Tuscany Bike Tour

  • Region: Italy
  • Destination: Tuscany
  • Duration: 6 Days / 5 Nights
  • Level: Three
  • Price From: $4895
  • Single Supplement: $950
Tour Dates
Apr 2 - Apr 7, 2017 $4895 Book Now
Apr 23 - Apr 28, 2017 $4895 Book Now
May 7 - May 12, 2017 $4895 Book Now
May 21 - May 26, 2017 $4895 Book Now
Jun 11 - Jun 16, 2017 $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; then we’ll get fitted on the bikes and head out into Tuscan countryside. Ride into the 13th century on the cobbled streets of tiny Petroio and wave at the old men 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, followed by an incredible Tuscan dinner.

Meals: Light Lunch / Dinner
Destinations: Montefollonico, Petroio
Accomplished: 14.5 miles / 23.2 km, elevation gain: 340 meters (Longer option: 20 miles / 32.2 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 friends, Domenico and 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. Climb up to Castiglione with its medieval fortress for a well-earned coffee. Then descend into the Val d’Orcia, an area so beautiful that UNESCO has designated it a World Heritage Site. (Remember the wheat field scenes from Gladiator? That was here.) Take in the views from lunch on a private terrace in Pienza. Wander the carefully laid out Renaissance streets and sample some local pecorino cheese before looping 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 with 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 to the hotel 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
Pedal through the olive and cypress trees as we ride deep into the hills of Chianti. The numerous fortified hamlets and castles are evidence of Florence and Siena’s 300-year struggle for regional dominance and now protect signature Chianti Classico wines aging in coveted antique cellars. Pedal past countless estates as we weave our way through forests and vineyards to lunch at our favorite local restaurant. 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
It’s our last day, and we’ll end with a bang: an incredible, epic final ride from one end of Chianti to the other for a triumphant finish at Florence’s Piazzale Michelangelo. We’ll say our goodbyes with the stunning Florentine skyline as a backdrop as we head onto our next adventure.

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