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All Caribbean Cruises with Windstar Cruises in February 2026

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5 cruises
Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, France, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $6,015
price per person Taxes included
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Wind Surf | Feb. 28, 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Deshaies,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Caribbean: Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Barbados
Philipsburg Itinerary Caribbean
External from $6,293
price per person Taxes included
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Wind Spirit | Feb. 28, 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Bridgetown
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. navigation,
5. Les Saintes,
6. Roseau,
7. Mayreau,
8. Bridgetown
sold out
Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $6,359
price per person Taxes included
Wind Spirit | Feb. 21, 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Saint Johns,
3. Tortola Island,
4. Virgin Gorda,
5. Tortola Island,
6. Tortola Island,
7. Jost Van Dyke,
8. Gustavia,
9. Philipsburg
sold out
Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $6,524
price per person Taxes included
Wind Spirit | Feb. 14, 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Saint Johns,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
Caribbean: Mexico, Cayman Islands, Jamaica, Dominican Republic, Virgin Islands, British Virgin Islands, Sint Maarten
Cozumel Island Itinerary Caribbean
External from $7,353
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | Feb. 17, 2026
Duration: 11 nights
Departure from: Cozumel Island Landing: Philipsburg
Itinerary:
1. Cozumel Island,
2. navigation,
3. George Town,
4. George Town,
5. Ocho Rios,
6. navigation,
7. Santo Domingo,
8. La Romana,
9. navigation,
10. Jost Van Dyke,
11. Virgin Gorda,
12. Philipsburg
5 cruises