Arrive in Naples and embark Sea Cloud II in the late afternoon.

Meals Included: Dinner

Gather on deck 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 II shows her full glory. Relax with a book on deck, and enjoy delicious meals and complimentary drinks. After lunch, anchor off Amalfi. This storied town, part of the Amalfi Coast UNESCO World Heritage site, is known for its pastel-hued houses that cling to the steep-sided mountains of this indented stretch of coastline. Stroll the waterfront with its marina and boutiques, visit the ornate cathedral with bronze doors dating to 1066, and wander the winding streets and alleyways to make your own discoveries. After exploring Amalfi, enjoy the captain’s welcome gathering this evening as Sea Cloud II makes her way to the Aeolian Islands.

Meals Included: Breakfast, Lunch, Dinner

The Aeolian Islands are famous not only for the winds of the god Aeolus, but also for some of the best-known classical volcanoes, recognized by UNESCO as a World Heritage site. Set sail in the morning with the islands of Vulcano and Stromboli in view, anchoring for the afternoon at Lipari. Go ashore for a drive around the perimeter of the entire island, with spectacular views of the other Aeolian volcanoes. Back in Lipari, visit the small but surprising archeological museum that has an extensive collection of Neolithic artifacts made from local obsidian—the foundation of the island’s prosperity during the Greco-Roman era. This evening, have dinner on deck as Sea Cloud II cruises the 25 miles to Stromboli; and perhaps witness some of this active volcano’s pyrotechnics.

Meals Included: Breakfast, Lunch, Dinner

In the early hours of the morning, pass through the narrow Strait of Messina that separates Sicily from the “boot” of Italy. It’s the purported location of Homer’s monsters Scylla and Charybdis, the rock and the hard place through which Odysseus sailed. Begin your day with a drive up to intoxicatingly beautiful Taormina, perched 250 meters above the azure Ionian Sea. With views of Mount Etna to the south, this stunning medieval town boasts the fashionable pedestrian Corso Umberto. Lined with exquisite architecture, it ends at the Greco-Roman Theater. This unforgettable theater was built right into the cliffside, overlooking the vast sea below, in the third century BC. Our special lunch today is at a privately owned villa, the Castello degli Schiavi, the setting for many scenes in The Godfather films. Meet the owners of this phenomenal 18th-century home and have time to explore it and its beautiful grounds. Return to Sea Cloud II, which has been at anchor under the watchful gaze of Mount Etna.

Meals Included: Breakfast, Lunch, Dinner

Weather permitting, spend the day with sails unfurled in the Ionian Sea, sailing across the southern part of Italy’s “boot” toward the Adriatic Sea.

Meals Included: Breakfast, Lunch, Dinner

Stop at the picturesque Adriatic town of Otranto, whose idyllic seaside appearance contrasts with its turbulent past. Explore the cathedral, which has a large, intricate, fanciful 12th-century mosaic floor depicting real and mythological animals, a tree of life, historical figures, and biblical scenes. The cathedral is also noted for a chapel displaying the skulls and bones of more than 800 martyrs of the Turkish invasion of 1480. A stroll along the town’s medieval walls offers panoramic views of the Aragonese Castle, the town, and the sea. Continue to Lecce, the “Florence of the South,” to explore its remarkable 17th-century baroque architecture, 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 resulting ornamented style was named “Lecce Baroque.” Our walking tour of Lecce takes us to 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 secondcentury Roman amphitheater. After visiting Lecce, return to our ship in time to witness the orange sun sinking into the Adriatic Sea.

Meals Included: Breakfast, Lunch, Dinner

With Sea Cloud II’s sails aloft, relax and take advantage of the ship’s amenities. Enjoy complimentary drinks, catch up on reading, sort photos, and learn from expedition staff presentations.

Meals Included: Breakfast, Lunch, Dinner

In the bustling port city of Split this morning, discover the UNESCO World Heritage-listed Diocletian’s Palace, more a small city than a single palace. Built by Emperor Diocletian as a sumptuous place to retire, this site is now a beguiling maze of marble streets, churches, and fortifications that tell the history of the city from the Romans and Byzantines to the modern day. It maintains a lively pulse of shops and street merchants to this day. An afternoon drive takes us along the Dalmatian coastline to medieval Trogir—a small island town also designated a UNESCO site—whose main square, cathedral, streets, and alleyways invite exploration. Return to Sea Cloud II, docked in Split, for an overnight sail to the island of Vis.

Meals Included: Breakfast, Lunch, Dinner

One of the outermost of Croatia’s many islands, Vis was ruled successively by the ancient Greeks, Romans, Venetians, Austrians, and Italians. It became a central Yugoslav military base during World War II, and only opened to tourists in 1990s, resulting in it now being less developed and less populated than many of its neighbors. On a walking tour of the fishing town of Komiža, see the traditional sailing vessels called falkušas, which have been used here since the 16th century, and hear about age-old regattas originally designed to keep pirates at bay. Take in expansive views from the rugged interior and visit a family-owned winery for a tasting and traditional peka lunch. See the extensive tunnels where Yugoslav resistance leader Josip Broz Tito hid troops and weapons at the end of World War II and into the Cold War, and venture to hillside barracks and hidden bunkers.

Meals Included: Breakfast, Lunch, Dinner

At the height of Venetian rule, Hvar was the region’s most prosperous center. Set off on a walking tour along the waterfront and around the delightful walled city. Visit the 15th-century Franciscan monastery, the arsenal, and Croatia’s oldest active theater. If you choose, hike up to the citadel for spectacular views of the island and the azure Adriatic beyond. This afternoon, take to the seas on our final sail and enjoy the captain’s farewell evening.

Meals Included: Breakfast, Lunch, Dinner

Arrive in Dubrovnik this morning. After breakfast, disembark and transfer to the airport for your flight home.

Meals Included: Breakfast