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

from $2,290.34
price per person Taxes included

17 reservations in 36 hours

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Wind Surf | Dec 2, 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

from $2,626.63
price per person Taxes included

19 reservations in 36 hours

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Wind Surf | Dec 7, 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, Antigua and Barbuda, United Kingdom, British Virgin Islands, Virgin Islands, Saint Barthelemy

from $2,756.23
price per person Taxes included

16 reservations in 48 hours

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Wind Surf | Dec 14, 2025

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Falmouth Harbour,

3. Anguilla,

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

from $3,073.53
price per person Taxes included

19 reservations in 48 hours

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Wind Surf | Dec 21, 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: Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Sri Lanka, Martinique

from $3,257.87
price per person Taxes included

18 reservations in 36 hours

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Wind Spirit | Dec 28, 2025

Duration: 7 nights

Departure from: Bridgetown Landing: Bridgetown

Itinerary:

1. Bridgetown,

2. navigation,

3. Basseterre,

4. Les Saintes,

5. Roseau,

6. Pigeon Island,

7. Fort de france,

8. Bridgetown

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

from $3,091.40
price per person Taxes included

15 reservations in 36 hours

See the cruise Book

Wind Surf | Dec 28, 2025

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Falmouth Harbour,

3. Anguilla,

4. Tortola Island,

5. Jost Van Dyke,

6. Jost Van Dyke,

7. Virgin Gorda,

8. Gustavia,

9. Philipsburg

All Caribbean Cruises with Windstar Cruises in December 2025

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

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

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

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

Caribbean: Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Sri Lanka, Martinique

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