Cruises on a Sailship to the Caribbean Islands

Promotions and offers for all Caribbean Sailing Ship Cruises! Experience the magic of a Sailing Ship Holiday with Star Clippers. Discover the thrill of a unique journey — the most exclusive ports await you, along with comfort, luxury, and adventure aboard the Star Clippers Sailing Ships for an original and different Caribbean cruise

2025
2026
2027

November 2025 December 2025

January 2026 February 2026 March 2026 April 2026 May 2026 June 2026 July 2026 August 2026 September 2026 October 2026 November 2026 December 2026

January 2027 February 2027 March 2027

Caribbean: Antigua and Barbuda, Guadeloupe, Dominica, Grenada, Saint Vincent and the Grenadines, Saint Martin, Saint Lucia, Barbados

from $3,272
price per person Taxes included

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Royal Clipper | Nov. 29, 2025

Duration: 7 nights

Departure from: Saint Johns

Itinerary:

1. Saint Johns,

2. Terre-de-Haut,

3. Cabritz Bay,

4. Saint George,

5. Tobago Cays,

6. Marigot,

7. Soufriere,

8. Bridgetown

Caribbean: Sint Maarten, Antigua and Barbuda, Dominica, Guadeloupe, France, Saint Barthelemy

from $3,846
price per person Taxes included

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Star Flyer | Nov. 29, 2025

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Barbuda,

3. Cabritz Bay,

4. Terre-de-Haut,

5. Deshaies,

6. Falmouth Harbour,

7. Gustavia,

8. Philipsburg

Caribbean: Barbados, Saint Vincent and the Grenadines, Grenada, Martinique, Saint Martin

from $3,272
price per person Taxes included

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Royal Clipper | Dec. 6, 2025

Duration: 7 nights

Departure from: Bridgetown

Itinerary:

1. Bridgetown,

2. Grenadine,

3. Saint George,

4. Tobago Cays,

5. Kingstown,

6. Fort de france,

7. Marigot,

8. Bridgetown

Caribbean: Sint Maarten, Antigua and Barbuda, Dominica, Guadeloupe, France, Saint Barthelemy

from $3,846
price per person Taxes included

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Star Flyer | Dec. 13, 2025

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Barbuda,

3. Cabritz Bay,

4. Terre-de-Haut,

5. Deshaies,

6. Falmouth Harbour,

7. Gustavia,

8. Philipsburg

Caribbean: Barbados, Saint Vincent and the Grenadines, Grenada, Martinique, Saint Martin

from $3,272
price per person Taxes included

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Royal Clipper | Dec. 20, 2025

Duration: 7 nights

Departure from: Bridgetown

Itinerary:

1. Bridgetown,

2. Grenadine,

3. Saint George,

4. Tobago Cays,

5. Kingstown,

6. Fort de france,

7. Marigot,

8. Bridgetown

Caribbean: Sint Maarten, Antigua and Barbuda, Dominica, Guadeloupe, France, Saint Barthelemy

from $3,951
price per person Taxes included

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Star Flyer | Dec. 27, 2025

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Barbuda,

3. Cabritz Bay,

4. Terre-de-Haut,

5. Deshaies,

6. Falmouth Harbour,

7. Gustavia,

8. Philipsburg

Caribbean: Barbados, Saint Vincent and the Grenadines, Grenada, Martinique, Saint Martin

from $3,272
price per person Taxes included

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Royal Clipper | Jan. 3, 2026

Duration: 7 nights

Departure from: Bridgetown

Itinerary:

1. Bridgetown,

2. Grenadine,

3. Saint George,

4. Tobago Cays,

5. Kingstown,

6. Fort de france,

7. Marigot,

8. Bridgetown

Caribbean: Sint Maarten, Antigua and Barbuda, Dominica, Guadeloupe, France, Saint Barthelemy

from $3,846
price per person Taxes included

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Star Flyer | Jan. 10, 2026

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Barbuda,

3. Cabritz Bay,

4. Terre-de-Haut,

5. Deshaies,

6. Falmouth Harbour,

7. Gustavia,

8. Philipsburg

Caribbean: Barbados, Saint Vincent and the Grenadines, Grenada, Martinique, Saint Martin

from $3,272
price per person Taxes included

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Royal Clipper | Jan. 17, 2026

Duration: 7 nights

Departure from: Bridgetown

Itinerary:

