Classic Caribbean

From $2,599 per person

8 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 - Feb. 28, 2026, Sat. - Philipsburg, St. Maarten
  • Day 2 - Mar. 1, 2026, Sun. - Charlestown
  • Day 3 - Mar. 2, 2026, Mon. - Roseau
  • Day 4 - Mar. 3, 2026, Tue. - Mayreau
  • Day 5 - Mar. 4, 2026, Wed. - Deshaies
  • Day 6 - Mar. 5, 2026, Thu. - Basseterre
  • Day 7 - Mar. 6, 2026, Fri. - Gustavia
  • Day 8 - Mar. 7, 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 - February 28, 2026

Philipsburg, St. Maarten

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

Day 2 - March 01, 2026

Charlestown

This capital of Nevis with its narrow streets and brightly painted Victorian and Georgian stone buildings is full of colonial history. Alexander Hamilton lived here as a child and you can see the ruins of the Hamilton Estate. Lovely Pinney&rsquo;s Beach is nearby and a group of volunteers work at night tagging sea turtles here and on the other beautiful beaches. Walk the main street and check out the Museum of Nevis History, St. Thomas Lowland Church and the Nevisian Heritage Village to name a few of the historic sites here.

Day 3 - March 02, 2026

Roseau

Get ready for a full day with plenty to do. Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break to enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. If you&rsquo;re up for an optional hike, don&rsquo;t miss Boiling Lake and the Valley of Desolation at Dominica&rsquo;s Morne Trois Pitons National Park, a UNESCO World Heritage Site.

Day 4 - March 03, 2026

Mayreau

With fewer than 300 inhabitants and miles of secluded beaches, it&#39;s easy to feel as if you&#39;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 5 - March 04, 2026

Deshaies

Situated near the Grand Anse beach, Deshaies has the deepest bay of all the Caribbean coasts with the best natural protection which made it a shelter for pirates of days gone by and is said to still be housing treasures on the Island. Grand Anse beach is one of the most beautiful of the islands with its over half a mile of fine golden sand and coconut palms.

Day 6 - March 05, 2026

Basseterre

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean&rsquo;s small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.

Day 7 - March 06, 2026

Gustavia

Affectionately known as St. Barts, the Caribbean&rsquo;s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island&rsquo;s signature ti punch as kite surfers fly by.

Day 8 - March 07, 2026

Philipsburg, St. Maarten

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

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Feb 28, 2026

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