WHAT'S INCLUDED
• Two professional tour guides throughout the program
• All accommodations in Boutique Hotel
• All breakfasts, all lunches, and all dinners
• Wine and beer with meals, coffee, cappuccino, and gelato stops
• Tastings of wine and local specialties
• Cooking demonstration with a local chef
• Logistical support during the tour and luggage transfer
• Shuttle at the beginning and at the end of the tour (Mercedes Vito/Ford Transit Custom)
• Bike rental with bike helmet and GPS navigation
SicilyCyclingTours gear(including a custom cycling jersey t-shirt, water bottle, and drawstring bag)
WHAT'S EXCLUDED: medical/travel insurance, and everything is not explicitly written in this page!
Price from €3.200/person
DAY 1
Welcome to Firenze.
Arrival in Firenze Airport, welcome from the staff and transfer to the Hotel.
Presentation of the trip, assembly and preparation of bikes.
Welcome drink.
Our ride begins at the postcard-perfect fishing village of Marzamemi, we’ll stop for a lunch of fresh seafood pasta at a local trattoria. We'll continue through the beautiful wine region of Nero d’Avola to our chic first hotel.
Meals: Lunch / Dinner
Destinations: Portopalo, Marzamemi
Accomplished: 21 miles / 34 km, elevation gain: 314 meters
Accommodations: Masseria della Volpe
Hotels may vary based on departure. Any variations will be displayed when selecting a departure Dates
DAY 2
The journey starts in Monte San Savino, a charming village in the Val di Chiana known for its Renaissance architecture and cobbled streets. Begin your day with a coffee in the main square and take a quick tour of the Castle of Monte San Savino. As you leave the village, you will cycle through fields of sunflowers and olive groves, setting the tone for a scenic ride.
The route takes you north along quiet country roads, framed by vineyards and tall cypress trees, leading you towards Castelnuovo Berardenga, the gateway to the Chianti Classico region. The landscape here is characterized by the distinctive red soil and rows of vines. Upon arrival, explore the village and visit the Villa Chigi Saracini, then enjoy a wine tasting session at a local winery.
Meals: Breakfast / Lunch / Dinner
Destinations: Castelluccio, Testa dell’Acqua, Noto
Accomplished: 26 miles / 42 km, elevation gain: 677 meters
Longer Option: 40 miles / 66 km, elevation gain: 984 meters
Accommodations: Masseria della Volpe
Hotels may vary based on departure. Any variations will be displayed when selecting a departure Dates
DAY 3
Start your day with a hearty breakfast before heading towards Gaiole in Chianti, a key stop in the Chianti region and home of the famous vintage bike race, “L’Eroica.” You will pedal through rolling hills and sections of strade bianche (white gravel roads), typical of this region. The route is lined with lush vineyards and offers fantastic views of the Tuscan countryside.
Make a stop at the Castle of Brolio, one of the oldest and most historic wine estates in Italy, where you can taste their renowned wines. From Gaiole, the road continues toward Siena, a city steeped in medieval history. Enter the city through Porta Romana and take in the iconic Piazza del Campo, home of the famous Palio horse race. Spend the afternoon exploring the magnificent Duomo of Siena and its vibrant streets.
Meals: Breakfast / Lunch
Destinations: Val di Noto, Ragusa Ibla, Ragusa
Accomplished 46 km
Elevation gain: 1,040 meters
Shorter Option: 17 miles / 27 km, elevation gain: 519 meters
Accommodations: Don Serafino or Relais Antica Badia
Hotels may vary based on departure. Any variations will be displayed when selecting a departure Dates
DAY 4
Departing from Siena, you head deeper into the Chianti region, cycling through a landscape of vineyards, olive groves, and small forests. The road to Radda in Chianti features rolling hills and offers stunning vistas of the region. Radda is a picturesque medieval village, encircled by ancient walls. Take a stroll through its historic center and visit the Chianti Wine Museum, where you can learn about the local winemaking traditions.
After a short break, continue your ride towards Castellina in Chianti, a charming town with a rich history. Here, you can explore the Via delle Volte, a covered passage along the old town walls, and visit the Rocca of Castellina, offering panoramic views over the vineyards.
Meals: Breakfast / Lunch / Dinner
Destinations: Giarratana, Buccheri, Vizzini
Accomplished: 37 miles / 60 km, elevation gain: 1,038 meters
Shorter Option: 23 miles / 37 km, elevation gain: 769 meters
Accommodations: Castello Camemi or Eremo della Giubiliana
Hotels may vary based on departure. Any variations will be displayed when selecting a departure Dates
DAY 5
This day’s ride takes you westward towards the medieval town of San Gimignano, also known as the “Manhattan of the Middle Ages” due to its iconic towers. The route passes through the rolling hills of the Val d’Elsa, a region dotted with vineyards, sunflower fields, and charming farmhouses.
As you approach San Gimignano, the skyline of its towers becomes visible from a distance. Once in the town, explore the Piazza della Cisterna and climb the Torre Grossa for an incredible view over the Tuscan landscape. Take time to wander the streets, visit artisan shops, and sample local delicacies such as saffron and the renowned Vernaccia di San Gimignano wine.
Meals: Breakfast / Lunch / Dinner
Destinations: Licodia Eubea, Gulfi Winery
Accomplished: 21 miles / 34 km, elevation gain: 495 meters
Longer Option: 46 miles / 74 km, elevation gain: 1,149 meters
Accommodations: Castello Camemi
Hotels may vary based on departure. Any variations will be displayed when selecting a departure Dates
DAY 6
Begin the day with a scenic ride southwards towards Tavarnelle Val di Pesa, located in the heart of the Chianti wine region. The route is dotted with rolling hills, olive groves, and vineyards. The landscape here is quintessentially Tuscan, with postcard-like views at every turn.
In Tavarnelle, visit the historic Abbey of Badia a Passignano, an ancient Benedictine monastery surrounded by vineyards. This is a perfect spot to take a break and perhaps enjoy a light lunch at a nearby enoteca (wine bar), where you can sample regional wines and local specialties
DAY 7
On the final day of your tour, you'll ride towards Florence, the jewell of the Reinassance. The road takes you through the Colli Fiorentini offering stunning views of the city as you approach. Stop at the Piazzale Michelangelo for a breathtaking panoramic view of Florence,with the Duomo and PonteVecchio standing out against the skyline. Upon arrival in the city, take some time to explore its incredible landmarks:the Cathedral of Santa Maria del Fiore, the Uffizi Gallery and the Ponte Vecchio. Celebrate the end of your bike tour with a well-deserved gelato and stroll along the Arno river.
WHAT PEOPLE SAY
Teo & Pam
"An unforgettable bike tour through Tuscany. Was a dream come true. The route was well-planned,offering a perfect mix of scenic landscapes and cultural stop and wine tasting."
Mark
"A fantastic way to explore the heart of Tuscany! The bike tour took us through charming villages, endless vineyards, and iconic landmark like Siena and Castellina in Chianti."
Togo
"An incredible cycling adventure through the Tuscan countryside! Highly recommended for anyone seeking an active and immersive travel experience."
