Florence to Pisa Self-Guided Cycling Tour Itinerary

Day 1 Arrival in Florence

Upon arrival in Florence, immerse yourself in the city’s rich history and beauty. Start your day by climbing Giotto’s Tower for a breathtaking view of the city below, with the Duomo framing the skyline. Explore the renowned Uffizi Gallery, or take a leisurely stroll across the iconic Ponte Vecchio bridge to enjoy unique views of the city. In the afternoon, meet for a tour briefing and bike fitting, followed by personalized suggestions for dinner to start your Tuscan adventure.
Overnight Location: Hotel in Florence
Distance: N/A
Meals: N/A

Day 2 Florence to Radda in Chianti

Depart Florence and begin your ascent through some of Chianti’s iconic hills, heading toward Radda in Chianti, where you’ll spend the night. Along the way, stop in the charming town of Greve to explore the main square and visit the famous Macelleria Falorni, renowned for its local salumi (cold cuts). Radda, a quaint and historic town, was once a key crossroads for travelers journeying north and south through Tuscany.
Overnight Location: Hotel in Chianti
Distance: 61km, 1,273m / 4176ft elevation gain
Meals: Breakfast

Day 3 Cycle to Siena

Pedal through the southern part of the Chianti Region, then spend the afternoon discovering Siena. Known as Italy’s best-preserved medieval city, Siena once rivaled Florence for power and influence in Tuscany during the 1300s. As you step inside its ancient city walls, you’ll feel as though you’ve traveled back in time.
Overnight Location: Hotel in Siena
Distance: 51km, 957m / 3,140ft elevation gain
Meals: Breakfast

Day 4 Ride to San Gimignano

Today’s ride takes you deep into the heart of Tuscany, cycling past vineyards, 17th-century villas, and charming small towns. Your destination is San Gimignano, a UNESCO World Heritage Site known for its well-preserved medieval architecture. Famous for its striking towers, remnants of the 13th and 14th centuries, San Gimignano offers a glimpse into Tuscany’s rich history.
Overnight Location: Hotel in San Gimignano
Distance: 50km, 774m / 2,540ft elevation gain
Meals: Breakfast

Day 5 From San Gimignano to Vinci

Today’s ride takes you through rolling hills, dotted with picturesque small towns. Your journey ends in Vinci, the birthplace of the renowned Leonardo da Vinci. Here, you’ll have the opportunity to visit his childhood home and explore a museum featuring scale models of his groundbreaking inventions.
Overnight Location: Agriturismo in Vinci
Distance: 74km, 936m / 3,070ft elevation gain
Meals: Breakfast

Day 6 Bicycle to Lucca

Climb the stairs to the Medici villa in Cerreto Guidi for stunning panoramic views, then continue your ride west to Lucca, where you’ll stay for the next two nights. Once a prosperous Roman town and medieval city-state, Lucca still preserves its charm with quaint shops, sidewalk cafés, and a beautifully intact 17th-century city wall.
Overnight Location: Hotel in Lucca
Distance: 59km, 439m/ 1,440ft elevation gain
Meals: Breakfast

Day 7 Loop ride to Pisa

On the final day of cycling, ride to Pisa to visit the iconic Leaning Tower and the Piazza dei Miracoli — arriving by bike adds to the excitement! Along the way, pass by Lake Massaciuccoli, where Puccini composed many of his famous operas. After exploring Pisa, return to Lucca for a relaxing evening “passeggiata” along the pedestrian streets or wander through its charming alleys and piazzas.

Choose from three options for your ride: cycle to Pisa and return by train (with your bike onboard), take a longer loop through scenic Tuscan hills, vineyards, and grand villas, or challenge yourself with an extended ride to the Tuscan coast to dip your toes in the Tyrrhenian Sea.
Overnight Location: Hotel in Lucca
Distance: Varies depending on the option selected.
Meals: Breakfast

Day 8 Departure

After enjoying a delicious breakfast buffet at your hotel, you’re free to continue your adventure wherever it may take you. We hope you’ve had a memorable time cycling through Tuscany and exploring its rich history, culture, and landscapes. Thank you for joining us on this unforgettable journey. “Buon viaggio!”
Overnight Location: N/A
Distance: N/A
Meals: Breakfast