Chianti Classico is one of Tuscany's most beautiful areas. Dense forests and medieval castles conjure images of falconers on horseback roaming through these woods. For modern-day cyclists, it offers rich rewards: quiet roads, challenging rides, and tables laden with fabulous food. See the castle where Chianti was invented. Visit Certaldo, the town where Decameron author Boccaccio was born. Tour medieval Siena and San Gimignano, and delve into Tuscan wines. Customizable tour for private groups of 4 and more persons.
Highlights:
- Wine estates: Volpaia, Dievole, Cesani & more
- Biking: 25-37 miles (plus optional loops)
- The medieval towns of San Gimignano & Certaldo
- Castello Brolio, the birthplace of Chianti.
Tour Itinerary:
Day 1: Ancient Abbeys
We begin with a short but challenging warm-up ride to a Chianti Classico landmark: Castello Volpaia, a medieval borgo on a hilltop whose ancient buildings are now occupied by wine making equipment and workers of this top Chianti Classico wine estate. Here we'll get a tour and our first taste of Chianti Classico and its Super Tuscan rival. For dinner we visit another medieval landmark: the Badia a Coltibuono, a former 11th century abbey where the monks produced some of Chianti's earliest wines, and where Lorenza di Medici now runs her famous cooking school. Dinner here begins our introduction to Tuscan cuisine, which includes such specialties as tomato soup (pappa pomodoro), rustic bread salad with tomatoes and basil (panzanella), and wild boar (cinghiale) (12 miles). Includes: (D).
Day 2: Chianti up close
Lush woods, mountain-ridge vistas, silvery olive groves, wispy poplars, rolling acres of Sangiovese vineyards, and quaint villages from the 13th C. Chianti League are what's in store on today's ride, which stops for lunch in the wine town of Gaiole in Chianti. Afternoon brings either more miles in the Chianti hills, or else takes us nearby to the family-run Cacchiano wine estate, located in a magnificent medieval castle, where we'll taste their splendid Chiantis. Afterwards, we'll stroll in the town of 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). Includes: (B), (D).
Day 3: The Gothic city of Siena
Today we'll take a break from biking and spend the day in Siena. We'll start with a cappuccino at Nanini, Siena's most famous coffee bar, and sample their panforte, a dense cake laced with nuts, candied fruits, and spices. We'll then tour Siena's splendid Palazzo Pubblico or City Hall, which houses masterpieces of Italian Gothic painting by Simone Martini and Ambrogio Lorenzetti. We'll also visit Siena's massive cathedral, home to artworks by Michelangelo and Pinturicchio. After lunch and time to shop, we'll continue onward to a tasting at Dievole. This property dates back over 700 years, but its owners know a few things about modern marketing, offerings an elaborate and entertaining presentation of their wines. Dinner is in a charming countryside trattoria with outdoor dining next to an olive grove. Includes: (B), (D).
Day 4: From Chianti to San Gimignano
Today we pass from Chianti Classico into the zone of Vernaccia of San Gimignano. We'll bike along a mountain ridge with winding roads and magnificent views, passing through the historic town of Castellina in Chianti. Once a fortified city, it's now a charming wine town with a well-preserved historical center. Our ride ends at our hotel, a restored country villa with a great view of San Gimignano. This region is home to Vernaccia, 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 out at the Panizzi winery (37 miles). Includes: (B), (D).
Day 5: The Wine Roads of Vernaccia
Our 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 along these back roads as we do a loop around San Gimignano. Rolling hills provide some biking challenges, while scenic provide the reward. Here we'll travel in the middle of the Vernaccia di San Gimignano wine zone, which we'll sample at our afternoon tasting at Panizzi. Here's 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, see its magnificent Italian Gothic frescos, and climb the tallest tower for an unbeatable view of the Tuscan countryside. Dinner on your own in San Gimignano (25 miles). Includes: (B).
Day 6: Bocaccio's Birthplace
This morning's ride loops through classic Tuscan landscapes with cypress trees, vineyards, and olive groves on our way to Certaldo, the birthplace of Decameron author Boccaccio. We'll visit the impressive Palazzo Pubblico of this towering hilltown, then bike back to San Gimignano for lunch. In the afternoon, we'll sample of variety of Vernaccia whites and Super Tuscans at Cesani, a relative newcomer to the area who makes award-winning wines. Our farewell dinner is in San Gimignano, allowing us to see the city in all its quiet magic at night (35 miles). Includes: (B), (D).
Day 7: Arrivederci. A shuttle to Florence and assistance with your travel plans. Includes: (B).
Notes:
Airfare is not included in the tour price.
Notes: Available for custom tours only. Minimum group size: 4. Itinerary can be customized, with more daily mileage and less wine tastings, greater or fewer days, upgrade in hotel accommodations, and/or exclusion of meals. Price varies accordingly. Departures on a custom-basis only, for groups of 4.
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