I’ve noticed a trend. Every time that I come back from travelling and write a blog about it I start with the words “only a fool would…” Spend a whole winter in Norway? Check. Three countries in one weekend? Count me in! Christmas in Iceland? Absolutely.

This time it was cycling from Prague to Meißen, nearly 230km or around 45km a day. If you get on your bike regularly that might not sound like much, but I’m what you’d call a fair weather cyclist. And the weather in the UK this summer has been neither fair nor summery. So as I sat on the plane at Heathrow I was both nervous and excited. I would get to see a lot of great towns and scenery en route, but I’d have to work for it.

The Cinque Terre — a series of small, connected coastal villages — has been on my, admittedly rather long, list of places to visit for some time, but when I first flew out to Tuscany I didn’t quite know how achievable it would be. Sure, Google Maps said that it would be a two hour drive from the villa, but I wasn’t completely sure that I was using the right address and I have been late several times when relying on directions cribbed from the Internet.

Walled cities are a Tuscan specialty. I’d been to a few in the last couple of weeks and, on paper, Arezzo looked to be another gem in the making.

However shortly after arriving things did not look quite so promising. Although an old city, much of what you can see on first entering the city is dull, generic office buildings, including one company amusingly called “multiass.”

Inside the city walls things immediately get… confusing. I walk down a street. To my right is a church, ahead are a mess of signs pointing in every direction, each one presumably a place of interest. With no guide book on the city I had no real idea what any of them were and arbitrarily picked “right.”

After the disappointment of Pisa¹ I was looking forward to the highly regarded city of Lucca, which is only twenty five kilometres north-east up the SS12.

Like Pisa the parking situation was dire and it took several attempts to find somewhere to put the car. The comparisons to Pisa end here, however, as I immediately liked what I saw.

Immediately inside the walls are those very typical narrow, cobbled streets. There were no shortage of shops with extensive displays of meats and cheeses, bread and cakes. These all needed investigating. While I’m sure that most of these places see a good number of tourists passing through, they’re certainly not at the level of tea towels or cheap models of local sites.

I really wanted to like Pisa. When I last visited in 2004 I came away fond of the area around the leaning tower but unimpressed with pretty much everything else I saw of the city. It was grey and bland and unattractive. But I was hoping that I had been wrong. It had been overcast and rainy, and I had had to rush around the place. Perhaps I had just not done the place justice?

A few days ago when I drive to Poppi I saw signs for Rufina and Borgo San Lorenzo. Today I decided to head for the latter and stop off in the former.

First stop was the Vine and Wine Museum, which I found at the end of this long row of tall trees.

After the last few days of rain I was annoyed with myself to be so relieved to get out of the hot, bright sun. Inside there were tables littered with leaflets publicising local events, wine tasting tours and the museum itself. In the distance were murmuring voices but by the entrance, near the tills where you’d expect someone to be taking tourists money, there was no-one.

After leaving Monteriggioni I aim the car towards Castelline in Chianti, an area well known for its wineries.

And, well, I passed a few. After they thinned out I did a U-turn and went back to the first one which looked the most promising. From the road there was a long, straight line of trees either side of the drive up to the farm house at the end. It was a bumpy drive and I pulled in next to a couple of other waiting cars. I got out and strolled towards the entrance.

A short distance from Colle di val d’Elsa is Monteriggioni. As with a few of the other places that I visited on this trip, I had not even heard of it when I woke up in the morning and, therefore, was pleasantly surprised with what I saw when I got there.

Monteriggioni is another one of Tuscany’s many pretty walled cities, this one smaller than most. You arrive on a steep, narrow path and enter underneath a tower. Inside you immediately find a large, mostly empty square. Around the periphery there are a number of parasols shading cafe tables and postcards and souvenirs spilling out of shop fronts.

When I first came to Colle di val d’Elsa I arrived on foot, having walked all the way from San Gimignano. This time it was easier, except for parking the car.

Colle di val d’Elsa is less famous than either San Gimignano or Siena but that’s not to say that it is without merit. It’s another attractive, small Tuscan town. This time made slightly less photogenic by the extensive maintenance work being performed on the main square.

One of the great things about this trip was that some days I’d just fall out of bed, flip open a map and decide where to go on a whim. My visit to Poppi was inspired by this process with a little coaxing from a book called “Most Beautiful Villages in Tuscany.” Such a title might lead to high expectations and the suspicion of imminent disappointment, but Poppi did not let me down. It’s a very pretty, compact town with a castle, a church and a long, cobbled main street. Even the weather was on my side.