Malta, Sicily and Greece Under Sail Aboard Sea Cloud II

Arrive in Valletta, Malta’s captivating capital and a UNESCO World Heritage site, where golden limestone fortifications—standing since the 16th century—guard a city rich in history and charm. In the late afternoon, step aboard the magnificent Sea Cloud II and settle into your new home at sea. As the sun begins to dip toward the horizon, raise a glass of champagne on deck and toast the unforgettable adventure that lies ahead. 

Arrival Time: Arrive before 4:00 p.m. local time. 
Arrival City: Valletta, Malta 

Be on deck this morning with cameras ready to enjoy one of the most attractive harbors in the Mediterranean bathed in early morning light. On tour, drive to the city’s highest point, the Upper Barrakka Gardens, and take in the sweeping view. Tour St. John’s Co-Cathedral with its elaborate inlaid marble tombstones and monumental artwork. After lunch onboard, opt for free time in Valletta, or continue your exploration with a guided visit the old capital of Mdina: walk along the ancient city walls and marvel at the feat of engineering undertaken to build the Rotunda of Mosta, one of the largest unsupported domes in the world. As evening falls, return to the ship for a festive welcome cocktail party and dinner hosted by the captain and officers as you sail to Gozo. 

In the morning, step ashore on Malta’s sister island, Gozo, a tranquil haven steeped in ancient mystery. Visit the awe-inspiring Ġgantija Temples, a UNESCO World Heritage site and one of the world’s oldest freestanding structures—predating both the Pyramids of Giza and Stonehenge by over a millennium. Explore these megalithic marvels, as well as the beautifully restored Ta’ Kola Windmill, a relic of the Knights of Malta’s enduring legacy. Back aboard the ship en route to Sicily, watch the crew climb high into the rigging to unfurl the sails by hand—a breathtaking display of traditional seamanship that brings the grandeur of square-rig sailing to life.  

Awaken this morning to the storied shores of Siracusa, a UNESCO site that was once a powerful rival to Athens and a beacon of ancient culture and commerce. Step ashore to explore its remarkable archaeological park, home to one of antiquity’s largest theaters—a 15,000-seat masterpiece carved from solid bedrock and still used for performances today. Wander through the atmospheric limestone quarries, including the legendary “Ear of Dionysius,” and visit the impressive Roman amphitheater, a testament to the city’s layered history. In the afternoon, enjoy the serenity of the open sea. Reflect on the morning’s discoveries, attend engaging talks with your expedition staff and sample a curated selection of Sicilian wines. Or simply relax on deck and revel in the thrill of sailing. 

Begin the day with a journey up to the enchanting hillside town of Taormina, gracefully perched at the foot of Mount Etna. With sweeping views of the Ionian Sea and a skyline dominated by the volcano’s majestic silhouette, Taormina is a jewel of Sicily. Stroll along the elegant Corso Umberto, a pedestrian promenade lined with historic architecture, boutique shops, and charming cafés. Visit the town’s crown jewel—the Greco-Roman Theater—an ancient amphitheater carved into the cliffside in the 3rd century B.C., offering breathtaking views of the sea and Mount Etna beyond. From Taormina, continue to the Castello degli Schiavi, an 18th-century private villa steeped in history and cinematic lore. Enjoy an exclusive lunch hosted by members of the family who still reside there and explore the villa’s atmospheric grounds, famously featured in several iconic scenes from The Godfather films. Return to Sea Cloud II for a relaxing evening at sea, beginning with happy hour on deck and followed by a delightful dinner as you set sail.  

As Sea Cloud II glides gracefully across the Ionian Sea, enjoy two leisurely days at sea—an ideal opportunity to unwind and embrace the rhythm of life aboard a classic tall ship. Claim your favorite deck chair, lose yourself in a captivating book and listen to the soothing sound of waves as the ship cuts through the surf en route to Greece. Marvel at the spectacle of the crew climbing high into the intricate rigging to hand-set the sails—a breathtaking display of seamanship and tradition. Enrich your voyage with engaging presentations by your onboard historian and experts, who bring the region’s fascinating past to life. Delight in exquisite meals and complimentary drinks, and connect with fellow travelers during lively social gatherings and shipboard events. Whether you're basking in the sun or diving into history, these days at sea promise relaxation, discovery and camaraderie.  

After docking in Katákolo, journey inland to the legendary site of Olympia—the birthplace of the Olympic Games, held every four years for over a millennium beginning in 776 B.C. This UNESCO World Heritage site offers a powerful glimpse into the ancient world’s reverence for athleticism, competition and the divine. Wander among the evocative ruins of the Temple of Zeus, once home to one of the Seven Wonders of the Ancient World, and admire the remnants of the Temple of Hera and the iconic statue of Nike. Stand in the original Olympic Stadium, where athletes once competed in honor of the gods, and explore the outstanding Archaeological Museum, which houses a remarkable collection of classical sculptures and artifacts that bring Olympia’s storied past to life. After lunch, visit Olympia Land Estate, a family-owned winery, for a tasting of exceptional vintages that reflect the history and tradition of the region.  

Nestled on the southwestern coast of the Peloponnese—named for the mythical King Pelops, founder of the Olympic Games—Pylos is a town steeped in history and myth. Once a vital center of Mycenaean civilization, it was home to King Nestor, the wise elder statesman of Homer’s Iliad. Today, explore the dramatic Methoni Castle, perched on a rocky cape jutting into the Ionian Sea. Built by the Venetians in the 12th century and expanded in the 17th, this fortress boasts a stone bridge, a deep moat, and towering walls that lead to a picturesque octagonal watchtower—perfect for photos and panoramic views.  

As Sea Cloud II rounds the southern tip of the Peloponnese and enters the Aegean Sea, you'll arrive at one of Greece’s most captivating destinations—Monemvasia. This dramatic fortress town clings to the side of a towering 1,000-foot rock that rises from the sea like a stone ship, hidden from view until you’re nearly upon it. Step ashore to explore the enchanting lower town, or kastro, a labyrinth of narrow cobbled lanes, Byzantine churches, and centuries-old stone houses. For those who opt to venture upward, a steep path leads to the upper town and the Church of Agia Sofia, perched high above the sea with sweeping views. With its timeless architecture and serene pace of life, Monemvasia feels like a living museum—where even the “newest” buildings are hundreds of years old. Spend your final afternoon at sea in quiet reflection, capture the ship’s graceful details through your lens, or simply savor the sea breeze as you recall the wonders of your journey. This evening, gather with fellow travelers for a festive farewell reception and dinner, celebrating the unforgettable voyage across the Ionian and Aegean seas aboard Sea Cloud II. 

Disembark in the port of Piraeus this morning and transfer to the airport in Athens for your flights home.  

Departure Time: After 12:00 p.m. 
Departure City: Athens, Greece 

Itineraries are subject to change.