Overview

Meet your Trek Travel host at your hotel, Villa Liberty, located in the heart of the medieval village of San Quirico d’Orcia. They'll give you a brief orientation of the adventures ahead and will fit you to your Trek bike, ensuring a comfortable ride for the week. Then, it's off on your self-guided bike tour in the enchanting landscape of the Val d’Orcia, famous for its unique and pristine views. Your first stop is the tiny medieval spa town of Bagno Vignoni, where you can dip your toes in the historic thermal springs and take pictures of the Roman baths located right at its center. Continue this scenic loop with a gentle climb up to Pienza, a UNESCO heritage site renowned for its pecorino cheese and considered one of the symbols of the Italian Renaissance. Wander through its streets and grab the best gelato in town at “Buon Gusto” before cycling back to your hotel at your leisure. Take some time to relax perhaps with a glass of wine in the garden and afterwards we suggest you walk to one of our favorite restaurants in the heart of San Quirico to enjoy your first Tuscan dinner!

Overview

This morning’s route lifts you high above the Val d’Orcia, a vista of rolling hills blanketed with vines and cypress trees. You'll 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. Your lunch destination is the walled village of Montalcino with its 14th-century fortress and steep cobblestone streets. 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.

Overview

Today you’ll head north following winding ribbons of road into gently undulating terrain into one of Italy’s most dramatic regions, the Crete Senesi. Here vineyards and olive trees give way to cultivated fields crossed occasionally by rows of cypress trees and a few solitary farmhouses. 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. After a lunch break in the town of Montisi or Asciano, 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.

Overview

Enjoy your morning cappuccino before venturing out 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 churches, but it is especially renowned for its noble wine “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!

Overview

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 host 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.