1. Bridgetown,

2. Grenadine,

3. Saint George,

4. Tobago Cays,

5. Kingstown,

6. Fort de france,

7. Marigot,

8. Bridgetown

Caribbean: Sint Maarten, Antigua and Barbuda, Dominica, Guadeloupe, France, Saint Barthelemy

from $3,846
price per person Taxes included

See the cruise Book

Star Flyer | Jan. 24, 2026

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Barbuda,

3. Cabritz Bay,

4. Terre-de-Haut,

5. Deshaies,

6. Falmouth Harbour,

7. Gustavia,

8. Philipsburg

Caribbean: Barbados, Saint Vincent and the Grenadines, Grenada, Martinique, Saint Martin

from $3,272
price per person Taxes included

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Royal Clipper | Jan. 31, 2026

Duration: 7 nights

Departure from: Bridgetown

Itinerary:

1. Bridgetown,

2. Grenadine,

3. Saint George,

4. Tobago Cays,

5. Kingstown,

6. Fort de france,

7. Marigot,

8. Bridgetown

Caribbean: Sint Maarten, Antigua and Barbuda, Dominica, Guadeloupe, France, Saint Barthelemy

from $3,846
price per person Taxes included

See the cruise Book

Star Flyer | Feb. 7, 2026

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Barbuda,

3. Cabritz Bay,

4. Terre-de-Haut,

5. Deshaies,

6. Falmouth Harbour,

7. Gustavia,

8. Philipsburg

Caribbean: Barbados, Saint Vincent and the Grenadines, Grenada, Martinique, Saint Martin

from $3,272
price per person Taxes included

See the cruise Book

Royal Clipper | Feb. 14, 2026

Duration: 7 nights

Departure from: Bridgetown

Itinerary:

1. Bridgetown,

2. Grenadine,

3. Saint George,

4. Tobago Cays,

5. Kingstown,

6. Fort de france,

7. Marigot,

8. Bridgetown

Caribbean: Sint Maarten, Antigua and Barbuda, Dominica, Guadeloupe, France, Saint Barthelemy

from $3,846
price per person Taxes included

See the cruise Book

Star Flyer | Feb. 21, 2026

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Barbuda,

3. Cabritz Bay,

4. Terre-de-Haut,

5. Deshaies,

6. Falmouth Harbour,

7. Gustavia,

8. Philipsburg

Caribbean: Barbados, Saint Vincent and the Grenadines, Grenada, Martinique, Saint Martin

from $3,272
price per person Taxes included

See the cruise Book

Royal Clipper | Feb. 28, 2026

Duration: 7 nights

Departure from: Bridgetown

Itinerary:

1. Bridgetown,

2. Grenadine,

3. Saint George,

4. Tobago Cays,

5. Kingstown,

6. Fort de france,

7. Marigot,

8. Bridgetown

Caribbean: Sint Maarten, Antigua and Barbuda, Dominica, Guadeloupe, France, Saint Barthelemy

from $3,846
price per person Taxes included

See the cruise Book

Star Flyer | Mar. 7, 2026

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Barbuda,

3. Cabritz Bay,

4. Terre-de-Haut,

5. Deshaies,

6. Falmouth Harbour,

7. Gustavia,

8. Philipsburg

Caribbean: Barbados, Saint Vincent and the Grenadines, Grenada, Martinique, Saint Martin

from $3,272
price per person Taxes included

See the cruise Book

Royal Clipper | Mar. 14, 2026

Duration: 7 nights

Departure from: Bridgetown

Itinerary:

1. Bridgetown,

2. Grenadine,

3. Saint George,

4. Tobago Cays,

5. Kingstown,

6. Fort de france,

7. Marigot,

8. Bridgetown

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

from $3,846
price per person Taxes included

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Star Clipper | Mar. 21, 2026

Duration: 7 nights

Departure from: Saint Johns

Itinerary:

1. Saint Johns,

2. Gustavia,

3. Norman Island,

4. Jost Van Dyke,

5. Virgin Gorda,

6. Philipsburg,

7. Basseterre,

8. Saint Johns

Caribbean: Antigua and Barbuda, Guadeloupe, Dominica, Grenada, Saint Vincent and the Grenadines, Saint Lucia, Barbados

from $4,331
price per person Taxes included

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Royal Clipper | Nov. 28, 2026

Duration: 7 nights

Departure from: Saint Johns

Itinerary:

