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

from $4,865
price per person Taxes included

Wind Surf | 4 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, Virgin Islands, Montserrat, Saint Lucia, Saint Vincent and the Grenadines, Guadeloupe

from $10,625
price per person Taxes included

Silver Shadow | 4 Jan 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, Dominica, Guadeloupe, France, Saint Barthelemy

from $4,437
price per person Taxes included

See the cruise Book

Star Flyer | 10 Jan 2026

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, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Sri Lanka, Saint Vincent and the Grenadines, Barbados

from $4,914
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, Saint Vincent and the Grenadines, Barbados

from $4,914
price per person Taxes included

See the cruise Book

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. Mayreau,

7. Kingstown,

8. Bridgetown

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

from $10,812
price per person Taxes included

Silver Shadow | 11 Jan 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, Dominica, Saint Lucia, Martinique, Guadeloupe, United States, British Virgin Islands, Virgin Islands, Saint Barthelemy

from $8,450
price per person Taxes included

5 reservations in 72 hours

See the cruise Book

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

from $6,772
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, British Virgin Islands, Saint Kitts and Nevis, Saint Pierre and Miquelon, Saint Vincent and the Grenadines, Grenada, Barbados

from $9,507
price per person Taxes included

See the cruise Book

Seabourn Ovation | 17 Jan 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Bridgetown

Itinerary:

1. Philipsburg,

2. Frenchman's Cay,

3. Basseterre,

4. navigation,

5. Saint Pierre,

6. Bequia,

7. Saint George,

8. Bridgetown

Caribbean: Sint Maarten, British Virgin Islands, Saint Kitts and Nevis, Saint Pierre and Miquelon, Saint Vincent and the Grenadines, Grenada, Barbados, Saint Lucia, United Kingdom, Antigua and Barbuda, Virgin Islands

from $17,150
price per person Taxes included

See the cruise Book

Seabourn Ovation | 17 Jan 2026

Duration: 14 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Frenchman's Cay,

3. Basseterre,

4. navigation,

5. Saint Pierre,

6. Bequia,

7. Saint George,

8. Bridgetown,

9. Castries,

10. navigation,

11. Montserrat,

12. Saint Johns,

13. Basseterre,

14. Jost Van Dyke,

15. Philipsburg

Caribbean: Sint Maarten, United Kingdom, United States, Guadeloupe, Netherlands, Saint Barthelemy, Puerto Rico

from $8,920
price per person Taxes included

4 reservations in 72 hours

See the cruise Book

SeaDream II | 18 Jan 2026

Duration: 7 nights

Departure from: Philipsburg Landing: San Juan

Itinerary:

1. Philipsburg,

2. Falmouth,

3. Charlestown,

4. Terre-de-Haut,

5. Saba,

6. Gustavia,

7. Gustavia,

8. navigation,

9. San Juan

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

from $4,958
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

from $5,145
price per person Taxes included

4 reservations in 72 hours

See the cruise Book

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, Dominica, Guadeloupe, France, Saint Barthelemy

from $4,437
price per person Taxes included

6 reservations in 72 hours

See the cruise Book

Star Flyer | 24 Jan 2026

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, British Virgin Islands, Virgin Islands, Saint Barthelemy

from $4,772
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

Caribbean: Sint Maarten, British Virgin Islands, Saint Kitts and Nevis, Saint Pierre and Miquelon, Saint Vincent and the Grenadines, Grenada, Barbados

from $9,507
price per person Taxes included

See the cruise Book

Seabourn Ovation | 31 Jan 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Bridgetown

Itinerary:

1. Philipsburg,

2. Frenchman's Cay,

3. Basseterre,

4. navigation,

5. Saint Pierre,

6. Bequia,

7. Saint George,

8. Bridgetown

Caribbean: Sint Maarten, British Virgin Islands, Saint Kitts and Nevis, Saint Pierre and Miquelon, Saint Vincent and the Grenadines, Grenada, Barbados, France, Guadeloupe, Dominica, Saint Lucia

from $17,150
price per person Taxes included

See the cruise Book

Seabourn Ovation | 31 Jan 2026

Duration: 14 nights

Departure from: Philipsburg Landing: Bridgetown

Itinerary:

1. Philipsburg,

2. Frenchman's Cay,

3. Basseterre,

4. navigation,

5. Saint Pierre,

6. Bequia,

7. Saint George,

8. Bridgetown,

9. navigation,

10. Basseterre,

11. Les Trois-Îlets,

12. Pointe à Pitre,

13. Roseau,

14. Rodney Bay,

15. Bridgetown

Cruises Sint Maarten in January 2026

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

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

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

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

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

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

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