Jewels of the Windward Islands

From $2,516 per person

7 days

Ship: Wind Spirit

Jewels of the Windward Islands
Windstar Cruises

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.

Journey Summary

  • Day 1 - Bridgetown
  • Day 2 - Tobago Cays
  • Day 3 - Pigeon Island
  • Day 4 - Pigeon Island
  • Day 5 - Castries
  • Day 6 - The Pitons
  • Day 7 - Mayreau

Detailed Itinerary

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

Day 1 - March 15, 2026

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 - March 16, 2026

Tobago Cays

Sail, snorkel, or beachcomb in complete seclusion in this unspoiled tropical paradise accessible only by boat. Quiet coves like Horseshoe Reef are home to fantastic coral reefs, while nearby Baradel offers an excellent opportunity to observe the area’s famous sea turtles. Crystalline waters and perfect weather make this an ideal spot to play in the sea

Day 3 - March 17, 2026

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 - March 18, 2026

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 - March 19, 2026

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 - March 20, 2026

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 - March 21, 2026

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.

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Jan 18, 2026

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