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Jewels of the Windward Islands
Nov 27, 2026 — Dec 4, 2026
Starting from
Beyond Inclusive Package
BRIDGETOWN, BARBADOS → BRIDGETOWN, BARBADOS
7 Nights on Star Legend
This is the Caribbean of days gone by — deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with paradise.





Popular Highlights
Enjoy St. Lucia's beachside resorts and national park.
Walk up Mount Pleasant and see the amazing view from Fort Hamilton on Bequia.
Make time for a visit to Grand Etang National Park on Grenada.
Savor the beauty of scenic sailing around St. Vincent & the Grenadines.
Indulge yourself at Windstar's Signature Beach Party with plenty of Caribbean flavors and spirit to savor and share.
Stand on deck for scenic sailing past the UNESCO World Heritage Site Pitons on St. Lucia.

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.
Bridgetown: Barbados Island Tour with Airport Transfer

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.
Anse Mitan, Snorkel Adventure Long
Anse Mitan, Martinique Heritage
Anse Mitan, Creole Village
Anse Mitan, Kayaking Mangrove Discovery
Anse Mitan, VIP Experience at La Mauny Plantation and Rum Tasting
Anse Mitan, Southern Panoramic Martinique

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.
Pigeon Island, Concierge Collection: Half Day Private Van & Guide
Pigeon Island, Aerial Tram Park
Pigeon Island, Panoramic St. Lucia
Pigeon Island, Rainforest Canopy Zip Line Adventure
Pigeon Island, Concierge Collection: Full Day Private Car & Guide
Pigeon Island, Catamaran Cruise to the Pitons
Pigeon Island, St. Lucian Walking Food Tour
Pigeon Island, Concierge Collection: Full Day Private Van & Guide
Pigeon Island, Concierge Collection: Half Day Private Car & Guide
Pigeon Island, Discover Sailing

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.

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.
Castries, Panoramic St. Lucia
Castries, Catamaran Cruise to the Pitons
Castries, Rainforest Canopy Zip Line Adventure
Castries, Concierge Collection: Lets Make Chocolate
Castries, Concierge Collection: Half Day Private Van with Guide
Castries, St. Lucian Walking Food Tour
Castries, Bamboo River Rafting & Rum (Easy-Moderate)
Castries, Heritage Highlights
Castries, Concierge Collection: Half Day Private Sedan with Guide

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.

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.
Mayreau, Grenadines Island Escape

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.
St. Georges, The Best of Grenada
St. Georges, Clear Bottom Kayaking
St Georges, Spice of Our Lives
St. Georges, Powerboat & Snorkeling at the Statues Park *

St. Georges, Certified One-Tank Dive
St. Georges, Discover Scuba
St. Georges, Certified Two-Tank Dive
St. Georges, Fort Frederick Rainforest & Waterfall
St. Georges, Izzie's Great House Discovery
St. Georges, Sailing Cruise to the Statue Park

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.
Bequia Snorkel Adventure
Bequia, Taste of Bequia
Bequia Highlights
Bequia, Bequia Fort & Lower Beach Getaway *
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Bequia, Concierge Collection: Rum Tasting at Firefly Plantation
Bequia, Mustique Magic with Lunch
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