City Guide: Siena, Italy

Nestled among Tuscany's rolling hills is a medieval labyrinth of cobbled streets and burnt-orange houses; it is not difficult to understand why Siena's historic centre has been declared a UNESCO World Heritage Site. Rich in history, art and ancient traditions, which continue to be honoured and celebrated, it is not only the city's storied beauty that sets it apart.

After waking to the chimes of Siena's spectacular 12th-century cathedral, wander through a warren of narrow streets flanked by frescos. Whilst stopping for an €1 shot of espresso and a chat, bear witness to processions of ornately decorated horses and patriotic, flag-waving Sienese troopers. Follow the tailing crowds of chanting civilians and you will be swept away in an extraordinary phenomenon. As you wind your way through a city built in the past, you will discover somewhere fit for the present. With its vibrant culture and Instagram opportunities on every street corner, it is only upon visiting this Italian gem that you can appreciate how the city of Siena is really like no other.

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Albergo Bernini

Siena, Italy

Located in the quieter backstreets of Siena, this traditional family-run hotel is perfect for those willing to forsake a few luxuries for a superb location at a very reasonable price. Set in a historic building, enjoy a buffet-style breakfast overlooking the Duomo or watch the sunset over the city from its outdoor terrace with a glass of crisp Italian wine.

Address

Via della Sapienza 15 53100

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Hotel Santa Caterina

Siena, Italy

This charming little 18th-century hotel located just outside the city walls offers the best of both worlds; sweeping views across the Tuscan countryside and easy access to Siena’s historic centre through Porta Romana. Breakfast al fresco in the tree-shaded garden or take in the countryside views towards Montalcino from the terracotta=tiled rooms.

Address

Via Enea Silvio Piccolomini 7 53100

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Antica Residenza Cicogna

Siena, Italy

Perfect for those with slightly deeper pockets, this medieval palazzo has been lovingly renovated into a beautiful family-run boutique residence. Standing in the heart of the city, no detail has been overlooked in the tastefully decorated rooms. Original frescos and characterful items add greatly to the hotel’s austere character. With an extensive buffet breakfast included, the shared lounge also has a fridge and offers complimentary Tuscan vin santo and cantucci biscuits – a truly Sienese stay.

Address

Via delle Terme 76 53100

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Rosewood Castiglion del Bosco

Siena, Italy

Overlooking the Unesco World Heritage Site of Val d’Orcia, this 800-year-old Tuscan estate offers hilltop romance at its best. Spend days pootling between the heated infinity pool – set atop a lavender- and bluebell-covered hill with views of Tuscany’s rolling fields – and the hotel’s spa located in the estate’s former wine cellars. Come evening, make your way through the estate’s vineyard for a wine tasting.

Address

Località Castiglion del Bosco Montalcino Siena 53024

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Rosewood Castiglione Del Bosco

Siena, Italy

This is where to live the Tuscan dolce vita. Serving as both a luxury resort and working wine estate, Rosewood Castiglione Del Bosco is countryside opulence at its peak. There are 23 suites, but we have our eye on of the estate’s nine huge villas – each of which are restored farmhouses. The attention to detail is impressive and whether staying two nights or two weeks, guests never seem ready to leave.

Address

Località Castiglion del Bosco 53024 Montalcino SI

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Monteverdi

Siena, Italy

With farm-to-table cuisine and an enoteca plating up exceedingly good burrata alongside chianti, Monteverdi rates high in the food stakes. Add rooms kitted with 18th-century copper bathtubs and exposed wooden beams to the mix, plus a spa that specialises in herb- and flower-infused treatments, and it’s game over for us.

Address

Via di Mezzo, Castiglioncello del Trinoro Sarteano 53047

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Castello Di Spaltenna

Siena, Italy

Castello di Spaltenna’s fanciful amenities – think four-poster beds and winding olive groves – make the case for a characterful stay. Choose between a boutique bedroom or country-style apartment for your lodgings and Romeo or Count Paris for your prince.

Address

Via Spaltenna 13 Località Pieve di Spaltenna Gaiole in Chianti Siena 53013

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Terre di Nano

Siena, Italy

With sprawling views of Montepulciano, this 19th-century country estate is surrounded by vineyards, olive groves and other niceties. Tuck into ravioli with truffle on arrival (because priorities) and after a few days holidaying, try to recreate your meal with the aid of Terre di Nano’s cookery classes.

Address

Villa Nano Monticchiello Pienza Siena 53026

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Borgo San Felice

Siena, Italy

This eighth-century borghi (hamlet) turned hotel is great for those looking to explore Chianti sans tourists. Positioned in the region’s south-eastern corner, this is a wine-lover’s Eden. With a Michelin-starred restaurant plus an informal osteria suitable for lighter lunches, there’s ample opportunity to toast to its splendour.

Address

Località San Felice Castelnuovo Berardenga 53019

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Campo Regio Relais

Step straight off a cobbled street onto the marbled floors of Campo Regio Relais. This is a top choice for boutique-style lovers and a gem in the heart of Siena’s old town, within strolling distance to restaurants and bars. With hints of French interiors, the restored building is a slightly toned-down version of more traditional Tuscan interiors yet comes with fresco-walled bedrooms, antique furniture, silk curtains and pastel-coloured details. The terrace overlooking the River Duomo, churches and medieval rooftops screams out for an evening Aperol as the sun goes down. Alternatively, head down to the sweetly named “honey bar” for a candlelit nightcap and selection of local snacks.

Address

Via della Sapienza 25 53100, Siena