Arrive into Pisa or Florence airport and you will be picked up and taken to your hotel in Florence. Spend the afternoon exploring the capital of Tuscany and take an evening stroll on the Ponte Vecchio.
Today you are given a chance to immerse yourself in Florence before you start your ride into the heart of Tuscany. The most important thing to do is find gelato and we know just the place. Marco Ottaviano Il Gelato on Matteo Palmieri is a favourite as they use seasonal fruits and not too much sugar.
Spend some time visiting Michelangelo’s ‘David’, wonder in the magnificence of the Duomo and watch life go by in this extraordinary city.
Your bike will be delivered today.
Leave your bags at the hotel for collection and begin your ride out of Florence and into the lush Chianti countryside. You will gently climb out of Florence towards San Casciano before another couple of larger hills stand in your way of some lovely gentle downhill through Certalo. Stop along the route in the quiet Tuscan countryside to enjoy a coffee and relax in your surroundings. To blend in, remember cappuccino is a morning drink in Italy and not to be drunk after lunch!
The rest of your journey is uphill but it is worth the effort as you arrive at your hotel. The grounds are stunning, the pool beautiful and the vista is endless.
There’s no need to pack your bags today as you will be returning to the same hotel this evening. Today is one of our favourite Tuscan routes. The morning will see you spend most of your time on downhill sections for about 20km. Then it’s a climb to San Gimignano, a sight for any seasoned traveller, and a UNESCO World Heritage Site. Encircled by its medieval walls and with it’s hilltop views, 12th century skyscrapers loom over the Piazza della Cisterna. We recommend a plate of Pappardelle, a favourite in Tuscany, in one of the numerous restaurants and cafes in the town.
From there, the route heads back out into the countryside finishing with a bit of climbing back up to the hotel.
You can leave your bags at the hotel as you will be returning there at the end of the day. Today’s route is a beautiful 60km loop taking in some climbing and some downhills through this undulating and hilly countryside.
You will pass through Radda in Chianti, a beautiful medieval town, perched on a hill with stunning views. From there, it’s on to Castellina in Chianti and some spectacular roads leading to this hidden Chianti landmark. Castellina’s history goes back to the Bronze Age and like Gaiole, it’s neighbour, it’s well known for its deep tasting, spicy and peppery olive oil. You will notice the colour and texture changes in the olive oils you taste as you ride through the region.
Pack up your bags today and they will be collected from the hotel. Today’s ride takes us down through the countryside and into Siena, a UNESCO World Heritage Site. The Piazza del Campo is the highlight with it’s open square featuring the Mangia Tower.
The city will be flying the flags of the local contrade, or city ward and the right to fly the flag is won and lost in an epic biannual horse race known as the Palio di Siena, that has been run since the 14th century. Run on 2 July and 16 August, the Piazza del Campo is turned from a popular square into a horse track featuring bareback riders being thrown from their mounts in ever tightening turns. If you happen to be travelling at this time, this is one of the ultimate Tuscan experiences.
Your hotel tonight is the stunning Castello di Casole. This is a hotel quite unlike any other. Offering stunning views over the countryside from the pool and sat within opulent grounds, this is our favourite luxury hotel in Tuscany.
Today is a day to rest your legs after a few days on the bike. You are in one of the finest hotels that Tuscany can offer so relax and unwind.
Today you will be transferred back to the airport for your return flight home.
If there is a better cycling experience than riding through Tuscany then we haven’t found it yet. Explore the medieval fortified towns of San Gimignano and Montepulciano, sip cappuccino in a Chianti town square and roll through the endless olive groves and vineyards.
Cypress trees will line your routes and, under the warm Tuscan sunshine, life’s daily stresses just melt away.