Star Collector: Grand Caribbean Adventure

From $19,846 per person

56 days

Ship: Wind Surf

Star Collector: Grand Caribbean Adventure
Windstar Cruises

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.

Journey Summary

  • Day 1 - Jan. 4, 2026, Sun. - Philipsburg, St. Maarten
  • Day 2 - Jan. 5, 2026, Mon. - Falmouth Harbour
  • Day 3 - Jan. 6, 2026, Tue. - Road Bay
  • Day 4 - Jan. 7, 2026, Wed. - Soper's Hole
  • Day 5 - Jan. 8, 2026, Thu. - Jost Van Dyke, Great Harbour
  • Day 6 - Jan. 9, 2026, Fri. - Jost Van Dyke, Great Harbour
  • Day 7 - Jan. 10, 2026, Sat. - Virgin Gorda / Prickly Pear, British Virgin Islands
  • Day 8 - Jan. 11, 2026, Sun. - Gustavia
  • Day 9 - Jan. 12, 2026, Mon. - Philipsburg, St. Maarten
  • Day 10 - Jan. 13, 2026, Tue. - Basseterre
  • Day 11 - Jan. 14, 2026, Wed. - Gustavia
  • Day 12 - Jan. 15, 2026, Thu. - St. John's
  • Day 13 - Jan. 16, 2026, Fri. - Les Saintes
  • Day 14 - Jan. 17, 2026, Sat. - Mayreau
  • Day 15 - Jan. 18, 2026, Sun. - Kingstown
  • Day 16 - Jan. 19, 2026, Mon. - Bridgetown
  • Day 17 - Jan. 20, 2026, Tue. - Anse Mitan
  • Day 18 - Jan. 21, 2026, Wed. - Castries
  • Day 19 - Jan. 22, 2026, Thu. - Pigeon Island
  • Day 20 - Jan. 23, 2026, Fri. - Pigeon Island
  • Day 21 - Jan. 24, 2026, Sat. - Bequia
  • Day 22 - Jan. 25, 2026, Sun. - Mayreau
  • Day 23 - Jan. 26, 2026, Mon. - St. George's
  • Day 24 - Jan. 27, 2026, Tue. - Bridgetown
  • Day 25 - Jan. 28, 2026, Wed. - Bequia
  • Day 26 - Jan. 29, 2026, Thu. - Mayreau
  • Day 27 - Jan. 30, 2026, Fri. - Soufriere
  • Day 28 - Jan. 31, 2026, Sat. -
  • Day 29 - Feb. 1, 2026, Sun. - Kralendijk
  • Day 30 - Feb. 2, 2026, Mon. - Willemstad
  • Day 31 - Feb. 3, 2026, Tue. - Oranjestad
  • Day 32 - Feb. 4, 2026, Wed. -
  • Day 33 - Feb. 5, 2026, Thu. - Cartagena
  • Day 34 - Feb. 6, 2026, Fri. - Cartagena
  • Day 35 - Feb. 7, 2026, Sat. -
  • Day 36 - Feb. 8, 2026, Sun. - Bocas del Toro
  • Day 37 - Feb. 9, 2026, Mon. -
  • Day 38 - Feb. 10, 2026, Tue. -
  • Day 39 - Feb. 11, 2026, Wed. - Colón
  • Day 40 - Feb. 12, 2026, Thu. - Bocas del Toro
  • Day 41 - Feb. 13, 2026, Fri. - Isla San Andres
  • Day 42 - Feb. 14, 2026, Sat. -
  • Day 43 - Feb. 15, 2026, Sun. -
  • Day 44 - Feb. 16, 2026, Mon. - Roatan
  • Day 45 - Feb. 17, 2026, Tue. - Belize City
  • Day 46 - Feb. 18, 2026, Wed. - Costa Maya
  • Day 47 - Feb. 19, 2026, Thu. - Cozumel
  • Day 48 - Feb. 20, 2026, Fri. -
  • Day 49 - Feb. 21, 2026, Sat. - Grand Cayman
  • Day 50 - Feb. 22, 2026, Sun. - Cayman Brac
  • Day 51 - Feb. 23, 2026, Mon. - Ocho Rios, Jamaica
  • Day 52 - Feb. 24, 2026, Tue. -
  • Day 53 - Feb. 25, 2026, Wed. - Santo Domingo
  • Day 54 - Feb. 26, 2026, Thu. - La Romana
  • Day 55 - Feb. 27, 2026, Fri. -
  • Day 56 - Feb. 28, 2026, Sat. - Jost Van Dyke, Great Harbour

Detailed Itinerary

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

Day 1 - January 04, 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 05, 2026

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.

Day 3 - January 06, 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.  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.

