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Cycling Trip Highlights
  • The Duomo and Michaelangelo’s David in Florence
  • San Giminano, the city of medieval skyscrapers
  • Val d’Orcia rolling countryside
  • Medieval cobbled squares in which to enjoy a morning cappuccino
Book your cycling holiday in Italy with us – 7 nights from£995.00
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Florence & Tuscany by Bike

A fully-flexible cycling holiday in Italy

What we love About your Tuscany and Florence cycling holiday

We love...The Views
There is nothing quite as dramatic as the views across Chianti. Olive groves and vineyards stretch out in front of you and the hills roll for miles and miles. Cypress trees line quiet roads and you can cycle on the famous Strada Bianchi, the famous Tuscan white roads.
We love...Florence & Its Architecture
Few cities are so associated with extraordinary architecture and art as Florence. You will explore cobbled streets leading you to magnificent palaces, medieval basilicas and famous art galleries in this revered city.
We love...Tuscan Lifestyle
You will be given lots of opportunities to relax and have a coffee in the many picturesque Tuscan villages. Take in the serene lifestyle and make sure to grab a bite to eat at one of the quaint restaurant's that you will ride past. The Pappardelle in San Gimignano is particularly good.

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Our suggested Tuscany cycling holiday

Day by Day

Day 1Arrival

Arrive into Pisa or Florence airport and Love Velo will pick you up and take you to your hotel in Florence. Spend the afternoon exploring the capital of Tuscany and take an evening stroll on the Ponte Vecchio.

Day 2Explore Florence

Today is a chance to immerse yourself in Florence before you start your ride into the heart of Tuscany. In our opinion, the most important thing to do is find gelato and we know just the place. Marco Ottaviano Il Gelato on Via 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.

Day 3Cycle into Chianti
Total distance48kmTotal climb865m

Leave your bags at hotel for collection and it’s time to ride out of Florence and into Chianti. You will cycle through undulating countryside for approximately 20km until you reach Strada in Chianti. As you head further south, you will notice the air changing, the smell of grapes drifting through the breeze and be greeted with miles and miles of vineyards. Stop in Greve in Chianti to discover the local town square, or should we say triangle, and enjoy a coffee. To blend in, remember cappuccino is a morning drink in Italy and not to be drunk after lunch!

From Greve you will head towards Panzano, a medieval town that has been fought over by Siena and Florence for hundreds of years. If you are riding this route on a Sunday, the town has a morning outdoor market selling cheeses, meats, flowers and other Chianti favourites. From Panzano you will ride 15km to the hotel, gently climbing as you go.

Day 4Explore San Gimignano
Total distance55kmTotal climb1035m

Leave your bags for collection in the morning and ride out today on our favourite Tuscan route. The morning will take you up some hills for about 10km before a long downhill through San Benedetto. Then it’s a climb to San Giminano, a sight for any seasoned traveler, and a UNESCO World Heritage Sight. 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 up to your hotel for the evening.

Day 5Exploring the South of Chianti
Total distance40kmTotal climb850m

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 40km 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 Gaiole in Chianti, famous for it’s green gold olive oil. Deep tasting, spicy and peppery olive oil, is a feature of Chianti and you will notice colour and texture changes as you ride through the region.

The route takes you past Castello di Brolio where Baron Bettino Ricasoli invented the Chianti formula in 1872 so feel free to stop and explore the castle. From there, it’s back through the Cypress tree lined roads to the hotel.

If you  fancy a longer or shorter route we have plenty of other loop rides in the area.

Day 6Cycle to Casole d'Elsa
Total distance45kmTotal climb850m

Your bags will be collected this morning and your ride today continues south. After a morning climb, it’s downhill for much of the way today, with the odd bump, but nothing too strenuous or difficult. You will pass through small Chianti towns, rolling vineyards and endless olive groves.

Day 7Cycle to Siena
Total distance75kmTotal climb1200m

You can leave your bags in the hotel as we will be returning later in the evening. Today’s ride takes us on a loop and into Siena, a UNESCO World Heritage Site. The Piazza del Campo is the highlight with its 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. The horse race has been run since the 14th century and the Piazza del Campo is turned from a square with people milling about, to a horse track featuring bareback riders being thrown from their mounts in ever tightening turns. If you happen to be in Siena on 2 July and 16 August, this is one of the most thrilling Tuscan experiences.

Leave a bit in the legs as the ride back to the hotel is mainly uphill.

If you fancy a longer or shorter route we have plenty of other loop rides in the area.

Day 8Departure

Enjoy a leisurely breakfast at the hotel and you will be transferred back to the airport for your return flight home.

How's the Weather? in Florence & Tuscany

The SpringMarch to May
Tuscany generally has a mild climate so Spring is a very pleasant time to ride, especially as you move through April into May. Temperatures are not sweltering and the summer crowds have not descended.
The SummerJune to August
The summer is hot and you're likely to experience good weather with warm temperatures. July & August are exceptionally warm and you are likely to want to ride early and stay out of the midday sun.
The AutumnSeptember to November
September is a great time to visit Tuscany as temperatures drop from the stifling summer heat. Cycling will be hugely enjoyable in the early Autumn. November has the most rainfall so plan your trip to be home before then.
The WinterDecember to February
The winter is best avoided for cycling in Tuscany as you're likely to experience cold weather and rain.

What to ExpectFrom vibrant countryside to famous cities

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 Giminano 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.

Your Florence & Tuscany Cycling TripPackage Details