Tuscany Bike Tour: 30 Year Riserva Edition

Meet your guides at the Chiusi train station for a transfer to our first of two hotels: Casa Newton is a noble estate transformed into a nine-room boutique property, tucked into Tuscany’s Val d’Orcia. Here, we’ll get fitted to our bikes before our first ride down memory lane. Encircling hill towns, these roads are the same ones we included on our first Tuscany tour in 2006—and they remain some of the best. Our destination is our friend Paolo’s farmhouse and olive mill, a de facto gathering place where locals bring their crates of handpicked olives to be pressed into olio nuovo. Paolo’s mother joins us for lunch, a meal that represents the earnest hospitality and simple, seasonal cooking of rural Italy—the way it’s been done for centuries. This evening is all about old friends: first, a visit with fabled local winemaker Vittorio Innocenti at his cellar in Montefollonico. We met Vittorio two decades ago; over the years he’s welcomed our countless visits to the home where his family has produced wine for seven generations, and where he recalls watching British troops as a boy during WWII. After, it’s dinner with Simone and Elena at the osteria that has earned a Michelin star in the time since we first began visiting.

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

The Val d’Orcia and Brunello wine region are home to some of the best wines in the world—and the best views imaginable from the bike—which is why this corner of Tuscany inspired our earliest tours of the region. Today we revisit a beloved route we’ve ridden hundreds of times: across the Val d’Orcia, beneath the eternal watch of medieval fortresses, and into the Brunello region. The sight of the Romanesque Abbey of Sant’Antimo never gets old, and its picture-perfect backdrop of olives and vineyards is an iconic Tuscan tableau. But the bigger highlight of today is our lunch in Lina’s garden. We’ve known Lina and her family for decades, and meeting her forever changed the way we design our tours—to seek and share meaningful connections with locals over a lovingly-made meal. After all, it’s one thing to travel around Tuscany eating in restaurants, but another thing entirely to break bread with Tuscans in their homes. Following our afternoon at Lina’s, ride or transfer back to Casa Newton with time for a dip in the pool or a game of bocce. Tonight’s dinner is picked straight from the hotel’s giardino antico and prepared by the chef.

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

This morning we depart Casa Newton for the hills of the Crete Senesi. Our first stop is the Abbey of Monte Oliveto, where a remarkable Renaissance fresco cycle adorns the courtyard. Your long-tenured guide is the one who originally insisted these frescoes be included on our tours, and his art history background paints its own picture of the artists and monks behind the masterpiece. Back on the bikes, we ride into the Chianti Classico region bound for one of our favorite family-run wineries where our friends are waiting to host us for lunch. This afternoon, check into our last hotel of the trip—the Relais & Châteaux Borgo San Felice, an exceptional property we’ve chosen year after year since 2010. In the birthplace of Chianti Classico, it’s only fair to spend our evening at another family-owned winery, and tonight is an exclusive affair at Castello di Brolio. The Ricasoli family has owned this property for over 1,000 years, making it one of the oldest businesses in the world; it also happens to be one of our longest-running partnerships in Tuscany. To celebrate over 20 years of friendship, we’ll sample vintages as old as DuVine and enter parts of the castle grounds otherwise closed to the public.

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

The Chianti hills weren’t always for winegrowing. In medieval times, they formed the strategic terrain that separated Siena from its rival city-state: Florence. In this age of fierce competition, castles dotted the hillsides in lines of defense—now, they stand like guideposts on our cycling route. Although it was eventually conquered by Florence, today Siena wins our attention. Spend the rest of the day exploring the culture of the Middle Ages that’s remarkably well preserved throughout the city. Our local guides illuminate how Siena was once impenetrable and more powerful than Paris, with influence reaching clear across Europe. Our visit ends with an aperitivo in a private tower, with views almost as far-reaching across the city’s Piazza del Campo. The evening is yours to spend in Siena before returning to Borgo San Felice for the night.

Meals: Breakfast / Lunch
Destinations: Siena, Gaiole in Chianti, Castagnoli
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

Federico Fellini once said “life is a combination of magic and pasta”—so today, we make Il Maestro proud. Our ride through the Chianti countryside has the magical quality of moving through a Renaissance painting: tidy rows of cypress, green swaying grasses, and roads as curvy as a Fellini muse, all bathed in cinematic golden light. And the pasta? Any Italian will tell you that homemade pasta is a celebration saved for long Sunday lunches, holidays, and—on this occasion—a milestone marking 30 years in the business of bike travel. Each family’s matriarch has her own style of pasta and the heirloom wooden board on which to prepare it. Today, the honors are carried out by a nonna who has known DuVine for decades, and we’ll leave lunch at her country home feeling like family. Pass the miles back to the hotel cycling side-by-side and reminiscing with Andy, DuVine Founder and CEO, or catch a ride in the van. There’s only one place we’d want our final dinner of the week: Borgo San Felice, our second home in Tuscany, where the estate’s wine fills (and re-fills) our glasses for toasts to the past, present, and future.

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

End on a high note with a classic ride that, for countless DuVine guests, has marked the finish of their time in Tuscany: a route all the way across Chianti, ending in Florence’s Piazzale Michelangelo. Whether you bike there or prefer to transfer, we say our goodbyes beneath the famous Florentine skyline as guides see you off to your next adventure.

Meals: Breakfast
Destinations: Radda, Panzano, 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