Chianti by Bike

Cycling the Wine Roads of San Gimignano and Chianti Classico



We meet in Florence, load up the van, and head to Radda in Chianti (approx. 1-1/4 hour drive). After arriving at our countryside hotel and doing a bike fit, we’ll tackle a challenging warm-up ride.

This takes us to a Chianti Classico landmark: Castello Volpaia, a medieval hamlet that tops a hill where fox (volpe() once roamed. (Being the highest village in this vicinity, we’re facing one of the tours’ longest climbs.) Today the entire village has been taken over and restored by the Castello Volpaia winery, which tucks its winemaking equipment discretely behind the ancient stone walls of this borgo. Those who wish can sample their first Chiantis and Super Tuscans at the winery’s drop-in tasting room. Then it’s a long descent all the way back to the hotel.

For dinner, we visit another medieval landmark: Badia a Coltibuono, an 11th century abbey where monks produced some of Chianti’s earliest wines and today Lorenza di Medici runs her cooking school. Dinner offers haute versions of Tuscany’s (cucina rustica(. [25 miles]
L, D • Le Noci


Today we do a loop ride through classic Chianti territory. That means we’ll be accompanied by stone walls hedged with lavender and rosemary, rustic sharecropper farmhouses, stately villas, ancient olive groves, and signs of the Black Rooster everywhere. Just as in medieval times, patches of cultivated land alternate with dense forests that seem ready to burst with Renaissance falconers on horseback. We’ll bike through some of the towns that were members of the Chianti League (a military coalition before it had anything to do with wine), including Gaiole in Chianti, where we’ll stop for lunch.

For our post-ride winery visit, we can go to the family-run Vecchie Terre di Montefili, a gorgeous old property once farmed by local monks. Here we’ll delve deeper into the noble sangiovese grape and the concept of terroir.

If there’s time afterwards, we can stroll in Radda in Chianti, once the capital of the Chianti League, and hear how the black rooster came to be Chianti Classico’s symbol. Dinner is at the cozy Le Vigne restaurant, located smack in the middle of a vineyard. [25 miles]
B, D • Le Noci


Today we take a break from biking and visit Siena. We'll start with a cappuccino at Nannini, Siena's most famous coffee bar, and sample their panforte, a dense cake laden with nuts, dried fruits, and spices (a medieval power bar, in effect).

We’ll then tour the Palazzo Pubblic, one of the most spectacular city halls in existence. Among its highlights are three masterpieces of Italian Gothic art: Simone Martini’s Maestá and Siege of Montemassi, and Ambrogio Lorenzetti’s Allegory of Good and Bad Government, the largest landscape since Roman times. We'll end up at Siena's striped cathedral, where you’ll have to option to visit artworks by Michelangelo, Pinturicchio, and Donatello.

Then you’re free for lunch, with time to shop or visit the Enoteca Nazionale, Italy's national wine museum/wine bar, located in a Medici fortress.

On our return to Radda in Chianti, we can stop for our afternoon tasting at Castello Brolio, the birthplace of Chianti. Owned by the Ricasoli family since 1141, this crenellated castle has seen its share of wars. You can visit its magnificent gardens and walk along the ramparts, then hear about Chianti’s creation by the “Iron Baron” Bettino Ricasoli, and finally taste their highly regarded Chianti Classicos and Super Tuscan, called Casalferro. Dinner offers scrumptious updates of Tuscany’s woodland cuisine, based on wild boar (cinghiale), guinea fowl, and other game.
B, D • Le Noci


Today we do a point-to-point ride from Chianti Classico to our hotel in San Gimignano. After biking along a scenic mountain ridge, we’ll encounter Castellina in Chianti. Once a fortified town, it’s now a charming wine village with a well-preserved historical center. We then cross into the San Gimignano zone and eventually climb to our hotel, a restored farmstead three miles outside of town.

