Tuscany Bike Tour

  • Region: Italy
  • Destination: Tuscany
  • Duration: 6 Days / 5 Nights
  • Level: Active
  • Price From: $4695
  • Single Supplement: $700
Tour Dates
Apr 3 - Apr 8, 2016 $4695 Book Now
Apr 24 - Apr 29, 2016 $4695 Book Now
May 8 - May 13, 2016 $4695 Book Now
May 22 - May 27, 2016 $4695 Book Now
Jun 5 - Jun 10, 2016 $4695 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 vine-covered hills to ancient Etruscan villages. Discover medieval fortresses and Renaissance masterpieces and delight in a visit to our friend 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 homemade pici pasta, pecorino cheese, garden-fresh bruschetta with local olive oil, and sample 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 in the sleepy village of Montefollonico, our home away from home for the next two nights. You’re in Italy, so the welcome always begins with a light lunch and glass of Prosecco; then we’ll get fitted on the bikes and head out into Tuscan countryside. Ride back in time to the 1200s on the cobbled streets of tiny Petroio and wave at the old men tending their olive groves. You’ll feel as if you’re cycling through a painting. Choose your own adventure with longer or shorter ride options. Regroup and relax with an après velo cocktail on the patio surrounded by breathtaking views. Tonight our chef Dania will delight you with gourmet specialties, and our host Umberto will welcome you as a friend and show you how to live like a local.

Meals: Light Lunch / Dinner
Destinations: Montefollonico, Petroio
Accomplished: 14.5 miles / 23.2 km, elevation gain: 642 meters (optional additional 20 miles/ 32 km)
Accommodations: La Chiusa

Day Two: The Renaissance Ride
Embark on a loop ride to the town of Pienza. Stop at the gorgeous Renaissance church of San Biagio on the outskirts of Montepulciano before pedaling along the lovely cypress-lined curves into Montichiello. These routes have inspired countless local postcards, and you’ll see why as we ride by. This area, known as the Val d’Orcia, is so beautiful that UNESCO has designated it a World Heritage Site. 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. Back in Montefollonico, we’ll be treated to a private visit at our friend Vittorio Innocenti’s cantina. Taste some traditional Vino Nobile and Vin Santo in his garden overlooking the Chiana Valley before heading next door for a true feast at our favorite local restaurant.

Meals: Breakfast / Lunch / Dinner
Destinations: Montefollonico, Montepulciano, Montichiello, Pienza
Accomplished: 26 miles / 43 km, elevation gain: 793 meters (optional additional 36 miles / 59 km)
Accommodations: La Chiusa

Day Three: Montalcino Castles, Brunello + Home-Cooking
Set off riding through pastures and forests to join the locals for a coffee in sleepy Montisi. Don’t forget your camera as the road opens up onto the bare ridgelines of the Crete Senesi. Take in panoramic views pedaling down the Asso Valley and 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 as we check into our stunning 5-star castle hotel. Spend the afternoon relaxing by the pool or getting pampered at the spa. 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: 732 meters (optional additional 46 miles / 76 km)
Accommodations: Castello di Velona

Day Four: Across the Crete Senesi
Wake up early to catch the monks greeting the new day with a Gregorian chant at the nearby Abbey of Sant’Antimo or sleep in at our castle hotel. Start the day with a ride across the Brunello region before an unforgettable visit to the Renaissance frescoes at the Abbey of Monte Oliveto. After a picnic lunch, continuing riding into the rolling wheat fields of this scenic landscape. If you’re eager to get into Siena, you can opt for an earlier van transfer to the hotel or continue cycling all the way into the city’s iconic Piazza del Campo on a truly unforgettable ride. Tonight you are free to explore the medieval city of Siena where your guides can provide great dining recommendations.

Meals: Breakfast / Lunch
Destinations: Buonconvento, Monte Oliveto, Asciano, Siena
Accomplished: 27 miles / 45 km, elevation gain: 1378 meters (optional additional 44 miles / 73 km)
Accommodations: Grand Hotel Continental

Day Five: The Tuscan Heartland
Pedal through the olive and cypress trees as we ride deep into the hills of Chianti. This area was at the center of Florence and Siena’s 300-year struggle for regional dominance, and the numerous fortified hamlets and castles are a testament to its unsettled past. More recently the locals have turned from war to wine, and these former fortresses now protect signature Chianti Classico wines as they age in coveted antique cellars. Pedal past Bossi, San Felice, Brolio and countless castles as we weave our way through forests and vineyards to the hilltop village of Radda. Here our friend Monica will welcome us to her family-run bottega for a lunch featuring bruschette, cheeses, homemade salads and inventive pastas. Ride the scenic ridgeline to the hotel, relax by the pool, and celebrate an incredible week of riding with a festive final dinner.

Meals: Breakfast / Lunch / Dinner
Destinations: Bossi, San Felice, Brolio
Accomplished: 25 miles / 40 km, elevation gain: 1186 meters (optional additional 34 miles / 57 km)
Accommodations: Locanda Le Piazze or Borgo di Vescine

Day Six: Ride to Florence
It’s our last day, and you can opt to sleep in, enjoy the hotel and take a late-morning shuttle to Florence; or make an epic final ride across Chianti for a triumphant finish at Florence’s Piazzale Michelangelo. Say your goodbyes with the stunning Florentine skyline for your backdrop as you head onto your next adventure.

Meals: Breakfast
Accomplished: Optional 29 mile/ 48 km ride into Florence