These are a few of my favourite towns that are not crawling with tourists and definitely worth a visit on your next trip to Siena.

5. Radicondoli

The first town I fell in love with in Italy, Radicondoli, will always be a favourite one to visit. Just 25km southwest of Siena, this small hilltop town is chock full of charm, amazing restaurants, and beautiful vistas that look out over the vast Tuscan landscape.

Stay in a nearby agriturismo and live like a local, enjoying fresh produce and a slower life. Podere La Fonte is one I’d recommend. La Fonte produces its own organic olive oil (delicious) and wine (steer clear).

Eat at Agriteca in Piazza among locals outside the nearby church, Parrochia Santi Simone E Guida. The day I visited they had just received the most delicious mozzarella di bufala Campana, which was the closest thing I’ve had to fresh-from-the-farm mozzarella at Caseificio Barlotti in Paestum.

4. Chiusdino

The last time I visited Chiusdino there was a truck parked in the piazza selling fresh fish and seafood. The best thing about visiting small and off-the-beaten-path towns like Chiusdino is that your Italian lifestyle fantasies don’t seem far off or cliché. Every morning at 9am nonni gather at the bar to chat over caffè and cornetti. Everything you picture when you think of small-town Italy is reality here without any romcom cheesiness.

Stay at Tenuta di Papena, a former monastery 10 minutes away from the town centre. Ginevra and her mother Fabiola run the estate and its six rustic apartments that all come equipped with a kitchenette and feel like your own private Tuscan home. Enjoy your wine in the courtyard and swim in their infinity pool with its to-die-for view. As a bonus, the owners speak perfect English and Gini also happens to be an amazing wedding planner. Papena hosts a wedding almost every week in the summer months (San Galgano Abbey is an eleven minute drive away) so make sure to book your stay well in advance.

If you’re looking for luxury, a stay at nearby Borgo Santo Pietro is a must.

Eat at Il Minestraio Di Il Cacciatore Di Maddalena Minocci. Their bruschetta is amazingly fresh and all pasta on the menu is worth ordering! Tip: if spaghetti alla carbonara is available then your decision making has been done for you.

3. Monticiano

This small Val di Merse town near Chiusdino is my favourite for a morning cappuccino.

Stay in all the same places as Chiusdino and you’ll be just a few minutes away from Monticiano!

Eat at Benedetto Vino in Piazza Sant’Agostino. Get the ‘tonno Toscana’ for a delicious treat. Order your coffee at Bar l’Incontro across the piazza and sit outside for some good people watching.

2. Torri

Torri is a tiny medieval village in the Comune of Sovicille, south of Siena. Think of a mini San Gimignano (but with no tourists!). It’s delightful to walk their winding streets and listen to the goings-on of people living in the apartments above you. The small gardens in this walled-in village are beautiful pops of green against the ancient stone.

Stay at the Torri Bed & Breakfast, which puts you directly in the town centre. There isn’t too much to do in Torri (nearly everything requires a drive to neighbouring Rosia) so I’d recommend staying in a larger town and visiting Torri for an evening.

East at La Sosta Del Cavaliere. Everything here is delicious, you can’t go wrong!

1. Colle di Val d’Elsa

Colle Val d’Elsa is made up of two towns: low (bassa) and high (alta). The lower town is newer and is worth visiting, if not exclusively for enjoying a gelato in Piazza Arnolfo di Cambio. Colle Alta, the old town, has a lengthy history and is Italy’s major producer of crystal glass.

Stay at Palazzo San Lorenzo Hotel & Spa in Colle Alta

Eat at Michelin starred Arnolfo for a meal as beautiful as it is delicious. For more wallet friendly options, visit Colle Bassa for Molino Il Moro‘s truffle and parmigiano reggiano sformato and Chicco‘s Neopolitan-style pizza with the best dough-y crust (tip: only eat on Chicco’s patio unless you’d rather sweat over your pizza).

 

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