All Caribbean Cruises with Windstar Cruises in February 2026

  • 2024
  • 2025
  • 2026
6 cruises

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

Philipsburg Itinerary Caribbean
from R 51 421,96
price per person Taxes included
21 reservations in 48 hours
Wind Spirit | 07 Feb 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Pigeon Island,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg

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

Philipsburg Itinerary Caribbean
from R 52 266,87
price per person Taxes included
19 reservations in 36 hours
Wind Spirit | 14 Feb 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. St. John ,
3. Anguilla,
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
from R 79 834,70
price per person Taxes included
18 reservations in 48 hours
Wind Surf | 17 Feb 2026
Duration: 11 nights
Departure from: Cozumel Island Landing: Philipsburg
Itinerary:
1. Cozumel Island,
2. navigation,
3. George Town,
4. George Town,
5. Port Antonio,
6. navigation,
7. Santo Domingo,
8. La Romana,
9. navigation,
10. Jost Van Dyke,
11. Virgin Gorda,
12. Philipsburg

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

Philipsburg Itinerary Caribbean
from R 52 266,87
price per person Taxes included
22 reservations in 36 hours
Wind Spirit | 21 Feb 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. St. John ,
3. Anguilla,
4. Virgin Gorda,
5. Tortola Island,
6. Tortola Island,
7. Jost Van Dyke,
8. Gustavia,
9. Philipsburg

Caribbean: Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Dominica, Sri Lanka, Barbados

Philipsburg Itinerary Caribbean
from R 49 515,98
price per person Taxes included
18 reservations in 36 hours
Wind Spirit | 28 Feb 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Bridgetown
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. St. John ,
5. Les Saintes,
6. Roseau,
7. Pigeon Island,
8. Bridgetown

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

Philipsburg Itinerary Caribbean
from R 50 125,11
price per person Taxes included
16 reservations in 36 hours
Wind Surf | 28 Feb 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Pigeon Island,
5. Les Saintes,
6. Gustavia,
7. Basseterre,
8. Philipsburg
6 cruises