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Classic Caribbean
Port to port
St. Maarten to St. Maarten
Dates
Dec 21, 2024 - Dec 28, 2024
View All 11 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$3,322
Cruise Only From
?
$2,699
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Dec 21, 2024 - Jan 4, 2025
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
All-Inclusive From
?
$2,799
Cruise Only From
?
$2,799
SPECIAL AVAILABLE
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Dec 28, 2024 - Jan 4, 2025
View All 18 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$7,622
Cruise Only From
?
$6,999
SPECIAL AVAILABLE
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Dec 28, 2024 - Jan 11, 2025
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
All-Inclusive From
?
$5,945
Cruise Only From
?
$4,699
Classic Caribbean
Port to port
St. Maarten to St. Maarten
Dates
Jan 4, 2025 - Jan 11, 2025
View All 11 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$3,522
Cruise Only From
?
$2,899
SPECIAL AVAILABLE
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Jan 4, 2025 - Jan 18, 2025
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
All-Inclusive From
?
$5,845
Cruise Only From
?
$4,599
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Jan 11, 2025 - Jan 18, 2025
View All 18 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$7,622
Cruise Only From
?
$6,999
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Jan 11, 2025 - Jan 25, 2025
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
All-Inclusive From
?
$7,445
Cruise Only From
?
$6,199
SPECIAL AVAILABLE
Classic Caribbean
Port to port
St. Maarten to St. Maarten
Dates
Jan 18, 2025 - Jan 25, 2025
View All 11 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$6,422
Cruise Only From
?
$5,799
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Jan 18, 2025 - Feb 1, 2025
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
All-Inclusive From
?
$6,945
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?
$5,699
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Jan 25, 2025 - Feb 1, 2025
View All 18 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
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Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Feb 1, 2025 - Feb 8, 2025
View All 18 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$7,622
Cruise Only From
?
$6,999
SPECIAL AVAILABLE
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Feb 1, 2025 - Feb 15, 2025
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
All-Inclusive From
?
$7,945
Cruise Only From
?
$6,699
Classic Caribbean
Port to port
St. Maarten to St. Maarten
Dates
Feb 8, 2025 - Feb 15, 2025
View All 11 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$5,422
Cruise Only From
?
$4,799
SPECIAL AVAILABLE
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Feb 8, 2025 - Feb 22, 2025
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
All-Inclusive From
?
$7,845
Cruise Only From
?
$6,599
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Feb 15, 2025 - Feb 22, 2025
View All 18 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$7,622
Cruise Only From
?
$6,999
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Feb 15, 2025 - Mar 1, 2025
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
All-Inclusive From
?
$9,445
Cruise Only From
?
$8,199
Classic Caribbean
Port to port
St. Maarten to St. Maarten
Dates
Feb 22, 2025 - Mar 1, 2025
View All 11 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$5,422
Cruise Only From
?
$4,799
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Feb 22, 2025 - Mar 8, 2025
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
All-Inclusive From
?
$8,945
Cruise Only From
?
$7,699
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Mar 1, 2025 - Mar 8, 2025
View All 18 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
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Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Mar 8, 2025 - Mar 15, 2025
View All 18 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$7,422
Cruise Only From
?
$6,799
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Mar 8, 2025 - Mar 22, 2025
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
Call for availability
Classic Caribbean
Port to port
St. Maarten to St. Maarten
Dates
Mar 15, 2025 - Mar 22, 2025
View All 11 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$5,422
Cruise Only From
?
$4,799
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Mar 15, 2025 - Mar 29, 2025
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
Call for availability
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Mar 22, 2025 - Mar 29, 2025
View All 18 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$7,422
Cruise Only From
?
$6,799
Barefoot Break in the British Virgin Islands
Port to port
St. Maarten to St. Maarten
Dates
Dec 2, 2025 - Dec 7, 2025
View Sailing Date and Fare
Ship
Wind Surf
Duration
5 Days
All-Inclusive From
?
$5,244
Cruise Only From
?
$4,799
Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean
Port to port
St. Maarten to St. Maarten
Dates
Dec 2, 2025 - Dec 14, 2025
View Sailing Date and Fare
Ship
Wind Surf
Duration
12 Days
Call for availability
Classic Caribbean
Port to port
St. Maarten to St. Maarten
Dates
Dec 7, 2025 - Dec 14, 2025
View All 11 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$5,422
Cruise Only From
?
