The Best Hotels to Book in San Gimignano, Italy

With a 1,000sqm (11,000sqft) spa, a pool amid the olive groves, and views across the mist-swathed cypress trees to the hilltop townscape of San Gimignano, Villa Sanpaolo is a serene hotel set in classic Tuscan countryside. Panoramas of pea-green rolling hills unfurl on all sides, and the restaurant and enoteca specialise in local wines and zero-kilometre produce. The resort’s superb GP olive oil comes from the surrounding 600 olive oil trees, grown in the rich fossil-shell soil.

With views across the medieval skyscrapers of San Gimignano, La Collegiata is housed in a former monastery that was founded in 1587, with a 19th-century turret that’s nevertheless in keeping with the whole. An aristocratic summer residence in the 20th century, it later turned into one of the most stunning hotels in San Gimignano. Antique-filled, white-walled rooms have a pared-back elegance, and there’s a large pool in the romantic, cypress-dotted gardens. You can take a tour from here in a most un-monk-like Lamborghini or Ferrari.

One of the loveliest hotels in San Gimignano, this is an agriturismo (farm stay), a mustard-walled rambling house on a hillside with big open fireplaces and brickwork ceilings. Rooms have wood-beamed ceilings, carved wooden headboards, chandeliers and polished terracotta floors. The views across cypress trees and vineyards will make your heart sing a veritable aria: there are great panoramas from the sunshade-surrounded swimming pool, as well as from the breakfast terrace – choose from a spread of crostini, fresh cornetti (croissants), home-baked cakes and more.

Hotel La Cisterna has been welcoming visitors since before San Gimignano was given its name. Once a place of rest for pilgrims, the hotel is now your home for however long you please. A glass of Chianti wine in the reading room will help you settle in quite nicely. Many rooms offer views of San Gimignano’s medieval streets, though savvy travellers can save a few extra euros by choosing a No View Room – you can spend hours marvelling at the village for free by simply stepping outside.

Spend your time in San Gimignano right on the main square, Piazza della Cisterna, at Hotel Leon Bianco. You’ll find that there’s no better way to embrace the location than in the Settecento Fiorentino Room: the mosaics inlaid in the furniture were created by Florentine artisans, while the spa-like bathroom was built out of the building’s ancient tower and contains an irresistible jacuzzi. Your “do not disturb” sign is sure to earn its keep, thanks to the soundproof windows and doors of your room.

Hotel Bel Soggiorno is all about convenience. You’ll find unobstructed countryside or historic-centre views by simply turning your head towards the window in your room. The hotel’s parking lot is a mere 100m (330ft) from the hotel, giving you prime access to the pedestrian-friendly San Gimignano – or a quick escape if desired. You’ll taste reinvented Tuscan cuisine at the fifth-generation restaurant on site, and, when nothing but a pool day will do, you’re welcome to visit the cool waters at Hotel Pescille, only 3km (2mi) away.

Hotel Casolare Le Terre Rosse is your escape into Tuscany. The hotel’s 10-acre (4ha) park is surrounded by the Siena hills and Castelvecchio Nature Reserve, leaving you to enjoy the private park and swimming pool in peace. More natural splendour and privacy await you in the Olivo Apartment, which has a private paved garden. Anytime you need a little nourishment, slide into the Bruschetta Snack Bar, where the chef will gladly prepare charcuterie and cheese platters with local wine pairings.

As you sit in the two-storey tower room at Hotel Pescille, gazing at panoramic views of San Gimignano, you’ll see relaxation stretched out before you. The lounge chairs lining the pool beg for an afternoon spent with a book in one hand and a cocktail in the other. Turn your attention in the opposite direction, and the shady garden chairs, pointing towards the valley, will entice you to sip a cup of tea and let your mind wander over the horizon.

The guest rooms of La Mormoraia, with their handmade terracotta floors, stone walls and exposed chestnut beams, are stunning – but you likely won’t spend much time admiring them. This organic farm will pack your schedule with hiking, massages, Turkish bath soaks and wine tastings. In between, you’ll be petting the farm’s livestock and deciding whether an adventure on horseback or on an electric mountain bike will give you the best views of the countryside.

Slip on a courtesy set of slippers, and stroll out into the private garden right from your room every morning at Hotel Sovestro. Views of the countryside are also included, as well as a free shuttle to Porta San Giovanni in San Gimignano. Whether sightseeing or swimming in the hotel’s pool is on your agenda, you’ll want to return in time for a Florentine-style steak dinner and superb wine at Ristorante Da Pode.