Star Collector: Caribbean Explorations

From $4,499 per person

15 days

Ship: Wind Spirit

Star Collector: Caribbean Explorations
Windstar Cruises

Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.

Journey Summary

  • Day 1 - Feb. 7, 2026, Sat. - Philipsburg, St. Maarten
  • Day 2 - Feb. 8, 2026, Sun. - Charlestown
  • Day 3 - Feb. 9, 2026, Mon. - Roseau
  • Day 4 - Feb. 10, 2026, Tue. - Mayreau
  • Day 5 - Feb. 11, 2026, Wed. - Anse Mitan
  • Day 6 - Feb. 12, 2026, Thu. - Basseterre
  • Day 7 - Feb. 13, 2026, Fri. - Gustavia
  • Day 8 - Feb. 14, 2026, Sat. - Philipsburg, St. Maarten
  • Day 9 - Feb. 15, 2026, Sun. - St. John's
  • Day 10 - Feb. 16, 2026, Mon. - Road Bay
  • Day 11 - Feb. 17, 2026, Tue. - Soper's Hole
  • Day 12 - Feb. 18, 2026, Wed. - Jost Van Dyke, Great Harbour
  • Day 13 - Feb. 19, 2026, Thu. - Virgin Gorda / Prickly Pear, British Virgin Islands
  • Day 14 - Feb. 20, 2026, Fri. - Gustavia
  • Day 15 - Feb. 21, 2026, Sat. - Philipsburg, St. Maarten

Itinerary Highlights

Enjoy Windstar&rsquo;s exclusive Signature Beach Party at Prickly Pear Beach<br />
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Detailed Itinerary

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

Day 1 - February 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.

Day 2 - February 08, 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 - February 09, 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 - February 10, 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 - February 11, 2026

Anse Mitan

Martinique offers a delightful and distinctive blend of French and Caribbean influences, with a bounty of historical sites, museums and a wide array of excellent shopping. Be sure to take a tour of the beautiful Jardin de Balata Botanical Gardens with exotic plants from around the world and a treetop walkway affording mountain views.

Day 6 - February 12, 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 - February 13, 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 - February 14, 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 9 - February 15, 2026

St. John's

St. John&rsquo;s is a city of Old World charm and elegance which lingers in the varied architecture of Georgian, Victorian, Vernacular, Romantic and International flavors.&nbsp; The picturesque seafront where tiny, colorful boats are moored, the cheerful wooden buildings carefully refurbished to retain their original features, the vibrant Market Street offering vegetables, fruit and fish and the duty-free Heritage Quay shopping area provide a delightful atmosphere to captivate you.&nbsp; Sites to see include St. John&rsquo;s Cathedral with its white Baroque towers, the Botanical Garden, St. John&rsquo;s Antigua Lighthouse, and Fort James.

Day 10 - February 16, 2026

Road Bay

With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean.&nbsp; It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats.&nbsp; Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.

Day 11 - February 17, 2026

Soper's Hole

Arrive at the boardwalk of Pusser&rsquo;s Landing and mingle with other yachtsmen in the utterly charming marina at Soper&rsquo;s Hole. Find a deserted stretch of beach to kick back and ponder this tiny port&rsquo;s rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime romantic sunset Sail Away.&nbsp;

Day 12 - February 18, 2026

Jost Van Dyke, Great Harbour

For an island comprised of a mere eight square miles, it&rsquo;s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis &nbsp;Drake Waterway. After all that, you&rsquo;ll be ready for an evening drink on the beach &mdash; where you can admire your Windstar ship aglow in the harbor.

Day 13 - February 19, 2026

Virgin Gorda / Prickly Pear, British Virgin Islands

<ul>
<li><strong>The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Although uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called &ldquo;The Baths,&rdquo; which form huge underground pools and caverns.</strong></li>
</ul>
&nbsp;<br />
<strong>Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.</strong>

Day 14 - February 20, 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 15 - February 21, 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 07, 2026

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