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All Caribbean Cruises with SeaDream Yacht Club

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91 cruises
sold out

Sint Maarten, Saint Barthelemy, United Kingdom

Philipsburg Itinerary Caribbean
from $3,678
price per person Taxes included
SeaDream I | Apr 9, 2025
Duration: 5 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. navigation,
3. Gustavia,
4. Gustavia,
5. Falmouth,
6. Philipsburg
sold out

Barbados, Saint Vincent and the Grenadines, Saint Lucia, Guadeloupe, Saint Barthelemy, British Virgin Islands, Sint Maarten

Bridgetown Itinerary Caribbean
from $4,670
price per person Taxes included
SeaDream I | Apr 12, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Philipsburg
Itinerary:
1. Bridgetown,
2. Bequia,
3. Rodney Bay,
4. Terre-de-Haut,
5. Gustavia,
6. navigation,
7. Tortola Island,
8. Norman Island,
9. Philipsburg
sold out

United States, Canada, Brazil, Bahamas

Palm Beach Itinerary Caribbean
from $8,788
price per person Taxes included
SeaDream II | Apr 12, 2025
Duration: 7 nights
Departure from: Palm Beach Landing: Palm Beach
Itinerary:
1. Palm Beach,
2. navigation,
3. Gordons Beach,
4. Salvador,
5. Staniel Cay,
6. Palm Beach
sold out

Sint Maarten, United Kingdom, Jamaica, British Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $4,310
price per person Taxes included
SeaDream I | Apr 13, 2025
Duration: 6 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Anguilla,
3. Spanish Town,
4. Norman Island,
5. navigation,
6. Gustavia,
7. Gustavia,
8. Philipsburg
sold out

Sint Maarten, Jamaica, British Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from $3,678
price per person Taxes included
SeaDream I | Apr 14, 2025
Duration: 5 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Spanish Town,
3. Norman Island,
4. navigation,
5. Gustavia,
6. Gustavia,
7. Philipsburg
sold out

Puerto Rico, Virgin Islands, United Kingdom, Saint Barthelemy

San Juan Itinerary Caribbean
from $4,690
price per person Taxes included
SeaDream I | Nov 15, 2025
Duration: 7 nights
Departure from: San Juan Landing: Charlotte Amalie
Itinerary:
1. San Juan,
2. St. John ,
3. navigation,
4. Anguilla,
5. Gustavia,
6. Gustavia,
7. Lovango Island,
8. Charlotte Amalie

Caribbean: Saint Martin, Guadeloupe, Saint Lucia, South Africa, Saint Vincent and the Grenadines, Barbados

Marigot Itinerary Caribbean
from $4,721
price per person Taxes included
5 reservations in 72 hours
See the cruise Book
SeaDream II | Nov 16, 2025
Duration: 7 nights
Departure from: Marigot Landing: Bridgetown
Itinerary:
1. Marigot,
2. Terre-de-Haut,
3. Rodney Bay,
4. Port Elizabeth,
5. Mayreau,
6. Tobago Cays,
7. Bridgetown
sold out

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

Charlotte Amalie Itinerary Caribbean
from $3,557
price per person Taxes included
SeaDream I | Nov 19, 2025
Duration: 5 nights
Departure from: Charlotte Amalie Landing: Charlotte Amalie
Itinerary:
1. Charlotte Amalie,
2. St. John ,
3. Anguilla,
4. Gustavia,
5. Gustavia,
6. Saint Johns,
7. Charlotte Amalie
sold out

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

Charlotte Amalie Itinerary Caribbean
from $4,690
price per person Taxes included
SeaDream I | Nov 22, 2025
Duration: 7 nights
Departure from: Charlotte Amalie Landing: Charlotte Amalie
Itinerary:
1. Charlotte Amalie,
2. Spanish Town,
3. Norman Island,
4. Saint Johns,
5. Philipsburg,
6. Gustavia,
7. Gustavia,
8. Charlestown,
9. Lovango Island,
10. Charlotte Amalie

