Star Collector: Grand Caribbean & Panamanian Adventure
 
Philipsburg, St. Maarten to Bridgetown
Sat Feb 21, 2026 - Sat Mar 21, 2026,
 28 days
 on Wind Spirit
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Starting from $8,299 USD
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Philipsburg, St. Maarten to Bridgetown
Get acquainted with the Caribbean’s most iconic and little-known vacation destinations during this comprehensive and romantic 28-port, 20-country voyage to the Windward and Leeward Islands, Colombia, and a guided daylight transit of the Panama Canal. Zipline through the shady Antigua Rainforest near Falmouth Harbour. Savor deep-fried pastries filled with warm and tasty seafood on Bonaire. Board a semi-submersible bound for underwater marine parks and sunken ships off the shores of St. Barts. Master delicious Creole cuisine during a beachside cooking class with a local Martinique chef. Swim and snorkel prior to an overnight stay in Jost Van Dyke. Cook up decadent chocolate confections from locally grown cocoa nibs near Castries. See Cartagena’s colonial architecture from a classic horse-drawn carriage perspective. Relax during a narrated daylight transit of the Panama Canal as you uncover how early engineers overcame formidable and deadly challenges.  Linger on deck on warm, moonlight nights with the gentle lapping of the water below and the sparkling plethora of stars above.
voyage map
Popular Highlights
Beach Party
Let yourself go – at Windstar’s Signature Beach Party, where the Caribbean spirit is in full swing.
Complimentary laundry
Pack light with complimentary daily laundry service
 
Cartagena
Appreciate the 400-year-old walls of Cartagena’s fortress, protecting the Old Town, a UNESCO site
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Sat Feb 21
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Feb 22
St. John's
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Feb 23
Road Bay
Arrive:  9:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Feb 24
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Feb 24
Soper's Hole
Arrive:  10:00 PM
Depart:  
Watersports Platform: 
Wed Feb 25
Soper's Hole
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Thu Feb 26
Jost Van Dyke, Great Harbour
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Feb 27
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Feb 28
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  7:00 PM
Watersports Platform: 
Sun Mar 1
Basseterre
Arrive:  8:00 AM
Depart:  9:00 PM
Watersports Platform: 
Mon Mar 2
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Tue Mar 3
St. John's
Arrive:  8:00 AM
Depart:  9:00 PM
Watersports Platform: 
Wed Mar 4
Les Saintes
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Thu Mar 5
Roseau
Arrive:  8:00 AM
Depart:  1:00 PM
Watersports Platform: 
Fri Mar 6
Mayreau
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Sat Mar 7
Bridgetown
Arrive:  7:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sun Mar 8
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Mar 9
Basseterre
Arrive:  9:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Mar 10
St. John's
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Mar 11
Les Saintes
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Mar 12
Roseau
Arrive:  8:00 AM
Depart:  1:00 PM
Watersports Platform: 
Fri Mar 13
Mayreau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Mar 14
Anse Mitan
Arrive:  7:30 AM
Depart:  2:00 PM
Watersports Platform: 
Sun Mar 15
Bridgetown
Arrive:  7:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Mar 16
Tobago Cays
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Mar 17
Pigeon Island
Arrive:  8:00 AM
Depart:  
Watersports Platform: 
Wed Mar 18
Pigeon Island
Arrive:  
Depart:  6:00 AM
Watersports Platform: 
Wed Mar 18
Castries
Arrive:  8:00 AM
Depart:  3:00 PM
Watersports Platform: 
Wed Mar 18
The Pitons
Arrive:  5:30 PM
Depart:  6:30 PM
Watersports Platform: 
Thu Mar 19
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Fri Mar 20
Bequia
Arrive:  8:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sat Mar 21
Bridgetown
Arrive:  5:00 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: 35 sun-kissed days, visiting 20 countries and 28 ports 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 Star Pride’s onboard Watersports Platform  — while being among those who enjoy the ship’s redesigned spa. 
  • 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
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
? 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
Sat, Feb 21 - Sat, Mar 21, 2026
WIND SPIRIT
$11,071
$8,299
THIS
SAILING