Detour | My Favourite Tuscany Towns and Villages

Tuscany Towns and Villages
Tuscany Towns and VillagesTuscany Towns and Villages

When you think of Tuscany, you likely conjure up images of never-ending vineyards, medieval towns, wine tastings and endless sunshine.  And you’d be right about all of those things.  Tuscany is one of those dreamy destinations where reality matches your imagination.

This was my third trip to Tuscany, and I was looking forward to revisiting some of my favourite Tuscany towns and villages as well as discovering new ones.  From exploring narrow, cobbled streets that wind through hilltop towns to tasting all sorts of gelato flavours at every stop we made.  And then there’s the local wine of course.

Below I’ve shared all the Tuscany Towns and Villages we visited on this particular trip….


Everyone has heard of Pisa, the Tuscan city made famous by the Leaning Tower.   Pisa has often been one of those fly in or fly out points when I’ve been travelling around Italy, and therefore I’ve somehow managed to end up there three times.  Is it a destination place?  In my opinion, no.  However, if you find yourself passing through, it’s worth spending a day, or one night (no more) and ticking the Leaning Tower of Pisa off your bucket list.  It’s a very walkable city, with plenty of bars and restaurants dotted around, and if you love gelato, then I recommend trying the Meringue flavour at La Bottega del Gelato.


Certaldo is the cutest medieval walled town, that feels like a movie set when you walk around.  It’s hard to believe something so charming is a real life, working town.  We accessed the town via a gondola and spent a couple of hours walking around, taking in every inch of how sweet this hilltop spot is.   I’d recommending staying for lunch or dinner as there are plenty of gorgeous restaurants and cafes dotted around.

San Gimingano

San Gimignano is a must-see on nearly every Tuscan tourist’s list.  It therefore makes it almost impossible to find a parking space during the day!  Because of this very reason, we paid two evening visits to San Gimignano for their famous gelato.  It is a magical town, full of buzzing piazza’s, medieval towers, and narrow stone streets.  You’ll be spoilt for choice with restaurants there, but as I already mentioned, it’s the gelato everyone talks about.  Gelateria Dondoli is world famous due to its many awards, and therefore is a necessity to try right?  A highlight there was the gorgonzola gelato, who knew blue cheese ice cream could actually taste good!


Monteriggioni, is one of my favourite spots.  A completely walled medieval village located on top of a hill, it is tiny, and a lovely place to visit.  With a large piazza in the centre, the village is filled with cute coffee shops, lovely home decor stores, and restaurants.  The city walls and its 14 towers are still intact, you can even take a walk alongside them on a walkway.  The saying ‘good things come in small packages’ rings true for Monteriggioni.


Volterra is a larger town, now made famous by the Twilight novels and movies.  I’ve been pre and post Twilight, and it was good to see that nothing had changed.  High up on a hilltop, you’ll find yourself wandering down alleyways and discovering piazzas at the end of them.  There are basilica’s, delicious deli’s, pretty shops, and plenty to see.  You can easily spend a day in Volterra walking inside the medieval walls.

Happy travels,

Annmaree x

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