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

External from $4,047
price per person Taxes included

Wind Surf | 2/12/2025

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

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

External from $4,245
price per person Taxes included

See the cruise Book

Wind Surf | 2/12/2025

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

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

External from $5,036
price per person Taxes included

See the cruise Book

Wind Surf | 7/12/2025

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

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

External from $4,641
price per person Taxes included

Wind Surf | 7/12/2025

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 $5,265
price per person Taxes included

See the cruise Book

Wind Surf | 14/12/2025

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 $4,870
price per person Taxes included

Wind Surf | 14/12/2025

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

External from $5,431
price per person Taxes included

Wind Surf | 21/12/2025

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

External from $6,023
price per person Taxes included

See the cruise Book

Wind Surf | 21/12/2025

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 $6,252
price per person Taxes included

See the cruise Book

Wind Surf | 28/12/2025

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 $5,463
price per person Taxes included

Wind Surf | 28/12/2025

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 $5,350
price per person Taxes included

See the cruise Book

Wind Surf | 4/01/2026

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

External from $5,153
price per person Taxes included

Wind Surf | 4/01/2026

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, Sri Lanka, Saint Vincent and the Grenadines, Barbados

External from $5,204
price per person Taxes included

Wind Surf | 11/01/2026

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

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

External from $5,401
price per person Taxes included

See the cruise Book

Wind Surf | 11/01/2026

Duration: 7 nights

Departure from: Philipsburg Landing: Bridgetown

Itinerary:

1. Philipsburg,

2. Basseterre,

3. Gustavia,

4. Saint Johns,

5. Les Saintes,

6. Mayreau,

7. Kingstown,

8. Bridgetown

Caribbean: Sint Maarten, Saint Kitts and Nevis, Dominica, Saint Lucia, Martinique, Guadeloupe, United States, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $8,554
price per person Taxes included

See the cruise Book

Wind Spirit | 14/01/2026

Duration: 10 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Basseterre,

3. Roseau,

4. Castries,

5. Fort de france,

6. Les Saintes,

7. Charlestown,

8. Virgin Gorda,

9. Jost Van Dyke,

10. Gustavia,

11. Philipsburg

Sint Maarten, Saint Kitts and Nevis, Dominica, Saint Lucia, Martinique, Guadeloupe, United States, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $7,172
price per person Taxes included

Wind Spirit | 14/01/2026

Duration: 10 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Basseterre,

3. Roseau,

4. Castries,

5. Fort de france,

6. Les Saintes,

7. Charlestown,

8. Virgin Gorda,

9. Jost Van Dyke,

10. Gustavia,

11. Philipsburg

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

External from $5,449
price per person Taxes included

See the cruise Book

Wind Spirit | 24/01/2026

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 $5,251
price per person Taxes included

Wind Spirit | 24/01/2026

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

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

External from $5,054
price per person Taxes included

See the cruise Book

Wind Spirit | 31/01/2026

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

External from $5,054
price per person Taxes included

Wind Spirit | 31/01/2026

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

External from $5,166
price per person Taxes included

Wind Spirit | 7/02/2026

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

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

External from $6,154
price per person Taxes included

See the cruise Book

Wind Spirit | 7/02/2026

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Charlestown,

3. Roseau,

4. Mayreau,

5. Fort de france,

6. Basseterre,

7. Gustavia,

8. Philipsburg

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

External from $5,449
price per person Taxes included

See the cruise Book

Wind Spirit | 14/02/2026

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

External from $5,251
price per person Taxes included

Wind Spirit | 14/02/2026

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 $5,251
price per person Taxes included

See the cruise Book

Wind Spirit | 21/02/2026

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 $5,251
price per person Taxes included

Wind Spirit | 21/02/2026

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

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

External from $5,431
price per person Taxes included

See the cruise Book

Wind Surf | 28/02/2026

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Charlestown,

3. Roseau,

4. Mayreau,

5. Deshaies,

6. Basseterre,

7. Gustavia,

8. Philipsburg

Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Dominica, Sri Lanka, Barbados

External from $4,975
price per person Taxes included

Wind Spirit | 28/02/2026

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

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

External from $5,370
price per person Taxes included

See the cruise Book

Wind Spirit | 28/02/2026

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

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

External from $5,036
price per person Taxes included

Wind Surf | 28/02/2026

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

Cruises of Windstar Cruises in Sint Maarten