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Self-Guided Florence to Siena Bike Tour

Self-Guided Florence to Siena Bike Tour
This two-day Tuscany bike tour takes you through the picture-perfect Chianti countryside as you slowly pedal from Florence to Siena. Cypress lined lanes and medieval villages create a scene right out of a Renaissance painting. You spend one night in Greve, the unofficial capital of Chianti, and one night in scenic Siena. You visit a 16th Century villa, tour their winery, and sample their wines and oils. Explore the bustling streets and piazzas of Siena as you search for the perfect gelato. Cycling in Italy can be hilly and this tour is no exception. However, the distances are not long and the views are spectacular. Bring your camera and curiosity, beautiful Chianti waits!
Day 1 Greve  We meet in the center of Florence and shuttle to our bicycle storage in the Chianti countryside (9 miles south of Florence). This 20-minute drive gets you past the traffic of the city. Together we cycle to a Chianti Classico winery for a private tour of their wine cellars and olive mill. Lunch at the winery includes a wine and oil tasting. After lunch the self-guided part of your bike tour begins. A panoramic downhill leads you to the village of Greve. Your hotel is right on the central piazza of town. Before dinner you can explore Montefioralle, a fortified medieval hamlet, or just find a nice spot in an outdoor cafe for a relaxing aperitif.

Day 2-3 Siena  You pedal the picturesque Chiantigiana road as it winds through the heart of Tuscany. Along the way you visit two Chianti villages. The town of Panzano was originally a medieval castle and still preserves some of its old walls and towers. A few miles down the road the town of Castellina offers a wealth of archaeological treasures including a 15th Century castle and Etruscan tombs from 700 BC. Climb the castle towers for 360 degree views. Inside the castle you will find a small archeological museum with bronze weapons, ornaments and Corinthian vases. Your cycling holiday ends in the traffic-free center of Siena. Today Siena offers Italy's best Gothic city experience. Frequent trains and busses make for an easy departure on day three.

Reserve This Tour Detailed Itinerary

US$ 600 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.

(Siena Palio Surcharge)

During the Palio (Siena's famous horse race) hotel prices
triple. A surcharge of US$ 100 (per person) will apply if you stay in Siena 6/29, 6/30, 7/1, 7/2, 8/13, 8/14, 8/15, or 8/16.

Save US$ 50 per person
Use our bike bags (panniers) instead of the luggage transfer
more info

Optional Charges
3rd night (US$ 200 per person)


Any date from March 1 to October 31
3 Days, 2 Nights
Route Rating
Moderate: Two rides, 15 and 27 miles (27 and 43 km) over hilly terrain.

Meet / Finish
Florence / Siena
  • Winery and olive oil mill tour with tastings
  • The towns of Greve, Castellina, and Siena
  • Beautiful vistas of vineyards and olive groves
  • Peaceful country back roads

What's Included
  • All lodging (3 and 4 star hotels)
  • All breakfasts
  • One lunch
  • Winery and olive mill visit with tastings
  • Luggage transfers from hotel to hotel
  • Private van transfer from Florence on day one
  • 2 beautiful rides. Extra miles available.
  • Use of a high-end bicycle

Cancellations: Terms and Conditions

Tour Summary
Map and Distances

Wineries and Castles
Want an easier tour?
Add a third night for US$ 200 (per person)

Instead of 27 miles on DAY 2 you ride:
DAY 1: 15 mi, Florence to Greve
DAY 2: 12 mi, Greve to Castellina
DAY 3: 15 mi, Castellina to Siena
DAY 4: Last Day

Recommended for less experienced cyclists.

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.