Cycling Tour in Tuscany

This cycling tour features the must-to-see places of Tuscany, including the UNESCO World Heritage sites of Pienza, Siena and Orcia Valley, and the scenic Chianti area and Crete Senesi. Other highlights include the towns of Greve, Radda and Gaiole in Chianti and other lesser-known villages such as Lucignano, Asciano and Rapolano. You will discover local wines, olive oil, and cheese through tastings and visits, and learn about local recipes during our meals and a hands-on cooking class.

See here for more info on Tuscany region.

Dates & Pricing

DATES (7 days)

May 11-17, 2025 | September 14-20, 2025

June 22-28, 2026

For other dates, info and availability please contact us.

TOUR PRICE

Per person in double occupancy: from $4,390 (from $4,490 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
Traditional accommodation in elegant and hand-selected 4-star hotel to get yourself immersed in the real Tuscan life
Strolls through must-see Tuscan towns such as Cortona, Panzano, Gaiole, Castellina and Radda in Chianti, and the small villages of Lucignano, and Asciano
Visit two UNESCO sites of Siena and Pienza in Orcia Valley
Exhilarating rides in Chiana and Orcia Valleys and Chianti and Crete Senesi areas with plenty of 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
4 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 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 Cortona, Asciano, Radda, Gaiole, Panzano, Castellina 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)
One group transfer to Montevarchi train station at the end of the tour
Local taxes & gratuities for luggage porters and restaurants servers during the tour

What's Not Included

3 lunches and 2 dinners on your own
Alcoholic beverages at group meals (including wine and spirits)
Round-trip airfare and expenses to/from the tour
Transfer to first hotel
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 in Cortona
Day 1 & 2 – Cortona and Chiana Valley

Cycling Route Info on Day 1: Main Route: 19mi/1360ft of elevation gain | Extra loop adds: 6mi/700ft

Cycling Route Info on Day 2: Main Route 34mi/1860ft | Extra loop adds: 11mi/900ft

Enjoy Cortona and relax in this medieval town before meeting your guides for a light lunch and introduction to the tour.

Tuscan life still adheres to the pace of older times. Over our first two days we ease into the rhythm of this special slice of Tuscany, which sits at the bullseye center of the Italian peninsula. First rides bring us in the area near Cortona, a quintessential Tuscan hilltop town, and Lucignano, another stunning example of medieval town planning, as well as through the Chiana Valley for an unforgettable wine tasting and visit to a local producer.

On these days, 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 3 & 4 – Orcia Valley and Crete Senesi

Cycling Route Info on Day 3: Main Route 32mi/2860ft | Extra loop adds: 13mi/1260ft

Cycling Route Info on Day 4: Main Route 32mi/3120ft | Extra loop adds: 11mi/780ft

In the next two days we’ll visit more of the Province of Siena, discovering the Abbey of Mount Oliveto, ambling the picture-book towns of Pienza, Asciano and Siena and cycling the UNESCO protected Val d’Orcia and world-famous Crete Senesi, which is like no place on Earth.

In Pienza, also recognized by UNESCO, we have the chance to hear from a local cheese maker about how ancient production methods are preserved to this day, and to taste the difference in a sampling.

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 5 & 6 – Chianti Area

Cycling Route Info on Day 5: Main Route 37mi/2890ft | Extra loop adds: 2mi/600ft

Cycling Route Info on Day 6: Main Route 30mi/2800ft | Extra loop adds: 11mi/1400ft

Having visited some of the lesser-known pockets of southern Tuscany, our last two days ensure the complete experience, with loops through the Chianti region and visits to its sun-soaked villages of Radda, Gaiole, Panzano and Castellina (add Greve on the extra loop scheduled for that day).

Here we drink in all that one has come to expect from Tuscany—gently undulating roads combed across open farmlands and punctuated by sharp cypress and the soft remnants of stone farmhouses. 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!