Stars of the Greater Antilles

From $4,363 per person

12 days

Ship: Wind Surf

A serene coastal scene featuring turquoise waters, palm trees, and huts, perfect for a Caribbean getaway.
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Cruise through the Greater Antilles discovering magical places that fell off the map and tiny gems that were never on it in the first place. Skip the crowds of Montego Bay and Ocho Rios and head instead for the silver screen beauty of Port Antonio, “discovered” by Errol Flynn and then long forgotten. Enjoy the retro-Caribbean vibe of Grand Cayman and the undersea wonderland of La Romana. Sink into the sand on perfect white beaches, dive to pirate shipwrecks, swim beneath waterfalls wrapped in jungle and fall in love with a Caribbean you didn’t know still existed.

Journey Summary

  • Day 1 - Feb. 17, 2026, Tue. - Cozumel
  • Day 2 - Feb. 18, 2026, Wed. -
  • Day 3 - Feb. 19, 2026, Thu. - Grand Cayman
  • Day 4 - Feb. 20, 2026, Fri. - Cayman Brac
  • Day 5 - Feb. 21, 2026, Sat. - Ocho Rios, Jamaica
  • Day 6 - Feb. 22, 2026, Sun. -
  • Day 7 - Feb. 23, 2026, Mon. - Santo Domingo
  • Day 8 - Feb. 24, 2026, Tue. - La Romana
  • Day 9 - Feb. 25, 2026, Wed. -
  • Day 10 - Feb. 26, 2026, Thu. - Jost Van Dyke, Great Harbour
  • Day 11 - Feb. 27, 2026, Fri. - Virgin Gorda / Prickly Pear, British Virgin Islands
  • Day 12 - Feb. 28, 2026, Sat. - Philipsburg, St. Maarten

Detailed Itinerary

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

Day 1 - February 17, 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.  Or take a ferry ride over to the mainland to explore the beaches of Playa del Carmen.

Day 2 - February 18, 2026

Day 3 - February 19, 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 4 - February 20, 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’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 5 - February 21, 2026

Ocho Rios, Jamaica

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

Day 6 - February 22, 2026

Day 7 - February 23, 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.  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 8 - February 24, 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 9 - February 25, 2026

Day 10 - February 26, 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.

Day 11 - February 27, 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>
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<strong>Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.</strong>

Day 12 - February 28, 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.

Dates and Prices

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Feb 17, 2026

Ship

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The Wind Surf sailing through clear blue waters, showcasing its iconic tall sails against a bright sky.
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