Day 4 - January 07, 2026

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 5 - January 08, 2026

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 6 - January 09, 2026

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 7 - January 10, 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 8 - January 11, 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 9 - January 12, 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 10 - January 13, 2026

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 11 - January 14, 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 12 - January 15, 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 16, 2026

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 14 - January 17, 2026

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 15 - January 18, 2026

Kingstown

Charming Kingstown, the capital and main commercial center of St. Vincent &amp; the Grenadines is known for its churches, cobblestone streets, colonial buildings and the St. Vincent Botanical Gardens, founded in 1765. &nbsp;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. &nbsp;Other sites to see include St. George&rsquo;s Anglican Cathedral, an 1820s structure adorned with stained glass windows, St. Mary&rsquo;s Catholic Cathedral, built in 1823, with its lovely Gothic spires and Romanesque columns and arches.

Day 16 - January 19, 2026

Bridgetown

Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you&rsquo;ll find historic sugar plantations and the fairyland magic of Harrison&rsquo;s Cave.

Day 17 - January 20, 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 18 - January 21, 2026

Castries

The capital and largest city of St. Lucia is a bustling port where shoppers flock.&nbsp; Most of the city&rsquo;s historic buildings were destroyed in major fires between 1785 and 1948 but you&rsquo;ll see the beautiful, scenic backdrop of Morne Fortune (elev. 2,795 ft.) and the bustling harbor.&nbsp; 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 19 - January 22, 2026

Pigeon Island

The UNESCO site Pitons&rsquo; 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.

Day 20 - January 23, 2026

Pigeon Island

The UNESCO site Pitons&rsquo; 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.

Day 21 - January 24, 2026

Bequia

The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia&rsquo;s whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island&rsquo;s famed model boat builders at work on their miniature masterpieces.

Day 22 - January 25, 2026

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 23 - January 26, 2026

St. George's

Inhale the intoxicating aroma of the &ldquo;Isle of Spice&rdquo; 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.

Day 24 - January 27, 2026

Bridgetown

Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you&rsquo;ll find historic sugar plantations and the fairyland magic of Harrison&rsquo;s Cave.

Day 25 - January 28, 2026

Bequia

The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia&rsquo;s whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island&rsquo;s famed model boat builders at work on their miniature masterpieces.

Day 26 - January 29, 2026

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 27 - January 30, 2026

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.

Day 28 - January 31, 2026

Day 29 - February 01, 2026

Kralendijk

The ice cream colors of the stucco houses will draw your lens, as will the pink flamingos on the salt pans. But you&rsquo;ll need a waterproof camera to complete the portrait since more than 400 fish species and 50 types of coral wait beneath the surface

Day 30 - February 02, 2026

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&rsquo;s the perfect appetizer for a day of watersports or an adventure below ground at the magical Hato Caves&mdash;filled with eerie limestone formations and ancient petroglyphs.

Day 31 - February 03, 2026

Oranjestad

Known for having some of the best beaches in the Caribbean, this Dutch port makes it easy to just &hellip; 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.

Day 32 - February 04, 2026

Day 33 - February 05, 2026

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.

Day 34 - February 06, 2026

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.

Day 35 - February 07, 2026

Day 36 - February 08, 2026

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 20<sup>th</sup> century.&nbsp;&nbsp; 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 <em>Extraneros </em>(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.

Day 37 - February 09, 2026

Day 38 - February 10, 2026

Day 39 - February 11, 2026

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.

Day 40 - February 12, 2026

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 20<sup>th</sup> century.&nbsp;&nbsp; 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 <em>Extraneros </em>(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.

Day 41 - February 13, 2026

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&rsquo;s a highlight to snorkel with puffer fish, angel fish, sea turtles and eels in the crystal-clear turquoise waters surrounding the island.

Day 42 - February 14, 2026

Day 43 - February 15, 2026

Day 44 - February 16, 2026

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

Day 45 - February 17, 2026

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 &ndash; 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.

Day 46 - February 18, 2026

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&rsquo;an Biosphere Reserve where jaguars, monkeys and hundreds of bird species live.

Day 47 - February 19, 2026

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.&nbsp; Or take a ferry ride over to the mainland to explore the beaches of Playa del Carmen.

Day 48 - February 20, 2026

Day 49 - February 21, 2026

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.

Day 50 - February 22, 2026

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&rsquo;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.

Day 51 - February 23, 2026

Ocho Rios, Jamaica

Tourist friendly Ocho Rios is situated in what the locals refer to as &ldquo;the garden parish&rdquo; with its abundance of greenery and scenery. See the popular Dunn&rsquo;s River Falls or zipline at Mystic Mountain Rainforest.&nbsp; Visit National Heritage Sites like the Port Maria Courthouse or Fort Haldane.&nbsp; See the estate made famous in the James Bond &ldquo;Goldeneye&rdquo; movie and weave through the variety of shops at the Ocho Rios Craft Market.

Day 52 - February 24, 2026

Day 53 - February 25, 2026

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.&nbsp; 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.

Day 54 - February 26, 2026

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 16<sup>th</sup> century Altos de Chavon, an amazing replica of a Mediterranean village.

Day 55 - February 27, 2026

Day 56 - February 28, 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.

Dates and Prices

Select year & month:

Unavailable dates are greyed out

JanFebMarAprMayJunJulAugSepOctNovDec

Available dates:

Jan 04, 2026

Ship

Your cruise ship

Ship image
Cruiseline

consultation

Need information to make a decision?

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