Tuscany Self-Guided Bike Tour

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 trees. After passing by the spa town of Bagno Vignoni, you will ride up to Castiglione d’Orcia, admiring the remains of what was once the mighty Rocca Aldobrandesca, a fortress that dominates the village. Your first stop today will be the renowned Abbazia di Sant’Antimo, a monumental 12th-century Romanesque abbey, where if you're lucky, you may arrive to the haunting choral harmonies of the monks' Gregorian chants—magical! Your lunch destination is the walled village of Montalcino with its 14th-century fortress and steep cobblestone streets that dominate the surrounding countryside. Here you can discover the delights of Brunello wine, one of the finest Italian varietals, and enjoy lunch at your leisure at one of Montalcino’s many trattorias. When you're ready, cycle back to San Quirico along winding roads and relax at the hotel before selecting a local bistro in town from the list of Trek Travel recommendations.

Today you’ll head north into one of Italy’s most dramatic regions, the Crete Senesi, following winding ribbons of road into gently undulating terrain. Here vineyards and olive trees give way to cultivated fields crossed occasionally by rows of cypress trees and a few solitary farmhouses. The particular dry grey terrain forms a sort of badlands typical of this area, which appears almost lunar, and are distinguished by the dramatic colors of the clay-dense soil. At the same time a barren landscape yet also some of the most stunning views in Tuscany. Riding here gives you a feeling of peace and, if you feel like adding some more mileage and elevation, take the avid route to Asciano, pedaling through meandering roads overlooking the surrounding ridges on an other-worldly route. We recommend you stop for lunch at our favourite restaurant in the tiny village of Montisi, Taverna da Roberto. Please, remember to make a reservation ahead of time because our friend and local chef Roberto only works with reservations. You'll be amazed by the passion and love he puts into preparing a delicious farm to table lunch for his guests! After lunch, continue your loop back to the medieval village of San Quirico d’Orcia where you can relax, perhaps with a spa session. The evening is yours to explore the cobbled streets of the town and to enjoy dinner at one of the many small bistros recommended by our local experts.

Enjoy your morning cappuccino and venture on a spectacular ride through the Val d'Orcia. Your destination today is one of Tuscany's prettiest towns, strung along a ridge at 605 meters above sea level and surrounded by walls and fortifications. Montepulciano is well known for its Renaissance buildings and lovely churches, but it is especially renowned for its noble wine called “Vino Nobile di Montepulciano", simply divine! Stop for lunch in this elegant town and don't miss the opportunity of tasting its high-level vintage made from Tuscan Sangiovese grapes. There are plenty of wineries where you can sample it. After lunch, continue your ride at your own pace surrounded by idyllic cultivated hills. Back at the hotel in San Quirico, take some time to relax with a stroll in town soaking up the tranquil atmosphere of this ancient medieval village. Tonight, we suggest you dine at the local trattoria Il Vecchio Forno to celebrate a trip of a lifetime in a magical region of Italy!

If you're up for it, close out your Tuscany self-guided bike tour by rising early for a final bike ride to Monticchiello as you watch the sunrise creeping over the classic Tuscan countryside. Or simply linger over a hot cappuccino and walk into town at your leisure, enjoying your final moments in this enchanting region. Your Trek Travel contact will meet you at the hotel at 11:00 AM to take your bike and say farewell before you leave for Florence or other destinations.