Star Collector: Grand Caribbean Adventure
 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sun Jan 4, 2026 - Sat Feb 28, 2026,
 55 days
 on Wind Surf
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Starting from $17,899 USD
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Philipsburg, St. Maarten to Philipsburg, St. Maarten
See all the flavors of the Caribbean as you visit 28 islands and 39 ports from the lush jungles of Dominica to arid Aruba, trendy French enclaves to quiet ports known only to yachtsmen. Then go beyond, to the shores of the conquistadors in Colombia, to the Mayan legacy in Belize, and to Mexico’s golden Yucatán. On Day 36, part-way through your 55-day voyage, explore one of mankind’s greatest achievements as you make a partial transit of the Panama Canal, passing through three sets of locks and sailing into Lake Gatun before returning to the Caribbean. There’s a little bit of everything on this voyage: cultures, cuisine, beaches, nature, history, and shopping. With this epic tour of the Caribbean, you’re sure to come home with unforgettable memories, new friends, and new perspectives.
voyage map
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Day 1: 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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Day 2: Falmouth Harbour
It’s said that Antigua has 365 beaches – one for every day of the year. See how many you can discover as our stay in port stretches into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.
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Day 3: 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.  It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats.  Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.
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Day 4: 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. 
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Day 4: 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.
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Day 5: 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.
VIEW THE JOURNEY
Day 6: Virgin Gorda / Prickly Pear, British Virgin Islands
  • 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 “The Baths,” which form huge underground pools and caverns.
 
Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.
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Day 7: Gustavia
Affectionately known as St. Barts, the Caribbean’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’s signature ti punch as kite surfers fly by.
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Day 8: 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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Day 9: 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.
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Day 10: Gustavia
Affectionately known as St. Barts, the Caribbean’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’s signature ti punch as kite surfers fly by.
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Day 11: St. John's
St. John’s is a city of Old World charm and elegance which lingers in the varied architecture of Georgian, Victorian, Vernacular, Romantic and International flavors.  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.  Sites to see include St. John’s Cathedral with its white Baroque towers, the Botanical Garden, St. John’s Antigua Lighthouse, and Fort James.
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Day 12: 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.
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Day 13: Pigeon Island
The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
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Day 14: Kingstown
Charming Kingstown, the capital and main commercial center of St. Vincent & the Grenadines is known for its churches, cobblestone streets, colonial buildings and the St. Vincent Botanical Gardens, founded in 1765.  Steep hills surround the town, with Fort Charlotte sitting high on a ridge north of the city, offering panoramic views of Kingstown and the surrounding islands.  Other sites to see include St. George’s Anglican Cathedral, an 1820s structure adorned with stained glass windows, St. Mary’s Catholic Cathedral, built in 1823, with its lovely Gothic spires and Romanesque columns and arches.
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Day 15: Bridgetown
Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you’ll find historic sugar plantations and the fairyland magic of Harrison’s Cave.
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Day 16: 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.
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Day 17: 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.
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Day 17: Pigeon Island
The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
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Day 18: Pigeon Island
The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
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Day 19: Bequia
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia’s whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island’s famed model boat builders at work on their miniature masterpieces.
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Day 20: Mayreau
With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you'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.
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Day 21: St. George's
Inhale the intoxicating aroma of the “Isle of Spice” as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.
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Day 22: Bridgetown
Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you’ll find historic sugar plantations and the fairyland magic of Harrison’s Cave.
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Day 23: Man-O-War Bay
Listen for the sound of a conch announcing the return of the fishing boats. Bobbing next to us are flotillas of pelicans – hinting at the excellent snorkeling waiting for you here and in neighboring Pirate’s Bay.
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Day 24: Mayreau
With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you'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.
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Day 25: Soufriere
Nestled in the shadows of the UNESCO Pitons, Soufriere represents the heart and soul of St. Lucia. The tiny town center is full of street vendors and stores and some of the best resorts on the island can be found here. Nearby are secluded waterfalls and the waters here boast some of the best diving around. Sights to see include the Edmund Rainforest Trail, fond Doux Holiday plantation, Robot Estate and the Gros Piton Nature Trail.
