Star Collector: Hidden Gems of the Caribbean

From $8,294 per person

18 days

Ship: Wind Spirit

Star Collector: Hidden Gems of the Caribbean
Windstar Cruises logo

Journey Summary

  • Day 1 - Jan. 14, 2026, Wed. - Philipsburg, St. Maarten
  • Day 2 - Jan. 15, 2026, Thu. - Basseterre
  • Day 3 - Jan. 16, 2026, Fri. - Roseau
  • Day 4 - Jan. 17, 2026, Sat. - Castries
  • Day 5 - Jan. 18, 2026, Sun. - Anse Mitan
  • Day 6 - Jan. 19, 2026, Mon. - Les Saintes
  • Day 7 - Jan. 20, 2026, Tue. - Charlestown
  • Day 8 - Jan. 21, 2026, Wed. - Virgin Gorda / Prickly Pear, British Virgin Islands
  • Day 9 - Jan. 22, 2026, Thu. - Jost Van Dyke, Great Harbour
  • Day 10 - Jan. 23, 2026, Fri. - Gustavia
  • Day 11 - Jan. 24, 2026, Sat. - Philipsburg, St. Maarten
  • Day 12 - Jan. 25, 2026, Sun. - St. John's
  • Day 13 - Jan. 26, 2026, Mon. - Road Bay
  • Day 14 - Jan. 27, 2026, Tue. - Virgin Gorda / Prickly Pear, British Virgin Islands
  • Day 15 - Jan. 28, 2026, Wed. - Soper's Hole
  • Day 16 - Jan. 29, 2026, Thu. - Soper's Hole
  • Day 17 - Jan. 30, 2026, Fri. - Jost Van Dyke, Great Harbour
  • Day 18 - Jan. 31, 2026, Sat. - Gustavia

Detailed Itinerary

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

Day 1 - January 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 2 - January 15, 2026

Basseterre

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean’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 3 - January 16, 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’re up for an optional hike, don’t miss Boiling Lake and the Valley of Desolation at Dominica’s Morne Trois Pitons National Park, a UNESCO World Heritage Site.

Day 4 - January 17, 2026

Castries

The capital and largest city of St. Lucia is a bustling port where shoppers flock.  Most of the city’s historic buildings were destroyed in major fires between 1785 and 1948 but you’ll see the beautiful, scenic backdrop of Morne Fortune (elev. 2,795 ft.) and the bustling harbor.  Visit the Castries Market for handicrafts, fruits and vegetables, see the murals painted by a local artist and housed in the Cathedral of the Immaculate Conception, and check out one of the many restaurants or Derek Walcott Square.

Day 5 - January 18, 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 - January 19, 2026

Les Saintes

This is the Caribbean as you’ve always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.

Day 7 - January 20, 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’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 8 - January 21, 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 9 - January 22, 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 10 - January 23, 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 11 - January 24, 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 12 - January 25, 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 13 - January 26, 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 14 - January 27, 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 15 - January 28, 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 16 - January 29, 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 17 - January 30, 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 18 - January 31, 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.

Dates and Prices

Select year & month:

Unavailable dates are greyed out

JanFebMarAprMayJunJulAugSepOctNovDec

Available dates:

Jan 14, 2026

Ship

Your cruise ship

The Wind Spirit sails through tranquil waters, flanked by lush green mountains under a clear sky.
Windstar Cruises logo

consultation

Need information to make a decision?

Reach out to our travel concierges today to create your perfect journey.