Windstar Cruises

LUSH & LOVELY ISLANDS OF THE LESSER ANTILLES

Enjoy the perfect mix of must-see Caribbean towns and harbors off the beaten path as you cruise and sail the royal beauties of the Lesser Antilles islands. Explore colonial history in pastel waterfronts, weathered forts and former sugar plantations. See the Caribbean at its most wild and beautiful on Dominica, St. Lucia and St. Kitts. Join the jetsetters on St. Barts, and everywhere you go, find delicious white beaches that turn rose and orange under Caribbean sunsets.

05/16/2025 through 02/22/2026
05/16/2025 through 03/07/2026

Day 1 The capital of Saint Maarten, the Dutch side of this two nation island, Philipsburg is located on the isthmus between Groot Baai (Great Bay) and the Salt Pond. Founded in 1733 as a free port, the city is now the home to outstanding shopping, casinos, and a variety of hotels and resorts, including nearby Mullet Bay Resort and Golf Club.
Day 2

Nestled under the imposing view of volcanic Mount Liamuiga, charming Basseterre is the best place to begin your next Caribbean adventure to St. Kitts. From the island’s untouched natural beauty, best seen by boarding the famous St. Kitts Scenic Railway, to the glittering beaches of Frigate Bay, perfect for snorkeling and jet skiing, there are plenty of excursions guaranteed to thrill you in Basseterre. Be sure to stop by the city center to visit Independence Square or venture thirty minutes outside of Basseterre to scenic Brimstone Hill Fortress; both sites will give you a glimpse into the area’s French colonial past. Set sail for this Caribbean capital and soak up the tropical sun!



Arrive Time: 8:00 AM – Depart Time: 9:00 PM
Day 3

The capital of picturesque St. Barthélemy, Gustavia is a veritable island paradise in the Caribbean. A former French colony, this small city on St. Barths’s west coast offers a variety of fine dining, designer shopping, and spectacular beachside activities to ensure a relaxing tropical getaway. Be sure to visit the historic site of Fort Karl for a panoramic view of Gustavia’s glittering harbor, then walk to Shell Beach to take a dip in warm, turquoise waters.



Arrive Time: 8:00 AM – Depart Time: 10:00 PM
Day 4

Saint John's, the vibrant capital of Antigua and Barbuda, is a captivating destination known for its colorful colonial architecture. The city offers visitors a charming mix of history, culture, and natural beauty. A must-see landmark is the stunning St. John's Cathedral, an iconic structure built in the 19th century, which offers visitors a glimpse into the island’s religious heritage. The city is also home to the bustling Heritage Quay, a popular shopping district where tourists can find everything from luxury items to local handicrafts. There visitors can bask in the lively atmosphere, peruse local markets offering fresh produce and seafood, and enjoy waterfront dining with views of the harbor.

One of the most enticing aspects of Saint John is its proximity to some of the island’s most stunning beaches. With 365 beaches to choose from, there’s a perfect spot for every type of beachgoer. Dickenson Bay, known for its white sandy shores and crystal-clear waters, is a favorite among visitors. The city’s vibrant atmosphere, combined with its natural beauty and historical charm, makes it a must-visit destination in the Caribbean.



Arrive Time: 8:00 AM – Depart Time: 9:00 PM
Day 5 Les Saintes (also known as Iles des Saintes) are perfect for the kind of traveler who relishes unspoiled tropical beauty and the serenity that comes from doing next to nothing on a vacation, but doing it à la française. While Guadeloupe's bustling epicenter, Pointe-à-Pitre, is just a l5-minute plane hop away, it seems continents apart from the eight pristine volcanic dots that comprise Les Saintes. There are about 3,000 inhabitants in the islands. About half of them live on Terre-de-Haut where only a few dozen four-wheeled vehicles travel its roads. There is just one doctor, and his home, designed to resemble a ship's bow, is something of a local landmark.

Arrive Time: 8:00 AM – Depart Time: 5:00 PM
Day 6 Roseau is the capital and largest city on Dominica, a small Caribbean island off the coast of Venezuela. This island getaway is renowned for its verdant rainforest landscape and natural wonders, including gorges, waterfalls, and geysers.

Arrive Time: 8:00 AM – Depart Time: 1:00 PM
Day 7 No airport, a single unnamed village, clear waters and white-sand beaches make Mayreau a quiet, rustic getaway. About 200 people live on this 1.5 mile (2.5km) long island just west of the Tobago Cays. Most visitors arrive via small cruise ships that dock at Saline Bay on the southwestern shore - making the island's other beaches best for seclusion. Salt Whistle Bay, at the northern end of the island, is protected from rough Atlantic breakers by a long narrow arm. This gorgeous bay has clear waters, beautiful white sands, calm swimming conditions and a protected anchorage for visiting yachts. The 20 minute walk from the village (near the middle of the western coast) to Salt Whistle Bay follows a path lined by cacti and scored by birdsong. There's a good view from the hilltop stone church at the northern side of the village.

Take a time machine to another century. One road, one pick up truck and more farm animals than citizens. Hunt for sea shells, sunbathe and surrender to the peace and quiet that make this a most serene island.

Arrive Time: 8:00 AM – Depart Time: 4:00 PM
Day 8

A former English colonial stronghold, Bridgetown, the capital of Barbados, will entice you with its unique Bajan flair and centuries-old English style architecture. This Caribbean haven, a favorite for Caribbean cruise-goers, offers plenty of adventurous and tropical excursions that will surely entertain you! Beachside attractions are a must – hop on a catamaran to go snorkeling offshore, plunge the ocean depths in a local submarine, or unwind on the sands of Carlisle Bay. Explore the historical remnants of Bridgetown’s English occupation, including St. Michael’s Cathedral, the Morgan Lewis Sugar Mill, Arlington House Museum, and Chamberlain Bridge. Better yet, sample the island’s best rums made from local sugarcane at St. Nicholas Abbey or Mount Gay Rum. Delight in Barbados’s natural wonders at Harrison’s Cave, the cavernous limestone grotto concealing striking calcite deposits and warm waters. Stroll the verdant walkways replete with hundreds of blooming flowers at Hunte’s Gardens or the Andromeda Botanic Gardens.

Travel to Bridgetown and immerse yourself in this Bajan paradise!


02/28/26 - 03/07/26

Starting At $2,499

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