excursions

The bike tours we have prepared will keep you busy from morning to early afternoon. Once  you return to the hotel you can choose whether to wait for dinner time in complete relaxation, or follow your guides to some interesting experiences that they have prepared for you.
Every day they are committed to offer you a unique experience, you will surely love!

Piazza del Campo: a surprise at first sight.
The Basilica of San Domanico: a historical gothic church which preserves the remains of Saint Catherine.
Via Francigena: a fundamental pilgrimage route in the history of the city where the most important buildings and monuments can be found: Palazzo Monte dei Paschi, Palazzo Tolomei, Palazzo Chigi Saracini.
Cathedral of the Assumption: a jewel of gothic architecture and treasure chest containing the famous works of Michelangelo, Donatello and Bernini.

An extraordinary 16th century hill top village that rests on the rolling hills of Siena like a natural balcony.
Montepulciano has Etruscan and Roman origins that developed in the Middle Ages and then acquired all its beauty during the Renaissance. It is an open-air set where several of the most famous movies have been filmed: The English Patient (1996), The Twilight Saga, New Moon (2009).
In addition to a guided tour of the city, you can take a “gourmet tour”,  including tasting the Nobile and Rosso di Montepulciano wines and enjoy a walk through the alleys of the historic center that lead to discovering the village and its history.

Pienza, the “Ideal Fortressed City” built by Pope Pius II (1458), which dominates Val d’Orcia (a UNESCO World Heritage Site since 2004). Let’s start the visit: The proportions of Piazza Pio II embody that sense of harmony sought in the Renaissance. The square is home to the main cathedral and Palazzo Piccolomini with access to the city walls.
The Cathedral dominates Piazza Pio II with a beautiful white stone façade. Different styles coexist here: the 3 naves recall German churches, the façade recalls Florentine infuence and there are also Gothic elements. The Bastions: Pienza was a fortified city with mighty bastions that now offer the opportunity to take a wonderful walk to admire a breathtaking view of Orcia.

Brunello di Montalcino is a Tuscan red wine, produced in the Montalcino area and is considered one of the longest-lived Italian red wines.
Officially “born” in 1869, it is obtained from a single type of grape: Sangiovese da Brunello.
It is undoubtedly one of the best red wines in the world and the best productions/vintages are admired by enthusiasts from all over the world.
Start with a tour of the vineyards followed by a tasing in a historical vat wine cellar starting from the younger Rosso di Montalcino  and then some Brunellos from different vineyards and vintages.

Culinary Highlights of Your Tuscany Bike Tour

Contrary to popular belief, Italy does not have a single gastronomic tradition like pizza, pasta and cannoli, but many traditions closely linked to their territory, which make up a very interesting mosaic. Our goal is to introduce you to it, and to immerse you in this culinary experiance.

Every evening we take you to the “Great Italian Trattorias” where the Italian culinary heritage is preserved and celebrated.
Experience the essence of Italian culture in the birthplace of the Italian language, where Dante Alighieri penned the Divine Comedy in 1321. Here, you’ll discover a culinary tradition deeply rooted in the Italian Renaissance, filled with robust flavors and rich aromas.

Tuscan cuisine is renowned for its mastery of meat dishes, with the Chianina steak standing as a symbol of excellence. Yet, there’s no shortage of variety for vegetarians—an array of vibrant, flavorful vegetable-based dishes awaits: Pappa al Pomodoro, Ribollita, Panzanella, Pici all’Aglione, Testaroli, Castagnaccio, and much more. Each bite is a taste of tradition, thoughtfully crafted to bring you the true flavors of Italy.

The restaurant is housed in the old walls of the village of Trequanda, a suggestive environment with wooden beams and pastel colors. The cuisine celebrates local meats, “Cinta Senese” and “Chianina”, combined with one of the cellars that we like the most. The restaurant and terrace overlook the hills of the Crete Senesi, a plus that alone justifies the trip.

Specialty Dishes:

Starter: Crispy artichokes on soft pecorino cheese with a mint flavored tomato mustard.
Pasta and Risotto: Egg spaghettini with creamed butter and “scorzone” black truffle from “Crete Senesi”.
Main course: “Chianina” Scottona Steak and Tuscan grilled Veal Florentine.

We are in Montalcino, home of Brunello, one of the world capitals of red wine. This historical  restaurant bases its success on the skills of Alessandra and Marina Fiorani. They offer high-level traditional culinary cusine in a very nice place with breathtaking views of  Val d’Orcia and Crete Senesi. It’s a must!

Specialty dishes:
Starter: Candied egg with a foamed Parmigiano Reggiano cheese cream and “Crete Senesi” white truffle.
Pasta and Risotto: Tagliatini with basil pesto and river shrimp tartare, served with crispy lemon infused polenta.
Main course: Local rabbit in porchetta stuffed with spinach and taggiasca olives, almonds, capers and thyme zucchini.

