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Cycling Tour in Tuscany

This cycling tour features either a 4-star hotel or a cozy agriturismo where you will be based for 6 nights to explore some of the must-to-see places of Tuscany, including the UNESCO World Heritage sites of Pienza, Siena and Orcia Valley. Other highlights include the towns of Montalcino, Cortona, Radda and Gaiole in Chianti and other lesser-known villages such as Lucignano 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

Minimum of 6 participants, maximum of 16, with a maximum guide-to-guest ratio of 1 to 8


DATES (7 days)

June 10-16, 2023

For dates, info and availability please contact us.



Per person in double occupancy: from $3,790 (upon request this tour will feature either an elegant 4-star hotel or an agriturismo)


Single Supplement: in 4-star hotel $690 | in agriturismo: $540


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 or cozy agriturismo
  • Strolls through must-see Tuscan towns such as Montalcino, Pienza, Cortona 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 hotel or agriturismo
  • 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
  • 1 entry fee at the local natural springs
  • Explore the UNESCO sites of Siena, Pienza and Orcia Valley; discover the historic towns of Montalcino, Asciano, Cortona, Gaiole, 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 from/to Terontola train station at the beginning and 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, with $150-250 surcharge depending on the type (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
  • 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!


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