Stars of the Greater Antilles
 
Cozumel to Philipsburg, St. Maarten
Tue Feb 17, 2026 - Sat Feb 28, 2026,
 11 days
 on Wind Surf
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Starting from $3,999 USD
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ITINERARY AND SHORE EXCURSIONS

The best on land brought to you by the best at sea. Get to the heart of local cultures with Windstar shore excursions. You don't want to just dip a toe in local culture, you want to dive into the deep end, and that's exactly what Windstar shore excursions are designed to do. All of our excursion are created to provide authentic local experience - the kind travelers like you are looking for. And with more than 2,500 excursions to choose from, you can experience your destination in whatever way is most meaningful to you. Whether you're an outdoor enthusiast, a foodie, a history buff, or someone who loves to get to know the faces behind the many places we travel.

Date
Port
Arrive
Depart
Watersports
Platform
Shore
Excursions
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Tue Feb 17
Cozumel
Arrive:
Depart:6:00 PM
Watersports Platform: 
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.
Wed Feb 18
AT SEA
Arrive:
Depart:
Watersports Platform: 
Thu Feb 19
Grand Cayman
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
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.
Fri Feb 20
Cayman Brac
Arrive:7:00 AM
Depart:1:00 PM
Watersports Platform: 
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.
Sat Feb 21
Port Antonio
Arrive:12:00 PM
Depart:6:00 PM
Watersports Platform: 
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.
Sun Feb 22
AT SEA
Arrive:
Depart:
Watersports Platform: 
Mon Feb 23
Santo Domingo
Arrive:1:00 PM
Depart:10:00 PM
Watersports Platform: 
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.
Tue Feb 24
La Romana
Arrive:7:00 AM
Depart:5:00 PM
Watersports Platform: 
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.
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: 
3 Available
+_
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.
3 Shore Excursions Available
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Jost Van Dyke, Catamaran Cruise and BeachBeach | Boating | Essentials Collection | Snorkeling
Duration4.5 Hours
Activity LevelModerate-Strenuous
$259
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Jost Van Dyke: Tortola Rib Boat TourBoating | Essentials Collection | Sightseeing | Refreshments | Watersports
Duration4 Hours
Activity LevelModerate
$199
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Jost Van Dyke, Sail and SnorkelBoating | Essentials Collection | Sightseeing | Refreshments | Watersports
Duration4 Hours
Activity LevelModerate-Strenuous
$159
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Fri Feb 27
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
2 Available
+_
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. Althought 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
2 Shore Excursions Available
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Virgin Gorda: Highlights & Bath TourBeach | Boating | Essentials Collection | Walking
Duration4 Hours
Activity LevelStrenuous
$89
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Virgin Gorda: Snorkel AdventureBoating | Essentials Collection | Refreshments | Snorkeling
Duration2.75 Hours
Activity LevelModerate-Strenuous
$239
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Sat Feb 28
Philipsburg, St. Maarten
Arrive:6:00 AM
Depart:
Watersports Platform: 
5 Available
+_
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.
5 Shore Excursions Available
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St. Maarten, Post Island Tour with Transfer to AirportEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$99
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St. Maarten, Post Island Tour with Transfer to HotelEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$99
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St. Maarten, Post Island Tour with Transfer to HotelEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$99
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St. Maarten: Americas Cup Sailboat Racing with Transfer to AirportBoating | Essentials Collection | Outdoors | Refreshments
Duration2.5 Hours
Activity LevelModerate
$179
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St. Maarten: Americas Cup Sailboat Racing with Transfer to Windstar Hotel Outdoors | Refreshments | Boating | Essentials Collection
Duration2.5 Hours
Activity LevelModerate
$179
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