TUSCANY 2025

After a transfer from Florence into the hills of Chianti, the week kicks off with an expert bike fitting under the guidance of a Colnago factory mechanic. Once you’re dialed in with your C68, set off along the vine-clad ridgelines, through the town of Panzano, and up to the village of Radda—a highlight reel of a route that gets us oriented to the region. Today happens to be a special day in Chianti: on the first Sunday each October, a Gran Fondo known as L’Eroica draws thousands of participants from around the world to ride vintage bikes through this pristine part of Tuscany. Seeing cyclists with wool jerseys and canvas panniers, it’s easy to imagine the greats like Coppi and Bartoli on these same roads. We’ll break away onto a secret cypress-lined road, passing hidden hamlets en route to lunch at a world-renowned winery. There’s only a few final kilometers before we reach Borgo San Felice, our village-turned-luxury hotel for the next three nights. Tonight we’ll have dinner with a Colnago designer for the chance to learn everything about these beautiful bikes.

Meals: Lunch / Dinner

Destinations: Panzano, Lucarelli, Brolio

Accomplished: 26 miles / 41 km, elevation gain: 2,400 feet / 732 meters

Shorter Option: 16 miles / 26 km, elevation gain: 1,600 feet / 497 meters

Accommodations: Borgo San Felice

Wake to the peaceful sounds of the Chianti countryside and begin the morning with a relaxed breakfast. A special guest will be joining today’s ride: we’ll share the road with local legend and former pro cyclist Andrea Tafi and chat about his iconic Paris Roubaix victory in 1999 on a Colnago C40. As we approach Siena, we’ll hop onto a section of the Strade Bianche—the iconic white gravel road where Tadej Pogačar earned his second race victory in the spring of 2024. Right on the route, on the slope of Colle Pinzuto, is our friend Serena’s home. Serena welcomes us as if she’s known us for decades, and together we’ll share a homemade lunch in her garden. After, transfer back to Borgo San Felice for extra time in the spa or by the pool, or rack up the miles and keep riding. Tonight finds us in a timeless hamlet for a traditional dinner at a local trattoria.

Meals: Breakfast / Lunch / Dinner

Destinations: Pianella, Montaperti, San Piero

Accomplished: 25 miles / 40 km, elevation gain: 1,929 feet / 588 meters

Longer Option: 34 miles / 56 km, elevation gain: 3,358 feet / 1,024 meters

Accommodations: Borgo San Felice

Olive and cypress trees surround us as we ride deep into the hills of Chianti. There’s no shortage of fortified hamlets and castles—relics of Florence and Siena’s 300-year struggle for regional ownership over the birthplace of Chianti Classico wines, historically found in ancient cellars around the area. Pedal past countless estates as we weave through forests and vineyards, completing a loop back to San Felice in time for lunch. This evening, meet a metalsmith in his 19th-century Siena workshop beneath the church of San Martino and get an inside glimpse at the enduring traditions of Italian craftmanship that suffuse Colnago’s DNA. Then, stroll through the lively Piazza del Campo to our private dinner atop one of the oldest medieval towers overlooking the square.

Meals: Breakfast / Lunch / Dinner

Destinations: Castelnuovo, Brolio, Castagnoli

Accomplished: 31 miles / 50 km, elevation gain: 2,673 feet / 815 meters

Longer Option: 44 miles / 71 km, elevation gain: 4,503 feet / 1,373 meters

Accommodations: Borgo San Felice

Say goodbye to San Felice as we ride out into the radiant morning light that bathes the Chianti vineyards. The landscape before us is the Crete Senesi—one of the most recognizable areas in Italy with its far-reaching vistas and cypress-lined lanes. At a family-owned olive mill, we’ll stop for a gourmet picnic lunch and demonstration of how Tuscans make their incomparable olive oil. From here, opt for a lift in the van or continue cycling all the way to our hotel for the final two nights: Castiglion del Bosco, an ancient estate lovingly restored by the Ferragamo family. For dinner, we head into Montalcino for an evening of Tuscan hospitality in the 15th-century home of our friend Lina.

Meals: Breakfast / Lunch / Dinner

Destinations: Asciano, Chiusure, Buonconvento

Accomplished: 38 miles / 68 km, elevation gain: 3,987 feet / 1,103 meters

Longer Option: 52 miles / 88 km, elevation gain: 5,447 feet / 1,486 meters

Accommodations: Castiglion del Bosco

This morning we pedal through Italy’s top Brunello vineyards starting right from Castiglion del Bosco (or Montalcino if you’re seeking some extra miles). Stop for a coffee in the medieval heart of San Quirico before heading into the scenic Val d’Orcia, where gentle breezes animate a living landscape of wildflowers and wheat fields. An olive-lined climb takes us over the shoulder of Mount Amiata, Tuscany’s towering dormant volcano, to lunch and a tasting at our favorite Brunello winery—the owner is a passionate cyclist and Colnago collector himself. Stop to take a picture of the beautiful Romanesque Abbey of Sant’Antimo on the return ride to Montalcino. Our final dinner is at the hotel: tonight, we toast to this cycling paradise known as Tuscany.

Meals: Breakfast / Lunch / Dinner

Destinations: Montalcino, San Quirico, Sant’Antimo

Accomplished: 31 miles / 50 km, elevation gain: 2,673 feet / 815 meters

Longer Option: 45 miles / 73 km, elevation gain: 5,120 feet / 1,561 meters

Accommodations: Castiglion del Bosco

Say goodbye to Tuscany any way you see fit: sleep in, stroll around the lovely grounds of Castiglion del Bosco with a coffee in hand, or opt for one last ride as dawn breaks over Montalcino. Your guides will see you off around mid-morning at the Chiusi-Chianciano train station.

Meals: Breakfast