We Bike Tuscany

Recommended in
Lonely Planet Florence &
Tuscany travel guides
Tuscany Self-Guided


If you're an experienced cyclist seeking a little extra adventure and independence (but not at the expense of comfort and peace of mind), then this trip is for you. With our detailed and easy-to-follow route notes and maps you will guide yourself in a five night/six day journey that takes in the best of the best of Tuscany, and some of its most scenic and unforgettable rides. Along with directions, you'll also receive our recommendations for sightseeing, wine tasting, shopping and restaurants -- both along the way and at your destination each day. Thinking all this sounds wonderful, exciting, romantic and yet... the idea of hauling heavy bags on a bike (uphill too!) is not exactly your idea of a relaxing vacation? Well, we couldn't agree more, which is why luggage transfers are included. You'll find your bags (as many and as heavy as you like) waiting in your room at the end of each day, delivered by one of our WBT guides. A guide who will also be available at all times for emergency breakdown assistance, van support in case of rain -- or just to answer any questions you may have during your trip (a cell phone will be provided so quick help is only a phone call away).

As if it couldn't get more perfect, this tour (like all of our trips) can be fully customized -- add or subtract a day or two, or take shorter or longer/more challenging routes (on some days) to your destination. It's all up to you. It's your ride, your adventure.


$2880 per person

  • Duration: 6 days/5 nights
  • Distance traveled: 30-40 miles per day
  • Area: Val di Chiana and Val d'Orcia
  • Nearest city: Arezzo-Siena
  • Places visited: Tuscany, Italy
  • Tour type: Road touring
  • Bike type: Hybrid
  • Skill level: Advanced
  • Season: April - October
  • Number of participants: 2-7
  • Minimum age: 16
  • Fully guided: no
  • Transportation to start site: yes



From Florence (or surroundings) we transfer by van to Cortona, famous setting of Under the Tuscan Sun. Enter the fortified walls of this beautiful village passing under the massive keystone of the 8th Century B.C. Etruscan gate. Orientation and warm-up ride with your (non) guide in the afternoon. Enjoy dinner and exploring the village in the evening, at last on your own. Let the adventure begin!

Accommodation: Villa San Michele - Cortona


From Cortona through the Val di Chiana, bike to your next inn, Locanda dell'Amorosa, one of the most romantic, charming and exclusive resorts of the area. In season, the countryside is covered in enormous sunflowers, making this ride (and your photographs!) even more spectacular. Optional short detour to a renowned winery for a taste of Vino Nobile di Montepulciano.

Accommodation: Locanda dell'Amorosa - Sinalunga


From Locanda dell'Amorosa you bike to the hilltop Reinassance town of Pienza, recently designated "Worldwide Heritage of Humanity" site by UNESCO. See the land slowly change, turning from green to ochre before arriving at your final destination.

Accommodation: Il Chiostro di Pienza


Today pedal into the wide open landscape of the Crete Senesi, past ancient hilltop towns, stone farmhouses, lone cypress trees and lush vineyards before reaching the medieval town of Montalcino. This is one of the loveliest little wine villages in Italy, and home to the famed Brunello di Montalcino wine (and some wonderful restaurants!).

Accommodation: Hotel La Vecchia Oliviera - Montalcino


Today is the most challenging but rewarding ride of the tour. Enroute to the medieval village of Bagno Vignoni, you'll spin through postcard perfect Tuscan scenary, pausing along the way for a brunello tasting (or two!) and the can't miss stop of Sant'Antimo Abbey -- perhaps in time to hear the monks' Gregorian chant. An unforgettable and magical experience.

Accommodation: Hotel Posta - Bagno Vignoni


Your last day features a loop ride with breathtaking views over the Val d'Orcia. At tour's end, reward yourself with a relaxing soak in the famous ancient thermal baths of Bagno Vignoni before your van transfer back to Florence or surroundings in the early evening.


  • Pick up/drop off in Florence or in the surroundings
  • Baggage transport
  • Accommodations at the best Tuscan Villas and inns of the region
  • All breakfasts
  • Maps and detailed route directions
  • 24 Speed high quality hybrid bikes, helmets, water bottles and handlebar bags


Please send us an email if you need more info. We will reply within 48 hours.