Lush & Lovely Islands of the Lesser Antilles

From $2,599 per person

7 days

Ship: Wind Surf

Lush & Lovely Islands of the Lesser Antilles
Windstar Cruises

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.

Journey Summary

  • Day 1 - Jan. 11, 2026, Sun. - Philipsburg, St. Maarten
  • Day 2 - Jan. 12, 2026, Mon. - Basseterre
  • Day 3 - Jan. 13, 2026, Tue. - Gustavia
  • Day 4 - Jan. 14, 2026, Wed. - St. John's
  • Day 5 - Jan. 15, 2026, Thu. - Les Saintes
  • Day 6 - Jan. 16, 2026, Fri. - Mayreau
  • Day 7 - Jan. 17, 2026, Sat. - Kingstown
  • Day 8 - Jan. 18, 2026, Sun. - Bridgetown

Itinerary Highlights

Grab your walking shoes and your credit card for the short walk from the Philipsburg pier to over 500 duty-free shops or find a cozy spot at one of the beachfront bars along the boardwalk, relax and take in some people watching.

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Detailed Itinerary

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

Day 1 - January 11, 2026

Philipsburg, St. Maarten

Welcome to the lively hub of Philipsburg, where the charm of pastel-colored buildings meets the irresistible allure of boutique stores packed with souvenirs. Nestled near the harbor on the Dutch side of St. Maarten, this destination bursts with character and history dating back to its discovery by Christopher Columbus in 1493. Today, Philipsburg offers an energizing mix of experiences, from savoring Creole dishes at local restaurants to exploring stylish shops, sparkling jewelry stores, and vibrant casinos along its famed Front Street. It's the perfect stop for a spirited island adventure.

Day 2 - January 12, 2026

Basseterre

Nestled between rolling green hills and the sparkling sea, Basseterre stands as one of the Caribbean's most picturesque capitals. The town's stunning Georgian architecture adds a touch of old-world charm to its vibrant character. Just beyond the city’s heart, the Brimstone Hill Fortress awaits. This UNESCO World Heritage Site, perched high with sweeping island views, offers both history and beauty to uncover. Lose yourself in its timeless appeal, where nature and heritage seamlessly come together.

Day 3 - January 13, 2026

Gustavia

St. Barts, the Caribbean's most sophisticated gem, blends French charm with tropical splendor. Stroll among quaint gingerbread cottages where you might spot a celebrity or two. From high-end shopping to vibrant seaside cafes, indulge in the island's breezy elegance. Relax on pristine beaches or enjoy the thrill of kite surfers gliding across the turquoise waters, all paired with the refreshing taste of the island's signature ti punch.

Day 4 - January 14, 2026

St. John's

St. John's is a charming city filled with both history and character. Its unique blend of Georgian, Victorian, and other traditional styles gives it an undeniable Old World elegance. Picture a delightful seafront, where vibrant boats are gently docked, and cheerful wooden buildings have been lovingly restored to their original beauty. Stroll along the bustling Market Street to find fresh vegetables, fruits, and fish, or explore the duty-free treasures at Heritage Quay. For those seeking landmarks, don't miss the striking white towers of St. John's Cathedral, the serene Botanical Garden, the historic Antigua Lighthouse, or the picturesque Fort James.

Day 5 - January 15, 2026

Les Saintes

Welcome to the Caribbean, where picture-perfect harbors brim with elegant yachts, majestic volcanic peaks frame the horizon, and inviting palm-lined beaches stretch endlessly before you. Beneath these turquoise waters lies a vibrant marine world so enchanting, even underwater legend Jacques Cousteau couldn't resist its charm. Whether you're an experienced diver or just dipping your toes into snorkeling, these crystal-clear seas promise unforgettable moments of discovery and wonder.

Day 6 - January 16, 2026

Mayreau

Discover the essence of seclusion in Mayreau, an untouched gem with fewer than 300 welcoming residents. Picture yourself on pristine beaches, where it feels like your very own private retreat. Saline Bay, a serene harbor nestled between the Caribbean and the Atlantic, invites you to relax, unwind, and dive into adventure. Make the most of your visit by enjoying the water sports available right off the ship. This is where tranquility meets a touch of indulgence.

Day 7 - January 17, 2026

Kingstown

Kingstown welcomes you with its timeless charm as the heart of St. Vincent & the Grenadines. Known for its cobblestone streets, beautiful colonial buildings, and historical landmarks, this bustling town offers something for every traveler. Wander through the 18th-century St. Vincent Botanical Gardens, one of the oldest in the Western Hemisphere, and enjoy the serenity of its vibrant plant life. For breathtaking views, venture up to Fort Charlotte, where you can soak in panoramic vistas of the town and nearby islands. Don’t miss St. George’s Anglican Cathedral, an architectural gem with spectacular stained glass windows, or St. Mary’s Catholic Cathedral, a lovely work of Gothic and Romanesque design.

Day 8 - January 18, 2026

Bridgetown

Dive into the rich charm of old England as you explore the city and its historic garrison, both remarkable UNESCO World Heritage Sites. Beyond the bustling streets, discover the fascinating tales of ancient sugar plantations and the enchanting beauty of Harrison’s Cave, a true natural wonder.

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Jan 11, 2026

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