Classic Caribbean

From $2,299 per person

7 days

Ship: Wind Surf

Classic Caribbean
Windstar Cruises

From the stunning drama of the Pitons to the captivating charm of Les Saintes. From hidden coves and secret beaches to exotic markets and lively cafés. Discover the best of this region with one single Caribbean cruise. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and&nbsp;<em>joie de vivre</em>&nbsp;unique to the Caribbean life.

Journey Summary

  • Day 1 - Mar. 21, 2026, Sat. - Philipsburg, St. Maarten
  • Day 2 - Mar. 22, 2026, Sun. - Charlestown
  • Day 3 - Mar. 23, 2026, Mon. - Roseau
  • Day 4 - Mar. 24, 2026, Tue. - Mayreau
  • Day 5 - Mar. 25, 2026, Wed. - Les Saintes
  • Day 6 - Mar. 26, 2026, Thu. - Basseterre
  • Day 7 - Mar. 27, 2026, Fri. - Gustavia
  • Day 8 - Mar. 28, 2026, Sat. - Philipsburg, St. Maarten

Itinerary Highlights

Let yourself go &ndash; at Windstar&rsquo;s Signature Beach Party, where the Caribbean spirit is in full swing.

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Detailed Itinerary

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

Day 1 - March 21, 2026

Philipsburg, St. Maarten

Nestled along the harbor, Philipsburg greets visitors with an inviting charm. Its streets are lined with pastel-colored buildings, home to an array of shops offering local treasures and island keepsakes. Once discovered by Christopher Columbus in 1493, this bustling port on the Dutch side of St. Maarten now thrives as a vibrant destination. Stroll along celebrated Front Street, where casual Creole eateries mingle with chic boutiques, glittering jewelry stores, and lively casinos, creating an energetic yet relaxed atmosphere unique to this Caribbean gem.

Day 2 - March 22, 2026

Charlestown

Step into Charlestown, the charming capital of Nevis, where history and culture are alive in every corner. Stroll its narrow streets, lined with bright Georgian and Victorian stone buildings that carry tales of the past. Did you know Alexander Hamilton spent his childhood here? You can visit the ruins of the Hamilton Estate and imagine life in those times. Explore Main Street to uncover treasures like the Museum of Nevis History and the fascinating St. Thomas Lowland Church. Feeling adventurous? Stop by Nevisian Heritage Village to travel back in time to the island's colonial days. For a touch of nature, head to serene Pinney’s Beach, where you might even witness volunteers tagging sea turtles under the moonlight. Charlestown seamlessly blends historic charm with natural beauty, offering a delightful escape for curious souls.

Day 3 - March 23, 2026

Roseau

Prepare yourself for a day of exciting discovery! Dive into the crystal-clear waters of Champagne Beach, where vibrant parrotfish and bubbling springs create an underwater paradise. At the botanical gardens, wander through lush landscapes and marvel at over 150 plant species, along with the striking red-necked Jaco parrots. Feeling adventurous? Embark on an optional hike to the dramatic Boiling Lake and the otherworldly Valley of Desolation, nestled in the heart of the UNESCO-listed Morne Trois Pitons National Park.

Day 4 - March 24, 2026

Mayreau

Welcome to the charming Mayreau, an untouched paradise with fewer than 300 friendly locals. Stretch out on miles of tranquil beaches that feel like your own secluded getaway. Saline Bay, nestled elegantly between the Caribbean and the Atlantic, offers pristine waters ideal for splashing, relaxing, or enjoying the water toys. This slice of heaven invites exploration, serenity, and unforgettable moments.

Day 5 - March 25, 2026

Les Saintes

Picture a tropical paradise straight out of your dreams—sparkling harbors filled with elegant yachts, framed by lush volcanic peaks and serene, golden beaches lined with swaying palms. These breathtaking waters, once explored by underwater legend Jacques Cousteau, are a welcoming playground for all explorers. Even first-time snorkelers can marvel at the vibrant marine life in these crystal-clear blues.

Day 6 - March 26, 2026

Basseterre

Discover the charm of Basseterre with its enchanting Georgian architecture nestled against lush, green hills. This captivating Caribbean capital offers both beauty and history. Venture beyond the town to explore Brimstone Hill Fortress National Park, an iconic UNESCO World Heritage Site. Over a quarter of St. Kitts is proudly preserved here, making it a must-see destination for both nature lovers and history enthusiasts.

Day 7 - March 27, 2026

Gustavia

Known for its effortless elegance, St. Barts is a Caribbean gem that marries stunning beaches with a chic French Riviera vibe. Stroll through charming streets lined with gingerbread-style cottages, explore designer boutiques, or relax with the island's signature ti punch while watching colorful kite surfers dance across the waves. This exclusive destination beautifully blends relaxation and sophistication.

Day 8 - March 28, 2026

Philipsburg, St. Maarten

Set against a vibrant backdrop of sunlit pastel facades, Philipsburg welcomes you with its charming streets brimming with inviting shops and local treasures. Nestled on the Dutch side of St. Maarten, this captivating harbor town has attracted explorers since Christopher Columbus first arrived in 1493. Discover Front Street, the beating heart of the town, where quaint Creole eateries mingle with elegant jewelry stores and chic boutiques. For those seeking a lively scene, the buzzing casinos are sure to entertain. Whether you're exploring its cultural charm or indulging in its spirited nightlife, Philipsburg delights every visitor.

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Mar 21, 2026

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