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

External from €2,050
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

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

External from €1,799
price per person Taxes included

See the cruise Book

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

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

External from €2,551
price per person Taxes included

See the cruise

Book Online

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

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

External from €2,351
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 €2,867
price per person Taxes included

See the cruise

Book Online

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 €2,467
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, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

External from €2,751
price per person Taxes included

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

External from €3,651
price per person Taxes included

See the cruise

Book Online

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, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from €3,867
price per person Taxes included

See the cruise

Book Online

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

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

External from €2,767
price per person Taxes included

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, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from €3,310
price per person Taxes included

See the cruise

Book Online

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, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from €2,610
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, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Sri Lanka, Saint Vincent and the Grenadines, Barbados

External from €2,636
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

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

External from €3,236
price per person Taxes included

See the cruise

Book Online

Wind Surf | 11 Jan 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

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

External from €5,333
price per person Taxes included

See the cruise

Book Online

Wind Spirit | 14 Jan 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 €3,633
price per person Taxes included

Wind Spirit | 14 Jan 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 €3,560
price per person Taxes included

See the cruise

Book Online

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 €2,660
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

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

External from €3,760
price per person Taxes included

See the cruise

Book Online

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

External from €2,560
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, United States, Dominica, Sri Lanka, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

External from €2,617
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

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

External from €3,717
price per person Taxes included

See the cruise

Book Online

Wind Spirit | 07 Feb 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 €3,560
price per person Taxes included

See the cruise

Book Online

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

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

External from €2,660
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 €3,460
price per person Taxes included

See the cruise

Book Online

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 €2,660
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

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

External from €3,151
price per person Taxes included

See the cruise

Book Online

Wind Surf | 28 Feb 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 €2,520
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

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

External from €3,420
price per person Taxes included

See the cruise

Book Online

Wind Spirit | 28 Feb 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Bridgetown

Itinerary:

1. Philipsburg,

2. Basseterre,

3. Gustavia,

4. navigation,

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 €2,551
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

Cruises of Windstar Cruises in Sint Maarten