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Itineraries and cruises Windstar Cruises departing from Sint Maarten December 2025

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December 2024
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5 cruises

Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

Sint Maarten Itinerary Caribbean
from $2,861.98
price per person Taxes included
16 reservations in 48 hours
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Wind Surf | Dec. 2, 2025
Duration: 5 nights
Departure from: Sint Maarten Landing: Sint Maarten
Itinerary:
1. Sint Maarten,
2. Tortola Island,
3. Jost Van Dyke,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Gustavia,
7. Sint Maarten

Caribbean: Sint Maarten, United States, Dominica, Sri Lanka, Guadeloupe, Saint Barthelemy, Saint Kitts and Nevis

Sint Maarten Itinerary Caribbean
from $3,464.82
price per person Taxes included
19 reservations in 36 hours
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Wind Surf | Dec. 7, 2025
Duration: 7 nights
Departure from: Sint Maarten Landing: Sint Maarten
Itinerary:
1. Sint Maarten,
2. Charlestown,
3. Roseau,
4. Pigeon Island,
5. Les Saintes,
6. Gustavia,
7. Basseterre,
8. Sint Maarten

Caribbean: Sint Maarten, Antigua and Barbuda, United Kingdom, British Virgin Islands, Virgin Islands, Saint Barthelemy

Sint Maarten Itinerary Caribbean
from $3,615.53
price per person Taxes included
16 reservations in 48 hours
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Wind Surf | Dec. 14, 2025
Duration: 7 nights
Departure from: Sint Maarten Landing: Sint Maarten
Itinerary:
1. Sint Maarten,
2. Falmouth Harbour,
3. Anguilla,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Sint Maarten

Caribbean: Sint Maarten, United States, Dominica, Sri Lanka, Guadeloupe, Saint Barthelemy, Saint Kitts and Nevis

Sint Maarten Itinerary Caribbean
from $4,067.66
price per person Taxes included
19 reservations in 48 hours
See the cruise
Wind Surf | Dec. 21, 2025
Duration: 7 nights
Departure from: Sint Maarten Landing: Sint Maarten
Itinerary:
1. Sint Maarten,
2. Charlestown,
3. Roseau,
4. Pigeon Island,
5. Les Saintes,
6. Gustavia,
7. Basseterre,
8. Sint Maarten

Caribbean: Sint Maarten, Antigua and Barbuda, United Kingdom, British Virgin Islands, Virgin Islands, Saint Barthelemy

Sint Maarten Itinerary Caribbean
from $4,067.66
price per person Taxes included
15 reservations in 36 hours
See the cruise
Wind Surf | Dec. 28, 2025
Duration: 7 nights
Departure from: Sint Maarten Landing: Sint Maarten
Itinerary:
1. Sint Maarten,
2. Falmouth Harbour,
3. Anguilla,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Sint Maarten
5 cruises