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home Port of departureJanuary 2026

Cruises from Philipsburg January 2026

  • 2025
  • 2026
  • 2027
17 cruises
sold out

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

Philipsburg Itinerary Caribbean
from $4,785
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
sold out

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

Philipsburg Itinerary Caribbean
from $10,449
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

Philipsburg Itinerary Caribbean
from $4,363
price per person Taxes included
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
sold out

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

Philipsburg Itinerary Caribbean
from $4,832
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

Philipsburg Itinerary Caribbean
from $5,016
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. Saint Johns,
5. Les Saintes,
6. Mayreau,
7. Kingstown,
8. Bridgetown
sold out

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

Philipsburg Itinerary Caribbean
from $10,633
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

Philipsburg Itinerary Caribbean
from $8,493
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
sold out

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

Philipsburg Itinerary Caribbean
from $6,660
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

Philipsburg Itinerary Caribbean
from $8,249
price per person Taxes included
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

Philipsburg Itinerary Caribbean
from $14,849
price per person Taxes included
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

Philipsburg Itinerary Caribbean
from $8,772
price per person Taxes included
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
sold out

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

Philipsburg Itinerary Caribbean
from $4,876
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

Philipsburg Itinerary Caribbean
from $5,060
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, Dominica, Guadeloupe, France, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $4,363
price per person Taxes included
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
sold out

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

Philipsburg Itinerary Caribbean
from $4,693
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

Philipsburg Itinerary Caribbean
from $8,249
price per person Taxes included
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

Philipsburg Itinerary Caribbean
from $14,849
price per person Taxes included
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
17 cruises