By Ferenc Máté
January 09, 2015
Most Romantic Hotels in Tuscany
Credit: Peter Horree / Alamy

Much of Tuscany is as romantic a place as exists on Earth. (The reason I chose to live there.) The beauty of the tranquil countryside, the drama of the coast, the charm of the medieval towns, the quaint family owned little restaurants, are all to a human scale. Romantic hotels abound mostly for their settings; Tuscan hotels themselves tend to be utilitarian, hence low on the bits and details that seem to make a place ‘romantic’ in the North American sense.

But opulent romantic hotels are found throughout the region. They are of all descriptions: a Renaissance palace in a city, a renovated monastery in a town, or a medieval castle or stone farmhouse in the boonies. You’ll find romance to fit any pocketbook; of course, the thicker the romance, the larger the pocket book has to be. The range is wide, from relaxing spa treatments at The St. Regis in Florence, to noble views of the biblical countryside in Siena, or the quiet luxury of villas in the wine country of Chianti and Montalcino. Expect beautiful rooms and excellent service, and depending on when you’re traveling, often an option to upgrade to an even better room.

The St. Regis (Florence)

The St. Regis Hotel on the shore of the Arno River, was originally a family palace designed by Filippo Bruneschelli, the celebrated Renaissance architect of the Duomo. The hotel succeeds in recapturing the Medici glory of the fifteenth century. Its public spaces and restaurant are courtly, even the simplest rooms are decorated with frescos and brocades, and the premium rooms and suites make you feel so regal you’ll be tempted to pass a royal proclamation or two. Service at the St. Regis is the pinnacle of attentiveness with butler service, high tea, and world-class spa treatments. Don’t forget to step out now and then. You’re minutes away from the greatest collection of Renaissance architecture, all the museums, the Ponte Vecchio, and of course Florence’s finest boutiques—of which there are so many, people have lost count.

Grand Hotel Continental (Siena)

In Italy’s most romantic city —after Venice of course— is a palace that is two centuries newer than Brunelleschi’s Florentine masterpiece. This seventeenth-century aristocratic residence was built as a wedding gift from Pope Alexander VII to his niece. Humble. Inside Siena’s medieval walls, the hotel is only minutes on foot—the city is closed to general traffic—from everything this unspoiled medieval city has to offer: the magnificent Gothic cathedral, the world’s best town square: Il Campo, and excellent restaurants and boutiques. Don’t let the name scare you; it’s a well-sized hotel with only fifty-one rooms and suites. It boasts a truly successful mix of ‘unashamedly opulent’ old and minimal, but still opulently modern. Carrera marble, frescos, and travertine floors are the norm. Their restaurant is renowned and wine cellar is unique.

Villa Bordoni (Chianti)

This peaceful villa high on a hill, in the heart of Chianti, is a luxurious romantic home-away-from-home while you explore the castle and villa-filled hills of Tuscany’s most romanticized region. A half-hour drive from Florence, and a bit more from Siena, it is the perfect non-city base. Beautiful gardens offer secluded nooks, the restaurant is cozy and serves outstanding food; and the nine rooms—each named after the castle it faces—have classic décor and modern everything. The doors are so soundproof you need a stethoscope to hear what passes outside. The breakfast, with excellent pastries and homemade jams, is so ample you can skip lunch and see more of this idyllic countryside. The service is not only friendly but also excellent.


Perhaps the most romantic of all in Tuscany even the name of it—Castiglioncello del Trinoro—sounds like a dream. Imagine an ancient stone hamlet (current population 11) on a two-thousand-foot hilltop, overlooking the least-changed valley in Tuscany with a volcano on the other side. Now imagine, scattered in it, a superbly designed, quality the best, hotel no-hotel. The reception room is an old stone cellar, the 11 rooms are here and there: one down a cobble-stoned lane, another up a twisting stairway near the tower. The tiny restaurant is carved out of the side of the hill, the bar hangs over a cliff next to the church. Get the picture? Add linen sheets, some amazing baths, a pool on top of the world, and some of the best meals and wines of your life. Half of Tuscany lies at your feet for a walk afterwards in the sunshine or the moonlight.

Torre di Cala Piccola

The Argentario Peninsula of Tuscany is one of the Italy’s best-hidden secrets. Almost intact (by an ingenious law) with dramatic bluffs, crystal clear azure seas, isolated tiny beaches, miniature vineyards and lemon groves clinging to the cliffs, amazing views, and some of the best and freshest seafood in the world, it is a romantic’s dream. At the bottom of a long winding road is a small hotel clinging to the hillside: pines, long views, the sea below in a rocky cove, and sunsets over the island of Giglio and Monte Cristo to take your breath away. The hotel is unpretentious but the location, the pool, and the walks are stunning. And in the nearby genuine fishing town of Porto Santo Stefano are two amazing (and acceptably-priced) restaurants, La Bussola, and a bit further Osteria dei Nobili Santi. Enjoy.