Relaxed Tuscany Bicycle Tour 7 Night

Your adventure begins in Florence, where you’ll meet your guide for a bike fitting and tour briefing. To help you navigate the busy city streets, your guide will ride with you out of Florence, leading the way into the stunning countryside of Chianti. Once beyond the city, enjoy a peaceful 32km ride through rolling vineyards and olive groves, arriving in Greve, a charming market town known for its Chianti wines and lively central piazza. Your luggage will be waiting for you at the hotel, so after checking in, take some time to explore. Perhaps enjoy a wine tasting at one of the local enotecas before settling in for an included welcome dinner.

Today’s ride takes you deeper into the heart of Chianti, cycling along quiet country roads toward Radda, a beautiful hilltop village with breathtaking views. On the way, stop in Castellina, a town with an Etruscan history, stone-paved streets, and panoramic terraces. If you want a bit more time in the saddle, an optional 20km extension allows for extra exploring. Arrive in Radda, where you’ll check into your hotel and enjoy a relaxing evening with a delicious included dinner.

Today’s ride is a gentle and scenic 33km route, taking you through Tuscan vineyards, medieval hamlets, and rolling countryside on your way to Siena. A stunning city known for its well-preserved medieval architecture and famous Piazza del Campo, Siena is a must-visit destination. Stroll through its narrow alleys, visit the breathtaking Duomo, and immerse yourself in its rich history. Dinner is on your own tonight, giving you the perfect opportunity to discover Siena’s fantastic local restaurants—don’t miss out on the region’s signature dish, pici pasta with wild boar ragu.

Today is a rest day designed for you to fully experience Siena. Wander through its cobblestone streets, visit the grand Palazzo Pubblico, and shop for local delicacies like pecorino cheese and Tuscan olive oil. If you’d like to keep riding, your guide can suggest a scenic loop route around Siena, offering more chances to soak in the region’s beautiful landscapes. Dinner is on your own, so explore Siena’s charming trattorias at your leisure.

Leaving Siena, you’ll ride through some of Tuscany’s most postcard-perfect countryside, heading toward the medieval wonder of San Gimignano. Along the way, stop in Colle di Val d’Elsa, a town famous for its beautiful crystal glassware and historic old town. As you approach your destination, you’ll see why San Gimignano is called the “City of Towers”—its medieval skyline is one of the most iconic in Italy. Your hotel is located near the historic center, making it easy to explore this UNESCO-listed town. Dinner is included tonight at a local restaurant, where you can enjoy a classic Tuscan meal with a glass of Vernaccia wine, unique to the region.

Today is another flexible day to explore at your own pace. Take in San Gimignano’s stunning medieval streets, artisan shops, and panoramic views. Don’t forget to visit Piazza della Cisterna for a scoop of world-famous gelato! If you’re up for another ride, work with your guide to plan an optional cycling route through the surrounding vineyards and rolling countryside. Dinner is included tonight at your hotel, giving you time to unwind and enjoy the peaceful atmosphere of this historic town.

Your final ride takes you further into Tuscany’s wilder, more rugged landscapes, as you head toward Volterra, one of the region’s most historically rich and picturesque hilltop towns. Set atop dramatic cliffs, Volterra boasts an incredible Etruscan and Roman history, with ancient city walls, a stunning Roman theater, and charming streets lined with artisan shops. After checking into your hotel, explore the town’s historic center or relax at a local café with a glass of Tuscan red wine. Your rental bike will be collected today. Dinner is on your own tonight, giving you the perfect chance to discover Volterra’s incredible culinary scene.

After breakfast, say goodbye to Tuscany as you prepare for your next adventure. Frequent buses connect Volterra to local train stations, making travel to Florence, Pisa, or beyond seamless. We’re happy to assist with travel arrangements to make your departure stress-free.