All Caribbean Cruises with Windstar Cruises in February 2026

  • 2025
  • 2027
10 cruises
sold out
Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Barbados
Philipsburg Itinerary Caribbean
External from $6,458
price per person Taxes included
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, United States, Dominica, Saint Vincent and the Grenadines, Martinique, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $6,618
price per person Taxes included
Wind Spirit | Feb. 7, 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
Philipsburg Itinerary Caribbean
External from $7,168
price per person Taxes included
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
Philipsburg Itinerary Caribbean
External from $7,183
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
Philipsburg Itinerary Caribbean
External from $7,183
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
Cozumel Island Itinerary Caribbean
External from $8,012
price per person Taxes included
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
Colon Itinerary Caribbean
External from $9,799
price per person Taxes included
Wind Surf | Feb. 9, 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
Philipsburg Itinerary Caribbean
External from $11,399
price per person Taxes included
Wind Surf | Feb. 28, 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 $12,911
price per person Taxes included
Wind Spirit | Feb. 28, 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
Cozumel Island Itinerary Caribbean
External from $13,699
price per person Taxes included
Wind Surf | Feb. 17, 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