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Day 27: Kralendijk
The ice cream colors of the stucco houses will draw your lens, as will the pink flamingos on the salt pans. But you’ll need a waterproof camera to complete the portrait since more than 400 fish species and 50 types of coral wait beneath the surface
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Day 28: Willemstad
Savor the pastel colors of the historic UNESCO site Old Town and the way the elaborate Dutch gables cut baroque curlicues from the sky. It’s the perfect appetizer for a day of watersports or an adventure below ground at the magical Hato Caves—filled with eerie limestone formations and ancient petroglyphs.
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Day 29: Oranjestad
Known for having some of the best beaches in the Caribbean, this Dutch port makes it easy to just … take it easy. Walk through town to choose your favorite carved wooden door, or spend the day like the Arubans do playing dominos at a beachside table.
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Day 31: Santa Marta
Romantic Santa Marta has it all: history (Colombia’s oldest city), natural beauty (from gentle bays and beaches to the highest coastal mountain range in the world), and its very own celebrity. Simon Bolivar  (“The Liberator”) is known as the George Washington of South America, and this was his Mount Vernon. Visit his beautiful estate or head to one of  the two UNESCO Biosphere Reserves nearby.
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Day 32: Cartagena
Welcome to the sparkling city of Cartagena, where the gold and jewels of the Spanish Main awaited shipment across the Atlantic. No pirate could resist, nor will you be able to when you visit this historic city. The Old Town, a UNESCO World Heritage Site, is surrounded by 400-year-old walls and contains a plethora of churches, fortresses, and restored colonial mansions. Outside the walls are more treasures: Climb the massive Castillo de San Felipe to investigate its maze of hidden tunnels, or shop for the perfect emerald.
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Day 34: Bocas del Toro
Bocas del Toro on Bastimentos island was visited by Columbus in 1502 and then built up with colorful and Caribbean-style clapboard houses by the United Fruit Company in the early 20th century.   Situated on the beautiful Bocas del Toro archipelago, the laid-back and friendly community is a great combination of races and ethnicities living harmoniously. West Indians, Latinos and Extraneros (the resident gringos) make this an easy place to feel right at home and embrace the relaxed Caribbean vibe of the town. Not far from town is the Smithsonian Tropical Research Institute, as well as two national parks, La Amistad and many banana plantations.
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Day 36: Colón
Explore the inner workings of the Panama Canal, head into the jungle to meet with Embera Indians, or take an aerial tram ride through the rainforest canopy.
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Day 37: Colón
Explore the inner workings of the Panama Canal, head into the jungle to meet with Embera Indians, or take an aerial tram ride through the rainforest canopy.
VIEW THE JOURNEY
Day 38: Bocas del Toro
Bocas del Toro on Bastimentos island was visited by Columbus in 1502 and then built up with colorful and Caribbean-style clapboard houses by the United Fruit Company in the early 20th century.   Situated on the beautiful Bocas del Toro archipelago, the laid-back and friendly community is a great combination of races and ethnicities living harmoniously. West Indians, Latinos and Extraneros (the resident gringos) make this an easy place to feel right at home and embrace the relaxed Caribbean vibe of the town. Not far from town is the Smithsonian Tropical Research Institute, as well as two national parks, La Amistad and many banana plantations.
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Day 39: Isla San Andres
At 10 square miles, the small island of San Andrés is considered a Colombia hot spot. The island, part of a UNESCO Biosphere Reserve, is multicultural and bilingual with the best beaches, and snorkeling spots. It’s a highlight to snorkel with puffer fish, angel fish, sea turtles and eels in the crystal-clear turquoise waters surrounding the island.
