Ciao, Bella: A Girls’ Guide to Southern Italy

Fly into Catania Airport and transfer along the coast to Taormina. Check into your hotel (like Villa Carlotta or a Belmond property), unpack, and ease into island mode. Spend the afternoon exploring Corso Umberto’s boutiques or sipping an Aperol spritz. Dinner can be casual tonight like fresh seafood at Trattoria da Nino.

Set out early for an epic full day at sea exploring the Aeolian Islands. Sail from Milazzo to Lipari and Vulcano. Swim, stroll, and soak in the wild Mediterranean charm before returning to Taormina in the evening, sun-kissed and sleepy.

Sleep in or lounge by the pool. Later, head out for a guided tasting tour through Taormina’s old town. Expect local cheeses, cured meats, seafood pastas, and Sicilian wines poured generously. It’s the perfect mix of culture and calories.

Your agenda: absolutely nothing. Grab your beach bag and spend the day at Isola Bella or one of the chic lidos below town. Optional detour: a quick cable-car ride up to Castelmola for panoramic views (and an icy granita).

All aboard: take the train from Taormina to Salerno, then ferry across the Tyrrhenian to Positano. Check into Il San Pietro di Positano, a hotel so beautiful you know it was made for the girls. Settle in, toast to arrival, and dine on your terrace overlooking the sea.

Spend the morning exploring Positano: shop the boutiques, lounge at Arienzo Beach Club, or take a dip in that unreal turquoise water. Tonight, roll up your sleeves for a ravioli and tagliatelle cooking class, complete with wine, laughter, and carb-fueled joy.

Cruise over to Capri for a full day of dolce vita. Visit the Blue Grotto, shop Via Camerelle, and take in the views from the Gardens of Augustus. Optional lunch at Da Paolino... yes, the lemon grove restaurant. Return to Positano by sunset.

Slow morning, long brunch, and an afternoon of sunbathing or spa time. As the sun dips, board a private sunset boat tour. Connect to the Bluetooth, drink champagne, and watch the golden light bouncing off the cliffs. Pure magic.

Catch the train north to Rome and check into Chapter Roma, your stylish home base in the heart of the city. Tonight’s plan: dinner with a view of the Colosseum—try Ristoro Della Salute.

Morning: guided Colosseum and Roman Forum tour (9 am–12 pm). Afternoon siesta or gelato stop, then uncover the city’s lesser-known secrets on an evening “Secrets of Rome” walking tour with the Gladiator Guide (6–8 pm).

Morning: explore the Vatican Museums and St. Peter’s Basilica... skip-the-line, obviously. Afternoon: wander through Trastevere, Rome’s most authentic neighborhood, and linger over your final dinner of the trip at Pasta e Vino.