Super Tuscany Bike Tour

  • Region: Italy
  • Destination: Tuscany
  • Duration: 6 days / 5 nights
  • Level: Three
  • Price From: $7095
  • Single Supplement: $1950


This tour is part of our private tours collection. Please complete a Private Tour Planning Form to start designing a private tour that is everything you want - and nothing you don't - where, when, and how you want it, to share with whomever you choose. Or, call 888-396-5383 to inquire about joining a future public date that may become available.

Go Private

Tuscany Explore More Promo

Region Highlights Tour Guides Accommodations Bikes What's Included Blogs

Michelin Star Icon-01Cycle the quiet roads of the scenic Italian countryside on a Super Tuscany Bike Tour. Marvel at landscapes that inspired Renaissance masterpieces. Indulge in the bounty of a lush land with gourmet dinners in Tuscany’s finest ristorante and private tastings at the region’s most renowned vineyards. Learn to cook like a true Tuscan during an exclusive cooking class. Drink in the sights and sounds of Siena’s bustling medieval streets, sip a glass of rich Brunello wine on your private terrace, and savor the freshest pecorino cheeses and olive oils. Sleep in grand style at the region’s most esteemed properties. Nothing is impossible on a Super Tuscany bike tour.


Tour by Day

Day One: Welcome to Tuscany
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: Light Lunch / Dinner
Destinations: Casole d’Elsa
Accomplished: 21 miles / 34 km
Accommodations: Castello di Casole

Day Two: San Gimignano
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: 25 miles / 40.5 km (Longer option: 48 miles / 78 km)
Accommodations: Castello di Casole

Day Three: From Casole to Siena
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: 16 miles / 26 km (Longer option: 36 miles / 58 km)
Accommodations: Castiglion del Bosco

Day Four: The Crete Senesi
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 in the hill town of Trequanda, a secret gem where we’ll eat authentic dishes on a private terrace. 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 fifteenth-century home of our dear friend Lina.

Meals: Breakfast / Lunch/ Dinner
Destinations: Buonconvento, Trequanda, Montisi, Montalcino
Accomplished: 27 miles / 43.5 km (Longer option: 65 miles / 105 km)
Accommodations: Castiglion del Bosco

Day Five: Val d’Orcia
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 and listen to the monks’ Gregorian chanting. 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: 30 miles / 50 km (Longer option: 42 miles / 70 km)
Accommodations: Castiglion del Bosco

Day Six: Ciao to Tuscany
Say goodbye to Tuscany any way you see fit. Sleep in, take a stroll around the grounds, or opt for a final ride. Later in the morning your guides will see you off with a private transfer from the hotel or the train station in Chiusi.

Meals: Breakfast
Accomplished: Optional ride