Overview

Welcome to your Tuscany cycling trip! Your Trek Travel guides will meet you at Piazza dell'Indipendenza in Florence at 10:30 AM on the first day of your Tuscany Bike Tour. 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 ride climbs high above the Val d’Orcia, revealing rolling hills lined with vines and cypress trees. Stop in the tiny spa town of Bagno Vignoni, famed for its sulfur springs and Medici‑era pool set in the main piazza, before continuing on to the magnificent 12th‑century Abbazia di Sant’Antimo—if you’re lucky, you may hear the monks’ Gregorian chants echoing through the abbey. Lunch awaits in the walled hilltop 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. Ride back on scenic roads or opt for a shuttle to enjoy more time at the hotel. This afternoon, relax by the pool maybe with a sunset cocktail, then spend the evening exploring San Quirico’s charming streets and enjoying dinner on your own at a local bistro.

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 gradually give way to shady chestnut forests. Stop to visit the Castello di Brolio and its famous L’Eroica Caffè, known for excellent espresso and cool cycling memorabilia. Back in Radda, we’ll return to our hotel and walk to the nearby Bar Dante for a delicious lunch, where our hosts pride themselves on serving the best bruschetta in town—if not all of Tuscany—perfectly paired with a glass of Chianti. Those eager to add a few more miles can hop back in the saddle for an optional afternoon loop to Lucarelli, stopping for an espresso with the locals. 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 roll through the hills, catch glimpses of Siena’s towers rising in the distance—a timeless view that speaks to Tuscany’s rich history. At midday, pause for a relaxed picnic lunch featuring hand‑cured prosciutto, local cheeses, and rich Frantoio olive oil at our friend Lapo’s farm, where he proudly shares the story of his land and craft. From here, shuttle back to the hotel and unwind with a few leisurely hours by the pool. This evening, we’ll take a 30-minute shuttle to 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. Together, 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.