Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean

From $4,002 per person

13 days

Ship: Wind Surf

Scenic view of a Caribbean coastline with vibrant blue waters, lush mountains, and a charming town.
Windstar Cruises logo

Escape on an extraordinary tropical vacation on this twelve-day cruise to hidden harbors and secluded beaches throughout the Lesser Antilles in the Caribbean. Board a catamaran bound for Norman Island off Tortola and listen to pirate legends and treasure tales prior to your secluded snorkeling excursion among pristine reefs and tropical fish. Set a course in your own rigid inflatable boat (RIB) across bays and inlets near Jost Van Dyke before hopping off for swimming and snorkeling near Great Harbour's scenic coastline. Cast deep lines for tuna, mahi-mahi, barracudas, and other delicious blue-water trophies off Nevis. Sample the sweetest of amber island ingredients in the thoughtful company of eco-minded beekeepers on St. Lucia. Admire sweeping harbor views as you sip local island rum with sweet cakes on a tasting tour of Fort Napoleon above Les Saintes. Sip Dominica’s Sea Moss non-alcoholic seaweed drink. Indulge your senses in classic Cuban cigars paired with spirits, wines, and cocktails at Basseterre, on St. Kitts.

Journey Summary

  • Day 1 - Dec. 2, 2025, Tue. - Philipsburg, St. Maarten
  • Day 2 - Dec. 3, 2025, Wed. - Soper's Hole
  • Day 3 - Dec. 4, 2025, Thu. - Jost Van Dyke, Great Harbour
  • Day 4 - Dec. 5, 2025, Fri. - Jost Van Dyke, Great Harbour
  • Day 5 - Dec. 6, 2025, Sat. - Virgin Gorda / Prickly Pear, British Virgin Islands
  • Day 6 - Dec. 7, 2025, Sun. - Gustavia
  • Day 7 - Dec. 8, 2025, Mon. - Philipsburg, St. Maarten
  • Day 8 - Dec. 9, 2025, Tue. - Charlestown
  • Day 9 - Dec. 10, 2025, Wed. - Roseau
  • Day 10 - Dec. 11, 2025, Thu. - Mayreau
  • Day 11 - Dec. 12, 2025, Fri. - Les Saintes
  • Day 12 - Dec. 13, 2025, Sat. - Basseterre
  • Day 13 - Dec. 14, 2025, Sun. - Gustavia

Detailed Itinerary

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

Day 1 - December 02, 2025

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 - December 03, 2025

Soper's Hole

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

Day 3 - December 04, 2025

Jost Van Dyke, Great Harbour

For an island comprised of a mere eight square miles, it’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  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.

Day 4 - December 05, 2025

Jost Van Dyke, Great Harbour

For an island comprised of a mere eight square miles, it’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  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.

Day 5 - December 06, 2025

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 6 - December 07, 2025

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 7 - December 08, 2025

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 8 - December 09, 2025

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 9 - December 10, 2025

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 10 - December 11, 2025

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 11 - December 12, 2025

Les Saintes

This is the Caribbean as you&rsquo;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 12 - December 13, 2025

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 13 - December 14, 2025

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:

Dec 02, 2025

Ship

Your cruise ship

The Wind Surf sailing through clear blue waters, showcasing its iconic tall sails against a bright sky.
Windstar Cruises logo

consultation

Need information to make a decision?

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