The Heart of Tuscany Bicycle Tour 6-Night

Your journey begins in Florence, where you’ll meet your local guide for a bike fitting and route briefing. You guide will ride with you through the iconic streets of Florence, navigating the city and then heading into the stunning Chianti countryside. Pedal through vineyard-covered hills and quiet backroads as you make your way to Panzano, a charming hilltop town known for its Chianti wines and breathtaking views. Upon arrival, check into your hotel, where your luggage will be waiting. Relax by the pool, sip a glass of Chianti Classico, and take in the sunset over the vineyards before enjoying an included welcome dinner featuring authentic Tuscan flavors.

Today’s ride takes you to one of Tuscany’s most famous towns—San Gimignano, the City of Towers. Cycle through rolling hills, past olive groves, and medieval villages, with plenty of opportunities to stop for photo-worthy views and local wine tastings. Arrive in San Gimignano, a UNESCO World Heritage site famous for its medieval skyline and world-renowned gelato. After checking into your hotel, explore the cobbled streets, artisan shops, and historic piazzas before enjoying an included dinner in the heart of town.

Today’s ride offers two options: a challenging 61km route through Tuscany’s rolling backroads or a more relaxed 41km ride with equally stunning scenery. Your journey culminates in Siena, one of Italy’s most beautiful medieval cities. Ride through vineyards, cypress-lined roads, and historic villages before entering Siena’s UNESCO-listed historic center. Check into your hotel, located inside the town gates, allowing you to easily explore Siena’s winding streets, stunning Duomo, and famous Piazza del Campo. Dinner is on your own tonight—take the opportunity to discover Siena’s renowned cuisine, perhaps trying pici pasta with wild boar ragu at a traditional trattoria.

Depart Siena along scenic quiet roads with stunning city views, heading south toward Montalcino, home of the world-famous Brunello wine. The rolling terrain offers panoramic vistas, charming farmhouses, and picturesque villages before you arrive in Montalcino, a medieval hilltop town surrounded by vineyards and fortresses. After checking into your hotel, take time to visit a local winery, explore the historic fortress, or simply relax with a glass of Brunello. Dinner is on your own tonight, allowing you to choose from Montalcino’s many excellent restaurants—from wine bars to Michelin-starred experiences.

Today’s ride takes you from Montalcino to Montepulciano, a 40km journey through the rolling hills of Tuscany. If you’re feeling adventurous, there are options to extend the ride with a few extra hills, giving you a chance to experience more of the scenic countryside. On your way, you’ll pass through Pienza, a lovely town perfect for a lunch stop and some exploration. Dinner is on your own tonight—explore the town and choose from a variety of local eateries.

Your final ride takes you across the border into Umbria, offering spectacular views of Lake Trasimeno. The route is mostly downhill toward Castiglione del Lago, a charming lakefront town with historic streets and fantastic lunch spots. From here, continue to Cortona, a stunning hilltop town known for its Etruscan history, breathtaking views, and rich culture. Check into your centrally located hotel, giving you easy access to Cortona’s museums, churches, and excellent dining options. Dinner is on your own tonight, and we highly recommend Il Falconiere, a Michelin-starred restaurant located just outside town, offering a spectacular final meal to celebrate your cycling adventure. This evening, your rental bikes will be collected, marking the end of your journey.

After breakfast, depart Cortona by train. Frequent connections make it easy to reach Florence, Rome, or your next destination. We’re happy to assist with travel arrangements.