Arrive in Naples and transfer from the airport to

the legendary Sea Cloud in the afternoon. Cast off

from Naples’ active harbor and pass by the rugged

coast of the island of Capri at sunset as we enter the

Tyrrhenian Sea

Marvel as Sea Cloud’s billowing sails are raised the old-fashioned way, by hand, and the ship heads across the Bay of Naples this morning.

Anchoring off the town of Agropoli this afternoon, we drive to Paestum, a UNESCO World Heritage site with some of the finest and best-preserved Greek temples anywhere. Founded around 600 B.C. by Greeks from Sybaris and called Poseidonia, it became a thriving city. Today, the three magnificent Doric temples—known as the Temple of Neptune, the “Basilica” of Hera, and the Temple of Ceres—can be explored up close. The Temple of Neptune (a misnomer, as it was likely dedicated to Hera) is especially intact and allows visitors to imagine what it must have been like 2,500 years ago. It is large and graceful, with elegant rows of columns.

The nearby museum has a superb collection of statues, paintings, and reliefs from the site, many of them richly evocative in how they depict life in ancient times. After exploring Paestum, we return to Sea Cloud and spend the afternoon sailing the Tyrrhenian Sea.

pend time exploring the historic city center of Salerno. Marvel at the 11th century Duomo of Salerno—a magnificent cathedral dedicated to Saint Matthew—and the gorgeous landscaped garden of Villa Comunale di Salerno. Or opt to visit the UNESCO-listed site of Pompeii, a once thriving city buried in pumice and ash when Vesuvius erupted in A.D. 79 that would not be rediscovered for 1,500 years. Pliny the Younger wrote, “Darkness fell, not the dark of a moonless or cloudy night, but as if the lamp had been put out in a dark room.” Walking the 2,000-year-old streets, we explore remarkably preserved villas, the forum, the splendid amphitheater (which seated 12,000), and temples.

This morning, we visit Amalfi. This storied town, part of the UNESCO World Heritage site that comprises the entire Amalfi Coast, has a glorious aspect, with pastel-hued houses clinging to the steep-sided mountains that comprise this indented stretch of coastline. Its pleasures are many: strolling the waterfront, with its marina and shops; visiting the ornate cathedral, with bronze doors dating from 1066; and just wandering the winding streets and alleyways to make your own discoveries. Spend the afternoon sailing.

The Aeolian Islands are not only famous for the winds of the god Aeolus, but also for some of the most well-known classical volcanoes. We set sails in the morning, anchoring for the afternoon at Lipari. Here we go ashore for a drive around the perimeter of the entire island, with spectacular views of the other Aeolian volcanoes, before returning to the main town. We visit the small but surprising archeological museum that has an extensive collection of Neolithic artifacts made from the local obsidian, which was also the foundation of the island’s prosperity during the Greco-Roman era. This evening, we have dinner on deck as Sea Cloud cruises the 25 miles to Stromboli, and with a little luck, we see some of the pyrotechnics of this active volcano.

In the wee hours of the morning, we pass through the narrow Strait of Messina, which separates Sicily from the “boot” of Italy. It is the purported location of Homer’s monsters Scylla and Charybdis, the rock and the hard place through which Odysseus had to sail. Later this morning, we drive up to the beautiful town of Taormina, perched 250 meters above the sea. With Mount Etna dominating to the south, this medieval town boasts the pedestrian-friendly Corso Umberto, lined with exquisite buildings, and one of the world’s most interesting cultural sites: the Greco-Roman Theater. This remarkable theater was built right into the cliffside, overlooking the vast sea below, in the third century B.C. Enjoy a special lunch at a privately owned castle, the Castello degli Schiavi. This impressive 18th-century home was the setting for many scenes in The Godfather films, and we meet members of the family that owns it and explore the extensive buildings and grounds. Return to Sea Cloud, which has been at anchor under the watchful gaze of Mount Etna.

Siracusa was the great rival to Athens, and its archaeological park features one of the largest theaters of antiquity. Its 15,000 seats are hewn out of bedrock, and the theater is still in use today. We also visit the nearby limestone quarry, the cave of “Dionysus’ Ear,” and the Roman amphitheater before returning to Sea Cloud for lunch. The afternoon features a walk through the medieval island town of Ortigia. The town is magical, with numerous little piazzas and narrow alleys, but the main feature is the Duomo, or Cathedral, which was built from the ruins of the ancient Temple of Athena. The history of Sicily can be told in the walls of this incredible construction. Enjoy time to explore on your own, if desired.

Weather permitting, we spend the day with sails unfurled in the Ionian Sea, sailing across the southern part of Italy’s “boot” toward Sicily. Join the expedition leader for a play-by-play description of the crew in the rigging and the action of setting square sails, staysails, and jibs as Sea Cloud shows her full glory. Relax with a book on deck, and enjoy delicious meals and complimentary drinks.

We stop at the picturesque Adriatic town of Otranto, whose idyllic seaside appearance contrasts with its turbulent past. We explore the cathedral, which has a large, intricate, 12th-century mosaic floor depicting real and mythological animals, a tree of life, historical figures, and biblical scenes. The cathedral is also noted for the chapel with the skulls and bones of more than 800 martyrs of the Turkish invasion of 1480. We also walk the medieval walls for great views of the Aragonese Castle, the town, and the sea.

We continue to Lecce, the “Florence of the South,” to explore its remarkable 17th-century baroque architecture and its narrow pedestrian streets and grand plazas on a walking excursion. Some of the greatest architectural masters of the time competed to see who could create the most beautiful buildings, and the highly fanciful, ornamented style was given its own name: Lecce Baroque. Our walking tour of Lecce shows us the Basilica di Santa Croce and the adjacent Palazzo del Governo; the extraordinary Piazza del Duomo, with its cathedral and the Palazzo Vescovile; and the second-century Roman amphitheater. After visiting Lecce, we return to our ship and sail into the Adriatic.

Sail across the Adriatic Sea, which sailing vessels have crossed for millennia. Sails on our ship are again raised the old-fashioned way, by hand, and the excitement is palpable. Hear presentations from our historian and naturalist, catch up on reading, and experience the five star service for which Sea Cloud is famous. We have a farewell dinner to toast our voyage.

We arrive in Dubrovnik this morning and disembark. Transfer to the airport for flights home.