Windstar Cruises from Philipsburg: 7 Set offures December 2025

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

External from £1,822
price per person Taxes included

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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

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

External from £1,835
price per person Taxes included

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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

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

External from £2,462
price per person Taxes included

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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, British Virgin Islands, Virgin Islands

External from £2,877
price per person Taxes included

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Wind Surf | 7 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

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 £4,107
price per person Taxes included

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Wind Surf | 14 Dec 2025

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, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from £4,324
price per person Taxes included

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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

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

External from £7,746
price per person Taxes included

See the cruise

Book Online

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

Itineraries and cruises Windstar Cruises set offing from Philipsburg December 2025 - 2026