Tuscany Harvest Bike Tour

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 on to our first hotel in Pienza; a jewel of Renaissance urban planning. This evening, head to a local farmhouse for dinner featuring cheeses, vegetables, grains, and meats all produced onsite.

Meals: Lunch / Dinner
Destinations: Pienza, Petroio
Accomplished: 19 miles / 29 km, elevation gain: 1,919 feet / 585 meters
Shorter Option: 14 miles / 22 km, elevation guide: 1,332 feet / 406 meters
Accommodations: Bandita Townhouse

Set off riding through pastures and forests to join the village of San Giovanni. Here we’ll meet up with our friend, 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 tartufi (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: San Giovanni, Torrenieri, Montalcino
Accomplished: 35 miles / 57 km, elevation gain: 2,486 feet / 758 meters
Shorter Option: 23 miles / 37 km, elevation gain: 1,184 feet / 361 meters
Accommodations: Castello di Velona

Today we will ride along the slopes of Monte 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 15th-century home of our friend Lina.

Meals: Breakfast / Lunch / Dinner
Destinations: Vivo d’Orcia, Pescina, Seggiano
Accomplished: 28 miles / 45 km, elevation gain: 3,818 feet / 1,164 meters
Longer Option: 43 miles / 69 km, elevation gain: 7,118 feet / 2,170 meters
Accommodations: Castello di Velona

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. Continue riding along the open ridges of this scenic landscape to meet up with Davide, our host at a small family-run Chianti winery. Taste their selection of wines, from full-bodied Chianti Classico to Super Tuscans and sparkling whites during a private tasting lunch. 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: 29 miles / 46 km, elevation gain: 2,083 feet / 635 meters
Longer Option: 48 miles / 77 km, elevation gain: 3,972 feet / 1,211 meters
Accommodations: Borgo San Felice or Le Fontanelle

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, completing the loop in time for a relaxed lunch at the hotel with time to enjoy the spa and grounds. Tonight we’ll convene for a joyous farewell dinner at our dear friend Serena’s Tuscan abode. Here, a bounty of autumn’s Tuscan specialties awaits, including cinghiale (wild boar).

Meals: Breakfast / Lunch / Dinner
Destinations: Castelnuovo, Brolio, Castagnoli
Accomplished: 31 miles / 50 km, elevation gain: 2,673 feet / 815 meters
Longer Option: 40 miles / 64 km, elevation gain: 3,575 feet / 1,090 meters
Accommodations: Borgo San Felice or Le Fontanelle

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
Optional ride: 32 miles / 52 km, elevation gain: 2,470 feet / 753 meters
Longer Option: 43 miles / 69 km, elevation gain: 3,477 feet / 1,060 meters