Self-Guided Florence to Siena Cycling Wineries

Price
US$ 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.

(Siena Palio Surcharge)

During the Palio (Siena's famous horserace) 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)

Dates
Any date from March 1 to October 31

3 Days, 2 Nights

Route Rating
Moderate: Two rides (15 and 27 miles) over hilly terrain.

Meet / Finish
Florence / Siena

Highlights

Winery visit with guided wine and oil tasting
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 visit and wine tasting
Luggage transfer from hotel to hotel
Private van transfer from Florence on day one
Two beautiful rides (15 and 27 miles). Extra miles available.
Use of high-end hybrid bicycle
Use of cell phone for emergencies

Cancellations: Terms and Conditions

» Tour Summary
» Map and Distances
» Hotels
» Photos
» Bicycles

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. We provide our guests with a cell phone. You can call in the morning and make arrangements for a lift.

Why Self-Guided?
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.

Winery and Castle Admission
All of these wineries and castles can be visited on this tour. Entrance fees, if applicable, are usually less than US$ 8.

Self-Guided Florence to Siena Cycling Wineries and Castles

All of these wineries and castles can be visited on this tour. Entrance fees, if applicable, are usually less than US$ 8.

Albergaccio Machiavelli Winery, San Casciano
The Albergaccio Machiavelli winery was founded in 1693. Today they produce 300,000 bottles of wine, primarily Chianti Classico and Chianti Classico Riserva. Sangiovese, Canaiolo, and Pinot Nero grapes grow on 27 hectares of land. Nicolo’ Machiavelli wrote The Prince while living on this estate.

Montefioralle Castle, Greve
The castle of Montefioralle was an important stronghold in the wars between Florence and Siena. It had two sets of walls and four gates, some of which survive today. During the middle ages it was one of the largest military fortifications of the area.

La Rocca Castle, Castellina
(Entrance not included in tour price)
The castle of Castellina called, “La Rocca” dates from the 15th century. Today it houses a museum with artifacts from nearby Etruscan tombs. Climb the stone towers for breathtaking views of the Chianti countryside.

Palazzo Squarcialupi Winery, Castellina
The 15th century Palazzo Squarcialupi was a built as a noble residence. Today it houses a winery and hotel. The winery produces Chianti Classico as well as extra virgin olive oil. Wines are aged for as long as three years in oak barrels.