Tuscany Bike Tour

  • Region: Italy
  • Destination: Tuscany
  • Duration: 6 Days / 5 Nights
  • Level: Three
  • Price From: $4895
  • Single Supplement: $950
Tour Dates
Tuscany Harvest Tour
Oct 29 - Nov 3, 2017 $4895 Call to book
Apr 1 - Apr 6, 2018 $4895 Book Now
Apr 22 - Apr 27, 2018 $4895 Book Now
Apr 29 - May 4, 2018 $4895 Book Now
May 13 - May 18, 2018 $4895 Book Now

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Explore the iconic Italian countryside as you ride through its gentle green hills and cypress-lined byways on the Tuscany Bike Tour. Climb into ancient Etruscan villages perched atop vine-covered hills. Discover medieval fortresses and Renaissance masterpieces and stop to visit Vittorio Innocenti’s private cantina. You’ll never forget the scent in the air as you ride along the ridges of the Crete Senesi or the sight of Siena’s Piazza del Campo at night. Savor local treats like fresh pici pasta, pecorino cheese, and garden fresh bruschetta with local olive oil, while sampling the finest Brunello, Super Tuscan, Vino Nobile, and Chianti Classico wines.


Tour by Day

Day One: La Dolce Vita
Meet our guides at the Chiusi train station for a transfer to La Chiusa, a former olive oil mill that is now a charming country inn. The welcome begins with a light lunch and glass of Prosecco, followed by a bike fitting and our first ride into the Tuscan countryside. You’ll feel as though you’ve traveled back to the 13th century while pedaling on the cobbled streets of tiny Petroio and passing generations-old farmers tending their olive groves. Choose your own adventure with longer or shorter ride options. This evening, stroll into the village of Montefollonico for a winetasting with our friend Vittorio and an incredible Tuscan dinner.

Meals: Light Lunch / Dinner
Destinations: Montefollonico, Petroio
Accomplished: 14 miles / 23 km, elevation gain: 340 meters (Longer option: 21 miles / 34 km)
Accommodations: La Chiusa

Day Two: Montalcino: Castles, Brunello, and Home-Cooking
Set off riding through pastures and forests to join the locals for a coffee in sleepy Montisi. Take in panoramic views of the bare ridgelines of the Crete Senesi and pedal down the Asso Valley into the Brunello wine-growing region. It’s a big climb up to Montalcino, the medieval hilltown at the heart of the Brunello zone, but the effort is well-rewarded with a tasting lunch at our favorite winery. Spend the afternoon relaxing by the pool or getting pampered at the spa of our five-star castle hotel. This evening we’ll head back into Montalcino for a cooking class and dinner in the fifteenth-century home of our friend Lina.

Meals: Breakfast / Lunch / Dinner
Destinations: Montefollonico, Montisi, Torrenieri, Montalcino
Accomplished: 30 miles / 50 km, elevation gain: 519 meters
Accommodations: Castello di Velona

Day Three: Pienza Loop: The Renaissance Ride
Embark on a loop ride to the town of Pienza, then climb up to Castiglione with its medieval fortress for a well-earned break. Descend into the Val d’Orcia, an area so beautiful that UNESCO designated it a World Heritage Site and the movie Gladiator’s famous wheat field scene was filmed here. Take in sprawling views during lunch on a private terrace in Pienza, then wander the carefully laid-out Renaissance streets. After a taste of some local Pecorino cheese, it’s time to complete the loop home to our hotel for another luxurious evening.

Meals: Breakfast / Lunch / Dinner
Destinations: Castiglione d’Orcia, Pienza, San Quirico d’Orcia
Accomplished: 26 miles / 41 km, elevation gain: 621 meters (Longer option: 41 miles / 65 km)
Accommodations: Castello di Velona

Day Four: Across the Crete Senesi: Monks and Masterpieces
Say goodbye to the Castello di Velona as we ride through the mystical morning light that bathes the Romanesque Abbey of Sant’Antimo. Pedal across the Brunello region before we stop for a visit of the Renaissance frescoes at the Abbey of Monte Oliveto. After a picnic lunch, continue riding along the open ridges of this scenic landscape. Opt for an earlier van transfer or continue cycling all the way to our final hotel, the Relais & Chateaux Borgo San Felice. Tonight, head into the medieval city of Siena to explore and dine there, or opt to dine at the hotel.

Meals: Breakfast / Lunch
Destinations: Buonconvento, Monte Oliveto, Asciano, Siena
Accomplished: 27 miles / 45 km, elevation gain: 923 meters (Longer option: 47 miles / 77 km)
Accommodations: Borgo San Felice or Le Fontanelle

Day Five: Chianti Classico: The Tuscan Heartland
Olive and cypress trees surround us as we ride deep into the hills of Chianti. We’ll see plenty of fortified hamlets and castles—relics of Florence and Siena’s 300-year struggle for regional dominance and ownership over the origin of Chianti Classico wines found in ancient cellars around the area. Pedal past countless estates as we weave our way through forests and vineyards to lunch with our friend Max at his innovative bistro. After lunch, opt for a longer ride or a straight shot back to the hotel. We’ll regroup in the evening for a tasting of San Felice’s famous wines and a festive final dinner.

Meals: Breakfast / Lunch / Dinner
Destinations: Castelnuovo, Brolio, Castagnoli
Accomplished: 30 miles / 50 km, elevation gain: 458 meters (Longer option: 40 miles / 66 km)
Accommodations: Borgo San Felice or Le Fontanelle

Day Six: Ride to Florence
On our last day, choose between a late morning at the hotel or ride all the way across Chianti for a triumphant finish in Florence’s Piazzale Michelangelo. Whether you rode here or took a transfer, we say our goodbyes with the stunning Florentine skyline as our backdrop as guides see you off to your next adventure.

Meals: Breakfast
Destinations: Panzano, Greve, Florence
Accomplished: Optional ride: 41 miles / 68 km, elevation gain: 776 meters