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

from $2,283.60
price per person Taxes included

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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

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

from $2,283.60
price per person Taxes included

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

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

from $2,618.90
price per person Taxes included

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

from $2,618.90
price per person Taxes included

2 reservations in 72 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, Dominica, Guadeloupe, France, Saint Barthelemy

from $2,651.20
price per person Taxes included

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Star Flyer | Dec 13, 2025

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Barbuda,

3. Cabritz Bay,

4. Terre-de-Haut,

5. Deshaies,

6. Falmouth Harbour,

7. Gustavia,

8. Philipsburg

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

from $2,748.11
price per person Taxes included

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

from $2,748.11
price per person Taxes included

See the cruise Book

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 Kingdom, United States, Saint Barthelemy, Antigua and Barbuda, Virgin Islands, Puerto Rico

from $4,474.74
price per person Taxes included

5 reservations in 72 hours

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SeaDream I | Dec 20, 2025

Duration: 7 nights

Departure from: Philipsburg Landing: San Juan

Itinerary:

1. Philipsburg,

2. Anguilla,

3. Charlestown,

4. Gustavia,

5. Gustavia,

6. Saint Johns,

7. Lovango Island,

8. San Juan

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

from $3,064.48
price per person Taxes included

5 reservations in 72 hours

See the cruise Book

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

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

from $3,064.48
price per person Taxes included

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: Sint Maarten, Antigua and Barbuda, Dominica, Guadeloupe, France, Saint Barthelemy

from $2,723.61
price per person Taxes included

See the cruise Book

Star Flyer | Dec 27, 2025

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Barbuda,

3. Cabritz Bay,

4. Terre-de-Haut,

5. Deshaies,

6. Falmouth Harbour,

7. Gustavia,

8. Philipsburg

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

from $3,082.30
price per person Taxes included

4 reservations in 72 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

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

from $3,082.30
price per person Taxes included

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

Cruises Sint Maarten in December 2025

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

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

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

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

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