Southern Tuscany towns itinerary (and what to eat)

Complete with beautiful hills, small towns, and quiet vineyards, Southern Tuscany is a sight to see. For those who value a slower experience of Italian life, this region offers much to do: whether it’s the culinary experience you’re looking for or the traditional landmarks you want to see, read on to find out more about the most renowned towns in Southern Tuscany (and what to do there!).

What are the towns in Southern Tuscany, and what can I do there?

Montepulciano: charming Renaissance architecture

• Places to see

  • Piazza Grande

  • Palazzo Comunale (bonus tips for the view from the tower!)

  • Wine cellars and artisan shops

• Things to eat

  • Pici all’aglione: Thick hand-rolled pasta with a garlicky tomato sauce.

  • Vino Nobile di Montepulciano: Taste one of Tuscany’s finest red wines!

  • Cantucci with Vin Santo: Almond biscotti and sweet Tuscan dessert wine.

Pienza: “ideal Renaissance city”

• Places to see

  • Fun fact: This is a UNESCO-listed town!

  • Val d’Orcia

• Things to eat

  • Pecorino di Pienza: Italian sheep’s milk cheese

  • Crostini with pecorino and pear or honey: A sweet-salty starter!

Monticchiello: unique "Teatro Povero" tradition

• Places to see

  • Cypress-lined roads

  • Central piazza

• Things to eat

  • Wild boar ragù

  • Rosso di Montalcino: Red wine that pairs great with game!

Montalcino & Sant’Antimo Abbey: Romanesque architecture

• Places to see

  • Medieval streets

  • Romanesque Abbey of Sant’Antimo

• Things to eat

  • Tagliatelle al tartufo (truffle): Truffle-infused pasta

  • Brunello di Montalcino: Red wine

  • Cinghiale: Wild boar that’s often served stewed or grilled.

Bagno Vignoni: thermal baths and natural hot springs

• Places to see

  • Central thermal pool

• Things to eat

  • Zuppa di farro: Farro soup

  • Tagliere di salumi e formaggi: Local cured meats and cheeses

San Quirico d’Orcia: a stop on the Via Francigena pilgrimage route

• Places to see

  • Horti Leonini gardens

• Things to eat

  • Panzanella: Bread salad with tomatoes, olive oil, and vinegar.

  • Olive oil from Val d’Orcia

Pitigliano: “Little Jerusalem”

• Places to see

  • Etruscan caves

• Things to eat

  • Sfratto dei Goym: Traditional Jewish pastry with honey, nuts, and spices

  • Cialdino: Local flatbread stuffed with vegetables or cured meats

Sovana: archaeological sites

• Places to see

  • Church of Santa Maria

• Things to eat

  • Acquacotta: Soup with vegetables, olive oil, and poached egg.

  • Ricotta and honey: A sweet treat!

What are some additional tips for my trip?

Here are some additional tips for your Southern Tuscany travels:

• Rent a car for maximum flexibility and scenic stops.

• Stay local for some great homemade meals and wine grown right by your stay!

We hope you enjoy the nooks and crannies of these beautiful towns on your next visit. With hills far and wide, enjoy the rich tradition Southern Tuscany has to offer!