Where?

San Gimignano, Italy.

Why now?

With medieval towers, a walled old town and charming trattorias
all surrounded by rolling vineyards, this Etruscan
hill town is quintessential Italy. Travel south from Florence
through verdant fields to reach San Gimignano’s crumbling
13th-century walls, through which you’ll find sand-hued buildings
and family-run business dating back generations.

Spend mornings sipping espresso in Piazza della Cisterna, a
square where locals gather for a morning gossip and nonnas wave
from doorways, before navigating the town’s cobbled backstreets.
Head to the 12th-century Duomo di San Gimignano, known locally as
the Collegiata, to admire frescoes by Domenico Ghirlandaio, and pop
into the Polo Museale Santa Chiara where three museums house
ancient ceramic jars, mosaics and artefacts.

Don’t miss…

This Unesco World Heritage Site appears to be stuck in its
medieval past, but dig a little deeper and San Gimignano may
surprise you. Don’t miss the Galleria Continua, a contemporary art gallery
showcasing artworks from world-famous artists such as Ai Weiwei,
Antony Gormley and Daniel Buren.

Who to take with you

Someone keen to learn about Estruscan history. Admire the
crumbling ruins of Rocca di Montestaffoli, the town’s 14th-century
fortress, and marvel at the Palazzo Comunale, a governmental
building dating back to the 13th century. Climb up the 218 steps of
the Torre Grossa for views across San Gimignano and the rolling
hills beyond.

When to go

June
is a popular month for holidaying in
Tuscany, as it’s when the region is at its best. Hot weather
can be quickly remedied with a cool glass of white wine.

Where to stay

Stay at Hotel La Collegiata, a converted
Franciscan convent originally built in 1587 just outside of San
Gimignano. Explore the building’s brick-laden cloisters and
renaissance architecture before heading out to stroll through
manicured gardens or take a dip in the pool.

Most likely to bump into…

Tuscan wine connoisseurs. Strike up a conversation and find out
where to head for the region’s best wine-tasting experiences.

Essentials to bring with you

This cute floral-print crepon midi dress from Faithfull the Brand is perfect
for floating through Tuscan vineyards and sipping coffee in town
squares.

How to get there

Fly into Florence airport, and transfer to San Gimignano in
under one and a half hours by car.