home Original Cruises to the Caribbean Islands on a Yacht
  • 2025
  • 2026
  • 2027
72 cruises

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

Marigot Itinerary Caribbean
from $7,699
price per person Taxes included
SeaDream II | 16 Nov 2025
Duration: 7 nights
Departure from: Marigot
Itinerary:
1. Marigot,
2. Terre-de-Haut,
3. Rodney Bay,
4. Port Elizabeth,
5. Mayreau,
6. Tobago Cays,
7. Bridgetown

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

Bridgetown Itinerary Caribbean
from $8,396
price per person Taxes included
SeaDream II | 23 Nov 2025
Duration: 7 nights
Departure from: 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 $7,139
price per person Taxes included
SeaDream I | 24 Nov 2025
Duration: 5 nights
Departure from: Charlotte Amalie
Itinerary:
1. Charlotte Amalie,
2. St. John ,
3. Philipsburg,
4. Gustavia,
5. Gustavia,
6. navigation,
7. Charlotte Amalie

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

San Juan Itinerary Caribbean
from $9,442
price per person Taxes included
SeaDream II | 7 Dec 2025
Duration: 7 nights
Departure from: 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 $7,699
price per person Taxes included
SeaDream I | 13 Dec 2025
Duration: 7 nights
Departure from: San Juan
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 $7,699
price per person Taxes included
SeaDream II | 14 Dec 2025
Duration: 7 nights
Departure from: San Juan
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 $9,442
price per person Taxes included
SeaDream I | 20 Dec 2025
Duration: 7 nights
Departure from: Philipsburg
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 $9,442
price per person Taxes included
SeaDream II | 21 Dec 2025
Duration: 7 nights
Departure from: Charlotte Amalie
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

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

Charlotte Amalie Itinerary Caribbean
from $8,396
price per person Taxes included
SeaDream I | 3 Jan 2026
Duration: 7 nights
Departure from: Charlotte Amalie
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 $8,571
price per person Taxes included
SeaDream II | 4 Jan 2026
Duration: 7 nights
Departure from: 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 $12,542
price per person Taxes included
SeaDream I | 10 Jan 2026
Duration: 10 nights
Departure from: San Juan
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 $8,920
price per person Taxes included
SeaDream II | 11 Jan 2026
Duration: 7 nights
Departure from: Charlotte Amalie
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 $8,920
price per person Taxes included
SeaDream II | 18 Jan 2026
Duration: 7 nights
Departure from: Philipsburg
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 $13,343
price per person Taxes included
SeaDream I | 20 Jan 2026
Duration: 11 nights
Departure from: Bridgetown
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 $8,920
price per person Taxes included
SeaDream II | 25 Jan 2026
Duration: 7 nights
Departure from: San Juan
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 $8,744
price per person Taxes included
SeaDream I | 31 Jan 2026
Duration: 7 nights
Departure from: San Juan
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 $12,542
price per person Taxes included
SeaDream II | 1 Feb 2026
Duration: 10 nights
Departure from: 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 $9,442
price per person Taxes included
SeaDream I | 7 Feb 2026
Duration: 7 nights
Departure from: Charlotte Amalie
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 $13,343
price per person Taxes included
SeaDream II | 11 Feb 2026
Duration: 11 nights
Departure from: 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 $8,744
price per person Taxes included
SeaDream I | 14 Feb 2026
Duration: 7 nights
Departure from: San Juan
Itinerary:
1. San Juan,
2. Lovango Island,
3. Charlestown,
4. Anguilla,
5. Gustavia,
6. Gustavia,
7. navigation,
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 $8,571
price per person Taxes included
SeaDream II | 22 Feb 2026
Duration: 7 nights
Departure from: Bridgetown
Itinerary:
1. Bridgetown,
2. Port Elizabeth,
3. Mayreau,
4. Rodney Bay,
5. Le Marin,
6. Terre-de-Haut,
7. Falmouth,
8. Philipsburg

