This former family farm has been painstakingly restored by Emmanuela Marino and partner Gareth Shaughnessy to give Siracusa a much-needed dose of style. Though close to the attractions of the city and the beach (plus the Sicilian Baroque towns of Noto, Modica and Ragusa Ibla), Marino built the hotel as a place to unplug rather than sightsee. There's a pretty raised infinity pool, secluded grounds, and décor that is modern but not out of place (design aficionados will like pieces such as the Edra Angel chaise lounge, a huge Hoesch tub, and a Davide Groppi test tube light). With only ten rooms (ask for one of the bigger ones), the property feels intimate but there are lots of communal areas to read and drink wine, which adds to the uncrowded feel. The nouveau Sicilian restaurant Zaffreano Bistrot is also a draw—try the grouper with ricotta and honey and the crudo, raw fish—as is the English-speaking, friendly staff. Plans are in place to arrange a boat transfer to and from Siracusa, which should make the journey even more romantic.

Named after the lighthouse at the front of the property, this new resort has a beautiful position overlooking the sea, with a big-decked pool and restaurant area that capitalizes on the views. The 20 rooms are spread out through low whitewashed buildings with shaded terraces (you'd be forgiven for thinking you had landed in the Greek isles, but this is actually the typical architectural style of the Aeolian Islands). Inside, the design is pared down but still luxurious, with butter-soft bedding and well kitted-out bathrooms. During the summer the hotel becomes more of a scene, with many tanned Italians crowding into the chic restaurant and bar, but off-season the place becomes positively sleepy. Regardless of the time of year, one of the best sights at night is Stromboli giving a little volcanic firework show in the distance. Ask someone at reception to arrange a boat trip to check out the nearby empty coves, and be sure to try the sweet Malvasia wine grown on the property's vineyards.

On a clear day you can see Malta from this property, in the region south of Ragusa known as Val de Noto. Built in the 12th century as an Arabic fortress/hermitage, it later became a Knights of Malta monastery. Owned by the Nifosì family for the last 300 years, it's now one of the most sumptuous hotels in southern Italy. The nine double rooms and three suites—formerly friars' quarters—have refurbished exposed-brick walls, arches, and wood beams, and are filled with 18th-century antiques. Splurge on the Tower Suite, in the oldest part of the building, with its two vaulted, stone-walled rooms, fireplace, and private garden. Privacy seekers prefer the five freestanding stone cottages, each with two or three bedrooms, a stone barbecue, a fireplace, and a kitchen. The hotel has its own airstrip for sightseeing tours and guests' private aircraft.

Falconara Charming House & Resort is the latest stylish addition to the new generation of Sicilian boutique hotels—a place known for grande dame, slightly fusty properties, or mom and pop bed & breakfasts. Despite its proximity to the highway and a stretch of built-up coastline, the new hideaway on the sea actually has an enviable position looking onto a private beach and a number of undeveloped coves. The one building in front of the property is a castle (which houses some of the bedrooms) that only adds to the vista, and the grounds also have a pretty pool and little beach club. The 65 rooms are simple but chic, with black stone floors, dark wood four-poster beds, and relatively small bathrooms that come with tubs and oversize showerheads—ask for a room with a terrace that looks onto the water. The restaurant is well priced and the bar area stylish, with oversize armchairs and chaises—though they could lose the pianist playing over recorded music. Perhaps best of all, service is warm and quick.

Taormina was one of the first Sicilian towns to be discovered by tourists in the 1800s—and the Timeo was first to roll out the welcome mat. The elegant grande dame, set on a panoramic hill just below the Greek Theater, has since hosted Liz Taylor and other Hollywood royalty. After a 2003 face-lift that added 31 new rooms in the adjacent Villa Flora, it's now the most glamorous place in town. The 87 antique-filled rooms are gussied up in Sicilian Baroque with heavy drapes, Oriental rugs, marble bathrooms, and killer views of Mount Etna. The hotel's private beach, dotted with loungers, is a ten-minute shuttle ride away at Timeo's sister property, Hotel Villa Sant'Andrea (137 Via Nazionale; 39-094-223-125). If you can't stay, at least drop by for a limoncello on the terrace at Il Dito e la Luna restaurant, the place to be seen during June's theater festival.

