Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean

From $3,399 per person

13 days

Ship: Wind Surf

Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean
Windstar Cruises

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. - Virgin Gorda / Prickly Pear, British Virgin Islands
  • Day 5 - Dec. 6, 2025, Sat. - Gustavia
  • Day 6 - Dec. 7, 2025, Sun. - Philipsburg, St. Maarten
  • Day 7 - Dec. 8, 2025, Mon. - Charlestown
  • Day 8 - Dec. 9, 2025, Tue. - Roseau
  • Day 9 - Dec. 10, 2025, Wed. - Mayreau
  • Day 10 - Dec. 11, 2025, Thu. - Les Saintes
  • Day 11 - Dec. 12, 2025, Fri. - Basseterre
  • Day 12 - Dec. 13, 2025, Sat. - Gustavia
  • Day 13 - Dec. 14, 2025, Sun. - Philipsburg, St. Maarten

Itinerary Highlights

Snorkel alongside brilliant parrot fish in the bubbly waters of Dominica’s Champagne Beach.

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Detailed Itinerary

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

Day 1 - December 02, 2025

Philipsburg, St. Maarten

Welcome to Phillipsburg—an island jewel that invites you with its pastel-hued buildings and warm, energetic streets. Nestled along the harbor on the Dutch side of St. Maarten, Philipsburg combines fascinating history with vibrant, contemporary charm. Walk along celebrated Front Street, where a blend of local Creole eateries, sparkling jewelry shops, and trendy boutiques await. Want a little adventure? Step into one of the lively casinos for a taste of the island's playful side. Whether you’re indulging in the culture or savoring the scenery, Philipsburg offers something truly special.

Day 2 - December 03, 2025

Soper's Hole

Step into the charm of Soper’s Hole, where the colorful boardwalk of Pusser’s Landing welcomes sailors and travelers alike. Explore the lively marina, a meeting point for yachts from around the globe, and soak in its unique blend of vibrancy and history. Tuck yourself away on a peaceful beach to relax or reflect on the area’s storied past filled with adventure and tales of pirates. As evening falls, set sail on an unforgettable journey, watching the sun dip below the horizon during a spectacular sunset departure. It’s a moment of serenity and magic you won’t forget.

Day 3 - December 04, 2025

Jost Van Dyke, Great Harbour

Imagine a serene escape to a Caribbean island just eight square miles in size, filled with adventure and charm. On Jost Van Dyke, start your journey at the national park on Diamond Cay or explore vibrant underwater scenes at Sandy Spit, where colorful angelfish dart among coral sponges. Feeling more adventurous? Glide your own boat along the picturesque Sir Francis Drake Waterway, soaking up the views. As the day winds down, let the golden hues of sunset lead you to a quiet beach, where a refreshing drink accompanies the peaceful sight of your beautifully illuminated Windstar ship resting in the harbor.

Day 4 - December 05, 2025

Virgin Gorda / Prickly Pear, British Virgin Islands

A hidden oasis of natural beauty and charm awaits as your ship sails along the tranquil waters, bringing you closer to Prickly Pear Island. This uninhabited gem, sprinkled with distinctive prickly pear cacti, is home to a beloved beach bar and a range of water activities. Keep an eye out for the breathtaking Barrier coral reef while approaching this serene bird sanctuary. Nearby, explore the fascinating geological formations of "The Baths," where massive boulders create spectacular underwater pools and caverns—a true natural wonder ready to be experienced.

Day 5 - December 06, 2025

Gustavia

Discover the allure of St. Barts, a glamorous Caribbean island where French sophistication meets sun-soaked beaches. Stroll through charming streets lined with pastel-colored cottages, and you might spot a celebrity or two. Explore exclusive boutiques showcasing designer fashion, or savor the island’s signature drink, ti punch, as you watch kite surfers dance across the waves.

Day 6 - December 07, 2025

Philipsburg, St. Maarten

Tucked along the waterfront on the Dutch side of the island, Philipsburg charms with its vibrant, pastel-colored streets and ocean breezes. This bustling Caribbean town, steeped in history since Christopher Columbus’s arrival in 1493, now offers a dynamic blend of old-world appeal and modern attractions. Stroll down lively Front Street and take your pick of chic boutiques, sparkling jewelry shops, and quaint Creole eateries filled with local flavor. Or, try your luck at one of the bustling casinos that add a lively spark to this sun-kissed getaway.

