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Cruises of Windstar Cruises in Sint Maarten

33 cruises

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

Philipsburg Itinerary Caribbean
from $4,002
price per person Taxes included
4 reservations in 72 hours
Wind Surf | 2 Dec 2025
Duration: 5 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Jost Van Dyke,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Gustavia,
7. Philipsburg
sold out

Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $3,816
price per person Taxes included
Wind Surf | 2 Dec 2025
Duration: 5 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Jost Van Dyke,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Gustavia,
7. Philipsburg

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

Philipsburg Itinerary Caribbean
from $4,376
price per person Taxes included
Wind Surf | 7 Dec 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
sold out

Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $4,376
price per person Taxes included
Wind Surf | 7 Dec 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
sold out

Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $4,592
price per person Taxes included
Wind Surf | 14 Dec 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. navigation,
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, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $5,121
price per person Taxes included
Wind Surf | 21 Dec 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg

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

Philipsburg Itinerary Caribbean
from $5,493
price per person Taxes included
Wind Surf | 21 Dec 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
sold out

Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $5,151
price per person Taxes included
Wind Surf | 28 Dec 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. navigation,
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, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $4,859
price per person Taxes included
Wind Surf | 4 Jan 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. navigation,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg

Caribbean: Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Saint Vincent and the Grenadines, Barbados

Philipsburg Itinerary Caribbean
from $4,907
price per person Taxes included
1 booking in 72 hours
Wind Surf | 11 Jan 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Bridgetown
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. Saint Johns,
5. Les Saintes,
6. Mayreau,
7. Kingstown,
8. Bridgetown
sold out

Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Sri Lanka, Saint Vincent and the Grenadines, Barbados

Philipsburg Itinerary Caribbean
from $4,907
price per person Taxes included
Wind Surf | 11 Jan 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Bridgetown
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. St. John ,
5. Les Saintes,
6. Pigeon Island,
7. Kingstown,
8. Bridgetown

Caribbean: Sint Maarten, Saint Kitts and Nevis, Dominica, Saint Lucia, Martinique, Guadeloupe, United States, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $8,438
price per person Taxes included
2 reservations in 72 hours
Wind Spirit | 14 Jan 2026
Duration: 10 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Roseau,
4. Castries,
5. Fort de france,
6. Les Saintes,
7. Charlestown,
8. Virgin Gorda,
9. Jost Van Dyke,
10. Gustavia,
11. Philipsburg
sold out

Sint Maarten, Saint Kitts and Nevis, Dominica, Saint Lucia, Martinique, Guadeloupe, United States, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $6,763
price per person Taxes included
Wind Spirit | 14 Jan 2026
Duration: 10 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Roseau,
4. Castries,
5. Fort de france,
6. Les Saintes,
7. Charlestown,
8. Virgin Gorda,
9. Jost Van Dyke,
10. Gustavia,
11. Philipsburg

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

Philipsburg Itinerary Caribbean
from $5,138
price per person Taxes included
Wind Spirit | 24 Jan 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, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $4,952
price per person Taxes included
Wind Spirit | 24 Jan 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, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $4,765
price per person Taxes included
Wind Spirit | 31 Jan 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

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

Philipsburg Itinerary Caribbean
from $5,058
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. 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 $4,872
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
from $4,952
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
from $4,952
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
sold out

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

Philipsburg Itinerary Caribbean
from $4,749
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

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

Philipsburg Itinerary Caribbean
from $4,935
price per person Taxes included
1 booking 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 $4,691
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 $4,691
price per person Taxes included
1 booking 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, Antigua and Barbuda, United Kingdom, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $5,151
price per person Taxes included
Wind Surf | 7 Mar 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Anguilla,
4. Virgin Gorda,
5. Tortola Island,
6. Tortola Island,
7. Jost Van Dyke,
8. Gustavia,
9. Philipsburg
sold out

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

Philipsburg Itinerary Caribbean
from $5,151
price per person Taxes included
Wind Surf | 7 Mar 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Anguilla,
4. Virgin Gorda,
5. Tortola Island,
6. Tortola Island,
7. Jost Van Dyke,
8. Gustavia,
9. Philipsburg
sold out

Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $4,592
price per person Taxes included
Wind Surf | 14 Mar 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. navigation,
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, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $4,592
price per person Taxes included
Wind Surf | 14 Mar 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. navigation,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg

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

Philipsburg Itinerary Caribbean
from $4,563
price per person Taxes included
Wind Surf | 21 Mar 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
sold out

Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $4,376
price per person Taxes included
Wind Surf | 21 Mar 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
33 cruises