Jewels of the Windward Islands

Jewels of the Windward Islands

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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 colourful 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.

Trip Name
Jewels of the Windward Islands
Vessel Type: 4-masted sailing yacht Length: 360 feet (110 meters) at waterline; 440 feet (134 meters) including bowsprit Passenger Capacity: 148 Built: 1987 Wind Spirit is a sleek, 4-masted sailing yacht accommodating 148 guests. With four decks and a gross tonnage of 5,736, Wind Spirit feels like your own private yacht. Wind Spirit features wide open, teak decks—quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda. All staterooms have ocean views, queen beds, and flat-screen TV with DVD player. The Owner’s Suite includes a sitting area. Wind Spirit offers two primary dining venues. Amphora restaurant offers gourmet, course-by-course cuisine in the evenings and Veranda restaurant offers casual buffet and full-service dining for breakfast and lunch. All dining is open seating. And, for dining under the stars, make a reservation for Candles which features steaks and skewers. Wind Spirit amenities include: World Spa by Windstar, Watersports Platform, Lounge, Library, Pool, and Hot Tub.


Day 1 - Day 1 - Bridgetown, Barbados
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 - Day 2 and 3 - Pigeon Island, St Lucia
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 3 - Day 3 - Castries and The Pitons St Lucia
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. 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 - Day 4 - Kingstown
Charming Kingstown, the capital and main commercial center of St. Vincent & the Grenadines is known for its churches, cobblestone streets, colonial buildings and the St. Vincent Botanical Gardens, founded in 1765.  Steep hills surround the town, with Fort Charlotte sitting high on a ridge north of the city, offering panoramic views of Kingstown and the surrounding islands.  Other sites to see include St. George’s Anglican Cathedral, an 1820s structure adorned with stained glass windows, St. Mary’s Catholic Cathedral, built in 1823, with its lovely Gothic spires and Romanesque columns and arches.
Day 5 - Day 5 - 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 6 - Day 6 - St Georges, Grenada
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.
Day 7 - Day 7 - 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 8 - Day 8 - Bridgetown, Barbados
Time to say farewell.

Trip Dates

StartEndPrice FromRoom Type


    • Enjoy the beachside resorts and national parks of Saint Lucia In Martinique visit Pagerie Habitation, where Empress Josephine lived as a child Walk up Mount Pleasant and see the amazing views from Fort Hamilton in Bequia Visit Grand Etang National Park on Grenada