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

External from R 43 784
price per person Taxes included

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

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

External from R 50 212
price per person Taxes included

Wind Surf | 21 Mar 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

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

External from R 50 212
price per person Taxes included

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, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from R 52 327
price per person Taxes included

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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

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

External from R 52 690
price per person Taxes included

Wind Surf | 28 Mar 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

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

External from R 52 690
price per person Taxes included

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

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

External from R 52 690
price per person Taxes included

Wind Surf | 14 Mar 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, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Dominica, Sri Lanka, Barbados

External from R 53 822
price per person Taxes included

Wind Spirit | 28 Feb 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Bridgetown

Itinerary:

1. Philipsburg,

2. Basseterre,

3. Gustavia,

4. St. John ,

5. Les Saintes,

6. Roseau,

7. Pigeon Island,

8. Bridgetown

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

External from R 54 484
price per person Taxes included

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Wind Surf | 09 Jan 2027

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Charlestown,

3. Les Saintes,

4. Mayreau,

5. Roseau,

6. Basseterre,

7. Gustavia,

8. Philipsburg

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

External from R 54 484
price per person Taxes included

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

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

External from R 54 676
price per person Taxes included

Wind Spirit | 31 Jan 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

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

External from R 54 826
price per person Taxes included

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Wind Surf | 02 Jan 2027

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

External from R 54 826
price per person Taxes included

See the cruise

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Wind Surf | 16 Jan 2027

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Tortola Island,

3. Tortola Island,

4. Jost Van Dyke,

5. Jost Van Dyke,

6. Virgin Gorda,

7. Gustavia,

8. navigation,

9. Philipsburg

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

External from R 55 744
price per person Taxes included

Wind Surf | 04 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

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

External from R 55 894
price per person Taxes included

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

Sint Maarten, Portugal

External from R 56 086
price per person Taxes included

Wind Surf | 04 Apr 2026

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

Ocean Cruises: Sint Maarten, Portugal

External from R 56 086
price per person Taxes included

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Wind Surf | 04 Apr 2026

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

Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Sri Lanka, Saint Vincent and the Grenadines, Barbados

External from R 56 299
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. St. John ,

5. Les Saintes,

6. Pigeon Island,

7. Kingstown,

8. Bridgetown

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

External from R 56 620
price per person Taxes included

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Wind Surf | 23 Jan 2027

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

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

External from R 56 620
price per person Taxes included

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Wind Surf | 06 Feb 2027

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

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

External from R 56 620
price per person Taxes included

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Wind Surf | 06 Mar 2027

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

External from R 56 620
price per person Taxes included

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Wind Surf | 21 Mar 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

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

External from R 56 620
price per person Taxes included

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Wind Surf | 20 Feb 2027

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

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

External from R 56 812
price per person Taxes included

Wind Spirit | 24 Jan 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Saint Johns,

3. Tortola Island,

4. Virgin Gorda,

5. Tortola Island,

6. Tortola Island,

7. Jost Van Dyke,

8. Gustavia,

9. Philipsburg

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

External from R 56 812
price per person Taxes included

Wind Spirit | 21 Feb 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Saint Johns,

3. Tortola Island,

4. Virgin Gorda,

5. Tortola Island,

6. Tortola Island,

7. Jost Van Dyke,

8. Gustavia,

9. Philipsburg

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

External from R 56 812
price per person Taxes included

Wind Spirit | 14 Feb 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

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

External from R 56 962
price per person Taxes included

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Wind Surf | 28 Mar 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

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

External from R 56 962
price per person Taxes included

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Wind Surf | 30 Jan 2027

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Tortola Island,

3. Tortola Island,

4. Jost Van Dyke,

5. Jost Van Dyke,

6. Virgin Gorda,

7. Gustavia,

8. navigation,

9. Philipsburg

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

External from R 56 962
price per person Taxes included

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Wind Surf | 13 Feb 2027

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

External from R 56 962
price per person Taxes included

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Wind Surf | 13 Mar 2027

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

Itineraries and cruises Windstar Cruises departing from Philipsburg