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Jewels of the Windward Islands

Jewels of the Windward Islands

At a glance

Duration: 8 Days, 7 Nights

Coverage: Roundtrip Bridgetown

From: $1,799

Season: January - March, November - December

Activities: Adventure, Culture, History, Wildlife

Book this Trip › or call us toll-free 1-888-815-5428

Wind Star Cruises

Experience the Caribbean’s private yachting scene during this voyage.

This is the Caribbean of days gone by – deep blue waters, quiet coves, and tropical islands dotted with powdery beaches and lush green hillsides.

Popular highlights:

  • Sail, swim and kayak off the Watersports Platform
  • St. Lucia’s beachside resorts and national park
  • Scenic cruising past the UNESCO World Heritage Site Pitons (volcanic spires on St. Lucia)
  • Beaches, sun, fun, and barbecue on your Island Experience on Mayreau*
  • Mount Pleasant and Fort Hamilton on Bequia
  • Grand Etang National Park on Grenada
  • Scenic cruising around St. Vincent & the Grenadines

*Weather dependant

On this Caribbean cruise you will 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.

Day-to-Day Itinerary

Day 1 - Bridgetown, Barbados

This infectiously happy island offers beautiful beaches, balmy weather, and a delightful British flair. Former sugar plantations furnished with Barbados mahogany and antiques vie for your attention with brightly painted wooden houses. The island’s centuries-old rum industry has divided the Bajan landscape into a pretty patchwork of fields dotted with coconut and royal palms, oleander, and aromatic citrus trees.

Day 2 - Pigeon Island, St. Lucia

With sunken ships surrounded by black coral trees, purple vase sponges, and a myriad of neon-hued fish, St. Lucia is a diver’s paradise. When you’re finished playing in the water, the mountainous rainforests of the interior await. Nature trails of every level lead you to the astonishing chatter and spectacular colors of 30 species of native birds — including the rare and beautiful Jacquot parrot.

Day 3 - At Sea

Day 4 - St. George's, Grenada

A lively blend of French and English cultures, St. George’s has steep hills to climb, spectacular views to drink in, and a fascinating rum distillery to tour. Shop for nutmeg, cinnamon, and other “Spice Island” specialties in one of the town’s bustling local markets. Or, as an option, you can hike past the postcard-perfect waterfalls and natural springs surrounding Grand Etang Lake on the island’s mountainous interior.

Day 5 - Tobago Cays, St. Vincent and the Grenadines

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 6 - Mayreau, St. Vincent and the Grenadines

Get away from it all on the idyllic island of 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. Crescent-shaped Salt Whistle 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 - Bequia, St. Vincent and the Grenadines

Once an active whaling station, Bequia today is a favorite among insiders for its unspoiled beauty and easy pace. Fishing nets dry in the sun in the pretty town of Port Elizabeth, situated on one of the loveliest harbors in the Caribbean. Pick a spot beneath a palm tree on the nearby beach and watch a schooner being hand built for a fortunate yacht owner. Or take home a perfectly detailed miniature version of your own.

Day 8 - Bridgetown

Disembark in Bridgetown for your travels home.

Dates & Rates

Dates Ships B BX A AX Owner's Suite
Nov 10, 2017 Wind Star $1,599 $1,799 $1,899 $1,999 $3,099
Nov 18, 2017 Wind Star $1,499 $1,599 $1,699 $1,899 $2,799


Yachtsman’s Caribbean


Wind Surf

Wind Surf Hosting only 310 privileged guests, the gleaming decks and sparkling sails of the Wind Surf invite you to discover a world of gracious indulgence. From sumptuous staterooms and suites to the cozy sophistication of the Yacht Club living room and library, every detail is designed for contemporary luxury. Treat your palate to the nouveau French cuisine of Stella Bistro. Work out in the state-of-the-art top deck Fitness Room with a sweeping sea view. Relax in the whirlpools or swimming pool. Or bask like royalty in the beautiful WindSpa. With an international crew of 191, your wish is our command. View ship details...