Overview

Welcome to your Tuscany cycling trip! Your Trek Travel guides will meet you at via Fiume, 12, directly outside the Hotel Albani in Florence at 10:30 AM on the first day of your in Florence. A two-hour shuttle will deliver you to your starting point for today's ride, a countryside trattoria set among the rolling hills of the Val d’orcia. After a delicious Tuscan lunch, your Trek Travel guides will ensure that you have an excellent fit to your Trek bicycle while offering specific cycling tips for riding in Italy. You’ll then start with a rolling, scenic loop ride among the cypress trees and olive groves to our first hotel in the charming medieval village of San Quirico d’Orcia. This evening, you and your companions will gather for an Italian aperitif on the hotel terrace before an exceptional dinner at our favorite restaurant in the heart of San Quirico. Enjoy a selection of traditional dishes with a modern twist, paired with a unique selection of regional wines.

Overview

This morning’s route lifts you high above the Val d’Orcia, a vista dotted with rolling hills blanketed with vines and rows of cypress. Your first stop is a tiny Roman spa town of Bagno Vignoni, known for its hot sulfurous springs. The town plaza is filled with a pool built by the Medici family centuries ago, where you can refresh your feet before you continue your ride to Abbazia di Sant’Antimo, a stunning 12th-century Romanesque abbey. If you're lucky, you may arrive to the choral harmonies of the monks' Gregorian chants—it is positively magical! Our lunch destination today is the walled village of Montalcino, whose 14th-century fortress and steep cobblestone streets dominate the surrounding countryside. Here you can discover the delights of Brunello wine, one of the finest Italian varietals together with lunch at the trattoria of your choice. Cycle back along winding roads or reward yourself with a shuttle and more time to enjoy yourself back at the hotel. This afternoon relax by the pool and perhaps order a sunset cocktail. This evening is yours to explore the cobbled streets of San Quirico to enjoy dinner at one of the many small bistros on your own.

Overview

Today you’ll head north into one of Italy’s most beloved regions—Chianti. Follow winding ribbons of road along cypress-lined ridges into the Crete Senesi, a landscape distinguished by its dramatic soil tones and some of the most breathtaking views in Tuscany. Your destination is the picturesque village of Villa Sesta, where a charming bistro awaits in a historic setting dating back more than 1,200 years. Sit back, relax, and enjoy fresh, farm-to-table cuisine. From here, you can choose to ride or shuttle the final stretch to Relais Vignale & Spa, a boutique hotel set among Chianti’s vineyards. After check-in, unwind with a dip in the pool or stroll the flower-lined paths of this elegant 18th-century residence. This evening, dine at the hotel’s Vignale restaurant and toast another unforgettable Tuscan sunset.

Overview

Don’t forget your camera as you descend into a valley where vineyards and olive groves give way to shady chestnut forests. Stop to visit the Castello di Brolio and its famous L’Eroica caffè, home to great espresso and cool cycling memorabilia. For lunch, we’ll stop at Bar Dante, where our hosts pride themselves on serving the best bruschetta in town—if not all of Tuscany—washed down with a glass of Chianti. Afterward, continue to Lucarelli for a mid-afternoon espresso with the locals, or spin back to the hotel to enjoy the spa. This evening is yours to explore the charming streets of Radda in Chianti, where you can pick up a local bike jersey or sample delicious regional specialties. Then, enjoy dinner in town while savoring the views and warm ambiance of this historic village.

Overview

Following your morning cappuccino, set out along quiet country roads lined with vineyards and shaded by forest. As you ride through the hills, catch glimpses of Siena’s towers rising in the distance—a timeless view that speaks to Tuscany’s rich history. Pause midday for a fresh picnic lunch of hand-cured prosciutto, local cheeses, and rich Frantoio olive oil. Back on the bike, enjoy sweeping vistas of Monteriggioni, a walled hilltop town crowned by 14 medieval towers. Stop for an espresso or gelato in the piazza before wandering its cobbled streets. From here, shuttle back to the hotel or continue pedaling through some of Chianti’s top wine-growing districts. Tonight, we shuttle to Fattoria di Corsignano, an agriturismo in the heart of the Chianti Classico wine region, for a lively private pasta-making masterclass. An Italian chef will guide you through the art of crafting fresh pasta, perfectly paired with local Chianti wines. We'll toast to a week of great riding, warm camaraderie, and unforgettable flavors.

Overview

It’s sadly time to bid farewell as your Tuscany cycling trip comes to a close. Rise early to soak in the soft morning light as a new day unfolds over the classic Tuscan countryside—or linger a little longer over a hot cappuccino and enjoy a slower-paced morning at the hotel. You’ll say goodbye to your guides at 11:00 AM before boarding a shuttle to Florence, continuing your travels with a piece of this beautiful region carried with you.