Tuscany Harvest Bike Tour

Your journey begins with a transfer to La Chiusa—a former olive mill that’s now a charming country inn—and there’s no better way to kick off harvest week than with a lunch featuring seasonal ingredients from the surrounding Tuscan countryside. But harvest season means there’s work to do, so we’ll jump straight into the action and pick olives from La Chiusa’s grove as a warm-up to our first ride. Then, we’ll hop on our bikes and follow the olives to our friend Paolo’s olive oil mill. Here, they’re pressed into the neon green olio nuovo (new oil), which we’ll sample on warm bruschetta. Ride the rest of the way to our first hotel in Pienza, a classic example of Renaissance architecture that has been exquisitely reimagined into a boutique property. For our first dinner of the week, we’re headed to a nearby farmhouse to feast on 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

Today is all about the truffle. Our search begins as we set off through golden pastures that give way to forests surrounding the village of San Giovanni. Our local friend and his truffle dog are awaiting our arrival, eager to begin their hunt. Together, we head deep into the oak groves that yield both black and white tartufi (truffles). Of course, we must taste our spoils—so back in San Giovanni, we’re treated to a truffle-infused lunch at a traditional, cozy osteria. Our afternoon ride is practically powered by truffles as we cycle 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 the five-star castle hotel we’ll call home for the next two nights.

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

Our route today follows the foothills of Monte Amiata, where volcanic soil has nurtured chestnut forests—which in turn means plenty of porcini mushrooms fruiting from the forest floor. In Tuscany, mushroom season is a sport: parked cars line the shoulders of country roads and families head into the woods en masse hoping to bring home the boletes. We’ll join the hunt just before our Michelin lunch at a mountain restaurant. After, ride back to our hotel for some downtime: perhaps a treatment at the spa or a glass of Brunello on the terrace. Later, we’ll regather and make our way into Montalcino for a cooking class and dinner at the 15th-century home of our friend Lina. On the menu: tender chestnuts and earthy porcini—what else?

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

This morning begins with a ride to a bakery for a different style of seasonal treat: we’re here for the pane coi santi, a rustic bread studded with nuts and raisins, made only in Tuscany around All Saints’ Day. It’s just the hearty fuel we need for the rest of our ride across the Crete Senesi and its iconic landscape of cypress-lined roads and swaying wheat fields. Pause at the Abbey of Monte Oliveto for a look at the remarkably intact Renaissance frescoes, then continue riding along the ridges to meet up with Davide, who welcomes us to his small, family-run winery. We’ll get to know Chianti intimately, tasting everything from full-bodied Chianti Classico to Super Tuscans and sparkling whites during our private wine-paired lunch. Tonight, the evening is yours to explore Siena; our guides are glad to make restaurant recommendations or reserve your table 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

Classic Tuscan cycling is on today’s menu. Our ride takes us through the silvery olive groves and cypress trees that lead deep into the hills of Chianti, then past fortified hamlets, estates, and castles that echo centuries of the region’s history. Keep spinning as forests turn into rust-red vineyards, indicating that we’ve completed our loop back to our hotel. The day’s riding is done—now it’s time for a leisurely lunch before an afternoon nap, a delicious massage, or a walk around the grounds to keep your legs moving. Our last dinner of the week is one you won’t soon forget: our friend Serena hosts us at home for a meal that reflects on all the flavors of the week, accompanied by the slow-cooked seasonal speciality of 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 and a few extra cups of coffee, or rise early for an epic final ride all the way across Chianti, with a triumphant finish in Florence’s Piazzale Michelangelo. Whether you biked here or took a transfer, we say our goodbyes in the most wonderful Renaissance city in the world as our guides see you off from Florence 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