Cycling in Tuscany | Tourissimo

Explore quintessential Tuscany: the Chianti area, Siena, Val d'Orcia, and Maremma on this mixed-terrain bike tour (gravel and paved).

We've designed an itinerary filled with “white roads,” intriguing stops, and authentic beauty. While Tuscany requires no introduction, it consistently lives up to its reputation and it never disappoints. The area south of Florence, around Siena and in the Val d’Orcia, will set the stage for the first part of our exploration by bike. You will visit medieval hilltop towns, abbeys, and wineries. The finish is on the Tyrrhenian seacoast in the Maremma region (a natural reserve).

Our journey kicks off in the village of Greve in the Chianti area. From there, we'll explore a portion of the Chianti production area, making a stop at a winery. Siena, embodying the essence of a medieval city, will be our home for one night. We've organized a walking tour, allowing you to fully appreciate this UNESCO site. Together, we'll immerse ourselves in the spirit of L’Eroica, a unique "race" that captures the essence of cycling's heroic era: sections on dirt roads, vintage refreshments, and scenic yet challenging roads. Noteworthy is the area’s historical fame since Roman times for its thermal springs. A visit to the thermal water site of Saturnia, featuring its unique pools, will be a highlight.

This itinerary belongs to Tourissimo's Ambitious Tours lineup and it is meant for experienced cyclists. But do remember that it is a vacation and that you can ride as little or as much as you want, or take a day off altogether. E-bikes are available.

Highlights

Two important wine regions: Chianti and Montalcino-Brunello
UNESCO World Heritage Site (Val d’Orcia)
Villages of Pienza and Montalcino
Stunning cycling along rolling hills covered with vineyards and quaint medieval villages
Some of the best regional food in Italy
Strade Bianche gravel roads
Gaiole in Chianti, the home of l’Eroica
The impressive medieval city of Siena
The lunar landscape of Crete Senesi
The historical Via Francigena (Francis Way, and ancient pilgrimage route)
Earthy food and uplifting wines
Espresso and cappuccino stops in charming medieval villages
The thermal waters of Saturnia
Lesser-known Maremma villages of Sorano, Capalbio, Pitigliano

Dates:

Ask for custom dates

Prices:

2025

USD 4,250

Private room (single supplement) USD 695

Duration:

8 days (7 nights)

Level:

Athletic

Share with others:

Request a Tour Summary

The tour was fabulous and far exceeded my expectations.

Mitch Stimac Tuscany Strade Bianche

[fa icon="quote-right"]

Day by Day

[fa icon="plus"] Day 1

Greve in Chianti - 23 mls - Rolling

Your guides will meet you at the Florence train station for a late-morning shuttle. You will settle into the picturesque village of Greve in the Chianti wine region. After preparing the bikes and some bike fitting, we will head out for a warmup ride. An overview of the tour will precede a typical Tuscan dinner.

Our table will be on the terrace right above the main square. Homemade pasta and a taste of the local Chianina beef - a Tuscan staple - will be part of our menu.

[fa icon="plus"] Day 2

Chianti - 52 mls - Hilly

Today's ride is a roller coaster journey along beautiful ridges and gentle hills through stunning countryside. We are in the Chianti Classico production area, and our route takes us on a loop through the region via Via Chiantigiana, a panoramic road that traverses north-to-south across vineyards and through hilltop villages such as Radda and Castellina. A regroup and wine tasting await us at the Castello di Brolio on the Barone Ricasoli estate, one of the largest and certainly the first among all Chianti Classico producers.

A highlight of the day is our stop at the sleepy village of Gaiole in Chianti. The Eroica ride has put Gaiole onto the map, with thousands of riders taking over the village every second weekend of October on their vintage bikes, adorned in pre-Lycra cycling kits. The village square transforms into a market featuring historical bicycles and other equipment. Just imagine all of that as we stop for a coffee in the piazza and grab an Eroica-branded souvenir.

[fa icon="plus"] Day 3

Siena - 45 or 68 mls - Hilly

Your Tuscany trip also includes Siena, where a medieval atmosphere lingers amidst the twisting streets of warm, brown brick. Strolling through Siena’s narrow maze of cobblestone walkways is an incredible architectural journey. The entire city, centered around the Piazza del Campo, is renowned for its horse race called Palio. The riding terrain is undulating, alternating between forests and farmland. We approach Siena via the Crete senesi landscape. Crete senesi, literally “Senese clays,” and the distinctive grey coloration of the soil give the landscape an appearance often described as lunar. We’ll regroup at a panoramic point near Asciano for photos.

The Strade Bianche pro race has had some epic finishes on the final cobblestone climb in Siena. That's where we will head for a walking tour and dinner.

[fa icon="plus"] Day 4

Montalcino - Val D'Orcia - 51 mls - Hilly

Today, we'll transition to a different area, heading a bit south to the Brunello di Montalcino wine production region. Pedaling on a ridge just above the Arbia River Valley, our first stop is at the Etruscan hamlet of Murlo, one of the loveliest sites in all of Tuscany. With Montalcino in sight, you'll be treated to lunch and a wine tasting at a small producer, learning more about Val d’Orcia and Brunello. Our next stop is the Sant’Antimo Abbey, a perfect example of Romanesque architecture surrounded by olive trees and cypress. The Abbey of Sant'Antimo, a former Benedictine monastery, is about 5 miles from the Via Francigena, the pilgrim route to Rome, making it a truly spiritual site.

