Take a quick spin through the birthplace of the Italian Renaissance with this five-day Tuscan cycling tour. This challenging bike route will take you through the medieval villages and cypress-spotted hills of the Tuscan wine region . Go from Florence to Siena as you take in the region's food, historic castles, and sun-kissed landscapes, accompanied, of course, by a good glass or two.


  • Explore the birthplace of the Renaissance in Florence
  • Sample the world's best Chianti in Tuscan wineries
  • Cycle through fields of flowers in the hills of Radda
  • Visit historic sites in the beautiful medieval city of Siena

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Florence Florence
Day 2 Florence to Radda-in-Chianti Radda-in-Chianti
Day 3 Radda-in-Chianti to Siena Siena
Day 4 Siena to Montalcino Loop Siena
Day 5 Depart Siena  

Detailed Itinerary

Day 1: Arrive in Florence

Florence Cathedral
Florence Cathedral

Start your trip in the city that inspired Da Vinci and Michelangelo, Dante and Petrarch. Find your inspiration in the cobblestone streets of Florence, the capital of Tuscany. Your first day's agenda is up to you, but the Duomo and Ponte Vecchio bridge are some particular highlights.

Day 2: Florence to Radda-in-Chianti

Countryside sunflowers
Countryside sunflowers

Time to get outfitted with your bike and get on the road. You'll start off heading toward Impruneta, a city known for its terracotta art, quaint villas, and a famous basilica called the Sanctuary of Santa Maria. Just 6 miles (10 km) down the road, you'll find Mercatele, a small town surrounded by the hills of Chianti, and famous for—you guessed it—its wineries. Make your way down the Tuscan wine road, stopping for a well-deserved break to indulge in the local reds in the unique triangular public square at Greve.

Today's trail winds down in the hills of Radda in Chianti, home to the medieval Pretorio Palace and where you'll spend the night.

Cycling distance: 43 miles (69 km)

Climb: 5,043 feet (1,537 meters)

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Day 3: Radda-in-Chianti to Siena

Chianti region
Chianti region


As you cycle down from the hills of the Chianti region towards Siena, keep an eye out for Meleto's Castle, an ancient fort that is now a Tuscan countryside villa. Proceed through Castagnolli and take a break at the Castle of Brolio for a quick Ricasoli wine tasting. If you keep up your pace, you'll soon reach the city of Siena, whose historic center is a UNESCO World Heritage Site.

Don't miss the Piazza del Campo, home of the Palio, Siena's famous biannual horse race. Other must-sees include the Siena Cathedral, with its strong Gothic-inspired architecture, and Palazzo Pubblico, which houses Siena's city hall.

Cycling distance: 27 miles (43 km)

Elevation: 2,470 feet (753 meters)

Day 4: Siena to Montalcino Loop


Take a second day to appreciate the walled city of Siena. Today's loop takes you through lush, green hills towards the renowned Brunello vineyards and a wine-tasting session at Montalcino. After a glass or two, start cycling your way to the walled city of Asciano and the nearby Monte Oliveto Abbey, the perfect place for a quiet break. This is the heart of the "Crete Senesi" region, home to all things Tuscan: rolling hills spanned by fields, olive groves, and vineyards, dotted with cypress trees and tiny villages that seem to disappear into the hillsides. 

If you want to keep exploring, cycle back to Siena, or you can give yourself a rest and take the train.

Cycling distance: 44-72 miles (70-116 km)

Day 5: Depart Siena

Say goodbye to Tuscany
Say goodbye to Tuscany

Spend your last morning in Tuscany wandering the city to visit one of Siena's many museums or picking up some souvenirs before you depart.


Map of Cycling Tuscany: Florence to Siena - 5 Days
Map of Cycling Tuscany: Florence to Siena - 5 Days