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Cruises of Windstar Cruises in Sint Maarten

  • 2024
  • 2025
  • 2026
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36 cruises

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

Philipsburg Itinerary Caribbean
from R 51 284,41
price per person Taxes included
19 reservations in 36 hours
Wind Surf | 21 Dec 2024
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, United Kingdom, Virgin Islands, British Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from R 85 808,06
price per person Taxes included
Wind Surf | 28 Dec 2024
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Anguilla,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Tortola Island,
7. Tortola Island,
8. Gustavia,
9. Philipsburg

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

Philipsburg Itinerary Caribbean
from R 63 879,55
price per person Taxes included
16 reservations in 48 hours
Wind Surf | 04 Jan 2025
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, Antigua and Barbuda, Saint Barthelemy, British Virgin Islands, Virgin Islands, United Kingdom

Philipsburg Itinerary Caribbean
from R 64 193,94
price per person Taxes included
18 reservations in 36 hours
Wind Surf | 11 Jan 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Gustavia,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Anguilla,
9. Philipsburg

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

Philipsburg Itinerary Caribbean
from R 63 879,55
price per person Taxes included
15 reservations in 48 hours
Wind Surf | 18 Jan 2025
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, Sri Lanka, Guadeloupe, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Anguilla, Virgin Islands, British Virgin Islands

Sint Maarten Itinerary Caribbean
from R 103 138,65
price per person Taxes included
22 reservations in 48 hours
Wind Surf | 18 Jan 2025
Duration: 14 nights
Departure from: Sint Maarten Landing: Sint Maarten
Itinerary:
1. Sint Maarten,
2. Charlestown,
3. Roseau,
4. Pigeon Island,
5. Les Saintes,
6. Gustavia,
7. Basseterre,
8. Sint Maarten,
9. Falmouth Harbour,
10. Baie Road,
11. Jost Van Dyke,
12. Jost Van Dyke,
13. Virgin Gorda,
14. Gustavia,
15. Sint Maarten

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

Philipsburg Itinerary Caribbean
from R 64 193,94
price per person Taxes included
19 reservations in 48 hours
Wind Surf | 25 Jan 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Anguilla,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg

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

Philipsburg Itinerary Caribbean
from R 70 088,70
price per person Taxes included
20 reservations in 48 hours
Wind Surf | 01 Feb 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Anguilla,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg

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

Philipsburg Itinerary Caribbean
from R 63 879,55
price per person Taxes included
17 reservations in 36 hours
Wind Surf | 08 Feb 2025
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, Antigua and Barbuda, Virgin Islands, British Virgin Islands, Saint Barthelemy, United Kingdom

Philipsburg Itinerary Caribbean
from R 64 193,94
price per person Taxes included
19 reservations in 48 hours
Wind Surf | 15 Feb 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Jost Van Dyke,
4. Virgin Gorda,
5. Tortola Island,
6. Gustavia,
7. Anguilla,
8. Philipsburg

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

Philipsburg Itinerary Caribbean
from R 63 879,55
price per person Taxes included
17 reservations in 48 hours
Wind Surf | 22 Feb 2025
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, Antigua and Barbuda, United Kingdom, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from R 68 123,78
price per person Taxes included
19 reservations in 48 hours
Wind Surf | 01 Mar 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Anguilla,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg

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

Philipsburg Itinerary Caribbean
from R 62 229,02
price per person Taxes included
17 reservations in 36 hours
Wind Surf | 08 Mar 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Anguilla,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg

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

Philipsburg Itinerary Caribbean
from R 63 879,55
price per person Taxes included
19 reservations in 48 hours
Wind Surf | 15 Mar 2025
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, Antigua and Barbuda, United Kingdom, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from R 64 193,94
price per person Taxes included
15 reservations in 48 hours
Wind Surf | 22 Mar 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Anguilla,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg

Ocean Cruises: Sint Maarten, Portugal

Philipsburg Itinerary Ocean Cruises
from R 49 633,88
price per person Taxes included
20 reservations in 36 hours
Wind Surf | 29 Mar 2025
Duration: 14 nights
Departure from: Philipsburg Landing: Lisbon
Itinerary:
1. Philipsburg,
2. navigation,
3. navigation,
4. navigation,
5. navigation,
6. navigation,
7. navigation,
8. navigation,
9. navigation,
10. navigation,
11. Ponta Delgada,
12. navigation,
13. navigation,
14. navigation,
15. Lisbon

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

Philipsburg Itinerary Caribbean
from R 40 280,86
price per person Taxes included
17 reservations in 36 hours
Wind Surf | 02 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 R 46 195,27
price per person Taxes included
19 reservations in 36 hours
Wind Surf | 07 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, Antigua and Barbuda, United Kingdom, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from R 48 474,58
price per person Taxes included
16 reservations in 48 hours
Wind Surf | 14 Dec 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Anguilla,
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 R 54 054,95
price per person Taxes included
19 reservations in 48 hours
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, Antigua and Barbuda, United Kingdom, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from R 54 369,34
price per person Taxes included
15 reservations in 36 hours
Wind Surf | 28 Dec 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Anguilla,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg

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

Philipsburg Itinerary Caribbean
from R 51 284,41
price per person Taxes included
16 reservations in 36 hours
Wind Surf | 04 Jan 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Anguilla,
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, Virgin Islands, Guadeloupe, Sri Lanka, Saint Vincent and the Grenadines, Barbados

Philipsburg Itinerary Caribbean
from R 51 795,29
price per person Taxes included
18 reservations in 36 hours
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 R 71 385,54
price per person Taxes included
19 reservations in 36 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

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 | 24 Jan 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, Virgin Islands, United Kingdom, British Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from R 50 301,95
price per person Taxes included
21 reservations in 36 hours
Wind Spirit | 31 Jan 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: 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: 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, 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
36 cruises