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Day 42: Roatan
The ocean playground around Roatan is part of the huge Mesoamerican Barrier Reef. These protected waters provide excellent snorkeling, kayaking, swimming with dolphins and other marine life and pristine powdery white beaches. Sample tradition island cuisine like conch, baleadas or pastilles in one of the many excellent cafes accompanied by delicious Honduran coffee
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Day 43: Belize City
With an origin as a logging camp and exporter of mahogany, Belize City is known now as the gateway to lovely nature and beautiful offshore islands. But stay in town long enough to check out the Swing Bridge – the only functioning manually operated bridge in the world. Then find the Cave Branch River for a float through ancient Mayan caves or visit the howler monkeys at the Community Baboon Sanctuary.
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Day 44: Costa Maya
Costa Maya is the closest gateway to the Chaccoben Mayan Ruins some of which you can climb to get an amazing view. The port features interesting shopping, local artisans and good restaurant and bars. It is part of the massive Mesoamerican Barrier Reef and the Banco Chinchorro Biosphere Reserve, home to sharks, dolphins and turtles and the Sian Ka’an Biosphere Reserve where jaguars, monkeys and hundreds of bird species live.
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Day 45: Cozumel
The Mesamerican Barrier Reef spans 14 miles around the Mexican island of Cozumel and the impressive marine diversity here makes it an excellent place for snorkeling and diving. Chankanaab, an eco-park surrounding a lagoon offers underwater caverns that are home to dolphins, manatees and sea turtles.  Or take a ferry ride over to the mainland to explore the beaches of Playa del Carmen.
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Day 47: Grand Cayman
The largest of the Cayman Islands, Grand Cayman is known for its beautiful beaches and coral reefs. Seven Mile Beach, for one is a long stretch of white sand, calm turquoise waters and shops and restaurants. Stingray City is the most popular attraction where the stingrays can be touched, fed and even held. The island has one cross-country walking path, the Mastic Trail and horseback riding on the beach may be the best way to experience the beauty of this place.
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Day 48: Cayman Brac
On tiny Cayman Brac, The Bluff, a limestone cliff running the length of the island contains numerous caves including the Bat Cave. It is a nature lover’s dream of lovely secluded beaches and lush green forests. Birdwatchers can search for endangered parrots, brown boobies and peregrine falcons or see the parrots at the Parrot Reserve. The hiking trails that crisscross the island lead to historic sites, reptilian habitats and unusual flora.
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Day 49: Port Antonio
Known as the gateway to the nearby Reach Falls, with its series of cascades tumbling from pool to pool, John Crow Mountains and tropical jungles, Port Antonio is a delightful hodgepodge of markets, street vendors, greenery, beaches and Georgian architecture. Experience the fun of taking a bamboo raft down the Rio River and don’t miss the world famous bottomless Blue Lagoon.
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Day 51: Santo Domingo
La Capital, as Santo Domingo is affectionately known, is a UNESCO site and one of the oldest cities in the Caribbean, with Zona Colonial buildings dating back to the 1500s. Santo Domingo is also considered the most modern metropolis in the Caribbean doing a great job of converging old and new.  At the heart of the Zona Colonial, a pedestrian-friendly maze of cobblestones and interesting architecture is the first cathedral built in the New World. Find time to sample the aromatic coffee and cacao.
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Day 52: La Romana
La Romana has something for every outdoor lover. White-sand beaches, pristine coral reefs, shallow and extreme depth waters teeming with marine life, fields of sugar cane, and cave-riddled forests where Taino rock art and fresh-water springs can be found. It is also home to the renowned Casa de Campo Resort with its award-winning golf course and 16th century Altos de Chavon, an amazing replica of a Mediterranean village.
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Day 54: 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.
VIEW THE JOURNEY
Day 55: Virgin Gorda / Prickly Pear, British Virgin Islands
  • 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 “The Baths,” which form huge underground pools and caverns.
 
Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.
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Day 56: 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.
