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Adventure of the Week: Tour of Tuscany: Florence to Montepulciano
3 Min Read
15 February 2018
Adventure of the Week: Tour of Tuscany: Florence to Montepulciano

Want to see the very best of Tuscany in a week? Well, it is either you spend the time fretting over directions and parking in an expensive hire car, or you could pack yourself onto a coach tour and elbow people for the best camera position to get that snap.  Or, you could push yourself, get onto two wheels and ride through classic Tuscan landscapes, conquering hills and taking in outstanding views far from the crowds. If you fancy the last option, then take a look at the Tour of Tuscany: Florence to Montepulciano.

cyclists in Tuscany

Quiet roads through the best of Tuscan scenery

In a nutshell:

Florence to Montepulciano is a road biking trip through the stunning backroads of Tuscany. Starting off in the classic renaissance city of Florence, you speed through the wine paradise of Chianti, take in the hill-top masterpieces of San Gimignano and Siena before finishing up in Montepulciano. The trip is a combination of world-class cycling, food, and wine that will bring tears of joy to your eye, rolling green scenery and towns built so beautifully that they almost defy belief.

Distance: The full trip is 170k, averaging about 55km per day.  However, if you don't have the whole week to do it, we offer the section from Florence to Siena as a standalone trip of three days cycling.

Grade: Moderate to Strenuous.  Make no mistake, this is no walk in the park, but with great effort comes great reward and we have designed this trip to get the best possible road cycling experience, while still allowing you space and freedom to immerse yourself in the Tuscan way of life. While an average of 55km is not too bad, there are some serious climbs involved each day, with several short hill-climbs between 5-8km with gradients of up to 12%.

Siena Tuscany

The classic skyline of Siena


Tuscany is arguably the most famous part of Italy (after Rome probably). It is the home of all we associate with classic Italy. Hill-top towns, big, bruising red wines, hearty but delicate food and ice cream so delicious that it will make you pedal that little bit harder. The towns and cities are inspirational, combining clean-cut beauty with ancient, crumbling beauty. Tuscany is a land of contrasts that seem to be entirely balanced.

Why Cycle Here?

Firstly, it is all about the cycling. It seems as if Tuscany has been made for road cycling, and indeed you will see loads of other cyclists while you are out there on the trail. You will be riding stages of the Giro d'Italia as you pedal your way through the classic Tuscan scenery. Climbing switchback roads lined with poplar trees or making that final ascent to the hill-top villages; you will need some power in the legs. However, what goes up......means you will find yourself flying down similar hills, sweeping around bends and whooping at the bottom as the adrenaline surges through you. Then there are the towns, villages, and cities. Still, to this day, Florence is one of the most beautiful cities I have visited. There is just something about a place of this size maintaining consistent attraction in its architecture and layout. The joy of this trip, however, is that there is better to come. While the scale may not be as large as Florence, the design of Siena or the layout of the 14 towers of San Gimignano are hard to beat. You will definitely finish this trip arguing about which of the stops you loved the most.

Montepulciano Tuscany

Montepulciano is a maze of beautiful twisting streets

The towns are not only physically beautiful. The lifestyle, passion, and friendliness of the people are a massive draw here too. Tuscan people are proud of where they live, what they produce and they are keen to make sure visitors see the very best of it. And, to be honest, there is a lot to be proud about. Tuscan wine is outstanding, and on this trip, you will get to pass through some of the best vineyards in Chianti. If you want to stop in at a few, feel free, your time is your own. If you would rather push on and get through the ride, the lovely winemakers of Chianti have come together so that you can taste a wide range of producers wines at Casa Chianti Classico, to save you going to the individual vineyards. And then the food. There is arguably nowhere better in the world to stock up on the carbs for a big bike ride. Pasta that is delicate to the palate smothered in rich, unctuous ragu. Or light, crisp pizza, fresh from the oven and made with passion. The keyword for Tuscan cuisine is always hearty, or earthy and they certainly know the secret of balancing comfort food, with flavour and mouthfeel, so you know you are eating something exceptional.

Tuscan food

Simple flavours made with outstanding produce

Planning and preparation

Cycling the Tour of Tuscany: Florence to Montepulciano is pretty straightforward. Florence and Pisa airports are serviced by many low-cost airlines, and even Rome is only a couple of hours away on the train. From Montepulciano, at the end of the trip, you can get to Chiusi rail station, with a short transfer and from there easily make your way back to your airport of choice. We have specialists who love all things Italian and know this trip inside out, so don't hesitate to get in touch with them with any questions you may have by emailing at info@macsadventure.com


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