Tuscany is a region on many people’s must see list, whether you are a cyclist or simply want to tour the region by any means.

We chose to travel in July.  Granted, it is quite warm and you’ll encounter a great number of tourists; but, there are many festivals & events that take place in the summer and are incredible to witness while the majority of tourists will either be on tour buses or cars.

This video shows highlights of the first day’s ride from a two week tour.  It starts from the departures exit at Aeroporto Internazionale Galileo Galilei in Pisa, passes through Pisa and goes north to Lucca.

Our tour was a loop; starting and ending in Pisa, with it’s iconic leaning tower. The airport is an easy ride from the tourist attractions and lodging in the center of the old town.  Follow the route on this map.

Stage 1:  Pisa to Lucca  22,8 km

Our first ride was from Pisa to Lucca.  After arriving on an evening flight from through London Heathrow, our bikes were delayed.  What can I say, things happens and we anxiously awaiting the arrival of the morning flight the next day so we could begin our first stage to Lucca.
After assembling the bikes and then making our way through Pisa and past the leaning tower, we exited onto the route to Lucca. Let me say that there are not a lot of roads between some towns and this makes it less easy to take a wrong turn and get lost. Since we were leaving later than our normal plan, we took the most direct route that included a significant tunnel. There is an alternative to this, that is an option.
The ride itself started with a level stretch and a steep climb to the tunnel. From there to the walled town of Lucca had no challenging hills.
Lucca is a marvelous town; circled by a walkable or cycleable wide wall for a nice view of the interior town and the area outside the wall. There is a lovely square with many restaurants and the Cathedral of St. Martin.
Also on the square, seven full grown oak trees grace the top the 14 story Tower of the Guinigis which dates back to the mid fourteenth century. By custom, a wealthy Tuscan family would build a tower whose height represented the status of the family. In some towns, the competition became quite fierce. The Guinigi family planted seven Holm Oak trees to represent rebirth and renewal. It offers a great view.
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Stage 2:  Lucca to Vinci  46,4 km

The next day we headed out through one of the wall portals on our way to the birthplace of Leonardo de Vinci; the hill town of Vinci. Beautiful countryside today with no major climbs and we arrived in time for a fascinating visit to the museum with exhibits of Leonardo’s drawings and replications of some of his inventions.
We also did a walk along the trail to his actual birthplace. All in all we found this to be a perfect halfway point overnight stop between Lucca and Florence.

Stage 3:  Vinci to Florence 42,4 km

Due to some road construction, our planned route required a bit of a change. These hiccups can happen, so it is good to be flexible.
The route was undulating; but without major climbs and brought us into Florence on an easy approach. The final portion into the city had more and more traffic; but, we could easily cycle by the stalled cars. Then, after checking in to our lodging, just over the Ponte Veccio bridge, we walked up through the extensive Boboli Gardens and admired the view back down to the rooftops of the city.
We stayed an extra day in Florence to see as much as possible of the art; both in the streets and in the museums and churches.
We also did a short side trip by public transportation to the hilltop Roman ruins at Fiesole.

Stage 4: Florence to Greve in Chianti  28,7 km

The road out of Florence starts level and then there is some climbing.
From Florence we headed out of town to ride State Route 222, or as the Italians call it, “the due, due, due”. Those in a hurry take the auto route and those who really want to see the beautiful Tuscan countryside ride the due, due, due. It winds and climbs and dips and you pass olive trees, cypresses and crowing roosters in country farms. This is Chianti wine country.
We stopped for a refreshment after a climb to Castellina in Chianti, then continued on to charming little town of Greve in Chianti, right in the heart of wine country.


Stage 5:  Greve in Chianti to Siena  40,6 km

Next day was a continuation of the ride through this beautiful countryside on the 222 to Sienna.
The city takes on the color of burnt sienna and if you are there, as we were, during the twice annual Il Palio, it doesn’t get more colorful than this. In the Campo, stands are erected and a dirt racetrack circuit draws a packed crowd on the event day to watch the 15th century costumed riders race bareback around the circuit. The streets are filled with banners and parties. It is AMAZING.
We stayed an extra day here as well to partake in the festivities.

Stage 6 Siena to San Gimignano

The next morning we waited out a morning rain and thunderstorm before we started out. Yes, it does rain in the region; but, fortunately it passed quickly and soon was heating up to another beautiful day.

This ride takes us to San Gimianno; a true hilltop town noted for it’s towers. On the way we pass sunflower fields and the walled city of Monteriggioni .



The final 6 km into San Gimianno is a series of switchbacks that seemed to go on and on as we climbed up and up; but, we had courteous driving waving and encouraging us as we pedaled upward. It was a welcome site to arrive in the lovely Piazza della Cisterna. The views from the hilltop made the climb seem all the more rewarding; as did the dinner and gelato.
It seemed like the whole town converged on the Piazza that evening to enjoy the gelato, the warm evening and the conversation. This town also had some of the most beautiful pottery we had seen.


Stage 7:  San Gimignano to Volterra  29,3 km

The route to the Etruscan town of Volterra begins with a downhill; but, soon there will be several climbing challenges before the final 3km push to enter the gate into Volterra; our last hilltop town of the tour. This ancient city boasts Roman ruins and and excellent Etruscan museum.

Stage 8:  Volterra to Casciana Terme  41,2 km

We leave the craggy terrain today for the lush countryside on our way to the Spa town of Casciana Terme. The route undulates and today’s ride was downright windy. We pass olive groves, peach orchards, vineyards and more sunflowers along the way. This was a good quiet half way point for our return tomorrow to Pisa. The thermal springs have been popular since the time of Augustus Caesar.


Stage 9:  Casciana Terme to Pisa  39,4 km

We complete our loop today, back to Pisa. This begins with a short climb out of town and the rest of the day in just some rolling hills; but, predominately downhill.

We took pleasure in the countryside of vineyards and more sunflowers along the way.

Once back in Pisa we visited the main attractions and found the interior of this town easy cycling or walking.