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

Charlotte Amalie Itinerary Caribbean
from $8,744
price per person Taxes included
SeaDream I | 28 Feb 2026
Duration: 7 nights
Departure from: Charlotte Amalie
Itinerary:
1. Charlotte Amalie,
2. Lovango Island,
3. Saint Johns,
4. Tortola Island,
5. Spanish Town,
6. Anguilla,
7. Gustavia,
8. Gustavia,
9. Philipsburg,
10. Charlotte Amalie

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

Charlotte Amalie Itinerary Caribbean
from $8,396
price per person Taxes included
SeaDream I | 7 Mar 2026
Duration: 7 nights
Departure from: Charlotte Amalie
Itinerary:
1. Charlotte Amalie,
2. St. John ,
3. Saint Johns,
4. Gustavia,
5. Anguilla,
6. Basseterre,
7. Spanish Town,
8. Norman Island,
9. San Juan

Caribbean: Sint Maarten, United Kingdom, United States, Guadeloupe, Netherlands, Saint Barthelemy, Virgin Islands

Philipsburg Itinerary Caribbean
from $9,442
price per person Taxes included
SeaDream II | 8 Mar 2026
Duration: 7 nights
Departure from: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth,
3. Charlestown,
4. Terre-de-Haut,
5. Saba,
6. Gustavia,
7. Gustavia,
8. navigation,
9. Charlotte Amalie

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

San Juan Itinerary Caribbean
from $8,744
price per person Taxes included
SeaDream I | 14 Mar 2026
Duration: 7 nights
Departure from: San Juan
Itinerary:
1. San Juan,
2. Lovango Island,
3. Charlestown,
4. Saba,
5. Gustavia,
6. Gustavia,
7. navigation,
8. Spanish Town,
9. Norman Island,
10. San Juan

Caribbean: Virgin Islands, Antigua and Barbuda, United Kingdom, Saint Barthelemy, Guadeloupe, France, Barbados

Charlotte Amalie Itinerary Caribbean
from $8,396
price per person Taxes included
SeaDream II | 15 Mar 2026
Duration: 7 nights
Departure from: Charlotte Amalie
Itinerary:
1. Charlotte Amalie,
2. Saint Johns,
3. Anguilla,
4. Gustavia,
5. Gustavia,
6. Falmouth,
7. Terre-de-Haut,
8. Le Marin,
9. Bridgetown

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

San Juan Itinerary Caribbean
from $8,396
price per person Taxes included
SeaDream I | 21 Mar 2026
Duration: 7 nights
Departure from: San Juan
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, France, Guadeloupe, United States, Netherlands, Saint Barthelemy, Antigua and Barbuda, Puerto Rico

Bridgetown Itinerary Caribbean
from $8,396
price per person Taxes included
SeaDream II | 22 Mar 2026
Duration: 7 nights
Departure from: Bridgetown
Itinerary:
1. Bridgetown,
2. Le Marin,
3. Terre-de-Haut,
4. Charlestown,
5. Sint Eustatius,
6. Gustavia,
7. Gustavia,
8. Saint Johns,
9. San Juan

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

Charlotte Amalie Itinerary Caribbean
from $8,396
price per person Taxes included
SeaDream I | 28 Mar 2026
Duration: 7 nights
Departure from: Charlotte Amalie
Itinerary:
1. Charlotte Amalie,
2. Anguilla,
3. Gustavia,
4. Gustavia,
5. Philipsburg,
6. Tortola Island,
7. Spanish Town,
8. navigation,
9. Lovango Island,
10. Charlotte Amalie

Caribbean: Puerto Rico, Dominican Republic, Turks and Caicos, Canada, United States

San Juan Itinerary Caribbean
from $10,661
price per person Taxes included
SeaDream II | 29 Mar 2026
Duration: 7 nights
Departure from: San Juan
Itinerary:
1. San Juan,
2. Samana,
3. Grand Turk,
4. Gordons Beach,
5. navigation,
6. navigation,
7. Palm Beach
72 cruises