Active travelers dreaming of a Tuscan retreat will love this six-days cycling itinerary that winds through medieval towns and quiet wine country. Begin in the artistically vital city of Pisa where you can learn about the Italian Renaissance before beginning your cycling trip through the lush countryside. You'll pass villas on your way to bustling Lucca, enjoy thermal spa treatments in Montecatini Terme, and visit the home of Leonardo da Vinci before enjoying a final night in the piazzas of Pisa.


  • Visit the famous Leaning Tower of Pisa
  • Sip wine in Lucca's medieval piazzas
  • Enjoy the thermal spas in Montecatini Terme
  • Visit the Leonardo da Vinci Museum in his hometown
  • Bike past scenic villas in the Arno Valley

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Pisa Pisa
Day 2 Ride to Lucca Lucca
Day 3 Ride to Montecatini Terme Montecatini Terme
Day 4 Ride to Vinci & San Miniato San Miniato
Day 5 Ride to Pisa Pisa
Day 6 Departure  

Detailed Itinerary

Day 1: Arrive in Pisa

Leaning tower of Pisa
Leaning Tower of Pisa

Welcome to Italy! When you land at Pisa International Airport (PSA), a driver will be waiting to transfer you to your hotel in town. After you check in and drop your baggage, you will have the rest of the day free to explore the city, visit the iconic leaning tower, and stroll around the Piazza dei Miracoli and the medieval downtown. 

Day 2: Ride to Lucca

A view of Lucca's old town
A view of Lucca's old town

After breakfast today, you will leave your hotel and rent the bikes that you will ride for the rest of your trip. You will then set off on your route to Lucca, which will take you about 20 miles (30 km) across the northern part of the Piana di Pisa and along the Serchio River.

As you ride along this beautiful path with views of the water, you will pass small medieval towns like Filettole and Ripafratta where you may wish to take a quick photograph of some of the city walls and crumbling towers. In the afternoon, you will reach Lucca's impressive city walls. 

After you check in at your hotel, you'll have the rest of the evening free to explore the city and make stops at places like the Lucca Cathedral, Piazza San Martino, Piazza dell Anfiteatro, or Guinigi Tower.

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Day 3: Ride to Montecatini Terme

Montecatini Terme
Terme Tettuccio

You'll set off on a 25-mile (45 km) ride along the base of the green Lucchesia Hills to your destination of Montecatini Terme. Enjoy the quiet of the country roads framed by majestic country villas before reaching the town of Collodi, which is famous for the serene garden of the Villa Garzoni and for being home to the author of Pinocchio.

You can also stop for a rest in the medieval hamlet of Pescia before arriving at the spa town of Montecatini in the late afternoon. After you check in at your hotel, you'll be able to enjoy the thermal spas that have made this town famous. For a panoramic view of the medieval city, you can take the funicular up the hill before dinner.

Day 4: Ride to Vinci & San Miniato

View from San Miniato
View from San Miniato

You'll start your 34-mile (55 km) ride in the morning and head south across the Padule di Fucecchio wetlands to San Miniato. Early along your route, you will reach the wooded Cerbaie Hills, and you can continue downhill to the town of Vinci, the hometown of Leonardo de Vinci where you can visit his home and the official museum.

When you get back on the route, you will cycle across the vineyard-covered ridge to reach the Medici villa of Cerreto Guidi where you can stop for a glass of wine, and then you will cross the Arno River to reach San Miniato.

After you check in at your accommodation, you can visit the Museo Diocesano di Arte Sacra, the Palazzo del Seminario, and some of the town's beautiful churches. 

Day 5: Ride to Pisa

Florence and Arno valley
The Arno Valley

You will ride 34 miles (55 km) back to Pisa today through the scenic hills of San Miniato. As you head into the Arno Valley to reach Santa Maria a Monte, you will have a steep climb on your way towards Bientina and the Vicopisano Castle.

When you reach the foot of Mount Pisano, you will reach the path that runs parallel to the Arno River once more time, and you will follow it all the way back to Pisa. 

When you reach your accommodation, you will be able to enjoy your final night in Italy as you'd like.

Day 6: Departure

Medieval stone bridge Ponte Vecchio over the Arno River
The Ponte Vecchio Bridge over the Arno River

It's time to say goodbye to Italy! After breakfast, a driver will pick you up at your hotel and return you to the Pisa International Airport for your flight home. 


Map of Cycling in Tuscany - 6 Days
Map of Cycling in Tuscany - 6 Days