Tuscany Bike Tour

Welcome to blissful Tuscany. From the Chiusi train station your guides will take you to Montefollonico and toast your arrival with a traditional Prosecco during your bike fitting, safety talk and map review. Our first outing will be a ride to the distinctive church of San Biagio on the outskirts of Montepulciano, home of Vino Nobile – famed as “the king of wines” since the 8th century. Returning to Montefollonico, we’ll have time to relax before beginning a marvelous Tuscan evening with our friends Dania and Umberto, the owners of the luxurious villa La Chiusa. Dania runs the kitchen of this Michelin-starred restaurant, and Umberto will be eager to welcome you as a friend, and show you how to live like a local. Enjoy the breathtaking views from this ancient olive mill while savoring the region's gourmet specialties, grown on La Chiusa’s estate, then unwind and let this heavenly Tuscan experience take over.

Meal: Dinner
Destinations visited: Montefollonico & Montepulciano
Distance cycled: 23.2 km / 14.50 miles

Embark on a loop ride to the town of Pienza, an architectural gem thanks to its namesake, Pope Pius II, who made it a pet project to turn his hometown into the ideal Renaissance city. The result is often described as the most beautiful village in Tuscany. In Pienza you will have time to meander the cobbled streets, practice your Italian at a local café, people watch, and taste the local wine-soaked or truffle-dusted pecorino cheese. Leaving Pienza, you’ll feel like you’re riding through a movie set, and you won’t be far from the truth. Gladiator and the English Patient were both filmed here. We’ll head past the monastery of Sant’Anna in Camprena and the villages of Castelmuzio and Petroio on cypress-lined roads, stopping for a picnic lunch complete with classic Tuscan bruschetta and an olive-oil tasting in an olive grove. Back in Montefollonico, we’ll have a very special private tour of our friend and local winemaker, philosopher and playwright, Vittorio Innocenti’s cantina. Then we’ll taste his traditional Vino Nobile and Vin Santo in his garden with the breathtaking Chiana Valley as a backdrop. Dinner is right next door at the warm, rustic Botte Piena.

Meals: Breakfast and Dinner
Destinations visited: Montefollonico, Pienza, St. Anna in Camprena & Petroio
Distance cycled: 37 km/23 miles

Today it’s off to the land of the Brunello wines, renowned as some as the world’s finest. The cycling route is stunning, beginning with rolling terrain through pastures and forests on the way to the sleepy village of Montisi where we will ride down the medieval streets. After Montisi, enjoy the panoramic views stretching from Mt. Amiata to Chianti as you cruise past poppies and sunflowers down the ridgeline to San Giovanni D’Asso and along the Asso River valley to Torrenieri. In Torrenieri we’ll stop for some Italian coffee to get the legs ready for the climb up to Montalcino. The road to Montalcino takes us right past some of the most famous Brunello wineries, including Casa Nova Dei Neri. Upon arrival, we’ll check into our hotel, Vecchia Oliviera, a converted olive mill built right into the walls of the town. With Montalcino’s many cafes, wine bars and pizzerias we’ll leave the choice of where to eat lunch up to you. After lunch you can join our guides for the 18km roundtrip ride down to the Abbey of Sant’ Antimo to hear the monks chant a Gregorian mass or spend the afternoon exploring Montalcino or relaxing by the pool. Montalcino is a picturesque town famous not only for its Brunello wines, gourmet honey and pecorino cheese, but also for its outstanding medieval architecture. We’ll have a private evening tasting at the 14th century fortress at the top of town followed by another exquisite Tuscan dinner with our friend Antonio, owner of local favorite, Re di Macchia.

Meals: Breakfast and Dinner
Destinations visited: Montefollonico, Montisi, San Giovanni D’Asso, Torrenieri, St. Antimo Abbey & Montalcino.
Distance cycled: Shorter Option: 40 km/25 miles. Longer Option: 58 km/36 miles

Enjoy an early-morning stroll around town, a sunrise visit to hear the chanting at Sant’Antimo or sleep in before another gorgeous day of cycling through the Tuscan countryside. We’ll spin to the 14th century Abbey of Monte Oliveto Maggiore to visit its outstanding Renaissance frescoes. After a gourmet Tuscan picnic featuring local pecorino cheeses, prosciuttos, and pates, washed down with a suitable regional wine, you can choose to take the van directly to the hotel in Siena or continue riding. Riders will cruise along the bare ridges of the Crete Senesi through Asciano and Vescona to Arbia, where we will once again have the option to take the van to the hotel. For truly ambitious cyclists, the final 11 km to the hotel is a real treat as we follow timeless back roads up a series of challenging hills to enter Siena in truly evocative fashion. Siena is gem of a medieval city with beautifully preserved Gothic architecture. The city is built around the Piazza del Campo, regarded by many as the most beautiful piazza in all of Italy. Here you’ll have time to shop while exploring the many hidden medieval walkways. The night is yours and your guides will be happy to point you to a favorite local trattoria for dinner.

Meals: Breakfast and Gourmet Picnic
Destinations visited: Abbey of Monte Oliveto di Maggiore, Asciano, Vescona, Arbia
Distance cycled: Shorter Option: 22 km/14 miles. Standard Option: 52.5 km/32.50 miles. Longer Option: 64km/40 miles.

From our hotel, we’ll transfer to Arbia, and then ride deep into the hills of Chianti. Passing rows of olives and cypresses, we’ll climb a ridge and break out of the trees as we ride through the gorgeous Chianti Classico estates of Bossi and San Felice before continuing to the Castello di Brolio. A Tuscan landmark for 1000 years, this imposing castle and the surrounding vineyards were given a facelift in the 19th century by the stern Baron Ricasoli who not only modernized local winemaking, but served as one of Italy’s first prime ministers. We’ll stop here for a tasting of the Iron Baron’s famous wine before continuing cycling, fully immersed in vast stretches of vineyards and winding panoramic roads, to Radda where our hostess, Monica, will delight us with
her unique antipasti and pastas. Our next stop will be our stunning hotel and winery, Borgo di Vescine, – a serene 13th century hamlet - for an intimate wine tasting with Vincenzo, the winemaker, and our final dinner.

Meals: Breakfast/ Lunch/ Dinner
Destinations visited: Arbia, Monteaperti, Castello di Brolio & Radda in Chianti
Distance cycled: 40.5 km/25 miles

On the last morning, we will shuttle you through the hills of Radda and Castellina on your way to visit San Gimignano, with its staggeringly beautiful medieval towers and its marvelously frescoed church of Santa Fina, a local saint. Shop for linens, ceramics, hand carved wooden ornaments, or perhaps a cycling jersey with the Chianti Classico black rooster. Be sure to stop at our favorite gelateria in the main piazza, international gelato champions for years running. We will continue on to Florence where we will end our tour at the train station of Santa Maria Novella.

Meal: Breakfast
Destinations visited: San Gimignano and Florence
Accomplished: Total Satisfaction