Often overlooked in favour of its older sister Florence, Siena has a heady mixture of Renaissance architecture and imposing Gothic triumphs. Every year, the Palio di Siena – a dramatic horse race that has drawn in visitors since medieval times – whips the city into a frenzy. Siena is otherwise laid-back: slow-paced streets lead to artisanal bakeries and intimate art galleries. Pair a city break in its history-laden district with a few languorous days in the romantic countryside.

When to go

Visit in September or October for still-warm temperatures and countryside in glorious autumn livery. Alternatively, time your visit for July or August for the Palio di Siena; make sure to book in advance – it’s very popular.

Food & Drink

One glance down a Sienese street and it’s clear that this city has a sweet tooth. Traditional bakeries serve indulgent regional treats such as the dense fruitcake panforte, or the delicate almond cookies known as ricciarelli. If you’re more savoury than sweet, Siena dishes up tantalising carnivorous fare: Tuscany’s melt-in-the-mouth pork and grass-fed beef are best enjoyed at Antica Osteria da Divo in the comfort of its ancient Etruscan rooms.

Not to miss

Set your alarm for an early morning start and dig out bargains at Fortezza Medicea’s Wednesday market.

Nightlife

Sienese culture lends itself to long evenings spent over a bottle of wine at a street café. Zesty hotspot Bar Il Palio is the best place in the city to watch the sunset with an apperitivo. For a more intimate experience, try the Tea Room, where delicious cocktails are expertly mixed and served with plenty of Italian charm.

Where to stay in Siena

While the city centre’s romantic atmosphere makes it perfect for a weekend break, Siena’s lush surroundings set the scene for quieter, more laid-back getaways. Hilltop Pienza offers gorgeous rural views; stay near Torrita di Siena for cosy B&Bs and luxury countryside villas.

How to get there

Fly to Florence, an hour’s drive away: Peretola Airport has links to both domestic and European destinations.

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