Jewels of the Windward Islands

From $2,638 per person

8 days

Ships: Star Legend, Wind Surf

Jewels of the Windward Islands

Journey Summary

  • Day 1 - Bridgetown
  • Day 2 - Anse Mitan
  • Day 3 - Castries
  • Day 4 - Pigeon Island
  • Day 5 - Pigeon Island
  • Day 6 - Bequia
  • Day 7 - Mayreau
  • Day 8 - St. George's

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

Anse Mitan

Martinique offers a delightful and distinctive blend of French and Caribbean influences, with a bounty of historical sites, museums and a wide array of excellent shopping. Be sure to take a tour of the beautiful Jardin de Balata Botanical Gardens with exotic plants from around the world and a treetop walkway affording mountain views.

Day 3

Pigeon Island

The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.

Day 4

Pigeon Island

The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.

Day 5

Castries

The capital and largest city of St. Lucia is a bustling port where shoppers flock.  Most of the city’s historic buildings were destroyed in major fires between 1785 and 1948 but you’ll see the beautiful, scenic backdrop of Morne Fortune (elev. 2,795 ft.) and the bustling harbor.  Visit the Castries Market for handicrafts, fruits and vegetables, see the murals painted by a local artist and housed in the Cathedral of the Immaculate Conception, and check out one of the many restaurants or Derek Walcott Square.

Day 6

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 7

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 8

St. George's

Inhale the intoxicating aroma of the “Isle of Spice” as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.

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.
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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

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