Siena is all shadows and spectacle. The Piazza del Campo, shell-shaped and sun-bleached, plays host to bareback horse races and a daily theatre of slow movement. From the heights of the Torre del Mangia — 102 thigh-burning metres — the city appears like a painted fan.

By nightfall, we dine by candlelight in the hotel’s wine vaults: venison, poached peaches, and a bottle chosen by the sommelier. Afterwards, a stroll to the Duomo under stars, where we slip inside for Sunday evening mass, surrounded by locals and centuries of quiet belief.

Aston Martins are available for purists, but we cycle through the rolling roads of Chianti — think The English Patient — stopping for fig tart and a bottle of red at the foot of a sun-warmed castle. Bond wouldn’t be caught on a bike, but it beats the gym.

This is Siena as she should be seen: cinematic, sensual, and slightly off-season.

Viewfinder: Siena

Roomkey

Grand Hotel Continental Siena – Starhotels Collezione

The only five-star property within Siena’s UNESCO-listed walls, the Grand Hotel Continental blends aristocratic Baroque architecture with museum-grade heritage and quietly confident service. Frescoed ceilings, Murano chandeliers, and travertine-clad bathrooms come as standard, while the noble piano nobile level offers 7m-high ceilings, mezzanine lounges, and 17th-century stuccowork. Once home to a noble Sienese family, the palazzo has hosted cardinals, counts, and — during Quantum of Solace — Daniel Craig. As discreet as it is cinematic.

Table With A View

Book a dinner in the hotel’s vaulted wine cellar — once part of the original noble estate — where courses are matched to local vintages by the in-house sommelier. Elsewhere, Sapordivino draws from seasonal Tuscan produce with flair. Off property, Guido is a low-lit local institution, favoured for decades by actors and musicians passing through town. Ask for the white truffle tagliolini.

Through the Lens

For sweeping rooftop views, take the back stairs from the Museo dell’Opera to the Facciatone lookout. Within the museum, Duccio’s Maestà remains one of the most poignant Marian portraits in all of European painting. The Santa Maria della Scala, once a medieval hospital for pilgrims, is now a vast, beautifully conserved museum complex whose underground vaults house archaeological remains and contemporary installations.

On The Road

Siena’s pedestrianised heart is best explored on foot — a rare treat for urbanists. For more dynamic escapes, hire a classic Alfa Spider or Jaguar E-type via Drive In Style, or opt for the electric two-seater Coupé courtesy of the hotel concierge — ideal for vineyard runs and zero-emissions city loops. Rossi Martino offers high-performance e-bikes with integrated GPS and climate-adaptive gearing — and can plot a route that snakes through Chianti’s hilltop villages and olive groves. Don’t be fooled: the inclines here are real.

Future Frame: For the Global Citizen

Siena leads by example in sustainable heritage. The Bottini tunnel system — now partially open to visitors — is a model of medieval water conservation, still studied by engineers. Adaptive reuse is quietly transformative here: Santa Maria della Scala, once a functioning hospital, is now a multidisciplinary cultural centre, while civic restrictions keep the historic centre car-free. The hotel group behind Grand Hotel Continental is also part of the I Prefer sustainable hospitality alliance, focusing on energy efficiency and locally-sourced design. In Siena, preservation and modern hospitality walk hand in hand.

Originally published in the Hampstead & Highgate Express (Ham & High), and syndicated across London titles.