Original Cruises to the Caribbean Islands on a Yacht

Caribbean: Sint Maarten, British Virgin Islands, Jamaica, Saint Barthelemy, Guadeloupe, Saint Vincent and the Grenadines, Barbados

from $5,124
price per person Taxes included

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SeaDream I | Nov 14, 2026

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Norman Island,

3. Tortola Island,

4. Spanish Town,

5. navigation,

6. Gustavia,

7. Gustavia,

8. Terre-de-Haut,

9. Mayreau,

10. Bridgetown

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

from $5,124
price per person Taxes included

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SeaDream I | Nov 21, 2026

Duration: 7 nights

Departure from: Bridgetown

Itinerary:

1. Bridgetown,

2. Castries,

3. Kingstown,

4. Port Elizabeth,

5. Port Elizabeth,

6. Tobago Cays,

7. Mayreau,

8. Saint George,

9. Bridgetown

Caribbean: Barbados, South Africa, Saint Vincent and the Grenadines, Saint Lucia, Guadeloupe, Sint Maarten, Saint Barthelemy

from $4,919
price per person Taxes included

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SeaDream I | Nov 28, 2026

Duration: 7 nights

Departure from: Bridgetown

Itinerary:

1. Bridgetown,

2. Port Elizabeth,

3. Mayreau,

4. Castries,

5. Terre-de-Haut,

6. Philipsburg,

7. Gustavia,

8. Gustavia,

9. navigation

Caribbean: Puerto Rico, Virgin Islands, Sint Maarten, Saint Barthelemy, Australia, Jamaica

from $4,919
price per person Taxes included

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SeaDream I | Dec 12, 2026

Duration: 7 nights

Departure from: San Juan

Itinerary:

1. San Juan,

2. navigation,

3. St. John ,

4. Philipsburg,

5. Gustavia,

6. Gustavia,

7. Sydney,

8. Spanish Town,

9. navigation,

10. Charlotte Amalie

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

from $4,919
price per person Taxes included

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SeaDream II | Dec 12, 2026

Duration: 7 nights

Departure from: Charlotte Amalie

Itinerary:

1. Charlotte Amalie,

2. Philipsburg,

3. Gustavia,

4. Gustavia,

5. Falmouth,

6. Charlestown,

7. Spanish Town,

8. Norman Island,

9. Sydney,

10. San Juan

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

from $6,103
price per person Taxes included

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SeaDream I | Dec 19, 2026

Duration: 8 nights

Departure from: Charlotte Amalie

Itinerary:

1. Charlotte Amalie,

2. St. John ,

3. navigation,

4. Norman Island,

5. Saint Johns,

6. Tortola Island,

7. Spanish Town,

8. Marigot,

9. Anguilla,

10. Gustavia,

11. Gustavia,

12. Charlotte Amalie

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

from $6,613
price per person Taxes included

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SeaDream II | Dec 19, 2026

Duration: 8 nights

Departure from: San Juan

Itinerary:

1. San Juan,

2. Gustavia,

3. Gustavia,

4. Anguilla,

5. Tortola Island,

6. Spanish Town,

7. navigation,

8. Tortola Island,

9. Norman Island,

10. Sydney,

11. San Juan

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

from $9,614
price per person Taxes included

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SeaDream I | Dec 27, 2026

Duration: 7 nights

Departure from: Charlotte Amalie

Itinerary:

1. Charlotte Amalie,

2. Spanish Town,

3. Norman Island,

4. Marigot,

5. Gustavia,

6. Gustavia,

7. Gustavia,

8. Saint Johns,

9. San Juan

Caribbean: Puerto Rico, Virgin Islands, Sint Maarten, Saint Barthelemy, Australia

from $11,656
price per person Taxes included

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SeaDream II | Dec 27, 2026

Duration: 7 nights

Departure from: San Juan

Itinerary:

1. San Juan,

2. St. John ,

3. Philipsburg,

4. Gustavia,

5. Gustavia,

6. Gustavia,

7. Sydney,

8. Charlotte Amalie

Caribbean: Puerto Rico, Virgin Islands, United Kingdom, Saint Barthelemy, Saint Martin, Antigua and Barbuda

from $4,041
price per person Taxes included

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SeaDream I | Jan 3, 2027

Duration: 6 nights

Departure from: San Juan

Itinerary:

1. San Juan,

2. St. John ,

3. Anguilla,

4. Gustavia,

5. Gustavia,

6. Marigot,

7. Saint Johns,

8. San Juan