Self guided bike tour in Tuscany

Itinerary

Day One: Montepulciano
 Welcome to blissful Tuscany. From the Chiusi train station your guide will take you to Montefollonico and toast your arrival with a traditional Prosecco during your bike fitting, safety talk and map review. Your 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, you’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

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. You’ll head past the monastery of Sant’Anna in Camprena and the villages of Castelmuzio and Petroio on cypress-lined roads. This is an ideal place to stop for a picnic lunch with prosciutto, fresh bread and pecorino cheese in an olive grove if you so desire. Back in Montefollonico, relax at the hotel before strolling into the village for dinner. We recommend the warm, rustic restaurant, Botte Piena.

Meals: Breakfast
Destinations visited: Montefollonico, Pienza, St. Anna in Camprena & 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, 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, you’ll check into your nest 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 may want to take an extra 18km ride down to the Abbey of Sant’ Antimo to hear the monks chant a Gregorian mass at 2:45pm. 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 evening we recommend a tasting at the 14th century fortress at the top of town followed by an exquisite Tuscan dinner with our friend Antonio, owner of local favorite, Re di Macchia.

Meals: Breakfast
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

Day Four: Montalcino - Siena
Enjoy an early-morning stroll around town, or sleep in before another gorgeous day of cycling through the Tuscan countryside. You’ll spin to the 14th century Abbey of Monte Oliveto Maggiore to visit its outstanding Renaissance frescoes. We recommend eating lunch at the abbey’s restaurant located in a medieval defensive tower. You will then cruise along the bare ridges of the Crete Senesi through Asciano and Vescona to Arbia. From here, the final 11 km to the hotel is a real treat as you 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 to enjoy a local trattoria for dinner.

Meals: Breakfast
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, you’ll ride deep into the hills of Chianti. Passing rows of olives and cypresses, you’ll climb a ridge and break out of the trees and 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. You can 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 at one of many local restaurants where you can sample fresh antipasti and pastas. Your final 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/ Dinner
Destinations visited: Arbia, Monteaperti, Castello di Brolio
Distance cycled: Shorter Option 34 km/ 21 miles; Longer Option 48 km/ 29 miles

Day Six: Radda – Florence
On the last morning, we will pick you up at your hotel and shuttle you through the hills of Radda and Castellina on your way to Florence where we will end our tour at the train station of Santa Maria Novella.

Meal: Breakfast
Destinations visited: Florence

Inclusions:

• Deluxe accommodations in luxurious properties with the best amenities Aluminum hybrid or road bicycle, handlebar bag, water bottle and optional toe straps
• Highlighted regional maps
• A list of restaurant and attraction suggestions along the cycling route
• All breakfasts, two gourmet dinners including wine
• Transportation from rendezvous to first hotel and from last hotel to drop-off
• All gratuities for baggage, porters, and hotel service
• All baggage transport
• DuVine Adventures t-shirt and luggage tag

Call or email us today to tell us the dates you would like to travel and we will confirm availability. Please note the price is based on 4 travelers and can start any day of the week, except Sunday. Contact - info@duvine.com or 617 776 4441 or 888.396.5383.