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.


Cycling Tour in Tuscany

Dates & Pricing

DATES (7 days)

September 15-21, 2024 | May 11-17, 2025 | September 14-20, 2025

For other dates, info and availability please contact us.



Per person in double occupancy: from $4,290 (from $4,390 in 2025)


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, Greve, Gaiole 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, Greve in Chianti, Panzano 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 (see more info here) and Garmin Touring Edge unit (if you have one, bring yours and we’ll upload the routes onto your unit)
  • 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 2 dinners on your own  
  • Alcoholic beverages (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



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