Windward Ways & Tobago Cays

From $3,119 per person

8 days

Ships: Star Legend, Wind Surf

Windward Ways & Tobago Cays

Journey Summary

  • Day 1 - Bridgetown
  • Day 2 - Bequia
  • Day 3 - Mayreau
  • Day 4 - Soufriere
  • Day 5 -
  • Day 6 - Kralendijk
  • Day 7 - Willemstad
  • Day 8 - Oranjestad

Detailed Itinerary

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

Day 1

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.

Day 2

Rodney Bay

Rodney Bay, Saint Lucia

Day 3

The Pitons

Located near the town of Soufriere, St. Lucia the Pitons are a UNESCO World Heritage Site and a spectacular landmark. Gros Piton is 2,619 feet high (798 meters) and Petit Piton is 2,438 feet high (743 meters). Gros Piton is home to at least 148 plant species and 27 bird species (5 of them endemic) and Petit Piton has 97 plant species with 8 rare tree species.

Day 4

Scarborough, Tobago

Scarborough, Tobago

Day 5

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.

Day 6

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.

Day 7

Day 8

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

Day 9

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.

Dates and Prices

(per person*)

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* Per double occupancy. Some pricing may reflect single traveler rate.

Ship

Your cruise ship

Two elegant ships, Star Legend and another, sail through calm blue waters under a partly cloudy sky.
Windstar Cruises logo
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.

Deckplans

Star Legend ship deck plan

consultation

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