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Cruises of Windstar Cruises in 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

favorite
Philipsburg Itinerary Caribbean
from $2,290.34
price per person Taxes included
17 reservations in 36 hours
See the cruise Book
Wind Surf | Dec 2, 2025
Duration: 5 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Jost Van Dyke,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Gustavia,
7. Philipsburg

Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

favorite
Philipsburg Itinerary Caribbean
from $2,626.63
price per person Taxes included
19 reservations in 36 hours
See the cruise Book
Wind Surf | Dec 7, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg

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

favorite
Philipsburg Itinerary Caribbean
from $2,756.23
price per person Taxes included
16 reservations in 48 hours
See the cruise Book
Wind Surf | Dec 14, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Anguilla,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg

Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

favorite
Philipsburg Itinerary Caribbean
from $3,073.53
price per person Taxes included
19 reservations in 48 hours
See the cruise Book
Wind Surf | Dec 21, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg

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

favorite
Philipsburg Itinerary Caribbean
from $3,091.40
price per person Taxes included
15 reservations in 36 hours
See the cruise Book
Wind Surf | Dec 28, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Anguilla,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
5 cruises