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

External from $5,037
price per person Taxes included

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Wind Spirit | Feb. 7, 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

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

External from $4,229
price per person Taxes included

Wind Spirit | Feb. 7, 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, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $4,460
price per person Taxes included

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Wind Spirit | Feb. 14, 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 $4,299
price per person Taxes included

Wind Spirit | Feb. 14, 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

Mexico, Cayman Islands, Jamaica, Dominican Republic, Virgin Islands, British Virgin Islands, Sint Maarten

External from $6,566
price per person Taxes included

Wind Surf | Feb. 17, 2026

Duration: 11 nights

Departure from: Cozumel Island Landing: Philipsburg

Itinerary:

1. Cozumel Island,

2. navigation,

3. George Town,

4. George Town,

5. Port Antonio,

6. navigation,

7. Santo Domingo,

8. La Romana,

9. navigation,

10. Jost Van Dyke,

11. Virgin Gorda,

12. Philipsburg

Caribbean: Mexico, Cayman Islands, Jamaica, Dominican Republic, Virgin Islands, British Virgin Islands, Sint Maarten

External from $6,566
price per person Taxes included

See the cruise Book

Wind Surf | Feb. 17, 2026

Duration: 11 nights

Departure from: Cozumel Island Landing: Philipsburg

Itinerary:

1. Cozumel Island,

2. navigation,

3. George Town,

4. George Town,

5. Ocho Rios,

6. navigation,

7. Santo Domingo,

8. La Romana,

9. navigation,

10. Jost Van Dyke,

11. Virgin Gorda,

12. Philipsburg

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

External from $4,299
price per person Taxes included

See the cruise Book

Wind Spirit | Feb. 21, 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 $4,299
price per person Taxes included

Wind Spirit | Feb. 21, 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 $4,446
price per person Taxes included

See the cruise Book

Wind Surf | Feb. 28, 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 $4,072
price per person Taxes included

Wind Spirit | Feb. 28, 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 $4,396
price per person Taxes included

See the cruise Book

Wind Spirit | Feb. 28, 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 $4,123
price per person Taxes included

Wind Surf | Feb. 28, 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

All Caribbean Cruises with Windstar Cruises in February 2026