All Caribbean Cruises with Windstar Cruises in February 2026

  • 2025
  • 2026
  • 2027
10 cruises

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

Philipsburg Itinerary Caribbean
from R 63 332
price per person Taxes included
Wind Spirit | 07 Feb 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
sold out

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

Philipsburg Itinerary Caribbean
from R 56 818
price per person Taxes included
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
sold out

Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from R 57 752
price per person Taxes included
Wind Spirit | 14 Feb 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

Mexico, Cayman Islands, Jamaica, Dominican Republic, Virgin Islands, British Virgin Islands, Sint Maarten

Cozumel Island Itinerary Caribbean
from R 88 213
price per person Taxes included
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: Mexico, Cayman Islands, Jamaica, Dominican Republic, Virgin Islands, British Virgin Islands, Sint Maarten

Cozumel Island Itinerary Caribbean
from R 88 213
price per person Taxes included
4 reservations in 72 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. 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, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from R 57 752
price per person Taxes included
Wind Spirit | 21 Feb 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

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

Philipsburg Itinerary Caribbean
from R 57 557
price per person Taxes included
2 reservations in 72 hours
Wind Surf | 28 Feb 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, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Dominica, Sri Lanka, Barbados

Philipsburg Itinerary Caribbean
from R 54 712
price per person Taxes included
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, Saint Kitts and Nevis, Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Barbados

Philipsburg Itinerary Caribbean
from R 54 712
price per person Taxes included
2 reservations in 72 hours
Wind Spirit | 28 Feb 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Bridgetown
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. Saint Johns,
5. Les Saintes,
6. Roseau,
7. Mayreau,
8. Bridgetown
sold out

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

Philipsburg Itinerary Caribbean
from R 55 386
price per person Taxes included
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
10 cruises