Star Collector: Grand Caribbean Adventure
 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sun Jan 4, 2026 - Sat Feb 28, 2026,
 55 days
 on Wind Surf
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Starting from $19,299 USD
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Philipsburg, St. Maarten to Philipsburg, St. Maarten
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.
voyage map
Popular Highlights
Complimentary laundry
Pack light with complimentary daily laundry service
 
Isla San Andres
Swim and snorkel with puffer fish and sea turtles, at Isla San Andres, part of a UNESCO Biosphere Reserve
Panama Canal
Get your favorite spot on deck for the daylight partial transit of the Panama Canal
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Sun Jan 4
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Mon Jan 5
Falmouth Harbour
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Jan 6
Road Bay
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Jan 7
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Jan 7
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
Depart:  
Watersports Platform: 
Thu Jan 8
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Fri Jan 9
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Jan 10
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sun Jan 11
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  7:00 PM
Watersports Platform: 
Mon Jan 12
Basseterre
Arrive:  8:00 AM
Depart:  9:00 PM
Watersports Platform: 
Tue Jan 13
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Jan 14
St. John's
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Jan 15
Les Saintes
Arrive:  8:00 AM
Depart:  1:00 PM
Watersports Platform: 
Fri Jan 16
Mayreau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Jan 17
Kingstown
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sun Jan 18
Bridgetown
Arrive:  5:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Jan 19
Anse Mitan
Arrive:  9:00 AM
Depart:  11:00 PM
Watersports Platform: 
Tue Jan 20
Castries
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Tue Jan 20
Pigeon Island
Arrive:  6:00 PM
Depart:  
Watersports Platform: 
Wed Jan 21
Pigeon Island
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Thu Jan 22
Bequia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Jan 23
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sat Jan 24
St. George's
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sun Jan 25
Bridgetown
Arrive:  6:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Jan 26
Bequia
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Jan 27
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Jan 28
Soufriere
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Thu Jan 29
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Jan 30
Kralendijk
Arrive:  1:00 PM
Depart:  10:00 PM
Watersports Platform: 
Sat Jan 31
Willemstad
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sun Feb 1
Oranjestad
Arrive:  6:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Feb 2
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Feb 3
Cartagena
Arrive:  8:00 AM
Depart:  
Watersports Platform: 
Wed Feb 4
Cartagena
Arrive:  
Depart:  3:30 PM
Watersports Platform: 
Thu Feb 5
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Feb 6
Bocas del Toro
Arrive:  12:00 PM
Depart:  6:00 PM
Watersports Platform: 
Sat Feb 7
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sun Feb 8
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Feb 9
Colón
Arrive:  7:00 AM
Depart:  4:00 PM
Watersports Platform: 
Tue Feb 10
Bocas del Toro
Arrive:  10:00 AM
Depart:  4:00 PM
Watersports Platform: 
Wed Feb 11
Isla San Andres
Arrive:  1:00 PM
Depart:  7:00 PM
Watersports Platform: 
Thu Feb 12
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Feb 13
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Feb 14
Roatan
Arrive:  9:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sun Feb 15
Belize City
Arrive:  9:00 AM
Depart:  7:00 PM
Watersports Platform: 
Mon Feb 16
Costa Maya
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Feb 17
Cozumel
Arrive:  8:00 AM
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: 
Favorite Part of the Job

“Finding out what new and exciting puzzles we get to solve each day.”
Chris Prelog
Windstar President
I have traveled extensively to many places in the world and have been in the travel industry for more than 20 years.
While plotting the course for this grand voyage, Chris Prelog encouraged his Windstar team to push the limits. “A lot of guests want to do a longer itinerary right after the first of the year; get away to someplace nice and warm for the winter,” says the cruise line’s President.  “This is an extended adventure they’ve never been able to have with Windstar before.”
 
And what an adventure it will be: 55 sun-kissed days, visiting 18 countries and 28 islands amid Caribbean Windward and Leeward pleasures, Colombia's coastal beaches and a guided daylight transit of the Panama Canal. Overnight port stays in Jost Van Dyke and St. Lucia offer ample opportunities to linger late into the evenings dining and socializing with locals.  Guests can take full advantage of Wind Surf’s onboard Watersports Platform or the wide-open decks and elegant outdoor spaces.


  • Take a catamaran cruise to St. Lucia’s twin Pitons, a UNESCO World Heritage Site — “I highly recommend this cruise; the island’s west coast is stunning, and the Pitons are an absolute must-see”
  • Stroll the streets of pastel-painted UNESCO-designated Willemstad, or head into Curacao’s famous Hato Caves, where “sloping trails lead through the coral-limestone chambers past still pools and even a fresh-water waterfall — a rare sight on this dry island”
  • Take advantage of late departures in St. Barts to “enjoy a sunset sail, linger over dinner at Eden Rock, and check out the night life at Nikki Beach”
  • Interact with the Kuna Indians of the San Blas Islands and learn about their culture
  • Explore Bequia, one of Chris’s favorite spots in the Caribbean — “This is truly a small-ship port … soak in the view of Admiralty Bay from Fort Hamilton, then grab a slice of Mac’s famous lobster pizza”
Accommodations & Pricing
Suite
Suite
With 376 square feet, you’ll find the perfect space for time together — and plenty of room for time to yourself. You’ll even enjoy two full separate bathrooms. All the amenities of the staterooms await you, plus a beautiful sitting area, and two flat-screen television sets with DVD players.
? Call for Availability
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
Sun, Jan 4 - Sat, Feb 28, 2026
WIND SURF
$24,744
$19,299
THIS
SAILING