Star Collector: Caribbean Explorations

From $4,499 per person

15 days

Ship: Wind Surf

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 - Dec. 14, 2025, Sun. - Philipsburg, St. Maarten
  • Day 2 - Dec. 15, 2025, Mon. - Falmouth Harbour
  • Day 3 - Dec. 16, 2025, Tue. - Road Bay
  • Day 4 - Dec. 17, 2025, Wed. - Soper's Hole
  • Day 5 - Dec. 18, 2025, Thu. - Jost Van Dyke, Great Harbour
  • Day 6 - Dec. 19, 2025, Fri. - Virgin Gorda / Prickly Pear, British Virgin Islands
  • Day 7 - Dec. 20, 2025, Sat. - Gustavia
  • Day 8 - Dec. 21, 2025, Sun. - Philipsburg, St. Maarten
  • Day 9 - Dec. 22, 2025, Mon. - Charlestown
  • Day 10 - Dec. 23, 2025, Tue. - Roseau
  • Day 11 - Dec. 24, 2025, Wed. - Mayreau
  • Day 12 - Dec. 25, 2025, Thu. - Les Saintes
  • Day 13 - Dec. 26, 2025, Fri. - Basseterre
  • Day 14 - Dec. 27, 2025, Sat. - Gustavia
  • Day 15 - Dec. 28, 2025, Sun. - 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 - December 14, 2025

Philipsburg, St. Maarten

Experience the vibrant charm of Philipsburg, a gem on the Dutch side of St. Maarten. Stroll along streets lined with colorful pastel buildings, where shops brim with unique souvenirs and keepsakes. Steeped in history since Christopher Columbus first sighted the island in 1493, today this lively town welcomes visitors to famed Front Street. Here, you’ll find everything from tempting Creole cuisine at local restaurants to glimmering jewelry stores and chic boutiques. Add a touch of excitement at the casinos and feel the dynamic pulse of island life.

Day 2 - December 15, 2025

Falmouth Harbour

Antigua is celebrated for its unrivaled charm, famously boasting 365 stunning beaches – one for each day of the year. With our extended port stop, you’ll have the time to soak in not just the turquoise waters but also the vibrant culture of this tropical paradise. As the sun sets, let the magic unfold under the starlit sky and indulge your imagination. It’s a place where the scenic beauty captivates every visitor, leaving memories of a lifetime.

Day 3 - December 16, 2025

Road Bay

Road Bay invites you to discover its charm, from tranquil waters and vibrant coral reefs to its soft, sandy shores. A favorite among sailors, this gem in Anguilla offers lively restaurants, welcoming bars, and quaint shops. As the sun sets, you'll witness some of the Caribbean’s finest moments, best enjoyed with a refreshing rum punch in hand. Nature lovers can spot Cuban tree frogs, red-footed tortoises, and playful iguanas—all calling this paradise home. Don't miss Wallblake House, nearby, an enchanting glimpse into the island's past as one of its oldest buildings and a heritage treasure.

Day 4 - December 17, 2025

Soper's Hole

Stroll along the vibrant boardwalk of Pusser’s Landing, where yachts bob gently in Soper’s Hole’s picturesque marina. This charming harbor invites you to relax and soak in its colorful history of swashbuckling pirates and romantic adventures. Find a quiet beach to enjoy the peaceful surroundings, then cap your day with an unforgettable sunset as your ship sails into the evening.

Day 5 - December 18, 2025

Jost Van Dyke, Great Harbour

Jost Van Dyke may only be eight square miles, but it’s brimming with adventures. Discover the natural beauty of Diamond Cay’s national park, or dive into crystal-clear waters at Sandy Spit to snorkel alongside vibrant sea life like swaying sponges and playful angelfish. Feeling adventurous? Navigate your own small boat through Sir Francis Drake Waterway and embrace the freedom of the open sea. As evening falls, relax with a refreshing drink on the beach while the soft glow of your Windstar ship shimmers in the harbor—an endearing reminder of your unforgettable journey.

Day 6 - December 19, 2025

Virgin Gorda / Prickly Pear, British Virgin Islands

As you glide towards the serene shores of Prickly Pear Island, the breathtaking Barrier coral reef shimmers just below the surface. The island, named for its prickly pear cacti, is a tranquil haven and home to a vibrant bird sanctuary. Although uninhabited, it offers a charming beach bar and opportunities for a splash of adventure with its water sports facilities. Nearby, discover the spectacular natural wonder of The Baths—a unique maze of massive granite boulders forming secret grottos and crystal-clear pools; nature’s perfect playground.