Popular Highlights
Complimentary laundry
Pack light with complimentary daily laundry service
 
Isla San Andres
Swim and snorkel with puffer fish and sea turtles, at Isla San Andres, part of a UNESCO Biosphere Reserve
Panama Canal
Get your favorite spot on deck for the daylight partial transit of the Panama Canal
Belize City
Belize City is known as the gateway to Maya ruins and a world of nature
Cayman Brac’s Bat Cave
Find Cayman Brac’s Bat Cave, one of the many caves found along The Bluff, a limestone cliff running the length of the island
St. Bart’s
Find a waterside café to try St. Bart’s signature ti punch in Gustavia
Cartagena
Explore charming Cartagena, a lovely venue
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sun Jan 4
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Mon Jan 5
Falmouth Harbour
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Jan 6
Road Bay
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Jan 7
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Jan 7
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
Depart:  
Watersports Platform: 
Thu Jan 8
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Fri Jan 9
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Jan 10
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sun Jan 11
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  7:00 PM
Watersports Platform: 
Mon Jan 12
Basseterre
Arrive:  8:00 AM
Depart:  9:00 PM
Watersports Platform: 
Tue Jan 13
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Jan 14
St. John's
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Jan 15
Les Saintes
Arrive:  8:00 AM
Depart:  9:00 PM
Watersports Platform: 
Fri Jan 16
Pigeon Island
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Jan 17
Kingstown
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sun Jan 18
Bridgetown
Arrive:  5:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Jan 19
Anse Mitan
Arrive:  9:00 AM
Depart:  11:00 PM
Watersports Platform: 
Tue Jan 20
Castries
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Tue Jan 20
Pigeon Island
Arrive:  6:00 PM
Depart:  
Watersports Platform: 
Wed Jan 21
Pigeon Island
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Thu Jan 22
Bequia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Jan 23
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sat Jan 24
St. George's
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sun Jan 25
Bridgetown
Arrive:  6:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Jan 26
Man-O-War Bay
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Jan 27
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Jan 28
Soufriere
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Thu Jan 29
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Jan 30
Kralendijk
Arrive:  1:00 PM
Depart:  10:00 PM
Watersports Platform: 
Sat Jan 31
Willemstad
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sun Feb 1
Oranjestad
Arrive:  6:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Feb 2
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Feb 3
Santa Marta
Arrive:  7:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Feb 4
Cartagena
Arrive:  8:00 AM
Depart:  3:30 PM
Watersports Platform: 
Thu Feb 5
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Feb 6
Bocas del Toro
Arrive:  12:00 PM
Depart:  5:30 PM
Watersports Platform: 
Sat Feb 7
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sun Feb 8
Colón
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Mon Feb 9
Colón
Arrive:  
Depart:  4:00 PM
Watersports Platform: 
Tue Feb 10
Bocas del Toro
Arrive:  10:00 AM
Depart:  4:00 PM
Watersports Platform: 
Wed Feb 11
Isla San Andres
Arrive:  1:00 PM
Depart:  7:00 PM
Watersports Platform: 
Thu Feb 12
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Feb 13
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Feb 14
Roatan
Arrive:  9:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sun Feb 15
Belize City
Arrive:  9:00 AM
Depart:  7:00 PM
Watersports Platform: 
Mon Feb 16
Costa Maya
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Feb 17
Cozumel
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Feb 18
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Feb 19
Grand Cayman
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Fri Feb 20
Cayman Brac
Arrive:  7:00 AM
Depart:  1:00 PM
Watersports Platform: 
Sat Feb 21
Port Antonio
Arrive:  12:00 PM
Depart:  6:00 PM
Watersports Platform: 
Sun Feb 22
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Feb 23
Santo Domingo
Arrive:  1:00 PM
Depart:  10:00 PM
Watersports Platform: 
Tue Feb 24
La Romana
Arrive:  7:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Feb 25
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Feb 26
Jost Van Dyke, Great Harbour
Arrive:  8:00 AM
Depart:  11:59 PM
Watersports Platform: 
Fri Feb 27
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Feb 28
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  
Watersports Platform: 
Favorite Part of the Job

“Finding out what new and exciting puzzles we get to solve each day.”
