Southern Italy & Sicily


Experience the picturesque towns and natural beauty of the Amalfi Coast as you explore the ruins of Pompeii, tour vineyards, and sail between hidden coves on the island of Capri. In Sicily, visit the Greco-Roman ruins of Syracuse and Taormina; swim, sail, hike, and savor the island’s rich wine and culinary traditions. With sun-soaked beaches, cinematic piazzas, and delicious seafood, this idyllic adventure will give you a true sense of Italy’s dolce vita.

Days: 13
Best time to visit: April-June, September, October
Ideal for: Couples

Trip Itinerary

Day 1 – Naples to Positano

Arriving in Naples this morning, you will be met at the airport for a private transfer to Positano on the Amalfi Coast. Settle into your hotel in this cliffside resort town that artfully blends luxury into its beautiful natural setting. Enjoy the rest of the day at your leisure to stroll through town, stretch out on the beach, or relax at your hotel with spectacular views over the Tyrrhenian Sea.


Day 2 – The Amalfi Coast

After breakfast, embark on a full-day, private boat tour along the jagged mountains of the Amalfi Coast, a seascape dotted with bays, inlets, and hidden coves like the Emerald Grotto in Conca dei Marini. Cruise along the Amalfi Coast around to the Sorrento Coast, visiting the Furore Fjord and the idyllic islands of Li Galli. Return to Positano for the night.


Day 3 – Tour Pompeii & Herculaneum

This morning, you will be picked up at your hotel for a full-day, private tour of Pompeii and Herculaneum. First, visit the incredible archaeological ruins of Pompeii, an entire city—mansions, markets, theaters, art, and even people—frozen in time by the 79 CE eruption of Mount Vesuvius. Continue the tour at the ruins of Herculaneum, once a vibrant fishing town, with its mosaics, public baths, and other buildings preserved in layers of molten lava and ash from the same eruption. You have the late afternoon and evening free to explore Positano.


Day 4 – Explore the Coast

Enjoy an open day in Positano to relax and do some sightseeing on your own. Tour a vineyard to learn about the region’s wines, produced from distinctive grape varieties grown at different elevations on ancient stone terraces. Down the coast, visit the picturesque town of Amalfi, with its narrow streets and hidden courtyards. Above Amalfi, you can hike up a pathway to the Torre dello Ziro, a mountaintop watchtower with amazing views over the coast.


Day 5 – Ferry to Capri

This morning, check out of your hotel in Positano and make your way down to the ferry port, where you will catch a ferry to Capri, a rugged, mountainous island set in blue-beyond-belief seas. Settle into your hotel and enjoy a relaxing lunch before taking a private tour of the island. Explore the towns of Capri and Anacapri, visit the luminescent Blue Grotto, and tour the Villa Jovis, the most extravagant and well-preserved of the dozen villas built by Roman emperors.


Day 6 – Enjoy Capri

Spend today relaxing on a private boat tour along the island’s dramatic coastal cliffs and mountains. Or stay closer to home and spend the day soaking up the sun along the coast, swimming and snorkeling in clear, calm seas. Capri is the perfect setting to enjoy seaside meals, crisp white wine, and the relaxed pace of island life.


Day 7 – Travel to Sicily

This morning, check out of your hotel in Capri and head to the port to catch a ferry to Naples, where you will be met and brought to the airport for an afternoon flight to Catania, Sicily. Arriving in Catania, travel onward to historic Syracuse, a city renowned for its Greek architecture. Spend the remainder of the day exploring this ancient city that once dared to take on Carthage and Rome.


Day 8 – Tour Syracuse

Delve into the rich heritage and history of Syracuse on a half-day, private walking tour of the city, focusing on the Greek and Roman ruins of the Parco Archeologico della Neapolis. Some of the main sites are the Teatro Greco, Paradis Quarry, and the Roman Amphitheater. Following your visit to the archaeological park, head to the Piazza del Duomo on the island of Ortygia, an area that boasts a large number of ancient monuments and churches.


Day 9 – Syracuse to Taormina

Leave Syracuse this morning and travel north to the hilltop town of Taormina, a coastal haven filled with ancient monuments and top-notch restaurants. Known for its Greco-Roman theater and rugged coastal beauty, Taormina offers comfort, culture, and mountainous walking trails. Take the next three days to immerse yourself in this majestic landscape, presided over by the active volcano, Mount Etna.


Day 10 – Beaches around Taormina

Taormina is inviting and accessible, and its town center is full of winding lanes and historic sites like the Teatro Greco, the Odeon, and the remains of port fortifications. Beautiful beaches, boutique shops, and an air or luxury make this the perfect stretch of coast to unwind and enjoy a taste of the dolce vita. A narrow strip of sand connects the tiny gem of a nature reserve, Isola Bella, to the mainland at low tide, which makes for an adventure right at your doorstep.


Day 11 – Mount Etna Tour

This morning, head off for a private tour of Mount Etna, including a visit to a local winery. The tallest active volcano in Europe for the past 270 years, Mount Etna is an enchanting landscape that offers unforgettable panoramic views over the Ionian Sea and the island. Next, tour a winery that grows grapes on ancient stone terraces at different elevations, and taste the delightful Nerello Mascalese, a unique wine produced almost exclusively in this region.


Day 12 – Half-Day Sail from Taormina

Today, gain a new appreciation for this idyllic stretch of Sicily’s coast on a half-day sailing excursion, stopping to swim and snorkel in the crystal-clear waters of tranquil bays and hidden coves. This evening, sip a glass of Sicilian wine with a relaxing meal featuring some of the island’s most famous dishes like artichoke frittella, red prawns, or a classic Pasta alla Norma.


Day 13 – Departure

Early this morning, you will be picked up at your hotel for a private transfer to the Catania airport. Fly to Rome and connect with your international flight home.

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