Day 7 - December 20, 2025

Gustavia

Discover the island affectionately called St. Barts, where Caribbean charm seamlessly meets French sophistication. Relax on picturesque beaches with Riviera-style flair or explore exclusive, duty-free boutiques. Wander amid quaint, gingerbread-styled cottages, perfect for a celebrity sighting or two. Indulge in designer shopping, then unwind with the island’s signature ti punch as vibrant kite surfers dance across the waves. Every moment here is a blend of luxury and cultural charm.

Day 8 - December 21, 2025

Philipsburg, St. Maarten

Soft hues of pastel facades and charming storefronts welcome you to vibrant Philipsburg. Tucked near the harbor on the Dutch side of St. Maarten, this lively town blends a rich history with modern flair. Discovered by Christopher Columbus in 1493, today it’s a hub of activity, where celebrated Front Street offers something for everyone. Savor local Creole dishes, shop stylish boutiques or jewelry, and try your luck at lively casinos. It’s a destination that’s as colorful as its sunsets.

Day 9 - December 22, 2025

Charlestown

Step into the charm and history of Nevis, a delightful capital steeped in colonial heritage. Stroll its narrow streets lined with colorful, centuries-old Victorian and Georgian buildings. Discover the place where Alexander Hamilton spent his childhood and visit the remains of the Hamilton Estate for a glimpse of his early world. For a touch of nature, nearby Pinney’s Beach beckons with its beauty. This serene spot is also a sanctuary where dedicated volunteers gently tag sea turtles under starlit skies. Wander along the main street to explore must-see historic treasures, including the Museum of Nevis History, the timeless St. Thomas Lowland Church, and the picturesque Nevisian Heritage Village. Immerse yourself in the vibrant culture and stories that make this little island unforgettable.

Day 10 - December 23, 2025

Roseau

Prepare for a day full of discovery and excitement at Dominica. Begin your adventure by snorkeling at Champagne Beach, where the warm waters bubble around you like a natural spa. Here, colorful parrotfish dart through the crystal-clear waters, offering a vibrant underwater show. Then, explore the botanical gardens, home to more than 150 plant species and the striking red-necked Jaco parrots. If you're feeling adventurous, set out on an optional hike to see Morne Trois Pitons National Park, a UNESCO World Heritage Site. There, you'll encounter dramatic landscapes, including the famous Boiling Lake and the rugged Valley of Desolation—a terrain unlike any other.

Day 11 - December 24, 2025

Mayreau

Nestled in the Caribbean with fewer than 300 residents, Mayreau feels like a hidden paradise. Saline Bay, a serene anchorage, is where the Caribbean and Atlantic meet, offering stunning surroundings and tranquility. Guests can savor the secluded beaches or enjoy the adventure of watersports, taking full advantage of the onboard platform. It’s small-ship cruising at its finest, combining exclusivity and unspoiled natural beauty.

Day 12 - December 25, 2025

Les Saintes

Imagine yourself strolling through yacht-filled harbors, surrounded by the emerald peaks of volcanic mountains and calm, sapphire waters. Les Saintes offers a picture-perfect escape—luxurious yet unpretentious. Here, golden beaches lined with swaying palms invite you to simply relax, while beneath the waves, a vibrant underwater paradise awaits. Whether you're an experienced diver or trying snorkeling for the first time, you'll find the waters impossibly clear and teeming with colorful life. It’s a playground for both adventure-seekers and serenity lovers alike.

Day 13 - December 26, 2025

Basseterre

Nestled between lush, green hills, Basseterre is one of the Caribbean’s most remarkable capitals. Its charming Georgian architecture creates a classic ambiance, while every corner of the city seems to whisper stories of its history. Nearby, discover Brimstone Hill Fortress National Park, a UNESCO World Heritage Site. Over 25% of St. Kitts is dedicated to this stunning preserve, where cultural heritage meets natural beauty.

Day 14 - December 27, 2025

Gustavia

Known locally as St. Barts, this Caribbean jewel exudes French charm with a glamorous twist. Stroll through lively streets lined with charming gingerbread cottages, or relax on sun-soaked beaches that rival France’s Riviera. Browse designer boutiques for a spot of duty-free shopping, or kick back with a refreshing ti punch as colorful kite surfers glide across the turquoise waters. A luxurious blend of cultural flair and island-style serenity awaits.

Day 15 - December 28, 2025

Philipsburg, St. Maarten

Philipsburg welcomes you with its charming pastel-colored buildings and enticing shops brimming with souvenirs. Nestled along the harbor on the Dutch side of St. Maarten, this vibrant town carries the legacy of Christopher Columbus, who discovered it in 1493. Stroll down celebrated Front Street to discover a lively atmosphere filled with Creole restaurants, glimmering jewelry stores, stylish boutiques, and bustling casinos. Whether you’re shopping, dining, or seeking entertainment, this lively destination offers something for everyone to enjoy.

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Dec 14, 2025

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