Windward Ways & Tobago Cays
From $2,819 per person
8 days
Ships: Star Legend, Wind Surf, Star Pride
From $2,819 per person
8 days
Ships: Star Legend, Wind Surf, Star Pride
Day-by-day description of your cruise and cruise activities.
Bridgetown
Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you’ll find historic sugar plantations and the fairyland magic of Harrison’s Cave.
Bequia
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia’s whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island’s famed model boat builders at work on their miniature masterpieces.
Mayreau
With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform.
Soufriere
Nestled in the shadows of the UNESCO Pitons, Soufriere represents the heart and soul of St. Lucia. The tiny town center is full of street vendors and stores and some of the best resorts on the island can be found here. Nearby are secluded waterfalls and the waters here boast some of the best diving around. Sights to see include the Edmund Rainforest Trail, fond Doux Holiday plantation, Robot Estate and the Gros Piton Nature Trail.
Kralendijk
The ice cream colors of the stucco houses will draw your lens, as will the pink flamingos on the salt pans. But you’ll need a waterproof camera to complete the portrait since more than 400 fish species and 50 types of coral wait beneath the surface
Willemstad
Savor the pastel colors of the historic UNESCO site Old Town and the way the elaborate Dutch gables cut baroque curlicues from the sky. It’s the perfect appetizer for a day of watersports or an adventure below ground at the magical Hato Caves—filled with eerie limestone formations and ancient petroglyphs.
Oranjestad
Known for having some of the best beaches in the Caribbean, this Dutch port makes it easy to just … take it easy. Walk through town to choose your favorite carved wooden door, or spend the day like the Arubans do playing dominos at a beachside table.
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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.
Reach out to our travel concierges today to create your perfect journey.