Caribbean: Barbados, Saint Vincent and the Grenadines, South Africa, France, Saint Lucia

Bridgetown Itinerary Caribbean
from $5,148
price per person Taxes included
See the cruise Book
SeaDream II | Nov 23, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Tobago Cays,
3. Mayreau,
4. Port Elizabeth,
5. Port Elizabeth,
6. Le Marin,
7. Rodney Bay,
8. Bridgetown

Caribbean: Virgin Islands, Sint Maarten, Saint Barthelemy

Charlotte Amalie Itinerary Caribbean
from $4,378
price per person Taxes included
See the cruise Book
SeaDream I | Nov 24, 2025
Duration: 5 nights
Departure from: Charlotte Amalie Landing: Charlotte Amalie
Itinerary:
1. Charlotte Amalie,
2. St. John ,
3. Philipsburg,
4. Gustavia,
5. Gustavia,
6. navigation,
7. Charlotte Amalie
sold out

Virgin Islands, United Kingdom, Saint Barthelemy, Sint Maarten

Charlotte Amalie Itinerary Caribbean
from $4,905
price per person Taxes included
SeaDream I | Nov 29, 2025
Duration: 7 nights
Departure from: Charlotte Amalie Landing: Charlotte Amalie
Itinerary:
1. Charlotte Amalie,
2. St. John ,
3. navigation,
4. Anguilla,
5. Gustavia,
6. Gustavia,
7. Philipsburg,
8. Charlotte Amalie
sold out

Barbados, Guadeloupe, Saint Martin, Saint Barthelemy, Virgin Islands, Puerto Rico

Bridgetown Itinerary Caribbean
from $4,721
price per person Taxes included
SeaDream II | Nov 30, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: San Juan
Itinerary:
1. Bridgetown,
2. Terre-de-Haut,
3. Marigot,
4. Gustavia,
5. Gustavia,
6. navigation,
7. St. John ,
8. San Juan
sold out

Virgin Islands, Netherlands, United States, Saint Barthelemy, Antigua and Barbuda, Jamaica, British Virgin Islands, Puerto Rico

Charlotte Amalie Itinerary Caribbean
from $4,905
price per person Taxes included
SeaDream I | Dec 6, 2025
Duration: 7 nights
Departure from: Charlotte Amalie Landing: San Juan
Itinerary:
1. Charlotte Amalie,
2. Sint Eustatius,
3. Charlestown,
4. Gustavia,
5. Gustavia,
6. Saint Johns,
7. Spanish Town,
8. Norman Island,
9. San Juan

Caribbean: Puerto Rico, Virgin Islands, Jamaica, British Virgin Islands, Saint Barthelemy, United Kingdom

San Juan Itinerary Caribbean
from $5,789
price per person Taxes included
See the cruise Book
SeaDream II | Dec 7, 2025
Duration: 7 nights
Departure from: San Juan Landing: San Juan
Itinerary:
1. San Juan,
2. St. John ,
3. navigation,
4. Spanish Town,
5. Norman Island,
6. Gustavia,
7. Gustavia,
8. Anguilla,
9. San Juan

Caribbean: Puerto Rico, Honduras, Antigua and Barbuda, United Kingdom, Saint Barthelemy, United States, Sint Maarten

San Juan Itinerary Caribbean
from $4,721
price per person Taxes included
4 reservations in 72 hours
See the cruise Book
SeaDream I | Dec 13, 2025
Duration: 7 nights
Departure from: San Juan Landing: Philipsburg
Itinerary:
1. San Juan,
2. La Esperanza,
3. Culebra,
4. Saint Johns,
5. Anguilla,
6. Gustavia,
7. Gustavia,
8. Charlestown,
9. Falmouth,
10. Philipsburg

