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Self-Guided Southern Tuscany Bike Tour

Self-Guided Southern Tuscany Bike Tour
Most Tuscany bike tours visit the northern part of the region including Florence, Chianti, and Siena. Fewer trips venture off the beaten path exploring southern Tuscany. Equally beautiful, but less touristy, southern Tuscany is known for its sun-drenched farmlands, picture perfect hill towns, and Italy's best red wines. Spend seven days cycling through beautiful hill towns including Montalcino, Pienza, and Cortona. Explore a 14th century castle. Tour a winery and sample their Brunello wine, Italy's best red. Soak in hot thermal waters at a Roman spa. Feast on local specialties including pici pasta (a thick spaghetti), wild boar, and a sheep cheese called pecorino. You will be enchanted by the warm people, quiet villages and natural splendor.
Day 1 Buonconvento  We meet in Florence and shuttle to Buonconvento. You have lunch in Buonconvento with your tour coordinator who reviews the tour and provides route notes and maps. Cycle to Monte Oliveto Maggiore a stunning abbey perched on top of a cliff.

Day 2-3 Montalcino  Ride to the perfectly preserved medieval village of Sant'Angelo in Colle. Listen to Gregorian chants in Tuscany's most beautiful Romanesque church. Enjoy a winery tour and learn how sangiovese grapes are transformed into the sublime Brunello wine.

Day 4 Pienza  Pedal at your own pace to Pienza, built by a Pope to represent the perfect Renaissance city. Swim or soak in the geo-thermal waters of Bagno Vignoni. Tiny Bagnoni Vignoni, population 16, has been soothing weary travellers since the Romans consecrated the waters to the Nymphs.

Day 5 Montepulciano  Zig-zag through the stone streets of Montichiello, a tiny village with great views. Cycle to Montepulciano, a town known for its ruby-red wine called Vino Nobile. Tour the cavernous cellars of an ancient winery.

Day 6-7 Cortona  Bike to the town made famous by Frances Mayes in her book Under the Tuscan Sun. Nestled high on a hill, Cortona is a delightful village with a medieval air. Tour ends in Cortona. Frequent trains make for an easy departure on day seven.

Reserve This Tour Detailed Itinerary

US$ 1,550 per person
(Single Supplement)

Traveling alone?
Join a self-guided tour that has already been scheduled. We can't run self-guided trips for one person, but we may have already booked a self-guided tour that works for you. More info

Group of three?
Tour prices are based on double room occupancy. Groups of three on self-guided trips have two options:
Option 1: Request a triple room. With a triple there is no single supplement. Option 2: Pay a single supplement (US$ 50/night) for the single room.

Save US$ 250 per person
Use our bike bags (panniers) instead of the luggage transfer
more info


Any date from March 1 to October 31
7 Days, 6 Nights
Route Rating
Moderate: 10-30 miles (15-50 km) per day cycling over hilly terrain.

Meet / Finish
Florence / Cortona
  • Winery tour with wine tasting
  • Swim at a thermal spa
  • 12th century castle visit
  • 8th century abbey
  • The Tuscan hill towns of Montalcino, Pienza, Montepulciano and Cortona
  • Beautiful vistas of vineyards and olive groves
  • Peaceful country back roads

What's Included
  • All lodging (3 and 4 star hotels)
  • All breakfasts
  • Lunch on Day 1
  • Winery visit and wine tasting
  • Luggage transfer from hotel to hotel
  • Private van transfer from Florence on day one
  • 6 beautiful rides. Extra miles available.
  • Use of high-end hybrid bicycle

Cancellations: Terms and Conditions

Tour Summary
Map and Distances

Wineries and Castles
What if it rains?

On self-guided bike tours there is no van support. However, we do move your luggage from hotel to hotel. In the event of rain you can catch a ride with us when we move your bags, just call and make arrangements for a lift.

Why a Self-Guided Bike Tour?
Explore Tuscany at your own pace. We provide detailed route notes, luggage transfers, great accommodations, restaurant suggestions, and sightseeing notes. You choose the dates. We take care of the details.