Tuscany Harvest Bike Tour

  • Region: Italy
  • Destination: Tuscany
  • Duration: 6 Days / 5 Nights
  • Level: Three
  • Price From: $4895
  • Single Supplement: $775
Tour Dates
Oct 29 - Nov 3, 2017 $4895 Book Now
Oct 21 - Oct 26, 2018 $4895 Book Now

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Michelin Star Icon-01The harvest season in Tuscany is a magical time to visit for gourmands, foodies, or anyone who loves to eat. Come celebrate the harvest with us as we cycle through the late-autumn sun into ancient Etruscan villages. Discover medieval fortresses and Renaissance masterpieces all while experiencing harvest season like a local. Pick olives and take them to the local mill, hunt for truffles, chestnuts, and porcini mushrooms, cook a seasonal dinner with our friend Lina, and share a wild-boar lunch with a bestselling author and boar-hunting expert. It’s a perfect combination of great cycling, great food, and great people at a great time to be in Tuscany.


Tour by Day

Day One: Raccolta | The Olive Harvest
Your journey begins with a transfer to La Chiusa, a former olive oil mill that is now a charming country inn. Enjoy lunch featuring ingredients from the surrounding countryside. Harvest time means there is work to do, and we will jump right into the action, picking olives from La Chiusa’s grove before hopping on our bikes and riding to our friend Paolo’s olive oil mill to get our olives pressed. Taste the alien green olio nuovo (new oil) on warm bruschetta before pedaling back to the hotel. 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 (Longer option: 20 miles / 32 km, elevation gain: 340 meters)
Accommodations: La Chiusa

Day Two: Tartufi | Truffles
Set off riding through pastures and forests to join the village of San Giovanni. Here we’ll meet up with our friend Topa, a local truffle dog, and her human companion. They’ll lead us into the oak forests that make this area famous for both its black and white truffles. Back in San Giovanni we’ll have a truffle-infused lunch at Donatella’s cozy Osteria. After lunch we’ll keep pedaling 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 when we check into our five-star castle hotel.

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

Day Three: Castagne + Porcini | Chestnuts + Mushrooms
Today we will ride along the slopes of Mt. Amiata, famous for the deep chestnut forests hiding a bounty of porcini mushrooms. Mushroom season in Tuscany means lines of cars parked along the sides of country roads as Tuscans head en-masse into the woods to search for these delicious prizes. We’ll join in the fun, going on our own hunt before a Michelin lunch at a mountain restaurant. After lunch, pedal back to our hotel to relax at the spa. This evening we’ll head back into Montalcino for a cooking class and dinner featuring porcini and chestnuts, of course, in the fifteenth-century home of our friend Lina.

Meals: Breakfast / Lunch / Dinner
Destinations: Vivo d’Orcia, Pescina, Seggiano
Accomplished: 27 miles / 44 kms (Longer option: 41 miles / 67 km)
Accommodations: Castello di Velona

Day Four: Pane dei Santi | An Autumn Treat
Ride to a local bakery for another seasonal treat, pane dei santi, a hearty bread with nuts and raisins made only around All Saints’ Day. Spend the rest of the day making your way across stunning Crete Senesi, stopping to visit the Renaissance frescoes at the Abbey of Monte Oliveto. After lunch, continue riding along the open ridges of this scenic landscape or opt for an earlier van transfer to the hotel. Tonight you are free to explore the medieval city of Siena or dine at the hotel.

Meals: Breakfast / Lunch
Destinations: Buonconvento, Monte Oliveto, Asciano, Siena
Accomplished: 27 miles / 45 km (Longer option: 40 miles / 64 km, elevation gain: 682 meters)
Accommodations: Castel Monastero

Day Five: Chianti Classico + Cinghiale | Wine + Wild Boar
Pedal through the olive and cypress trees deep into the hills of Chianti where fortified hamlets and castles are a testament to the area’s unsettled past. Pass countless estates as we weave our way through forests and vineyards to meet up with Dario Castagno, a best-selling author and local boar hunting expert, for a cinghiale-themed lunch. Learn about the local traditions and politics surrounding the battuta (boar hunt). After lunch, opt for a longer ride or a straight shot back to the hotel. We’ll regroup in the evening for a festive final dinner at our friend Serena’s house featuring the full bounty of the Tuscan autumn.

Meals: Breakfast / Lunch / Dinner
Destinations: Castelnuovo, Brolio, San Sano
Accomplished: 36 miles / 50 km, elevation gain: 640 meters (Longer option: 56 miles / 92 km)
Accommodations: Castel Monastero

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