Sic i-l-y
ortigia
stay.
Grand Hotel Ortigia. Although not exactly the 5-star hotel that's advertised, this hotel still has a perfect roofdeck for enjoying a beautiful seascape at breakfast, is on the quaint island of Ortigia, offers a boat shuttle to a private beach and is walking distance to the market and best restaurants.
eat.
Ristorante Porta Marina da Salvo, Perle d'Ortigia & Ristorante Dioniso for the squid ink pasta.
do.
Visit Ortigia's historic street market, stopping at Caseificio Borderi for amazing cheese; explore the island & port of Ortigia on foot. If you're interested in what was rather than what is, visit the Roman Amphitheater, Teatro Greco and Orecchio di Dionisio at the Neapolis, and the Museo Archeologico Regionale Paolo Orsi, but don't expect to be terribly impressed by the preservation efforts of these ancient ruins.
taormina
stay.
Porta del Tocco Design Suites in the old town center; Villino Gallo d'Oro on the beach; or Grand Hotel Mazzaro Sea Palace for a truly luxe seaside experience and private beach.
eat.
Stecco Natura popsicles are the highlight. Any restaurant here is as good as the next, but nothing to write home about.
do.
Stroll the historic center at twilight; visit Isola Bella beach for people watching - but beware of the rocky shore; lounge on the more private Mazzarò beach; visit the beautiful, well-preserved and still used Teatro Greco.
Panarea
stay.
Lisca Bianca; Hotel Raya; Hotel Cincotta.
eat.
Bridge Bar for sunset cocktails; Da Franceso for the famous pasta; Raya for cocktails and live music at dusk until the early hours of the morning.
do.
Take the beautiful, scenic walk along the Via Drautto to the little beach at Caletta de Zimmari and relax there for the day, continuing on to the prehistoric village for a dose of history, the origins of Panarea, and beautiful cliffside views of daytrippers on their yachts along the way; walk even further to Junco Cove Beach; stroll the downtown/port area for quaint and high-end boutique shops, not skipping the famous Raya Boutique, or just relax at one of the many cafes with a cappuccino or cocktail.
lipari
stay.
somewhere else. This island is best enjoyed in a day trip.
eat.
Ristorante Fillipino. Order any or everything on the menu, but especially a fresh tomato and caper salad, and even on a 90 degree day, the clam and mussel zuppe is the best you'll ever have. Try each of the olive oils that come with the bread for sampling.
do.
Stroll down the via Garibaldi, adorned with small shops and boutiques, and buy a local, artisan painted and ornament-adorned colorful straw bag at La Casa Eoliana; stroll down the Corso Emanuele, laden with restaurants and knickknack shops, and stop into the sculptor Giovanni Spada's shop, or buy any number of the local pastries or delicacies; visit the astonishingly impressive Archaeological Museum on via del Castello, replete with bronze age pottery, miniatures from the Greek tragedies, IV to III centuries BC tombs, Roman era statues, pottery, jewelry (home to what I've branded as the original flower crown), and prehistoric tools; check out Marina Corta, a small, quaint port, and order the refreshing, local obsession, Aperol spritz.