$4,799
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Dec 7, 2025 - Dec 21, 2025
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
All-Inclusive From
?
$7,545
Cruise Only From
?
$6,299
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Dec 14, 2025 - Dec 21, 2025
View All 18 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$7,722
Cruise Only From
?
$7,099
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Dec 14, 2025 - Dec 28, 2025
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
All-Inclusive From
?
$6,645
Cruise Only From
?
$5,399
SPECIAL AVAILABLE
Classic Caribbean
Port to port
St. Maarten to St. Maarten
Dates
Dec 21, 2025 - Dec 28, 2025
View All 11 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$5,422
Cruise Only From
?
$4,799
SPECIAL AVAILABLE
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Dec 21, 2025 - Jan 4, 2026
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
All-Inclusive From
?
$4,545
Cruise Only From
?
$3,299
SPECIAL AVAILABLE
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Dec 28, 2025 - Jan 4, 2026
View All 18 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
All-Inclusive From
?
$7,222
Cruise Only From
?
$6,599
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Jan 4, 2026 - Jan 11, 2026
View All 18 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
Call for availability
Star Collector: Grand Caribbean Adventure
Port to port
St. Maarten to St. Maarten
Dates
Jan 4, 2026 - Feb 28, 2026
View Sailing Date and Fare
Ship
Wind Surf
Duration
55 Days
Call for availability
Blue Waters of the Leeward Islands
Port to port
St. Maarten to St. Maarten
Dates
Jan 14, 2026 - Jan 24, 2026
View Sailing Date and Fare
Ship
Wind Spirit
Duration
10 Days
Call for availability
Star Collector: Hidden Gems of the Caribbean
Port to port
St. Maarten to St. Maarten
Dates
Jan 14, 2026 - Jan 31, 2026
View Sailing Date and Fare
Ship
Wind Spirit
Duration
17 Days
Call for availability
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Jan 24, 2026 - Jan 31, 2026
View All 18 Sailing Dates and Fares
Ship
Wind Spirit
Duration
7 Days
Call for availability
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Jan 31, 2026 - Feb 7, 2026
View All 18 Sailing Dates and Fares
Ship
Wind Spirit
Duration
7 Days
Call for availability
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Jan 31, 2026 - Feb 14, 2026
View All 19 Sailing Dates and Fares
Ship
Wind Spirit
Duration
14 Days
Call for availability
Classic Caribbean
Port to port
St. Maarten to St. Maarten
Dates
Feb 7, 2026 - Feb 14, 2026
View All 11 Sailing Dates and Fares
Ship
Wind Spirit
Duration
7 Days
Call for availability
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Feb 7, 2026 - Feb 21, 2026
View All 19 Sailing Dates and Fares
Ship
Wind Spirit
Duration
14 Days
Call for availability
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Feb 14, 2026 - Feb 21, 2026
View All 18 Sailing Dates and Fares
Ship
Wind Spirit
Duration
7 Days
Call for availability
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Feb 21, 2026 - Feb 28, 2026
View All 18 Sailing Dates and Fares
Ship
Wind Spirit
Duration
7 Days
Call for availability
Classic Caribbean
Port to port
St. Maarten to St. Maarten
Dates
Feb 28, 2026 - Mar 7, 2026
View All 11 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
Call for availability
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Feb 28, 2026 - Mar 14, 2026
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
Call for availability
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Mar 7, 2026 - Mar 14, 2026
View All 18 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
Call for availability
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Mar 14, 2026 - Mar 21, 2026
View All 18 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
Call for availability
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Mar 14, 2026 - Mar 28, 2026
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
Call for availability
Classic Caribbean
Port to port
St. Maarten to St. Maarten
Dates
Mar 21, 2026 - Mar 28, 2026
View All 11 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
Call for availability
Star Collector: Caribbean Explorations
Port to port
St. Maarten to St. Maarten
Dates
Mar 21, 2026 - Apr 4, 2026
View All 19 Sailing Dates and Fares
Ship
Wind Surf
Duration
14 Days
Call for availability
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
St. Maarten to St. Maarten
Dates
Mar 28, 2026 - Apr 4, 2026
View All 18 Sailing Dates and Fares
Ship
Wind Surf
Duration
7 Days
Call for availability
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