Cycling Tour in Tuscany and Eroica

Top your cycling experience of Tuscany with the quintessential L’Eroica, which celebrates the sport as it was done in times past. The exhilarating amateur ride uses vintage bikes and gears, and includes rest stops that offer local foods and wines. L’Eroica started as an effort to protect the last strade bianche (the ancient gravel ‘white roads’ of the area that were threatened with paving). Enjoy the heart of Tuscany on a vintage bike surrounded by more than 5,000 riders passionate about preserving tradition!

Beyond l’Erioca and other great rides, this tour includes the must-see UNESCO World Heritage sites of Pienza, Siena, and the Orcia Valley, towns of Montalcino, Radda, and Gaiole in Chianti, and the charming villages of Lucignano and Rapolano. Off the bike, we savor local wines, olive oils, and cheeses, and taste and learn about the other unique recipes of the heart of Italy.

See here for more info on Tuscany region.

Dates & Pricing

DATES (7 days)

September 30-October 6, 2025

For more info and availability please contact us.

TOUR PRICE

Per person in double occupancy: from $4,290 (from $4,390 in 2026)

Single Supplement: $690

For travel in 2021 and beyond, your tour is carbon neutral! In addition, we donate more than 1% of your trip price to food-literacy and environmental non-profits that share our values. (Details here)

Tour Highlights

Exposure to local culture and history with native, bilingual, experienced Tour Leaders
Tastings of regional Slow Food Presidia and visits to local wine, cheese, and olive oil makers
Experience the authentic Tuscan cuisine featuring fresh and seasonal ingredients
Enjoy some of the best white wines of the region such as Vernaccia of San
Gimignano and Vermentino and the red wines of Brunello, Chianti and Super Tuscans
Elegant and traditional accommodation in hand-selected 4-star hotels
Be part of the exciting event of L’Eroica and experience cycling as the pioneers of this sport used to do in the last century
Strolls through must-see Tuscan towns such as Montalcino, Pienza and Siena, and the small villages of Lucignano, Gaiole and Radda in Chianti
Exhilarating rides and opportunities to improve your cycling skills with your Tour Leaders
Traditional, local recipes to bring home with you!

Cycling Level 3 – Antipasto, Primo and Secondo (Entrée)

What's Included

6 nights accommodation in 4-star hotels
5 dinners and 3 lunches
1 olive oil tasting in agriturismo and 1 visit and tasting to a cheese maker
Visit at Abbey of Mount Oliveto
Exhilarating rides in Crete Senesi, Chianti area and in Orcia, Arbia and Chiana valleys
1 wine tasting and visit to local winery
Explore the UNESCO sites of Siena, Pienza and Orcia Valley; discover the historic towns of Montalcino, Gaiole, Radda and Castelnuovo Berardenga
2 bilingual professional Tour Leaders
1 comfortable 9-seat van available for transportation and assistance during bike rides including water, fresh fruits and snacks
Bike rental and navigation system (see more info here)
Guaranteed entry for the Eroica (medical certification is required)
2-day vintage bike rental and 1 vintage wool cycling jersey
One group transfer from Terontola train station at the beginning of tour
One group transfer to Montevarchi train station at the end of the tour
Local taxes & gratuities for luggage porters and restaurants servers during tour

What's Not Included

3 lunches and 1 dinner on your own
Alcoholic beverages at group meals (including wine and spirits)
Round-trip airfare and expenses to/from the tour
E-bike, upon request and availability. (See more info here)
Trip cancellation, baggage loss or travel delay insurance (this optional coverage is highly recommended. See more info here)
Gratuities for your Tour Leaders. (Info here)
Personal expenses, such as, but not limited to, phone calls, laundry, emails, snacks, gifts

Itinerary

Optional Pre-Tour Night near Trequanda
Day 1 & 2 – Terontola-Cortona Train Station, Around Crete Senesi and Chiana Valley

Cycling Route Info on Day 1: Main Route: 21mi/1500ft of elevation gain | Extra loop adds: 4mi/150ft

Cycling Route Info on Day 2: Main Route 33mi/2270ft | Extra loop adds: 15mi/1530ft

Catch our 45-mins group transfer to our 4-star hotel for the next four nights. Check in and relax before meeting your guides for a light lunch and introduction to the tour.

The white roads of Tuscany are a rite of passage for many Italian cyclists. Our journey begins in the Province of Siena, at the geographic heart of the Italian peninsula. First spins take us to the quintessential hilltop town of Rapolano and charming village of Lucignano, a stunning example of medieval town planning.

Later, we ride the Chiana Valley for an unforgettable olive oil and wine tasting. Other highlights include a visit at the farm of a local breeder of the Chianina cow to learn about this former Slow Food presidium.
Day 3 & 4 – Orcia Valley and Crete Senesi

Cycling Route Info on Day 3: Main Route 33mi/3090ft | Extra loop adds: 7mi/200ft

Cycling Route Info on Day 4: Main Route 35mi/2220ft | Extra loop adds: 19mi/1950ft

In the next two days we’ll visit more of the Province of Siena, with rides through the Val d’Orcia, offering extra loops on some L’Eroica gravel roads (for a preview), and the world-famous Crete Senesi, which looks like nowhere else on Earth.

Of course, no exploration of southern Tuscany could be complete without visits to the fabled towns of Pienza, and Montalcino. In Pienza, we hear from a local cheese maker how ancient production methods are preserved to this day, and see if we can taste the difference.

A hands-on cooking class and dinner will be featured and you will be invited to join us for a team effort off the bike to celebrate at the table the Tuscan food and wines!
Day 5 & 6 – Chianti Area and Eroica!

Cycling Route Info on Day 5: Main Route 37mi/2930ft | Extra loop adds: 8mi/900ft

Cycling Route Info on Day 6: Eroica routes range between 29-129mi and elev. gain 2300-12000ft | Not riding Eroica? Ride in Chianti 32mi/2880ft

Our final two days will be spent in another 4-star hotel and include an invigorating climb up to Radda in Chianti enclosed in its formidable walls, and visit to Gaiole just to its east, starting point of L’Eroica. Today you will not only pick up your bib number, but you will also start to experience the Eroica atmosphere with the local vintage clothing market, the food and wine exhibitors, surrounded by cyclists from all over the world.

Those who will be riding “the hero’s journey” on the last day can try out the vintage bikes on some gravel in advance. Collectively, we will commemorate the tour over an utterly Tuscan final dinner, replete with local flavors and wines, and celebrate our hero riders. Benvenuti in Toscana!
Day 7 – Montevarchi Train Station

To request the itinerary as a PDF or to ask us any questions please contact us today!