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

from $4,400
price per person Taxes included

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Star Flyer | 29 Nov 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: Antigua and Barbuda, Guadeloupe, Dominica, Grenada, Saint Vincent and the Grenadines, Saint Martin, Saint Lucia, Barbados

from $3,743
price per person Taxes included

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Royal Clipper | 29 Nov 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: Barbados, Saint Vincent and the Grenadines, Grenada, Martinique, Saint Martin

from $3,743
price per person Taxes included

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Royal Clipper | 6 Dec 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 $4,400
price per person Taxes included

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Star Flyer | 13 Dec 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 $3,743
price per person Taxes included

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Royal Clipper | 20 Dec 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 $4,520
price per person Taxes included

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Star Flyer | 27 Dec 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 $3,743
price per person Taxes included

See the cruise Book

Royal Clipper | 3 Jan 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 $4,400
price per person Taxes included

See the cruise Book

Star Flyer | 10 Jan 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 $3,743
price per person Taxes included

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Royal Clipper | 17 Jan 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 $4,400
price per person Taxes included

See the cruise Book

Star Flyer | 24 Jan 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 $3,743
price per person Taxes included

See the cruise Book

Royal Clipper | 31 Jan 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 $4,400
price per person Taxes included

See the cruise Book

Star Flyer | 7 Feb 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 $3,743
price per person Taxes included

See the cruise Book

Royal Clipper | 14 Feb 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 $4,400
price per person Taxes included

See the cruise Book

Star Flyer | 21 Feb 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 $3,743
price per person Taxes included

See the cruise Book

Royal Clipper | 28 Feb 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 $4,400
price per person Taxes included

See the cruise Book

Star Flyer | 7 Mar 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 $3,743
price per person Taxes included

See the cruise Book

Royal Clipper | 14 Mar 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 $4,400
price per person Taxes included

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Star Clipper | 21 Mar 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: Sint Maarten, Anguilla, Virgin Islands, British Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy

from $4,492
price per person Taxes included

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Star Flyer | 28 Nov 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: Antigua and Barbuda, Guadeloupe, Dominica, Grenada, Saint Vincent and the Grenadines, Saint Lucia, Barbados

from $4,954
price per person Taxes included

See the cruise Book

Royal Clipper | 28 Nov 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, Saint Kitts and Nevis, Dominica, Guadeloupe, France, Antigua and Barbuda

from $4,492
price per person Taxes included

See the cruise Book

Star Flyer | 5 Dec 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 $4,816
price per person Taxes included

See the cruise Book

Royal Clipper | 12 Dec 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 $4,372
price per person Taxes included

See the cruise Book

Star Flyer | 12 Dec 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 $4,677
price per person Taxes included

See the cruise Book

Star Flyer | 19 Dec 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 $5,093
price per person Taxes included

See the cruise Book

Royal Clipper | 26 Dec 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 $4,612
price per person Taxes included

See the cruise Book

Star Flyer | 26 Dec 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 $4,492
price per person Taxes included

See the cruise Book

Star Flyer | 2 Jan 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 $4,816
price per person Taxes included

See the cruise Book

Royal Clipper | 9 Jan 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 $4,492
price per person Taxes included

See the cruise Book

Star Flyer | 9 Jan 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 $4,492
price per person Taxes included

See the cruise Book

Star Flyer | 16 Jan 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