In the afternoon, we'll set aside time for a leisurely stroll in Montalcino, offering more stunning views.

[fa icon="plus"] Day 5

Sorano - 53 mls - Hilly

We continue our journey through the Val d’Orcia (a UNESCO site), but soon we enter a less-visited, wilder Tuscany. Our starting point is San Quirico d’Orcia, and our first stop is in the hilltop village of Pienza. Pienza is renowned for Pope Pio II, its perfectly-preserved medieval center, and for pecorino cheese (are you ready to taste pecorino cheese gelato?). Its location also offers a stunning view of the valley. After descending and crossing the Orcia River, we embark on a long climb to the highest point of the entire week: Radicofani, at 814 meters (2,670 feet). Lunch is planned at this scenic spot. Our final destination is a journey back in time.

The fortress of Sorano is as unique as it is charming, and while it may seem intimidating from afar, it is also very welcoming to cyclists.

[fa icon="plus"] Day 6

Saturnia - 50 mls - Hilly

From Sorano, we quickly reach Pitigliano. We then traverse several small but scenic valleys on our way to Saturnia, the highlight of the day. The site is situated over an ancient Etruscan settlement, undoubtedly the reason they settled there in the first place. The sulphurous spring water maintains a temperature of around 37.5 °C. Notable thermal waterfalls include the Mill Falls, located at an old mill, as well as the Gorello waterfalls. We take our time here (remember to pack a swimming suit and towel). We are about halfway through the ride, but you also have the option to ride back in the van if you prefer not to hop back on the saddle. The ride to Sorano is beautiful and ascends a canyon that suddenly reveals Rocca degli Orsini (or Orsini castle), which dominates the village of Sorano.

[fa icon="plus"] Day 7

Maremma and Talamone - 58 mls - Rolling and flat

Today’s ride takes us toward the seacoast and the charming village of Talamone. We traverse vineyards and open farmland in the Sovana and Capalbio production areas, making our first stop for lunch in Capalbio—one of the gems you'll discover on this bike trip. Soon, we find ourselves in the coastal Maremma area, one of the very few territories in Tuscany that remains true to its wild roots, untouched by mass tourism. We conclude the ride, and our tour, on the Tyrrhenian Sea.

Our hotel will spoil us with its terraces overlooking the sea. Pay a visit to Talamone village, perched on a promontory, before gathering for our final dinner and celebrations at our favorite seafood place. Our final dinner is in the central piazza, honoring Garibaldi’s Expedition of the Thousand (they docked in Talamone on the way to Sicily).

[fa icon="plus"] Day 8

Departure

After breakfast we say goodbye and your guides will give you a lift to the Florence airport.

What's Included

• Professional tour guides throughout the program

• All accommodations

• All breakfasts, all lunches (some picnics), and six dinners

• Local wine with dinner

• Wine tastings

• Guided tour of Siena

• Support vehicle during the tour and luggage transfer

• Shuttle at the beginning, during, and at the end of the tour

• All activities mentioned in the day-by-day description

• Bike rental

• GPS navigation and maps (digital)

More Info

Food and Wine

It's often noted that Tuscan cooking has its roots in "cucina povera" or peasant cooking. However, this can be said of most Italian cuisines. True to form, Tuscan cooking is simple—no reductions, no fancy sauces, no elaborate creations, and no heavy, complicated seasoning. Throughout Tuscany, olive groves and wild herbs abound. Many of the finest olive oils produced in Tuscany are reserved for use as a condiment at the table rather than as an ingredient in kitchen cooking. Tuscany also boasts some of the best Italian reds, including Chianti, Brunello, Nobile di Montepulciano, not to mention the super-tuscans.

Strade Bianche Pro Race

The Strade Bianche (formerly Eroica Pro) is organized by RCS Gazzetta dello Sport, the same organizers as the Giro d’Italia, making it a “newer” race in the international pro circuit. However, the fact that it is ridden on the strade bianche unpaved roads has given the race an epic aura that few other races possess. Cobblestone and dusty strade bianche await the best riders each year on the 1st weekend in March. The race starts and ends in Siena.

Val d’Orcia Natural and Cultural Park

The natural features of the valley, coupled with the cultural identity of the community that has lived there for centuries, make Val d’Orcia a unique area, earning it the designation of a World Heritage site by UNESCO. The municipalities of Val d’Orcia include Castiglione d’Orcia, Montalcino, Pienza, Radicofani, and San Quirico d’Orcia.

Libere Terme

Thermal springs endlessly flow (as the Romans knew) from deep underground, creating little bubbles of paradise. Terme di Saturnia belongs to the Libere Terme, a circuit of self-governing and free thermal spas. However, for a more luxurious option, there is a spa hotel in town.