home › Cruises on a Sailship to the Caribbean Islands
  • 2027
November 2026 December 2026
January 2027 February 2027 March 2027
28 cruises
Caribbean: Antigua and Barbuda, Guadeloupe, Dominica, Grenada, Saint Vincent and the Grenadines, Saint Lucia, Barbados
Saint Johns Itinerary Caribbean
from R 57 239
price per person Taxes included
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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, Anguilla, Virgin Islands, British Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
from R 51 900
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: Sint Maarten, Saint Kitts and Nevis, Dominica, Guadeloupe, France, Antigua and Barbuda
Philipsburg Itinerary Caribbean
from R 51 900
price per person Taxes included
See the cruise Book
Star Flyer | 05 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: Sint Maarten, Anguilla, Virgin Islands, British Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
from R 50 511
price per person Taxes included
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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: Barbados, Grenada, Saint Vincent and the Grenadines, Martinique, Saint Martin
Bridgetown Itinerary Caribbean
from R 55 637
price per person Taxes included
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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, Saint Kitts and Nevis, Dominica, Guadeloupe, France, Antigua and Barbuda
Philipsburg Itinerary Caribbean
from R 54 035
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
Bridgetown Itinerary Caribbean
from R 58 841
price per person Taxes included
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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
Philipsburg Itinerary Caribbean
from R 53 288
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
Philipsburg Itinerary Caribbean
from R 51 900
price per person Taxes included
See the cruise Book
Star Flyer | 02 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
Bridgetown Itinerary Caribbean
from R 55 637
price per person Taxes included
See the cruise Book
Royal Clipper | 09 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
28 cruises