Tuscany Harvest Bike Tour

Meet your guides at the Chiusi train station for a transfer to our first hotel, a noble estate perched on a hill outside Pienza that has been refashioned into a boutique retreat. Get fitted on the bikes and set off on a ride on our favorite roads through quintessential Tuscan countryside. Our destination is our friend Paolo’s olive mill where locals arrive with crates of handpicked olives to be pressed into neon green olio nuovo (new oil). Meet Paolo’s mother and savor the warm hospitality and simple flavors of Italian rural life during lunch in the family’s farmhouse. From there, cycle back to the hotel where there’s time to relax and enjoy a glass of wine by the pool. Later we’ll regather to watch the sun set over the Val d’Orcia as the chef welcomes us with a seasonal dinner served just steps from the hotel’s garden.

Meals: Lunch / Dinner
Destinations: Pienza, Montisi
Accomplished: 24 miles / 38 km, elevation gain: 2,388 feet / 728 meters
Shorter Option: 13 miles / 22 km, elevation gain: 1,171 feet / 357 meters
Accommodations: Casa Newton

Today’s ride takes us through the Val d’Orcia and Brunello wine regions, home to some of Tuscany’s most beautifully manicured landscapes. Yet just above, neat rows of vines meet the wild forests of Mount Amiata, a dormant volcano that has long shaped the surrounding terroir. Amiata’s forests nurture chestnuts, porcini mushrooms, and the elusive cinghiale (wild boar), while the vineyards below produce some of Italy’s finest wines. This intersection of farm and forage is a gift to the palate. We’ll celebrate the season’s bounty over a homemade lunch at the 15th-century home of our friend Lina in the heart of Montalcino. After, opt to ride or transfer back to the hotel for a relaxed afternoon. This evening we’ll head to dinner at a neighboring farm. Here, the day’s harvest becomes tonight’s feast as everything on the table—from the cheese to the vegetables to the organic wines—is made or grown right on site.

Meals: Breakfast / Lunch / Dinner
Destinations: Castiglione d’Orcia, Castelnuovo dell’Abate, Montalcino
Accomplished: 30 miles / 48 km, elevation gain: 3,188 feet / 972 meters
Longer Option: 51 miles / 82 km, elevation gain: 5,087 feet / 1,551 meters
Accommodations: Casa Newton

Today is all about the truffle. Our search begins as we ride through golden pastures that give way to forests surrounding the village of San Giovanni. A local friend and his truffle dog await our arrival, eager to begin their hunt. Together, we head deep into the oak groves that conceal 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 cozy osteria. Our afternoon ride is practically powered by truffles as we pedal along the cypress-lined roads of the Crete Senesi, bathed in warm autumn light. Our ride ends at the luxurious hotel that will be our home for the next three nights. Relax and get settled then regroup for dinner. We’ll spend the evening at a charming, family-owned osteria, where locals gather to share a glass of Chianti and feast on seasonal favorites.

Meals: Breakfast / Lunch / Dinner
Destinations: Monte Oliveto, Asciano, Monteaperti
Accomplished: 37 miles / 60 km, elevation gain: 3,096 feet / 944 meters
Longer Option: 43 miles / 70 km, elevation gain: 3,841 feet / 1,171 meters
Accommodations: Borgo San Felice or Castel Monastero

As patient winemakers gather the last bunches of grapes, the vineyards themselves seem to celebrate the vendemmia (grape harvest) with a fireworks display of fall color. The leaves of Sangiovese glow a warm amber that contrasts beautifully with the brilliant yellows of the Malvasia and the scarlet pops of Colorino and Canaiolo. Today’s scenic loop is one of our favorites. We’ll wind through the vivid patchwork of the Chianti Classico, pausing for plenty of photos along the way. Stop for coffee in the picturesque village of Gaiole, then complete the loop back to the hotel. The day’s riding is done—now it’s time for a leisurely lunch followed by an afternoon nap, a delicious massage, or a walk around the grounds to keep your legs moving. Tonight the evening is yours to explore Siena, Italy’s quintessential medieval city. Stroll the cobbled streets, browse the shops, and enjoy dinner on your own—your guides are happy to recommend the perfect local restaurant.

Meals: Breakfast / Lunch
Destinations: Castagnoli, Gaiole, Siena
Accomplished: 25 miles / 41 km, elevation gain: 2,529 feet / 771 meters
Longer Option: 32 miles / 52 km, elevation gain: 3,483 feet / 1,062 meters
Accommodations: Borgo San Felice or Castel Monastero

The kitchen garden has long been the creative heart of Tuscan cuisine and the Mediterranean diet, now so widely acclaimed, has its roots in Tuscany’s mezzadria—or sharecropping—system. While wheat, transformed into bread and pasta, created the foundation of the diet, the addition of fresh garden-grown produce gave rise to the classic Tuscan dishes we enjoy today. Today we’ll ride into the Chianti hills to visit our friend Serena, whose bountiful garden and love of cooking brings those flavors to life during an unforgettable al fresco lunch. Choose to cycle back to the hotel or hop in the van for a transfer. Tonight we’ll raise a glass to the abundance of the season before a final gourmet dinner paired with renowned wines produced right on the estate.

Meals: Breakfast / Lunch / Dinner
Destinations: Castelnuovo, Pianella, Bossi
Accomplished: 32 miles / 52 km, elevation gain: 2,906 feet / 886 meters
Longer Option: 42 miles / 68 km, elevation gain: 3,874 feet / 1,181 meters
Accommodations: Borgo San Felice or Castel Monastero

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: Radda, Florence
Optional ride: 36 miles / 58 km, elevation gain: 2,270 feet / 692 meters
Longer Option: 48 miles / 78 km, elevation gain: 3,611 feet / 1,101 meters