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All Caribbean Cruises with Windstar Cruises in February 2026

  • 2027
  • 2028
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January 2028 February 2028 March 2028
10 cruises
Caribbean: Mexico, Cayman Islands, Jamaica, Dominican Republic, Virgin Islands, British Virgin Islands, Sint Maarten
Cozumel Island Itinerary Caribbean
External from $6,844
price per person Taxes included
See the cruise Book
Wind Surf | 17/02/2026
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
sold out
Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Barbados
Philipsburg Itinerary Caribbean
External from $7,838
price per person Taxes included
Wind Spirit | 28/02/2026
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
Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, France, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $8,700
price per person Taxes included
See the cruise Book
Wind Surf | 28/02/2026
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
sold out
Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $8,718
price per person Taxes included
Wind Spirit | 14/02/2026
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
sold out
Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $9,118
price per person Taxes included
Wind Spirit | 21/02/2026
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, United States, Dominica, Saint Vincent and the Grenadines, Martinique, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $9,832
price per person Taxes included
Wind Spirit | 7/02/2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Fort de france,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Caribbean: Panama, Colombia, Honduras, Belize, Mexico, Cayman Islands, Jamaica, Dominican Republic, Virgin Islands, British Virgin Islands, Sint Maarten
Colon Itinerary Caribbean
External from $11,893
price per person Taxes included
See the cruise Book
Wind Surf | 9/02/2026
Duration: 19 nights
Departure from: Colon Landing: Philipsburg
Itinerary:
1. Colon,
2. Bocas del Toro,
3. San Andres,
4. navigation,
5. navigation,
6. Roatan,
7. Belize City,
8. Costa Maya,
9. Cozumel Island,
10. navigation,
11. George Town,
12. George Town,
13. Ocho Rios,
14. navigation,
15. Santo Domingo,
16. La Romana,
17. navigation,
18. Jost Van Dyke,
19. Virgin Gorda,
20. Philipsburg
sold out
Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, France, Saint Kitts and Nevis, Saint Barthelemy, British Virgin Islands, Virgin Islands
Philipsburg Itinerary Caribbean
External from $13,835
price per person Taxes included
Wind Surf | 28/02/2026
Duration: 14 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Deshaies,
6. Basseterre,
7. Gustavia,
8. Philipsburg,
9. navigation,
10. Tortola Island,
11. Virgin Gorda,
12. Tortola Island,
13. Tortola Island,
14. Jost Van Dyke,
15. Gustavia,
16. Philipsburg
sold out
Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Barbados, Antigua and Barbuda, Martinique
Philipsburg Itinerary Caribbean
External from $15,670
price per person Taxes included
Wind Spirit | 28/02/2026
Duration: 15 nights
Departure from: Philipsburg Landing: Bridgetown
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. navigation,
5. Les Saintes,
6. Roseau,
7. Mayreau,
8. Bridgetown,
9. navigation,
10. Basseterre,
11. Saint Johns,
12. Les Saintes,
13. Roseau,
14. Mayreau,
15. Fort de france,
16. Bridgetown
sold out
Mexico, Cayman Islands, Jamaica, Dominican Republic, Virgin Islands, British Virgin Islands, Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, France, Saint Kitts and Nevis, Saint Barthelemy
Cozumel Island Itinerary Caribbean
External from $20,225
price per person Taxes included
Wind Surf | 17/02/2026
Duration: 18 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,
13. Charlestown,
14. Roseau,
15. Mayreau,
16. Deshaies,
17. Basseterre,
18. Gustavia,
19. Philipsburg
10 cruises