Tuscany Private Bike Tour

Day 1: Chianti Classico
Welcome to blissful Tuscany. Your guides will transfer you deep into the hills of Chianti to your first hotel, a 5-star Tuscan castle and winery.  After toasting your arrival with a traditional Prosecco during your bike fitting, we will head out on our first ride. Our first outing will be a ride to the Chianti Classico-producing town of Radda in Chianti.  Along the way we will pass plenty of vineyards and villas amidst the characteristic forested hills of this region.  In town we will stop for a light lunch in our friend Monica’s cozy restaurant.  After lunch, explore the medieval streets before hopping back onto the bikes.  We will experience some winding switchbacks on the loop back, giving you a great chance to warm up your legs.  Back at the hotel, relax amidst the vineyards before regrouping for a wine-tasting and your first Tuscan dinner at the hotel’s charming restaurant. 

Meals: Lunch / Dinner
Accommodations: Castello di Spaltenna
Destinations visited: Gaiole and Radda
Distance cycled: 25 km / 15 miles

Day 2: Siena
From our hotel, we’ll ride deep into the hills of Chianti. Passing rows of olives and cypresses, we’ll climb a ridge and stop at the picturesque San Felice estate for a tasting of their award-winning wines. Leaving San Felice we’ll get our first views of the towers of Siena, our eventual destination.  Before reaching Siena, our ride takes us through the wheat fields past the hamlet of Monteaperti.  In 1260 this peaceful landscape witnessed the epoch-making victory of an outnumbered Sienese army over the invading Florentines that sparked Siena’s medieval Golden Age.  We’ll eat lunch nearby at a delightful country restaurant before our final spin into the city.  Riding down the cobbled streets of Tuscany’s second city, we will arrive at our 5-star hotel, the nicest in town, located conveniently on the main pedestrian street.  Siena is a 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.  Tonight your guides will take you to the city’s most highly-regarded restaurant for a dining experience you won’t soon forget.

Meals: Breakfast / Lunch / Dinner
Accommodations: Grand Hotel Continental
Destinations visited: Brolio, San Felice, Monteaperti, Curina, Siena
Distance cycled: 50 km/30 miles

Day 3: Siena – San Quirico
Today it’s off to the land of Brunello wines, renowned as some as the world’s finest. The cycling route is stunning, beginning with rolling terrain through pastures and opening up onto the Crete Senesi, bare wheat-covered hills that have historically been the “breadbasket of Siena”.   The panoramic views here are world famous and we will get a great work-out on the long climbs to lunch.   The historic Abbey of Monte Oliveto di Maggiore is our destination where your guides will have a picnic prepared with fresh local products.   After lunch you can choose to take the shorter riding option through the walled town of San Giovanni D’Asso and down the Asso River valley to Torrenieri.  In Torrenieri we’ll stop for some Italian coffee to get the legs ready for the last bit of cycling up to our hotel in the medieval village of San Quirico.  The hotel has a great restaurant and spa for a relaxing afternoon and evening in this peaceful village.  If you’re up for an extra challenge after lunch, you can choose to ride to Montalcino.  Montalcino is a picturesque town famous not only for its Brunello wines, gourmet honey and pecorino cheese, but also for its outstanding medieval architecture.  It’s a big climb, but the views more than make up for it and the downhill to San Quirico is sublime.  This evening we recommend the hotel’s restaurant, but you are free to dine anywhere in town.

Meals: Breakfast and Lunch
Accommodations: Palazzo Del Capitano
Destinations visited: Asciano, Monte Oliveto di Maggiore, San Quirico d’Orcia
Distance cycled: Shorter Option: 56 km/34 miles. Longer Option: 65 km/39 miles

Day 4: Montichiello and Montepulciano Loop
Enjoy an early-morning stroll around town or sleep in before departing for another great ride.  We will start out in the beautiful Orcia Valley riding through the wheat fields where Gladiator was filmed.  After crossing the valley we will climb to the isolated village of Montichiello where we will stop in at the café for a coffee with the locals.  Above Montichiello the famous cypress-lined switchbacks that are featured on countless postcards beckon.  Cresting the ridge we’ll loop over to Montepulciano, one of Italy’s most beautiful hilltowns.  You are free to explore the town, stop at a local trattoria for lunch and join the guides for a tasting at the evocative Cantina del Redi.  From Montepulciano it is a gorgeous ride along the ridge to Petroio, our final destination.  Our hotel in this small hilltown has a fantastic view from its peaceful terrace.  Relax, sip a glass of local wine and chat with Ousmane, our colorful host, before regrouping for a dinner prepared by the hotel’s chef. 

Meals: Breakfast / Dinner
Accommodations: Palazzo Brandano
Destinations visited: Montichiello, Montepulciano, Petroio
Distance cycled: 42 km/ 25 miles

Day 5: Pienza Loop
Embark on a loop ride to the town of Pienza.  Often called the ideal Renaissance city, Pienza’s neatly laid-out streets and architecturally unified main square are unique in the region.  This was all the work of the town’s namesake and most famous son, Pope Pius II, who made it a pet project to apply Renaissance principles to city planning.  The result is often described as the most beautiful village in Tuscany.  Here 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.  Stop for lunch at a local café before looping home through olive groves and vineyards.  This evening we’ll take you to our favorite little village of Montefollonico where 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; a perfect way to spend our final evening together.

Meals: Breakfast / Dinner
Accommodations: Palazzo Brandano 
Destinations visited: Pienza, Petroio, Castelmuzio
Distance cycled: 38 km/ 23 miles

Day 6: Farewell
On the last morning, we will shuttle you through the hills to the Chiusi train station where we will say farewell as you head off to your next destination.

Meal: Breakfast
Accomplished: Total Satisfaction

TRIP TOTAL: 211 KM/ 126 MILES, averaging 15-25 miles per day. Optional longer rides available each day.