Chris Prelog
Windstar President
I have traveled extensively to many places in the world and have been in the travel industry for more than 20 years.
While plotting the course for this grand voyage, Chris Prelog encouraged his Windstar team to push the limits. “A lot of guests want to do a longer itinerary right after the first of the year; get away to someplace nice and warm for the winter,” says the cruise line’s President.  “This is an extended adventure they’ve never been able to have with Windstar before.”
 
And what an adventure it will be: 55 sun-kissed days, visiting 18 countries and 28 islands amid Caribbean Windward and Leeward pleasures, Colombia's coastal beaches and a guided daylight transit of the Panama Canal. Overnight port stays in Jost Van Dyke and St. Lucia offer ample opportunities to linger late into the evenings dining and socializing with locals.  Guests can take full advantage of Wind Surf’s onboard Watersports Platform or the wide-open decks and elegant outdoor spaces.


  • Take a catamaran cruise to St. Lucia’s twin Pitons, a UNESCO World Heritage Site — “I highly recommend this cruise; the island’s west coast is stunning, and the Pitons are an absolute must-see”
  • Stroll the streets of pastel-painted UNESCO-designated Willemstad, or head into Curacao’s famous Hato Caves, where “sloping trails lead through the coral-limestone chambers past still pools and even a fresh-water waterfall — a rare sight on this dry island”
  • Take advantage of late departures in St. Barts to “enjoy a sunset sail, linger over dinner at Eden Rock, and check out the night life at Nikki Beach”
  • Interact with the Kuna Indians of the San Blas Islands and learn about their culture
  • Explore Bequia, one of Chris’s favorite spots in the Caribbean — “This is truly a small-ship port … soak in the view of Admiralty Bay from Fort Hamilton, then grab a slice of Mac’s famous lobster pizza”
Wind Surf
On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.
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Accommodations & Pricing
Boutique cruising with fewer than 350 guests. Our expertly designed itineraries and unexpected shore excursions bring you closer to each destination.
Category B
Category B
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $17,899 per guest
? All-inclusive price from $23,344 per guest
Category BX Deluxe
Category BX Deluxe
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $19,299 per guest
? All-inclusive price from $24,744 per guest
Category A
Category A
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $20,349 per guest
? All-inclusive price from $25,794 per guest
Category AX Deluxe
Category AX Deluxe
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $22,129 per guest
? All-inclusive price from $27,574 per guest
Category TX Deluxe
Category TX Deluxe
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $24,199 per guest
? All-inclusive price from $29,644 per guest
Suite
Suite
With 376 square feet, you’ll find the perfect space for time together — and plenty of room for time to yourself. You’ll even enjoy two full separate bathrooms. All the amenities of the staterooms await you, plus a beautiful sitting area, and two flat-screen television sets with DVD players.
? Cruise only from $37,999 per guest
? All-inclusive price from $43,444 per guest
Officer's Suite
Officer's Suite
For the ultimate in nautical experiences, reserve the new Officer’s Suite located close to the Bridge where our own ship’s officers have their quarters. With its unique “insider” location and 242 square feet of comfort, the nautically appointed Officer’s Suite offers an experience you won’t find on any other cruise line.
? Call for Availability
Bridge Suite
Bridge Suite
The ultimate in space and style surrounds you in 495 square feet of pure indulgence. Separate bedroom and living room with an in-suite dining area is an invitation to relaxation. And possibly best of all, your expansive bathroom features both a whirlpool spa tub and a massage shower.
? Call for Availability
The Windstar Life
The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations
Genuine and Thoughtful Crew
Crew Talent Show
Open Bridge
Local and Live Performances
Relax at the Pool or Hot Tub
Complimentary 24 Hour Room Service
Signature Sail Away
Shopping With The Chef
Take In The Sun
Watersports Platform
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sun, Jan 4 - Sat, Feb 28, 2026
WIND SURF
$23,344
$17,899
THIS
SAILING