1. Saint Johns,

2. Terre-de-Haut,

3. Cabritz Bay,

4. navigation,

5. Grenada,

6. Tobago Cays,

7. Soufriere,

8. Bridgetown

Caribbean: Sint Maarten, Anguilla, Virgin Islands, British Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy

from $3,927
price per person Taxes included

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Star Flyer | Nov. 28, 2026

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Baie Road,

3. Jost Van Dyke,

4. Norman Island,

5. Spanish Town - Virgin Gorda,

6. Basseterre,

7. Gustavia,

8. Philipsburg

Caribbean: Sint Maarten, Saint Kitts and Nevis, Dominica, Guadeloupe, France, Antigua and Barbuda

from $3,927
price per person Taxes included

See the cruise Book

Star Flyer | Dec. 5, 2026

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Charlestown,

3. Cabritz Bay,

4. Terre-de-Haut,

5. Deshaies,

6. Falmouth Harbour,

7. Basseterre,

8. Philipsburg

Caribbean: Barbados, Grenada, Saint Vincent and the Grenadines, Martinique, Saint Martin

from $4,209
price per person Taxes included

See the cruise Book

Royal Clipper | Dec. 12, 2026

Duration: 7 nights

Departure from: Bridgetown

Itinerary:

1. Bridgetown,

3. Saint George,

4. Tobago Cays,

5. Kingstown,

6. Fort de france,

7. Marigot,

8. Bridgetown

Caribbean: Sint Maarten, Anguilla, Virgin Islands, British Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy

from $3,822
price per person Taxes included

See the cruise Book

Star Flyer | Dec. 12, 2026

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Baie Road,

3. Jost Van Dyke,

4. Norman Island,

5. Spanish Town - Virgin Gorda,

6. Basseterre,

7. Gustavia,

8. Philipsburg

Caribbean: Sint Maarten, Saint Kitts and Nevis, Dominica, Guadeloupe, France, Antigua and Barbuda

from $4,088
price per person Taxes included

See the cruise Book

Star Flyer | Dec. 19, 2026

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Charlestown,

3. Cabritz Bay,

4. Terre-de-Haut,

5. Deshaies,

6. Falmouth Harbour,

7. Basseterre,

8. Philipsburg

Caribbean: Sint Maarten, Anguilla, Virgin Islands, British Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy

from $4,032
price per person Taxes included

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Star Flyer | Dec. 26, 2026

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Baie Road,

3. Jost Van Dyke,

4. Norman Island,

5. Spanish Town - Virgin Gorda,

6. Basseterre,

7. Gustavia,

8. Philipsburg

Caribbean: Barbados, Grenada, Saint Vincent and the Grenadines, Martinique, Saint Martin

from $4,452
price per person Taxes included

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Royal Clipper | Dec. 26, 2026

Duration: 7 nights

Departure from: Bridgetown

Itinerary:

1. Bridgetown,

3. Saint George,

4. Tobago Cays,

5. Kingstown,

6. Fort de france,

7. Marigot,

8. Bridgetown

Caribbean: Sint Maarten, Saint Kitts and Nevis, Dominica, Guadeloupe, France, Antigua and Barbuda

from $3,927
price per person Taxes included

See the cruise Book

Star Flyer | Jan. 2, 2027

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Charlestown,

3. Cabritz Bay,

4. Terre-de-Haut,

5. Deshaies,

6. Falmouth Harbour,

7. Basseterre,

8. Philipsburg

Caribbean: Barbados, Grenada, Saint Vincent and the Grenadines, Martinique, Saint Martin

from $4,209
price per person Taxes included

See the cruise Book

Royal Clipper | Jan. 9, 2027

Duration: 7 nights

Departure from: Bridgetown

Itinerary:

1. Bridgetown,

3. Saint George,

4. Tobago Cays,

5. Kingstown,

6. Fort de france,

7. Marigot,

8. Bridgetown

Caribbean: Sint Maarten, Anguilla, Virgin Islands, British Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy

from $3,927
price per person Taxes included

See the cruise Book

Star Flyer | Jan. 9, 2027

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Baie Road,

3. Jost Van Dyke,

4. Norman Island,

5. Spanish Town - Virgin Gorda,

6. Basseterre,

7. Gustavia,

8. Philipsburg

Caribbean: Sint Maarten, Saint Kitts and Nevis, Dominica, Guadeloupe, France, Antigua and Barbuda

from $3,927
price per person Taxes included

See the cruise Book

Star Flyer | Jan. 16, 2027

Duration: 7 nights

Departure from: Philipsburg

Itinerary:

1. Philipsburg,

2. Charlestown,

3. Cabritz Bay,

4. Terre-de-Haut,

5. Deshaies,

6. Falmouth Harbour,

7. Basseterre,

8. Philipsburg