All Caribbean Cruises with Windstar Cruises in February 2026

12 cruises
sold out
Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Dominica, Sri Lanka, Barbados
Philipsburg Itinerary Caribbean
External from £2,239
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
sold out
Sint Maarten, United States, Dominica, Sri Lanka, Guadeloupe, Saint Barthelemy, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
External from £2,266
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
sold out
Sint Maarten, United States, Dominica, Sri Lanka, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from £2,325
price per person Taxes included
Wind Spirit | 7 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
External from £2,363
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
Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from £2,363
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
Philipsburg Itinerary Caribbean
External from £2,541
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
Philipsburg Itinerary Caribbean
External from £2,622
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. Mayreau,
5. Deshaies,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Philipsburg Itinerary Caribbean
External from £2,772
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. navigation,
5. Les Saintes,
6. Roseau,
7. Mayreau,
8. Bridgetown
Philipsburg Itinerary Caribbean
External from £2,896
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
Philipsburg Itinerary Caribbean
External from £3,391
price per person Taxes included
Wind Spirit | 7 Feb 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Basseterre,
6. Gustavia,
7. Philipsburg
sold out
Mexico, Cayman Islands, Jamaica, Dominican Republic, Virgin Islands, British Virgin Islands, Sint Maarten
Cozumel Island Itinerary Caribbean
External from £3,609
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
Cozumel Island Itinerary Caribbean
External from £3,876
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. Ocho Rios,
6. navigation,
7. Santo Domingo,
8. La Romana,
9. navigation,
10. Jost Van Dyke,
11. Virgin Gorda,
12. Philipsburg
12 cruises