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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Cozumel to Philipsburg, St. Maarten
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.
voyage map
Popular Highlights
Blue Lagoon
Peer into the world-famous bottomless Blue Lagoon of Jamaica.
El Meco
 Find the Mayan Temple of El Meco.
Grand Cayman
See Jamaica beyond the crowded cruise ports, head off the map to Grand Cayman, and spend a day snorkeling the gorgeous waters of La Romana.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Tue Feb 17
Cozumel
Arrive:  
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
Ocho Rios, Jamaica
Arrive:  8:30 AM
Depart:  2:00 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:  10:00 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: 
Accommodations & Pricing
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar) 
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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
ALL DATES &
FARES
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited select beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Tue, Feb 17 - Sat, Feb 28, 2026
WIND SURF
$5,088
$3,999
THIS
SAILING