The seasons mark the times of this former tavern where in the kitchen Eliana skillfully combines fresh and local ingredients, many of which are of her own production, to give life to the genuine dishes of the Tuscan tradition. Enjoy your meal in a beautiful environment surrounded by nature.

Specialty dishes:

Starter: Cardoncello mushrooms, creamed cannellini beans and sweet gorgonzola sauce.
Pasta and Risotto: Rice “Gnudo” (Tuscan gnocchi), Pienza ricotta and spinach.
Main course: Cheek peposo (tuscany stew with pepper) and mashed potatoes.

One of the most beautiful late medieval villages in all of Tuscany and home of the red wine “Nobile di Montepulciano” and home to this elegant restaurant. This restaurant offers a refreshing welcome and a extraordinary culinary menu, offerering high quality service to its international clientele. Local traditional dishes and excellent bottles of “Nobile di Montepulciano” await us.

Specialty dishes:
:
Starter: Montalcino-style tripe with saffron and “Cinta Senese” sausage with pecorino cheese.
Pasta and Risotto: Risotto Carnaroli Grand Reserve with garlic, creamed goat cheese and anchovies.
Main course: Seared pigeon with seasonal side dish and red chilli mustard.

A stone’s throw from Piazza del Campo this is the place where time has stood still with the aim of bringing guests back to Siena, as it was. The cuisine is a modern one evolved from local tradition which keeps its identity intact, yet opens it towards new sensory horizons. Do not miss a visit to the 4-story wine cellar.

Specialty dishes:
Starter: Marinated anchovies, vanilla, raspberries, rocket pesto.
Pasta and Risotto: Handmade tagliatelle with Tuscan ragout.
Main course: “Priest’s hat” (type of beef), garden vegetables, beef garum.

Nestled in one of Tuscany’s most picturesque medieval villages, this refined restaurant invites you to experience authentic Italian elegance. Recently refreshed to enhance its warm hospitality and culinary offerings, it caters to a discerning international crowd with impeccable service. Savor traditional local dishes crafted with passion and paired with prestigious bottles of “Nobile di Montepulciano” wine—a true taste of Tuscany awaits you here.

Specialty dishes:
Starter: Liver pâté, coffee bread and spiced pear with cooked wine sauce.
Pasta and Risotto: Pici pasta, black garlic, Pientino cheese, breadcrumbs, thyme & pepper.
Main course: Chamomile marinated lamb with heirloom mustard, popcorn crust, pickled vegetables.

 Tuscany Bike Tour Accommodation

We’ve curated a selection of exquisite hotels, charming historic homes, and vineyard estates where you can unwind in total relaxation after your day of biking adventures. Many offer exclusive spa treatments in enchanting, serene settings. Our tours are designed for a deeper experience, allowing you to stay in a single hotel for the entire holiday—immersing yourself fully in the local culture and the beauty of Tuscany.

In the enchanting medieval village of San Quirico, at the heart of Val d’Orcia, the Capitano Collection offers a unique blend of Luxury & Design Boutique hotels, villas, and historic residences. Located both within and just beyond the village walls, each suite and room is distinctively designed, providing a personalized retreat for every guest. Immerse yourself in the charm and heritage of Tuscany, just steps from each captivating corner of this ancient village.

Amid the historic charm of San Quirico and a medieval gem in the heart of Val d’Orcia, the Palazzo del Capitano invites you to experience Tuscany’s finest. This unique collection of Luxury & Design Boutique hotels, villas, palaces, and historic residences is nestled within and just beyond the village walls, each only a few steps apart. With individually styled suites and rooms, every guest can discover a space that resonates with their personal sense of comfort and elegance. Embrace the essence of Italian heritage and hospitality in this breathtaking setting.

What’s included in our Tuscany Bicycle Tours

* All breakfasts, lunches, dinners
* One certified regional guide for every 8 guests, one bike mechanic and one SAG van driver
* Snacks, sport drinks, beverages, energy bars during the tour
* 2 different itineraries every day with different experience levels
* Guest pick-up / drop-off to and from the airport or other meeting point
* Daily bike maintenance and cleaning
* Daily laundry service for bike gear
* Custom Hirides.com cycling kit: bib shorts, jersey and socks
* Private guided tours at museums, historical sites, wineries and other select attractions as noted in the Travel Planner
* All gratuities at hotels and restaurants
* Special events, including wine tastings and other select attractions as mentioned in the Travel Planner
* Professional bicycle rental (e-bike or muscle) or transport of your beloved bicycle to Italy
* Baggage transfers, handling and assistance
* Civil Liability Insurance and Italian health insurance for non European citizens

  • Guide gratuities
  • Transportation to and from your HiRides trip start & end locations
  • On-your-own meals & activities
  • Additional cycling kit
  • Travel Protection Plan (highly recommended).

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