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All Caribbean Cruises with SeaDream Yacht Club

  • 2025
  • 2026
  • 2027
86 cruises
sold out

Puerto Rico, Virgin Islands, United Kingdom, Saint Barthelemy

San Juan Itinerary Caribbean
from $7,522
price per person Taxes included
SeaDream I | 15 Nov 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 $7,571
price per person Taxes included
SeaDream II | 16 Nov 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 $5,705
price per person Taxes included
SeaDream I | 19 Nov 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 $7,522
price per person Taxes included
SeaDream I | 22 Nov 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 $8,257
price per person Taxes included
SeaDream II | 23 Nov 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 $7,021
price per person Taxes included
SeaDream I | 24 Nov 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 $7,866
price per person Taxes included
SeaDream I | 29 Nov 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 $7,571
price per person Taxes included
SeaDream II | 30 Nov 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 $7,866
price per person Taxes included
SeaDream I | 6 Dec 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 $9,285
price per person Taxes included
SeaDream II | 7 Dec 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 $7,571
price per person Taxes included
SeaDream I | 13 Dec 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 $7,571
price per person Taxes included
SeaDream II | 14 Dec 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 $9,285
price per person Taxes included
SeaDream I | 20 Dec 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 $9,285
price per person Taxes included
SeaDream II | 21 Dec 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 $9,936
price per person Taxes included
SeaDream I | 27 Dec 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
sold out

Puerto Rico, Saint Barthelemy, United Kingdom, Virgin Islands

San Juan Itinerary Caribbean
from $17,852
price per person Taxes included
SeaDream II | 28 Dec 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 $8,257
price per person Taxes included
SeaDream I | 3 Jan 2026
Duration: 7 nights
Departure from: Charlotte Amalie Landing: San Juan
Itinerary:
1. Charlotte Amalie,
2. St. John ,
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 $8,429
price per person Taxes included
SeaDream II | 4 Jan 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. St. John ,
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 $12,334
price per person Taxes included
SeaDream I | 10 Jan 2026
Duration: 10 nights
Departure from: San Juan Landing: Bridgetown
Itinerary:
1. San Juan,
2. St. John ,
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 $8,772
price per person Taxes included
SeaDream II | 11 Jan 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 $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

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 $13,122
price per person Taxes included
SeaDream I | 20 Jan 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 $8,772
price per person Taxes included
SeaDream II | 25 Jan 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 $8,599
price per person Taxes included
SeaDream I | 31 Jan 2026
Duration: 7 nights
Departure from: San Juan Landing: Charlotte Amalie
Itinerary:
1. San Juan,
2. Tortola Island,
3. St. John ,
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 $12,334
price per person Taxes included
SeaDream II | 1 Feb 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

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

Charlotte Amalie Itinerary Caribbean
from $9,285
price per person Taxes included
SeaDream I | 7 Feb 2026
Duration: 7 nights
Departure from: Charlotte Amalie Landing: San Juan
Itinerary:
1. Charlotte Amalie,
2. St. John ,
3. Saint Johns,
4. Sint Eustatius,
5. Gustavia,
6. Gustavia,
7. Charlestown,
8. Spanish Town,
9. Norman Island,
10. San Juan

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

Bridgetown Itinerary Caribbean
from $13,122
price per person Taxes included
SeaDream II | 11 Feb 2026
Duration: 11 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Rodney Bay,
3. Portsmouth (USA),
4. Gustavia,
5. Gustavia,
6. Basseterre,
7. Charlestown,
8. Terre-de-Haut,
9. Terre-de-Haut,
10. Mayreau,
11. Tobago Cays,
12. Port Elizabeth,
13. Port Elizabeth,
14. Bridgetown

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

San Juan Itinerary Caribbean
from $8,599
price per person Taxes included
SeaDream I | 14 Feb 2026
Duration: 7 nights
Departure from: San Juan Landing: Charlotte Amalie
Itinerary:
1. San Juan,
2. St. John ,
3. Charlestown,
4. Anguilla,
5. Gustavia,
6. Gustavia,
7. navigation,
8. Spanish Town,
9. Norman Island,
10. Charlotte Amalie
sold out

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

San Juan Itinerary Caribbean
from $7,666
price per person Taxes included
SeaDream I | 21 Feb 2026
Duration: 7 nights
Departure from: San Juan Landing: Charlotte Amalie
Itinerary:
1. San Juan,
2. La Esperanza,
3. Culebra,
4. Lovango Island,
5. Saint Johns,
6. Gustavia,
7. Charlestown,
8. Spanish Town,
9. Norman Island,
10. Charlotte Amalie

Caribbean: Barbados, South Africa, Saint Vincent and the Grenadines, Saint Lucia, France, Guadeloupe, United Kingdom, Sint Maarten

Bridgetown Itinerary Caribbean
from $8,429
price per person Taxes included
SeaDream II | 22 Feb 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Philipsburg
Itinerary:
1. Bridgetown,
2. Port Elizabeth,
3. Mayreau,
4. Rodney Bay,
5. Le Marin,
6. Terre-de-Haut,
7. Falmouth,
8. Philipsburg
86 cruises