11 nights onboard Wind Surf

Stars of the Greater Antilles

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.
Leaving from: Cozumel
Cruise ship: Wind Surf
Visiting: Cozumel Georgetown, Grand Cayman West End Port Antonio
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Windstar Cruises

Windstar Cruises operates a fleet of small luxury cruise ships. The cruise line has six yachts - three of which are masted sailing ships - and offers laid-back luxury with a tinge of historic seafaring adventure.

Wind Star and Wind Spirit each carry 148 guests, whereas Wind Surf carries 342. 'Power yachts' Star Pride, Star Breeze and Star Legend all carry 312 passengers. It's a unique experience, by all means!

342
Passengers
210
Crew
1998
Launched
2019
Last refit
14745t
Tonnage
162m
Length
20m
Width
12kts
Speed
6
Decks
USD
Currency
Cruise Itinerary
Day 1
Cozumel, Mexico
Day 3
Georgetown, Grand Cayman, Cayman Islands
Day 4
West End, Bahamas
Day 5
Port Antonio, Jamaica
Day 7
Santo Domingo, Dominican Republic
Day 8
La Romana, Dominican Republic
Day 10
Great Harbour, Jost Van Dyke, British Virgin Islands
Day 11
Virgin Gorda, British Virgin Islands
Day 12
Philipsburg, Sint Maarten (Dutch part)
Cozumel, Mexico image
Day 1
Cozumel, Mexico

Cozumel is the largest island in Mexico’s Yucatan peninsula and a microcosm of the very best that the Mayan Riviera has to offer: think sugar white beaches, a jungle rich with Mayan ruins and some of the world’s most impressive diving sites teeming with technicolour fish. This once sleepy island has come a long way from its humble fishing roots but remains far less commercialised than neighbouring Playa del Carmen in Cancun, just across the bay. Removed from the raucous pace of the mainland by around 20km of Caribbean Sea, a cruise to Cozumel offers a peaceful respite and a leisurely chance to relax into the rhythm of the tropics.

Georgetown, Grand Cayman, Cayman Islands image
Day 3
Georgetown, Grand Cayman, Cayman Islands
Begin exploring the capital by strolling along the waterfront Harbour Drive to Elmslie Memorial United Church, named after the first Presbyterian missionary to serve in Cayman. Its vaulted ceiling, wooden arches, and sedate nave reflect the religious nature of island residents. In front of the court building, in the center of town, names of influential Caymanians are inscribed on the Wall of History, which commemorates the islands' quincentennial in 2003. Across the street is the Cayman Islands Legislative Assembly Building, next door to the 1919 Peace Memorial Building. In the middle of the financial district is the General Post Office, built in 1939. Let the kids pet the big blue iguana statues.
West End, Bahamas image
Day 4
West End, Bahamas
Port Antonio, Jamaica image
Day 5
Port Antonio, Jamaica
Port Antonio, on the Northeast coast of Jamaica, is the islands third largest port, mainly for bananas and coconuts. It is also an important tourist destination. In fact, it has been featured as a model of paradise in several famous Hollywood films such as Club Paradise and Cocktail. Port Antonio was a sleepy coastal town until the 1880s, when Lorenzo Dow Baker, an American businessman, started the banana trade in Jamaica and promoted Port Antonio as a vacation spot for wealthy Americans. "Portie", as it is nicknamed, became a boom town. Even the movie star Errol Flynn was enamoured and ended up buying property here after his yacht washed ashore in 1946. Today it is still a major destination with plenty to do and see, from stunning scenery, creative arts and crafts, and cultural and historical sites.
Santo Domingo, Dominican Republic image
Day 7
Santo Domingo, Dominican Republic
La Romana, Dominican Republic image
Day 8
La Romana, Dominican Republic
Neither pretty nor quaint, La Romana has a central park, an interesting market, a couple of good restaurants, banks and small businesses, a public beach, and Jumbo, a major supermarket. If you are staying for a week or more you may want to buy a Dominican cell phone at Jumbo. It’s a mere $20 for a basic one, plus minutes. It can save you untold money if you'll be making local calls from your hotel/resort. It is, at least, a real slice of Dominican life. Casa de Campo is just outside La Romana, and other resorts are found in the vicinity of nearby Bayahibe. Although there are now more resorts in the area, this 7,000-acre luxury enclave put the town on the map. Casa de Campo Marina, with its Mediterranean design and impressive yacht club and villa complex, is as fine a marina facility as can be found anywhere; the shops and restaurants at the marina are a big draw for all tourists to the area.
Great Harbour, Jost Van Dyke, British Virgin Islands image
Day 10
Great Harbour, Jost Van Dyke, British Virgin Islands
Jost Van Dyke, four miles long, is truly known as the 'barefoot island'. The smallest of the British Virgin Islands, it is known as a popular destination for yachts and is celebrated for its casual lifestyle, protected anchorages, fine beaches and beachfront restaurants and bars. The island has fewer than 200 inhabitants and they are widely known as a welcoming people. The island's name conjures up its rich, colorful past. Jost Van Dyke is said to have been named for an early Dutch settler, a former pirate. At Great Harbour, Little Harbour, and White Bay there are safe, protected bays and pristine beaches shaded with coconut palms and seagrape trees. Discover inviting shops selling local treasures, restaurants, and bars. 'The Painkiller', one of the Caribbean’s most popular drinks, originated at the Soggy Dollar Bar. Foxy’s and Gertrude's in White Bay are renowned for drinks made with the island's famous rum, frosty beers, and tales of pirates and sunken treasure. Explore Jost Van Dyke's history in the vegetation-covered ruins of centuries-old sugar mills, or on the old trails that crisscross the island. Revel in the natural beauty of the pristine, untouched beaches. Hike up to the highest spot on the island, Majohnny Point, and take in a stunning 360 degree view of the Caribbean. Relax in the natural 'bubble pool', a popular tourist attraction. Jost Van Dyke conjures up images of what the British Virgin Islands may have looked like many years ago.
Virgin Gorda, British Virgin Islands image
Day 11
Virgin Gorda, British Virgin Islands
Philipsburg, Sint Maarten (Dutch part) image
Day 12
Philipsburg, Sint Maarten (Dutch part)
The capital of Dutch St. Maarten stretches about a mile (1½ km) along an isthmus between Great Bay and the Salt Pond and has five parallel streets. Most of the village's dozens of shops and restaurants are on Front Street, narrow and cobblestone, closest to Great Bay. It's generally congested when cruise ships are in port, because of its many duty-free shops and several casinos. Little lanes called steegjes connect Front Street with Back Street, which has fewer shops and considerably less congestion. Along the beach is a ½-mile-long (1-km-long) boardwalk with restaurants and several Wi-Fi hot spots.Wathey Square (pronounced watty) is in the heart of the village. Directly across from the square are the town hall and the courthouse, in a striking white building with cupola. The structure was built in 1793 and has served as the commander's home, a fire station, a jail, and a post office. The streets surrounding the square are lined with hotels, duty-free shops, restaurants, and cafés. The Captain Hodge Pier, just off the square, is a good spot to view Great Bay and the beach that stretches alongside.
Ship Details
Windstar Cruises
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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