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Cruises of Windstar Cruises in Sint Maarten

  • 2026
  • 2027
January 2026 February 2026 March 2026 April 2026 May 2026 June 2026 July 2026 August 2026 September 2026 October 2026 November 2026 December 2026
58 cruises
sold out
Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy, British Virgin Islands, Virgin Islands
Philipsburg Itinerary Caribbean
External from £7,746
price per person Taxes included
Wind Surf | 21 Dec 2025
Duration: 14 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg,
9. navigation,
10. Tortola Island,
11. Tortola Island,
12. Jost Van Dyke,
13. Jost Van Dyke,
14. Virgin Gorda,
15. Gustavia,
16. Philipsburg
Philipsburg Itinerary Caribbean
External from £3,865
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
Philipsburg Itinerary Caribbean
External from £3,791
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
Philipsburg Itinerary Caribbean
External from £3,740
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
sold out
Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Barbados, Martinique, Saint Lucia, Sri Lanka, Grenada, Netherlands Antilles, Aruba, Colombia, Panama, Honduras, Belize, Mexico, Cayman Islands, Jamaica, Dominican Republic
Philipsburg Itinerary
External from £25,448
price per person Taxes included
Wind Surf | 4 Jan 2026
Duration: 55 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,
10. Basseterre,
11. Gustavia,
12. Saint Johns,
13. Les Saintes,
14. Roseau,
15. Mayreau,
16. Bridgetown,
17. Fort de france,
18. Castries,
19. Pigeon Island,
20. Pigeon Island,
21. Bequia,
22. Mayreau,
23. Saint George,
24. Bridgetown,
25. Bequia,
26. Mayreau,
27. Soufriere,
28. navigation,
29. Kralendijk,
30. Willemstad,
31. Oranjestad,
32. navigation,
33. Cartagena De Indias,
34. Cartagena De Indias,
35. San Blas Island,
36. navigation,
37. Bocas del Toro,
38. Colon,
39. Colon,
40. Bocas del Toro,
41. San Andres,
42. navigation,
43. navigation,
44. Roatan,
45. Belize City,
46. Costa Maya,
47. Cozumel Island,
48. navigation,
49. George Town,
50. George Town,
51. Ocho Rios,
52. navigation,
53. Santo Domingo,
54. La Romana,
55. navigation,
56. Jost Van Dyke,
57. Virgin Gorda,
58. Philipsburg
sold out
Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Barbados, Martinique, Saint Lucia, Sri Lanka, Grenada, Netherlands Antilles, Aruba
Philipsburg Itinerary
External from £13,854
price per person Taxes included
Wind Surf | 4 Jan 2026
Duration: 28 nights
Departure from: Philipsburg Landing: Oranjestad
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,
10. Basseterre,
11. Gustavia,
12. Saint Johns,
13. Les Saintes,
14. Roseau,
15. Mayreau,
16. Bridgetown,
17. Fort de france,
18. Castries,
19. Pigeon Island,
20. Pigeon Island,
21. Bequia,
22. Mayreau,
23. Saint George,
24. Bridgetown,
25. Bequia,
26. Mayreau,
27. Soufriere,
28. navigation,
29. Kralendijk,
30. Willemstad,
31. Oranjestad
Philipsburg Itinerary Caribbean
External from £10,278
price per person Taxes included
Wind Surf | 4 Jan 2026
Duration: 21 nights
Departure from: Philipsburg Landing: Bridgetown
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,
10. Basseterre,
11. Gustavia,
12. Saint Johns,
13. Les Saintes,
14. Roseau,
15. Mayreau,
16. Bridgetown,
17. Fort de france,
18. Castries,
19. Pigeon Island,
20. Pigeon Island,
21. Bequia,
22. Mayreau,
23. Saint George,
24. Bridgetown
Philipsburg Itinerary Caribbean
External from £6,793
price per person Taxes included
Wind Surf | 4 Jan 2026
Duration: 14 nights
Departure from: Philipsburg Landing: Bridgetown
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,
10. Basseterre,
11. Gustavia,
12. Saint Johns,
13. Les Saintes,
14. Roseau,
15. Mayreau,
16. Bridgetown
Philipsburg Itinerary Caribbean
External from £7,248
price per person Taxes included
Wind Surf | 11 Jan 2026
Duration: 14 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,
9. Fort de france,
10. Castries,
11. Pigeon Island,
12. Pigeon Island,
13. Bequia,
14. Mayreau,
15. Saint George,
16. Bridgetown
Philipsburg Itinerary Caribbean
External from £3,763
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. Saint Johns,
5. Les Saintes,
6. Roseau,
7. Mayreau,
8. Bridgetown
58 cruises