Day 7 - December 08, 2025

Charlestown

Nestled along the shores of Nevis, Charlestown is a delightful blend of vibrant history and natural beauty. Its narrow streets are dotted with charming Victorian and Georgian stone buildings, radiating an old-world charm. Once the childhood home of Alexander Hamilton, the town invites you to explore fascinating ruins at the Hamilton Estate. For those seeking a slice of paradise, nearby Pinney’s Beach offers golden sands where sea turtles are carefully tagged by dedicated volunteers beneath the moonlit sky. Wander down the main street to discover the Museum of Nevis History, the St. Thomas Lowland Church, and the Nevisian Heritage Village, each brimming with stories of the island's rich past.

Day 8 - December 09, 2025

Roseau

Discover the unparalleled beauty and adventure of Dominica with this unforgettable day. Immerse yourself in the Caribbean waters of Champagne Beach, where vibrant parrotfish swim gracefully in warm, bubbling shallows. Stroll through the lush botanical gardens, home to over 150 plant species and the striking red-necked Jaco parrots. Feeling adventurous? Choose an optional hike to witness the breathtaking Boiling Lake and Valley of Desolation, both nestled in the pristine Morne Trois Pitons National Park—recognized as a UNESCO World Heritage Site. Every moment is designed to awaken your senses and celebrate the natural wonders of this island paradise.

Day 9 - December 10, 2025

Mayreau

Mayreau boasts an air of tranquil seclusion, making it feel like your own hidden paradise. With fewer than 300 warm-hearted locals and miles of unspoiled beaches, this is where serenity thrives. Tucked away in Saline Bay, a perfect anchorage separating the gentle Caribbean from the untamed Atlantic, you’ll find the perfect spot for leisurely relaxation. Don’t miss the chance to dive into adventure, taking advantage of the yacht’s Watersports Platform for some fun in the sun.

Day 10 - December 11, 2025

Les Saintes

Dream of the Caribbean in vivid color as majestic yachts fill turquoise bays, framed by lush volcanic peaks and pristine stretches of palm-lined shores. Beneath the surface, an underwater paradise awaits—a region so enchanting it drew Jacques Cousteau himself. Even first-time snorkelers can immerse themselves in these crystal-clear waters, discovering marine wonders like nowhere else.

Day 11 - December 12, 2025

Basseterre

Nestled between lush emerald hills, Basseterre offers a picture-perfect setting with its charming Georgian architecture. This Caribbean gem boasts captivating sights, but the true treasure lies beyond its streets. Over a quarter of St. Kitts is devoted to Brimstone Hill Fortress National Park, a UNESCO World Heritage Site that invites travelers to explore history, beauty, and culture amidst awe-inspiring surroundings.

Day 12 - December 13, 2025

Gustavia

Welcome to the glamorous island of St. Barts, a Caribbean jewel blending French charm with tranquil beauty. Stroll through charming streets adorned with pastel-colored gingerbread houses. Delight in designer shopping or join the crowd watching kite surfers glide across sparkling waves. Feeling adventurous? Hunt for celebrity hangouts. Need to unwind? Savor a refreshing ti punch, the island’s signature drink, while soaking in the chic, relaxed vibe.

Day 13 - December 14, 2025

Philipsburg, St. Maarten

Immerse yourself in the charming vibe of Philipsburg, where pastel-colored buildings line the bustling streets. Nestled on the Dutch side of St. Maarten near its lively harbor, this vibrant town welcomes visitors with its unique island spirit. Front Street, the town’s heart, is a must-see and offers something for everyone. Savor the flavors of local Creole cuisine at cozy restaurants, sip on refreshing tropical drinks, or peruse boutiques brimmed with stylish finds. You’ll also find world-renowned jewelry stores and casinos that pulse with energy for those feeling lucky. Steeped in history, this enticing destination is a doorway to both traditional culture and modern indulgence.

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Dec 02, 2025

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