Sicilian Splendors

Detailed Itinerary

Day-by-day description of your cruise and cruise activities.

Day 1

Rome

In this enchanting city the past and present intersect in perfect harmony. Casually intermingled among ancient ruins and majestic cathedrals are the trappings of a modern metropolis: Skyscrapers,cafes, boutiques selling designer footwear. But of course what you seek first in the heart of Rome is its breathtaking history. A good place to begin is the Vatican, with its Sistine Chapel and St. Peter’s Basilica. Works by Bernini, Michelangelo, Caravaggio, and Raphael are just a few of those on display, any one of which is worth hours of contemplation. Then the ancient ruins—Colosseum, Forum, Circus Maximus. And of course the Trevi Fountain for the obligatory coins promising your return to the Eternal City.

Day 2

Cruising Stromboli, Italy

Weather conditions depending, you will see the volcano that never sleeps as you cruise by Stromboli and with any luck observe the active lava stream by day or the glowing lava at night.

Day 3

Lipari

Take time on shore to explore the beautiful village and enjoy the exclusive access that only a small ship can provide in a port large cruise ships cannot reach. An optional tour will introduce you to the highlights of the largest of the seven Aeolian Islands, well-known for its mythological connections and a UNESCO World Heritage Site.

Day 4

Palermo, Italy

Palermo, the vibrant capital of Sicily, is a city where history, culture, and flavor come alive. Known for its stunning mix of Arab-Norman architecture, bustling markets, and rich culinary traditions, it offers a unique blend of Mediterranean charm and timeless heritage. From ornate cathedrals and grand theaters to lively piazzas and street food stalls, Palermo is a feast for the senses and a true gateway to Sicily’s soul.

Day 5

Trapani

At once ancient and contemporary, Trapani is a city of contrasts. From the salt marshes that produce much of the Mediterranean’s signature colored salts, to the intricate mosaics of Mozia and the famous wines of Marsala, to the best view in all of Sicily from the medieval hill town of Erice where the colorful gardens are rivaled only by the cannolis for pure sensory delight. The line of 17th century windmills, still hard at work in ancient Phoenician salt marshes beckons you to return to Trapani again and again.

Day 6

Valletta

Malta’s capital city, a UNESCO World Heritage Site, is among the world’s smallest, yet definitely most charming. Graced with the paintings of Caravaggio and kissed by beautiful shorelines, you’ll find photographic icons at almost every turn. Not to be missed is a visit to the stately Palazzo Parisio to glimpse the enchanting lifestyle of Malta’s nobility.

Day 7

Porto Empedocle

Here you’ll find what are widely acclaimed as the best, ancient ruins in the entire Mediterranean. Imagine the wonders of Athens, of Ephesus, of legendary Olympia itself. Then imagine them all in one place, at Agrigento, a UNESCO World Heritage Site. As you wander the verdant ridge overlooking the Mediterranean you will be transported to the 5th and 6th centuries. The irresistible scent of olive, almond, and eucalyptus trees will entice you back to the present. This is one of the world’s most beautiful sites.

Day 8

Syracuse, Italy

Rich in both Greek and Roman history and home of the mathematician Archimedes, Syracuse is full of ancient ruins including the Roman Amphitheater, Teatro Greco, and the Orecchio di Dionisio. The Ortigia, or Old Town is full of sites to see like the Ortigia Cathedral which houses a number of relics of St. Lucy, the patron saint of Syracuse.

Day 9

Giardini Naxos

Today you’ll discover one of Sicily’s jewels, the charming village of Giardini Naxos, nestled in one of the world’s most beautiful bays. An optional excursion to the popular hillside town of Taormina will be a highlight of your voyage — from the stunning setting of the iconic Greek Theater to the sparkling beaches along the Ionian Sea. Take a more adventurous tack and explore the UNESCO site of Mount Etna, Europe’s most active volcano.

Day 10

Transit Straits of Messina

The Straits of Messina, a narrow passage between Sicily and mainland Italy, are famed for their dramatic scenery, strong currents, and mythological legends. Linking the Tyrrhenian and Ionian Seas, this strategic waterway has long been a crossroads of history and culture. As you sail through, you’ll be treated to views of rugged coastlines, picturesque villages, and possibly even the whirlpools that inspired the ancient tales of Scylla and Charybdis.

Day 11

Sorrento

UNESCO World Heritage Sites abound in Sorrento. Optional tours will take you to the archaeological areas of Pompeii and Torre Annunziata, or the 4^th century B.C. city of Herculaneum. Perhaps your choice will be a boat ride to Positano, the legendary home of the Sirens. Perched on a terrace on the spectacular Amalfi Coast, Sorrento offers exceptional views of the Bay of Naples and Mount Vesuvius.

Ship

Your cruise ship

About this ship

Star Legend

Star Legend is a boutique, all-suite yacht that exemplifies Windstar Cruises’ signature style of immersive, small-ship luxury. Carrying just 312 guests, the vessel offers a relaxed yet sophisticated atmosphere, designed for discerning travelers who seek personal space, attentive service, and the ability to reach off-the-beaten-path destinations in comfort and style.

Originally launched in 1992 and transformed in 2021 as part of Windstar’s ambitious $250 million Star Plus Initiative, Star Legend emerged from its renovation with a new vitality. The ship was lengthened by 84 feet, allowing for expanded public areas, new dining concepts, and additional all-suite accommodations—all while preserving the sense of intimacy that defines the Windstar experience.

The 156 suites onboard range from 277 to 820 square feet, all offering sweeping ocean views. Interiors are designed with a contemporary, understated elegance, featuring warm wood tones, plush furnishings, and a palette drawn from the sea and sky. Many suites include private verandas or French balconies, while all offer walk-in closets, marble bathrooms with dual vanities, and fine details such as L’Occitane bath amenities, high-thread-count linens, and Illy espresso machines.

Dining on Star Legend is a true highlight. Guests enjoy a variety of culinary venues, all included in the fare and all rooted in Windstar’s commitment to quality and creativity. Amphora, the main dining room, serves globally inspired dishes in an open-seating setting. Candles, the ship’s romantic outdoor venue, offers expertly prepared steaks under the stars. Cuadro 44 by James Beard Award–nominated chef Anthony Sasso presents modern Spanish cuisine in a cozy, wine-bar-style space, while the Star Grill by Steven Raichlen delivers global barbecue flavors in an al fresco setting. The Yacht Club Café provides a more casual option for coffee, pastries, and light bites throughout the day.

Life onboard is designed for both enrichment and relaxation. The World Spa by Windstar offers a full menu of treatments, a thermal suite, and a serene atmosphere, while the fitness center features modern equipment and instructor-led wellness classes. The open decks include an infinity-style pool and whirlpools with panoramic views, while the ship’s watersports platform at the stern offers complimentary access to kayaks, paddle boards, snorkeling gear, and more—available when anchored in select destinations.

Because of its size and advanced maneuverability, Star Legend is uniquely equipped to access smaller ports and remote harbors. Whether exploring the storied coastlines of the Mediterranean, the rugged beauty of Northern Europe, or the exotic islands of Southeast Asia, the ship brings guests closer to the cultures and landscapes they’ve come to discover.

Blending elegance, intimacy, and destination-driven itineraries, Star Legend offers a yachting experience that is as enriching as it is indulgent—perfect for travelers who seek the freedom of the open sea without sacrificing the comforts of modern luxury.

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