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STAR COLLECTOR: LOVELY LEEWARDS on Star Pride

Star Pride New York
Exterior view of Star Pride sailing near Manhattan, New York
  • Exterior view of Star Pride sailing near Manhattan, New York
  • Exterior view of Star Pride beyond palm trees in Mayreau
  • View of Star Pride crossing the Corinth Canal in Greece
  • View of bed and balcony in Star Pride suite - Photo Credit: Gil Stose Photography
  • View of dining table and living area in Star Pride suite - Photo Credit: Gil Stose Photography
Whether you’re passionate about swimming among rarely seen undersea wildlife or the intricate cultures and intertwined European histories of the Windward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty. Shop unique designer apparel in St. Barts, where you’ll discover a fashionable confluence of high-end brands normally associated with places like Madison Avenue, but displayed in an ambiance that’s anything but intimidating. Master the art of cooking with distinct spices like nutmeg, cloves, and allspice in authentic Caribbean cuisine while taking direction from a highly-skilled native chef in Philipsburg. This Caribbean getaway is the perfect duration for lovers of island life and those who want to spend more time exploring the Windward Islands overlooked by other cruise lines.
About Star Pride
About Windstar Cruises
Windstar Cruises logo

THE WORLD'S BEST SMALL SHIP CRUISE LINE

NO ONE ELSE GOES SO FAR TO GET TRAVELERS SO CLOSE …
You’re closer to secluded coves, tiny villages, misty fjords. To ancient ruins, medieval alleyways, quaint marinas. To unspoiled beaches, unfamiliar cultures, undiscovered atolls. To enlivening your curiosity and awakening your sense of wonder. You’re closer than ever to the kind of authentic and unforgettable exper

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Nov 08, 2026 through
Nov 22, 2026
Nov 2, 2026 7:00 PM
14 Nights from
$3,999.00 (USD)
Per Person
+ $94.00 taxes/fees
Category sp
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$3,999.00
Cat:SP
$285.64 per night
8751544
Nov 09, 2025 through
Nov 23, 2025
Nov 3, 2025 7:00 PM
14 Nights from
$4,099.00 (USD)
Per Person
+ $94.00 taxes/fees
Category sp
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$4,099.00
Cat:SP
$292.79 per night
8709461
Jan 03, 2027 through
Jan 17, 2027
Dec 28, 2026 7:00 PM
14 Nights from
$3,999.00 (USD)
Per Person
+ $94.00 taxes/fees
Category sp
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$3,999.00
Cat:SP
$285.64 per night
8751543

Itinerary

Day Port Arrive Depart
1 San Juan 7:00 PM
2 At Sea
3 St. George's 9:00 AM 10:00 PM
4 Bequia 8:00 AM 10:00 PM
5 Mayreau 8:00 AM 5:00 PM
6 Les Saintes 10:00 AM 5:00 PM
7 Marigot, St. Martin 8:00 AM 3:00 PM
8 San Juan 7:00 AM 7:00 PM
9 CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) 8:00 AM 6:00 PM
10 Basseterre 8:00 AM 5:00 PM
11 Gustavia 7:00 AM 10:00 PM
12 Philipsburg, St. Maarten 8:00 AM 10:00 PM
13 Jost Van Dyke, Great Harbour 9:00 AM 10:00 PM
14 Virgin Gorda / Prickly Pear, British Virgin Islands 8:00 AM 5:00 PM
15 San Juan 7:00 AM
Prices are per-person based on double occupancy, unless otherwise noted.