Itinerary

Day One: Montepulciano
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 and light lunch
Destinations visited: Montefollonico & Montepulciano
Distance cycled: 23.2 km / 14.50 miles

Day Two: Pienza
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 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 & Petroio
Distance cycled: 37 km/23 miles

Day Three: Montefollonico - Montalcino
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. This is a great opportunity to stop into a local wine shop and try some great Brunello vintages. This evening we'll walk from our hotel to a very local Tuscan dinner featuring traditional local recipes and wines.

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

Day Four: Montalcino - Siena
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.

Day Five: Siena –  Chianti
From our hotel, we’ll 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 lunch where we will sample fresh antipasti and pastas. Our next stop will be our stunning hotel and winery, nestled amidst the woods and vineyards - for an intimate wine tasting and our final dinner.

Meals: Breakfast/ Lunch/ Dinner
Destinations visited: Bossi, San Felice & Brolio
Distance cycled: Shorter Option 34 km/ 21 miles; Longer Option 48 km/ 29 miles

Day Six: Florence
On the last morning, say goodbye to Tuscany as you see fit; sleep in and enjoy the peaceful quiet of the Chianti countryside, or savor a cappucino on the terrace.  Later in the morning we will shuttle you to Florence where we will end our tour at the train station of Santa Maria Novella.

Meal: Breakfast
Destinations visited: Florence
Accomplished: Total Satisfaction

TRIP TOTAL: 208.9 KM/ 129 MILES, averaging 40-50 km/ 25-30 miles per day. Optional longer rides available each day.

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