Palazzo Gaurdati, Sorrento | 3 Nights
A classic, 4-star hotel in the very heart of Sorrento, Palazzo Gaurdati is one of the oldest noble buildings in the city. Just 50 feet from central Piazza Tasso and short walk from the beaches, the hotel makes the perfect base for enjoying Sorrento. Its elegant rooms are set over 3 floors of an ancient palace and are furnished with marble bathrooms, parquet floors, antique furniture, and Murano-glass chandeliers. Palazzo Guardati offers stunning views of the harbor and the Bay of Naples from its roof terrace, where you can relax on lounge chairs, enjoy a drink from the bar, or cool off with a dip in the pool.

Eurostars Monte Tauro, Taormina | 1 Night
Just a five-minute walk from the ancient Greco-Roman theatre and the main piazzas of the town, Hotel Monte Tauro in Taormina provides a tranquil oasis with panoramic views of Naxos Bay. Each of its spacious and elegantly-furnished rooms includes a balcony or terrace with views over the Ionian Sea. The hotel also offers an enormous pool with hydro-massage jets, a sea-view restaurant, and a delightful, rooftop cocktail bar. Taormina’s main shopping and dining area is just 500 feet away and a short cable-car ride from there connects the town with the sands of Isola Bella Beach below.

Mari del Sud Resort, Vulcano | 2 Nights
Oozing with the quintessential charm of the Aeolian islands, Mari del Sud resort is built in the typical island style of whitewashed stone. Its bright, airy rooms are adorned with decorative ceramic tiles and feature private patios for relaxing. The resort offers stunning views over the sea and invites relaxation with plenty of sun loungers and parasols around both the expansive swimming pool—which features a hydro-massage area—and along its stretch of volcanic sand beach.

Badia Nuova Residence, Trapani| 2 Nights
A former noble residence, today Badia Nuova is a modern and welcoming abode in the very heart of Trapani’s old town. The hotel takes its name from a wonderful nearby church, dating back to the 15th century, which used to be a monastery. The location of Badia Nuova couldn’t be more ideal as everything Trapani has to offer – sites, beaches, dining, and shopping – is just outside. Each of its spacious and stylish rooms includes a kitchenette and the mesmerizing views from its chic rooftop terrace make it the perfect spot to watch the sunset and enjoy a cocktail before heading out to experience the passeggiata.

Royal Maniace Hotel, Syracuse| 2 Nights
A superbly-situated, 4-star hotel in the historic city center of Syracuse, the Royal Maniace offers panoramic views of emerald-blue seas combined with breathtaking beauty and elegantly-styled, modern rooms to make your stay relaxing and comfortable. Located along the waterfront of the ancient island of Ortigia, the hotel makes the perfect base for getting the most out of your stay in Syracuse. The historic streets and all the architectural wonders that the ancient city has to offer are just outside and the amazing, 7th-Century Duomo is just five minutes away.