Tuscany with Charm

Tour briefing and bike handover. Take your time to explore the surroundings before you hop in the saddle the next day. A leisurely stroll through the famous spa town is a perfect start—or perhaps a ride on the funicular up to Montecatini Alto?

The small medieval wine town of Montecarlo—where one of Tuscany’s rare white wines flourishes—lies along the route to Lucca (alternatively, you can reach Montecarlo independently by train). Cycling atop its nearly fully preserved city walls offers an unforgettable experience. The journey then continues to Lake Massacciuccoli, also known as Giacomo Puccini’s lake, boasting breathtaking views all the way to the sea and Pisa’s “Piazza dei Miracoli,” home to the world-famous Leaning Tower.

The cycling route first follows the Arno River, accompanied by fertile fields. Next, you’ll pass through the hills of the Pisa region, where gentle slopes are dotted with sweet vineyards, juicy olives, and ripe peaches. Small medieval villages cling to the hilltops like swallows’ nests. With these enchanting sights, you’ll soon arrive at today’s destination, the spa town of Casciana Terme.

You’ll pedal through vineyards and softly rolling hills along picturesque paths toward San Gimignano, surrounded by the timeless beauty of the authentic Tuscan countryside. Just before you arrive, the iconic silhouette of the world-famous medieval towers will come into view. Once owned by noble families, these historic towers still define the town’s charming skyline today.

The stunning Tuscan landscape along today’s route makes the occasional small climb barely noticeable. By the time you reach the fortified village of Monteriggioni, you’ll feel transported back to the Middle Ages. But the undeniable highlight of the day is the architectural gem that is Siena.

Enjoy great views over the vineyards on a beautiful mountain road. Take a break in the stone village of Vagliali and enjoy a good Italian cappuccino before cycling along a white road through vineyards and deciduous forests to Radda. Fortify yourself for lunch with a typical plate of pasta and savour the atmosphere of this village gem before the tour continues into the heart of Chianti to Castellina.

The last day of cycling takes you over a plateau with great views and then hilly to Greve with its enchanting old town centre. The capital of Tuscany draws ever closer and you cycle comfortably on a long descent to the Ponte Vecchio. You are sure to have found your favourite Tuscan wine this week. Treat yourself to it again at the end of your trip in beautiful Florence.

Flexible departure options, extensions, or combination with “Florence to Rome” tours are all available.