Chianti by Bike

Cycling the Wine Roads of San Gimignano and Chianti Classico

Trip Notes:

Biking Level of Difficulty

As Virgil said, “Bacchus love hills.” So it’s no surprise that Chianti and San Gimignano are full of hills. Rolling and gentle, short and abrupt, you’ll find all kinds here. In general, they’re shorter, but steeper, than in Piedmont. But these are not mountains, so any seasoned biker should be able to tackle them with resolve, patience, and a good granny gear. As in Piedmont, the country roads are nicely paved and without much traffic, and the drivers are very respectful of bikers (having all biked themselves; it’s Italy’s main sport after soccer). The bike routes on CHIANTI BY BIKE are around 50 km/35 miles per day, but since this is a customizable itinerary, we can add or subtract miles (as well as other activities, such as winery visits or cooking lessons), depending on the wishes of your group. Keep in mind that these are hilly miles, so 35 miles might seem longer in the saddle than on the page—or on your club rides, if you live on the flatlands. As in Piedmont, this is not the place to begin a biking hobby. If you’re not already a biker, we suggest our walking tours as a better alternative for an active vacation.


Florence or Pisa (continental), or Rome (intercontinental). To land in Florence or Pisa, you’ll need to connect somewhere in Europe. From the Florence airport to the city center, it’s a 20-minute taxi ride. If arriving in Pisa, the airport has its own train stop and is only an hour from Florence. Rome is the closest intercontinental airport, with direct flights to the US. If arriving in Rome, you’ll need to take a train from the airport to town (30 min.). Then from Rome’s main train station, it’s only 95 minutes to Florence on the fast train (EuroStar); the latter requires reservations.


Plan to land in Italy at least a day before the tour begins; that’s necessary to be at our starting point on time. Most people spend the preceding night in Florence. For hotel suggestions, email us or consult a good hotel search engine, such as If you’re spending just one night, we recommend staying near the main train station, Stazione Santa Maria Maggiore, since that is our meeting point. Otherwise, take your pick of neighborhoods. Florence is not a huge city, and it’s very walkable. In fact, we encourage you to get out and walk around; the streets are a living museum!

Meeting point

Our meeting point is in Florence’s main train station, Santa Maria Maggiore (details will be indicated in your information packet). From here, we shuttle to Chianti (about 1 hour), where the tour gets underway. (We cannot pick up from individual hotels because only taxis and permanent residents are allowed in Florence‘s city center.)

Departure day

On our final day, we’ll have you back at the Florence train station by 11 A.M. (Drive time from San Gimignano is approximately 1 hour.)

Italian train schedule

Click here for the Trenitalia schedule in English. Be aware that the schedule is posted just a few months in advance, so if you’re looking for long-range dates, try something sooner, if only to get an idea of departure frequency and trip length.

Trip extensions

Because CHIANTI BY BIKE does not include any time in Florence, we recommend spending a few days in this fabulous art city, either before or after our tour. Florence is easy to navigate on your own. But there are also excellent thematic walking tours offered by our friends at CONTEXTTRAVEL.COM. If you’d like to explore other small-sized cities in Tuscany, Florence is well connected with Lucca (1 hr, 20 min) and Arezzo (1 hr) by train. And it’s just a hop and a skip to Rome on the EuroStar express train (1 hr 35 min).

Travel insurance

This is recommended to protect you from needless loss caused by last-minute cancellations, lost luggage, and more. One source is Travelex Insurance (800) 228-9792 (please use our compay code: 21-0043 LDV).


Go to to find out average temperatures in Tuscany for any week of the year. This site is also useful to see the forecast when you’re packing, as is Go to to “Radda in Chianti, Italy” and “Siena, Italy” to see the 7-day forecast.


Articles by La Dolce Vita Wine Tours cofounder Patricia Thomson:
“Vernaccia: A Medieval Wine for Modern Times”
“Everyone to the Table: 3 Days at a Cooking School in Chianti”
“Wines in Florence: Frescobaldi and the Rise of the Wine Bar”


Dispatches from the wine road
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