- Sail the waters of the Mediterranean, Tyrrhenian, Ionian and Adriatic seas aboard the magnificent square-rigger yacht Sea Cloud.
- Set out with a historian to visit 5 UNESCO World Heritage Sites, including the volcanic Aeolian Islands and the haunting ruins at Pompeii and Paestum.
- Explore the picturesque city of Lecce, known as the “Florence of the South,” and wander the winding streets of Amalfi and Ravello in the company of local guides.
- Discover the medieval treasures of Taormina, Sicily and enjoy a private dinner at a historic castle.
Set sail aboard the majestic four-masted yacht Sea Cloud on a voyage across the Adriatic Sea to the fabled shores of Sicily and Southern Italy. Step back in time as you venture into stunning Greek temples, ancient theaters, splendid cathedrals and grand plazas steeped in history. Discover the great baroque city of Lecce, the “Florence of the South,” and experience small-town life while exploring the winding streets of Otranto and Gerace. Delve into the Greco-Roman treasures of Sicily and savor the island’s renowned cuisine, before a walk amid the stunning volcanic landscapes of the Aeolian Islands. Cap off your journey by exploring the gorgeous Amalfi Coast and the legendary ruins of Pompeii and Paestum.
This trip is operated in collaboration with Lindblad Expeditions.
Depart on an overnight flight to Dubrovnik, Croatia. Time permitting, you’ll briefly explore the city before you board the ship and cast off.
Travel as sailors have for millennia as you cross the Adriatic Sea. Begin the morning on deck, where sailors climb the lines to raise Sea Cloud’s sails by hand. Learn about the art of sailing as you follow the action. Attend talks by our onboard historian and naturalist, relax with a book and experience the five‐star service for which Sea Cloud is known.
Your first stop is the picturesque Adriatic town of Otranto, whose idyllic seaside appearance contrasts with its turbulent past. Explore the cathedral, viewing its intricate 12th-century mosaic floor, and venture into a chapel containing the bones of more than 800 martyrs of the Turkish invasion of 1480. Then walk the city’s medieval walls, taking in sweeping views. Continue to Lecce to explore its 17th-century baroque architecture, narrow pedestrian streets and grand plazas. Visit the Basilica di Santa Croce and the adjacent Palazzo del Governo; the Piazza del Duomo, with its impressive cathedral; and the 2nd-century Roman amphitheater. Afterward, return to the ship and sail into the Ionian Sea.
Spend the morning with sails unfurled, voyaging across the southern part of Italy’s “boot.” Anchor off Roccella Ionica and drive to the hilltop village of Gerace, which occupies a spectacular setting facing the mountains and valleys of Calabria on one side and the sea on the other. Enjoy a glimpse of small-town life in Southern Italy, meandering along the town’s winding streets. Explore the borgo antico (old town) and visit the Byzantine-Norman cathedral, which dates from 1045 and houses an interesting museum. Then return to Sea Cloud and sail toward Sicily.
Sail south to the UNESCO World Heritage Site of Syracuse, a city that once rivaled Athens in cultural and economic wealth. Explore the archaeological park, which showcases one of the world’s largest theaters of antiquity, a 15,000-seat arena still in use today. After lunch, visit the enchanting island town of Ortigia to discover its charming piazzas, twisting alleyways and magnificent Duomo, built from the ruins of Sicily’s ancient Temple of Athena. Enjoy time to explore on your own, if you wish.
Anchor off the coast of Taormina, perched more than 600 feet above the sea. With Mount Etna dominating to the southwest, this stunning medieval town boasts the fashionable Corso Umberto, lined with exquisite buildings, and a 3rd-century B.C. Greco-Roman theater, built directly into the cliff. Tonight, you’re invited to a private dinner at the historic Castello degli Schiavi. At this 18th-century home, which was featured in several Godfather films, you’ll meet members of the family that owns it and explore the extensive buildings and grounds.
Pass through the narrow Strait of Messina, which separates Sicily from the boot of Italy. It’s also the purported location of Homer’s mythical monsters Scylla and Charybdis, between which Odysseus had to sail. Arrive at the Aeolian Islands, a World Heritage Site known for its breathtaking landscapes and simmering volcanoes. Sail amid the islands of Vulcano and Stromboli, anchoring at Lipari. You’ll take a scenic drive around the perimeter of the entire island and spend time in Lipari Town, browsing the impressive collection of Neolithic artifacts at the archeological museum. This evening, have dinner on deck as you sail to Stromboli—with luck, you’ll see some of the island’s volcanic pyrotechnics as the ship approaches.
Spend the morning at sea, sailing to the western coast of Italy. In the afternoon, visit the storied town of Amalfi, part of the World Heritage Site that comprises the entire Amalfi Coast. Explore this enchanting town, where pastel-hued houses cling to the mountainside above the sea. Stroll the waterfront, peruse local shops and boutiques, and visit the Romanesque cathedral, whose bronze doors date from around 1066. Later, drive up the mountain along a series of hairpin turns to Ravello, which overlooks the coastline from high above. Ravello has long been a haunt of artists and intellectuals, including Gore Vidal, Greta Garbo, and D.H. Lawrence, who wrote Lady Chatterley’s Lover here. Explore the Villa Rufolo, originally built in the 13th century and restored in the mid-19th century. Meander through its gardens and stately buildings and climb the tower, if you wish, for sweeping views.
This day, you'll anchor off the town of Agropoli and drive to Paestum, a World Heritage Site with some of the best-preserved Greek temples in the world. Founded around 600 B.C. by Greeks from Sybaris, it became a thriving city. Three magnificent Doric temples—known as the Temple of Neptune, the Basilica of Hera and the Temple of Ceres—can be explored up close. Explore the nearby museum’s superb collection of statues, paintings and reliefs from the site, which depict life in ancient times. Later, return to Sea Cloud and spend the afternoon sailing the Tyrrhenian Sea.
Spend the morning in Pompeii, a city frozen in time when Mount Vesuvius erupted in 79 A.D., blanketing the area in a thick layer of ash and debris. The site was only discovered many centuries later, when, in 1748, explorers excavated dwellings, everyday objects and the bodies of Pompeii’s residents, all remarkably preserved in the volcanic ash. Venture into this splendid and haunting city, see its frescoed villas and get a rare glimpse of daily life nearly 2,000 years ago. Return to Sea Cloud this afternoon, where the ship will raise its sails a final time as it makes its way toward the Bay of Naples. Toast your journey at a farewell dinner on board.
Arrive in Naples after breakfast and disembark the ship. Transfer to the airport for your flight home, or join our 2-day optional extension exploring historic Naples.