Sint Maarten, Virgin Islands, Montserrat, Saint Lucia, Saint Vincent and the Grenadines, Guadeloupe

from $6,368.27
price per person Taxes included

Silver Shadow | Jan 4, 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. navigation,

3. Saint Thomas,

4. Little Bay,

5. Castries,

6. Mayreau,

7. Les Saintes,

8. Philipsburg

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

from $2,916.00
price per person Taxes included

16 reservations in 36 hours

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Wind Surf | Jan 4, 2026

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, Virgin Islands, Montserrat, Saint Lucia, Saint Vincent and the Grenadines, Guadeloupe

from $6,479.99
price per person Taxes included

Silver Shadow | Jan 11, 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. navigation,

3. Saint Thomas,

4. Little Bay,

5. Castries,

6. Mayreau,

7. Les Saintes,

8. Philipsburg

Caribbean: Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Sri Lanka, Saint Vincent and the Grenadines, Barbados

from $2,945.04
price per person Taxes included

18 reservations in 36 hours

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Wind Surf | Jan 11, 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, Dominica, Saint Lucia, Martinique, Guadeloupe, United States, British Virgin Islands, Virgin Islands, Saint Barthelemy

from $4,058.93
price per person Taxes included

19 reservations in 36 hours

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Wind Spirit | Jan 14, 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, Virgin Islands, United Kingdom, British Virgin Islands, Saint Barthelemy

from $2,971.86
price per person Taxes included

19 reservations in 36 hours

See the cruise Book

Wind Spirit | Jan 24, 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. St. John ,

3. Anguilla,

4. Virgin Gorda,

5. Tortola Island,

6. Tortola Island,

7. Jost Van Dyke,

8. Gustavia,

9. Philipsburg

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

from $2,860.13
price per person Taxes included

21 reservations in 36 hours

See the cruise Book

Wind Spirit | Jan 31, 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. St. John ,

3. Anguilla,

4. Tortola Island,

5. Jost Van Dyke,

6. Jost Van Dyke,

7. Virgin Gorda,

8. Gustavia,

9. Philipsburg

Cruises from Philipsburg January 2026

Sint Maarten, Virgin Islands, Montserrat, Saint Lucia, Saint Vincent and the Grenadines, Guadeloupe

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

Sint Maarten, Virgin Islands, Montserrat, Saint Lucia, Saint Vincent and the Grenadines, Guadeloupe

Caribbean: Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Sri Lanka, Saint Vincent and the Grenadines, Barbados

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

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

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