This new five star is providing a bit of competition for the older grande dames in town—a good thing since a number of them are becoming more fusty than charming in their old age. Housed in a neoclassical palace on the street where the composer Richard Wagner lived for a couple of years, it's well located and a close walk to places like the Politeama Theater and Via Liberta. The 61 rooms have plush carpets, upholstered furniture, and heavy silk drapery, but because the property is new they feel more luxurious and intimate than dusty. NB: The chandelier in the lobby was used in the ballroom scene in the Sicilian cinematic classic, The Leopard.

The secret is out: Hotel Gutkowski is the best bargain in ancient, seaside Siracusa. You'll need to book way ahead for one of the 26 rooms at this pale-blue villa, on the city's island of Ortygia. All are decorated with rustic simplicity: plain white walls, white linens and drapes, basic wood furniture, and tiled or hardwood floors. But all come with satellite TVs and fridges, and seven have Mediterranean views. Your room rate includes one of the best continental breakfasts in Siracusa, with fresh-squeezed juices, homemade jams and pastries, and organic fruit.

Opened by a local couple, Hotel Signum is located in a low-key gorgeous landscape between twin volcanoes that spills down to the pristine sea. The 30 rooms are charming rather than slick (snag one with a Tyrrhenian sea view), and the grounds have an incredible vista of Panarea and Stromboli in the distance. The sunset terrace in particular is a perfect location for doing absolutely nothing but staring off into the distance. If you must move, rent a moped and spend your time exploring the island's gorgeous fishing villages, or hike one of the dormant volcano trails. The included breakfast here is one of Sicily's best and dinner isn't shabby either, though you'll have to let the staff know if you are staying for the meal that morning. One caveat: the ferry schedule can be sporadic when the seas are rough and the staff seems completely clueless about whether they are running—a frustration when you turn up at the port and there is no way to get back to the mainland.

There's no better deal in touristy Taormina than this pretty-in-pink hillside mansion, which turned a century old in 2005. The former Schuler residence (it's still run by the family) sits on prime real estate, adjacent to the city's botanical gardens and only two minutes from the pedestrian shopping stretch of the Corso Umberto. Most of the 26 affordable rooms and suites have balconies with stunning views of the gardens and the sea. Families will appreciate the separate Garden Villa, with two bathrooms, Jacuzzi, kitchen, living room, and patio. The hotel's many freebies include a piano and TV room, a small library, mountain bikes, and shuttle service to local beaches.

When this luxury resort opened in 2005 it quickly became the place to book for a stay on the western part of the island—with easy day trips to places such as Erice, the salt pans of Trapani, and the ruins of Segesta, Selinunte and Agrigento. Most of the hotel is new build though there are some original sections that are around 150 years old, and it is obvious that the property has benefited from a great deal of investment. The 91 rooms are huge, the Daniele Steiner spa suitably soothing and worth a treatment or two, and the garden and pool area is well-landscaped. In many ways the resort doesn't have a great sense of place from inside its walls, and it doesn't feel particularly Sicilian in its décor, but it's definitely the most luxurious pad around. A plus is the private beach club accessible by hotel shuttle—it has a charming blue-tiled restaurant, chaise lounges set out on the sand, and a bar on the small dock—but be forewarned that though the hotel says it is a ten-minute drive from the property, it's really half an hour.

It has been called the most majestic hotel in Sicily, and the legendary San Domenico doesn't disappoint. Built around a 15th-century monastery, the hotel offers incredible views, dreamy gardens, serious in-room luxury, and old-world charm (17th-century painting lines the walls). Not surprisingly, the hotel draws a wealthy international clientele who park themselves around the swimming pool, or at one of four sensational restaurants. The 108 rooms are located in two wings, one old (the Ancient Convent) and one new.