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Florence & Tuscany by Bike

6 nights from £995.00

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
Florence & Tuscany by Bike
6 nights from £995.00
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WE LOVEThe 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 LOVEFlorence & 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.

What's Included

Our suggested Tuscany cycling holiday

We can tailor make this trip for you
Day 1Arrival in Florence

Arrive into Pisa or Florence airport, where a private transfer 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. If it’s romance you’re after, there are an abundance of restaurants sitting on the banks of the Ponte Vecchio, where you can wine and dine by the reflecting sunset.

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 to Radda in Chianti

Today’s route is a beautiful 50km taking in some climbing and some downhills through this undulating and hilly countryside. You will make your way to Radda in Chianti, a beautiful medieval town, perched on a hill with stunning views. 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. From there, you will cycle through the Cypress tree lined roads to your hotel.

Total distance50kmTotal climb750m
Day 4Cycle to San Gimignano

Today is one of our favourite Tuscan routes. You will head west through quiet Chianti countryside towards Poggibonsi. Then it’s a climb to San Gimignano, a sight for any seasoned traveler, and a UNESCO World Heritage Site. Encircled by its medieval walls and with its 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. Your overnight stay will be just outside the walls of this famous city.

Total distance45kmTotal climb790m
Day 5Loop Ride From San Gimignano

Your loop ride today circles the Castelvecchio Nature Reserve, so you can be guaranteed spectacular scenery. Although there is a fair bit of ascent, you will find plenty of Tuscan towns to hop off the saddle to rest, eat and drink coffee. Gambassi Terme boasts quaint alleyways that create a maze within the town.  The middle part of your route travels through the tranquil nature reserve’s rolling hills, so have your camera to hand.

If you  fancy a longer or shorter route we have plenty of other loop rides in the area, including to Monteriggioni and Voleterra.

Total distance67kmTotal climb1396m
Day 6Cycle to Siena

Today’s ride takes you further into the heart of Tuscany on your way to Siena, a UNESCO World Heritage Site. The Piazza del Campo is the highlight with its open square featuring the Mangia Tower. If you happen to be in Siena on 2 July and 16 August, one of the most thrilling Tuscan experiences is 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.

Total distance41kmTotal climb725m
Day 7Loop Ride From Siena

Head out into the rural countryside surrounding Siena, passing through small villages that encapsulate what Tuscan living is all about. We have loop rides to suit you. Explore Rosia’s religious landmarks, including the beautifully structured Abbazia di Torri, or ride west into the heart of the Val d’Orcia. After your loop ride, say goodbye to Siena as you travel back to Florence airport via private transfer or if you’d like to spend more time in Tuscany, choose to extend your stay. If you’re after rural consider our alternative loop ride, which takes you into the quiet hills.

Total distance35kmTotal climb365m

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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.

8day holiday
Or tailor your trip
48km avg
Expect to ride about 48km per day

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.

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