Windstar Cruises from Philipsburg: 7 Departures March 2026

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

External from $4,081
price per person Taxes included

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Wind Surf | Mar 14, 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, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $4,202
price per person Taxes included

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Wind Surf | Mar 7, 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. navigation,

3. Tortola Island,

4. Virgin Gorda,

5. Tortola Island,

6. Tortola Island,

7. Jost Van Dyke,

8. Gustavia,

9. Philipsburg

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

External from $4,425
price per person Taxes included

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Wind Surf | Mar 21, 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

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

External from $4,566
price per person Taxes included

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Wind Surf | Mar 28, 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

Ocean Cruises: Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy, Portugal

External from $6,719
price per person Taxes included

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Wind Surf | Mar 28, 2026

Duration: 21 nights

Departure from: Philipsburg Landing: Lisbon

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,

10. navigation,

11. navigation,

12. navigation,

13. navigation,

14. navigation,

15. navigation,

16. navigation,

17. navigation,

18. navigation,

19. Ponta Delgada,

20. navigation,

21. navigation,

22. navigation,

23. Lisbon

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

External from $7,416
price per person Taxes included

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Wind Surf | Mar 14, 2026

Duration: 14 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. Charlestown,

11. Roseau,

12. Mayreau,

13. Les Saintes,

14. Basseterre,

15. Gustavia,

16. Philipsburg

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

External from $7,659
price per person Taxes included

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Wind Surf | Mar 21, 2026

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. Saint Johns,

10. Tortola Island,

11. Tortola Island,

12. Jost Van Dyke,

13. Jost Van Dyke,

14. Virgin Gorda,

15. Gustavia,

16. Philipsburg

Itineraries and cruises Windstar Cruises departing from Philipsburg March 2026 - 2027