Super Tuscany Bike Tour

After a private transfer from Florence to your first hotel, your guides will greet you with a light lunch at this private castle. Then we’ll set out on our first ride through the surrounding countryside, with stunning vistas over fields of wheat, sunflowers, and dense oak forests. No ride here is complete without the customary coffee break at a local café, and we will honor this tradition with a stop in the medieval hill town of Casole. Back at the hotel we’ll sample the local wines before our first gourmet dinner prepared by the castle’s chef.

Meals: Lunch / Dinner
Destinations: Casole d’Elsa
Accomplished: 21 miles / 34 km, elevation gain: 1,765 feet / 538 meters
Accommodations: Castello di Casole

Wake up to a frothy cappuccino and delectable breakfast before setting out on a ride over the open ridges to San Gimignano. Explore the bustling streets of this famous hill town and climb the tallest remaining medieval tower for one of Tuscany’s most astonishing views. We’ll enjoy lunch at a charming local restaurant, and after you can opt to cycle home or take the van for some relaxation at the hotel. Dinner tonight is a true culinary experience featuring refined Tuscan cuisine at a Michelin-starred restaurant, Arnolfo, in nearby Colle Val d’Elsa.

Meals: Breakfast / Lunch / Dinner
Destinations: San Gimignano, Colle Val d’Elsa, San Donato
Accomplished: 23 miles / 37 km, elevation gain: 2,211 feet / 674 meters
Longer Option: 46 miles / 74 km, elevation gain: 4,474 feet / 1,364 meters
Accommodations: Castello di Casole

Say goodbye to the wilds of Casole as we pedal through the forested hills and onto the refined city of Siena. This storied city is like an open-air museum of Gothic architecture, home to prosperous citizens fiercely proud of their traditions like the Palio, a thrilling bareback horse race held in the main piazza. Explore the city and enjoy lunch in the medieval environs of our favorite local restaurant. In the afternoon you can once again opt for an early transfer to our hotel or cycle there through the wheat-covered hills south of Siena. We will spend the next three nights at Massimo Ferragamo’s incredible Castiglion del Bosco hotel. Tonight you can choose to dine here or in the nearby village.

Meals: Breakfast / Lunch
Destinations: Siena, Ville di Corsano, Bibbiano
Accomplished: 40 miles / 65 km, elevation gain: 3,795 feet / 1,157 meters
Shorter Option: 20 miles / 32 km, elevation gain: 1,745 feet / 532 meters
Accommodations: Castiglion del Bosco

Wake up to the absolute peace of your tranquil Tuscan villa. Pedal through walled Buonconvento on the way to the Abbey of Monte Oliveto to take in its unique Renaissance fresco. From here the landscape opens up as we ride along the bare ridges of the Crete Senesi, one of the most photographed roads in the world. Lunch is a family affair prepared by our friends Mariella and Paolo at their farmhouse and olive mill outside Castelmuzio. More panoramic views await us on the ride home as well as an optional challenging climb up to the wine-producing village of Montalcino. We’ll all return to Montalcino this evening for a special cooking class and dinner in the 15th-century home of our dear friend Lina.

Meals: Breakfast / Lunch/ Dinner
Destinations: Buonconvento, Trequanda, Montisi, Montalcino
Accomplished: 33 miles / 54 km, elevation gain: 2,654 feet / 809 meters
Longer Option: 48 miles / 77 km, elevation gain: 3,759 feet / 1,146 meters
Accommodations: Castiglion del Bosco

Ride this morning from Montalcino and through Italy’s top Brunello vineyards. Stop for a coffee in the medieval heart of San Quirico before heading into the scenic Val d’Orcia, where the iconic wheat field scenes from Gladiator were filmed. Then we’ll ride along the shoulder of Mount Amiata, Tuscany’s towering dormant volcano to lunch and a tasting at our favorite Brunello winery. Stop to take a picture of the beautiful Romanesque Abbey of Sant’Antimo as we pedal back to Montalcino. Our final dinner tonight is at the hotel as we raise a toast to this paradise known as Tuscany.

Meals: Breakfast / Lunch / Dinner
Destinations: Montalcino, San Quirico, Sant’Antimo
Accomplished: 31 miles / 50 km, elevation gain: 3,542 feet / 1,080 meters
Shorter Option: 26 miles / 42 km, elevation gain: 2,713 feet / 827 meters
Accommodations: Castiglion del Bosco

Say goodbye to Tuscany any way you see fit. Sleep in, stroll around the grounds, or opt for a final early morning ride. Later in the morning, your guides will see you off at the Chiusi Chianciano train station.

Meals: Breakfast