Caribbean: Puerto Rico, Jamaica, British Virgin Islands, Antigua and Barbuda, Saint Martin, Saint Barthelemy, Saint Kitts and Nevis, United States, Virgin Islands

San Juan Itinerary Caribbean
from $4,721
price per person Taxes included
4 reservations in 72 hours
See the cruise Book
SeaDream II | Dec 14, 2025
Duration: 7 nights
Departure from: San Juan Landing: Charlotte Amalie
Itinerary:
1. San Juan,
2. Spanish Town,
3. Norman Island,
4. Saint Johns,
5. Marigot,
6. Gustavia,
7. Gustavia,
8. Basseterre,
9. Charlestown,
10. Charlotte Amalie

Caribbean: Sint Maarten, United Kingdom, United States, Saint Barthelemy, Antigua and Barbuda, Virgin Islands, Puerto Rico

Philipsburg Itinerary Caribbean
from $5,789
price per person Taxes included
See the cruise Book
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. St. John ,
8. San Juan

Caribbean: Virgin Islands, United States, Saint Barthelemy, Antigua and Barbuda, Jamaica, British Virgin Islands, Puerto Rico

Charlotte Amalie Itinerary Caribbean
from $5,789
price per person Taxes included
See the cruise Book
SeaDream II | Dec 21, 2025
Duration: 7 nights
Departure from: Charlotte Amalie Landing: San Juan
Itinerary:
1. Charlotte Amalie,
2. St. John ,
3. Charlestown,
4. Gustavia,
5. Gustavia,
6. Saint Johns,
7. Spanish Town,
8. Norman Island,
9. San Juan
sold out

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

San Juan Itinerary Caribbean
from $6,195
price per person Taxes included
SeaDream I | Dec 27, 2025
Duration: 7 nights
Departure from: San Juan Landing: Charlotte Amalie
Itinerary:
1. San Juan,
2. Spanish Town,
3. Norman Island,
4. Saint Johns,
5. Gustavia,
6. Gustavia,
7. Gustavia,
8. Charlestown,
9. Charlotte Amalie

Caribbean: Puerto Rico, Saint Barthelemy, United Kingdom, Virgin Islands

San Juan Itinerary Caribbean
from $11,130
price per person Taxes included
See the cruise Book
SeaDream II | Dec 28, 2025
Duration: 7 nights
Departure from: San Juan Landing: Charlotte Amalie
Itinerary:
1. San Juan,
2. navigation,
3. Gustavia,
4. Gustavia,
5. Gustavia,
6. Anguilla,
7. St. John ,
8. Charlotte Amalie

Caribbean: Virgin Islands, Antigua and Barbuda, United Kingdom, Saint Barthelemy, United States, Jamaica, British Virgin Islands, Puerto Rico

Charlotte Amalie Itinerary Caribbean
from $5,148
price per person Taxes included
4 reservations in 72 hours
See the cruise Book
SeaDream I | Jan 3, 2026
Duration: 7 nights
Departure from: Charlotte Amalie Landing: San Juan
Itinerary:
1. Charlotte Amalie,
2. Lovango Island,
3. Saint Johns,
4. Anguilla,
5. Gustavia,
6. Gustavia,
7. Charlestown,
8. Spanish Town,
9. Norman Island,
10. San Juan

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

Charlotte Amalie Itinerary Caribbean
from $5,255
price per person Taxes included
2 reservations in 72 hours
See the cruise Book
SeaDream II | Jan 4, 2026
Duration: 7 nights
Departure from: Charlotte Amalie Landing: Charlotte Amalie
Itinerary:
1. Charlotte Amalie,
2. Spanish Town,
3. navigation,
4. Saint Johns,
5. Anguilla,
6. Philipsburg,
7. Gustavia,
8. Gustavia,
9. Lovango Island,
10. Charlotte Amalie

Caribbean: Puerto Rico, Virgin Islands, Antigua and Barbuda, United Kingdom, Saint Barthelemy, United States, Guadeloupe, South Africa, Saint Vincent and the Grenadines, Barbados