Still bristling with towers, San Gimignano is one of the most perfectly preserved medieval towns in Europe, earning it UNESCO World Heritage status. This region is also home to Vernaccia di San Gimignano, a white wine acclaimed ever since the 1200s. In 1643 Michelangelo Buonarotti the Younger wrote that it “kisses, licks, bites, slaps and stings.”

We’ll test out that theory before dinner, when we meet on the hotel patio for an informal tasting of Vernaccia in its various incarnations. Dinner is family-style at San Donato, a winery and agriturismo in a medieval borgo. Here the buffet table sags with a huge number of mouthwatering antipasti, followed by homemade pasta, then a Tuscan dessert staple: cantucci (almond biscotti) dipped in our vin santo made by our host. [37 miles]
B, D • Pescille


Today’s loop ride takes us on ancient roads that once hosted pilgrims on their journey to Rome. Nowadays you’re likely to see more pheasants than pilgrims. Our route traverses the countryside surrounding San Gimignano. We’ll pass by San Donato (last night’s dinner spot), then Castel San Gimginano as we move west, crossing the border into the province of Pisa. Again, pristine Vernaccia vineyards alternate with fields of wild flowers and woods thick with chestnut trees, porcini, and black truffles. The terrain is rolling and scenic.

In the late afternoon, we’ll head to Panizzi, a pioneering producer that produces six different kinds of Vernaccia. Here we’ll also get acquainted with this region’s Chianti, known as Chianti Colli Senesi.

We’ll then spend time in the city of towers, San Gimignano, visiting the magnificent Italian Gothic frescos in its cathedral. Those whose leg muscles aren’t spent can climb the tallest tower for an unbeatable view of the Tuscan countryside. Dinner is on your own in San Gimignano, where you can look for such classic Tuscan dishes as pappa pomodoro (tomato soup), panzanella (bread salad with tomatoes and basil), and cinghiale (wild boar). [25 miles]
B • Pescille


This morning’s ride is a loop ride to Certaldo, the birthplace of Decameron author Boccaccio. We’ll again be treated to quiet roads surrounded by classic Tuscan landscapes, with cypress trees, vineyards, and olive groves lining the way.

In Certaldo, we’ll visit the impressive Palazzo Pubblico (Town Hall), then bike back to San Gimignano in time for lunch. In the afternoon, we’ll sample of variety of Vernaccia whites and Super Tuscans at Cesani, a small, family-run estate that produces a super Super Tuscan, as well as two excellent versions of Vernaccia. Our farewell dinner is in San Gimignano, allowing us to see the city in all its quiet magic at night. [25 miles]
B, D • Pescille


A shuttle to Florence by noon and assistance with your travel plans. B

Please bear in mind that this is a sample itinerary, which is customizable. Longer rides, less wineries, more sightseeing or less—all this and more is possible upon request.

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Dates & fees:

7 days (flexible)

Tour available for custom groups only, minimum size: 4. Inquire about prospective dates.


$3,695 (based on the accompanying 7-day itinerary; modifications are possible, including the number of days, the level of accommodation, daily mileage on bike, the inclusion of wine tastings, the inclusion of meals)

Single supplement: $400 (for 6 nights)

Bike rental: $300 (for 7 days)

Meet and Depart

Florence train station [map]

What's included:

  • 6 nights accommodations (double room) in two 3-star hotels, with breakfast buffet
  • 5 gourmet dinners (three courses with wine)
  • All wine tastings mentioned
  • Shuttle at beginning/end of tour, as described
  • Bike maps/route notes; saddle bag; cage pedals
  • SAG wagon support during bike rides

What's not included:

  • Air travel
  • 1 dinner on your own and all lunches
  • After-dinner drinks, or special wines at tastings that are not part of what is provided to the group
  • Bike and helmet rental (optional)
  • Items of a personal nature
  • Anything not specified as included

“I’ve never had better support on a bike tour. I learned a lot about wine, but also about architecture, art, food, and Italian culture. Keep up the good work!”

– Valerie Moore, Midland Park, NJ

Dispatches from the wine road
– Livin' La Dolce Vita


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