Cruises of Windstar Cruises in Sint Maarten

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

External from $14,364
price per person Taxes included

Wind Surf | Dec. 21, 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

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

External from $7,168
price per person Taxes included

See the cruise

Book Online

Wind Surf | Dec. 21, 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, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $7,030
price per person Taxes included

See the cruise

Book Online

Wind Surf | Dec. 28, 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

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

External from $6,936
price per person Taxes included

See the cruise

Book Online

Wind Surf | Jan. 4, 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

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

External from $47,194
price per person Taxes included

Wind Surf | Jan. 4, 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

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

External from $25,693
price per person Taxes included

Wind Surf | Jan. 4, 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

Caribbean: 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

External from $19,061
price per person Taxes included

See the cruise

Book Online

Wind Surf | Jan. 4, 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

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

External from $12,598
price per person Taxes included

See the cruise

Book Online

Wind Surf | Jan. 4, 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

Caribbean: Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Barbados, Martinique, Saint Lucia, Sri Lanka, Grenada

External from $13,442
price per person Taxes included

See the cruise

Book Online

Wind Surf | Jan. 11, 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

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

External from $6,979
price per person Taxes included

See the cruise

Book Online

Wind Surf | Jan. 11, 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