San Juan Itinerary Caribbean
from $7,690
price per person Taxes included
See the cruise Book
SeaDream I | Jan 10, 2026
Duration: 10 nights
Departure from: San Juan Landing: Bridgetown
Itinerary:
1. San Juan,
2. Lovango Island,
3. Saint Johns,
4. Anguilla,
5. Gustavia,
6. Gustavia,
7. Charlestown,
8. Terre-de-Haut,
9. Port Elizabeth,
10. Port Elizabeth,
11. Tobago Cays,
12. Bridgetown

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

Charlotte Amalie Itinerary Caribbean
from $5,469
price per person Taxes included
5 reservations in 72 hours
See the cruise Book
SeaDream II | Jan 11, 2026
Duration: 7 nights
Departure from: Charlotte Amalie Landing: Philipsburg
Itinerary:
1. Charlotte Amalie,
2. St. John ,
3. Saint Johns,
4. Anguilla,
5. Gustavia,
6. Gustavia,
7. Basseterre,
8. Falmouth,
9. Philipsburg

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

Philipsburg Itinerary Caribbean
from $5,469
price per person Taxes included
See the cruise Book
SeaDream II | Jan 18, 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

Caribbean: Barbados, Grenada, Saint Vincent and the Grenadines, South Africa, Guadeloupe, Saint Kitts and Nevis, United States, Saint Barthelemy, Jamaica, British Virgin Islands, Virgin Islands, Puerto Rico

Bridgetown Itinerary Caribbean
from $8,182
price per person Taxes included
See the cruise Book
SeaDream I | Jan 20, 2026
Duration: 11 nights
Departure from: Bridgetown Landing: San Juan
Itinerary:
1. Bridgetown,
2. Saint George,
3. Mayreau,
4. Tobago Cays,
5. Port Elizabeth,
6. Port Elizabeth,
7. Terre-de-Haut,
8. Basseterre,
9. Charlestown,
10. Gustavia,
11. Gustavia,
12. Spanish Town,
13. Norman Island,
14. St. John ,
15. San Juan

Caribbean: Puerto Rico, Netherlands, Saint Barthelemy, United Kingdom, Guadeloupe, France, Barbados

San Juan Itinerary Caribbean
from $5,469
price per person Taxes included
See the cruise Book
SeaDream II | Jan 25, 2026
Duration: 7 nights
Departure from: San Juan Landing: Bridgetown
Itinerary:
1. San Juan,
2. navigation,
3. Sint Eustatius,
4. Gustavia,
5. Gustavia,
6. Falmouth,
7. Terre-de-Haut,
8. Le Marin,
9. Bridgetown

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

San Juan Itinerary Caribbean
from $5,362
price per person Taxes included
5 reservations in 72 hours
See the cruise Book
SeaDream I | Jan 31, 2026
Duration: 7 nights
Departure from: San Juan Landing: Charlotte Amalie
Itinerary:
1. San Juan,
2. Tortola Island,
3. Lovango Island,
4. Anguilla,
5. Gustavia,
6. Gustavia,
7. Philipsburg,
8. navigation,
9. Spanish Town,
10. Norman Island,
11. Charlotte Amalie

Caribbean: Barbados, Saint Lucia, Saint Kitts and Nevis, Netherlands, Saint Barthelemy, Guadeloupe, Saint Vincent and the Grenadines, South Africa

Bridgetown Itinerary Caribbean
from $7,690
price per person Taxes included
See the cruise Book
SeaDream II | Feb 1, 2026
Duration: 10 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Rodney Bay,
3. Basseterre,
4. Sint Eustatius,
5. Gustavia,
6. Gustavia,
7. Terre-de-Haut,
8. Terre-de-Haut,
9. Mayreau,
10. Tobago Cays,
11. Port Elizabeth,
12. Port Elizabeth,
13. Bridgetown
91 cruises