home Cruises on a Sailship to the Caribbean Islands
18 cruises

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

Philipsburg Itinerary Caribbean
from $3,860
price per person Taxes included
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: Antigua and Barbuda, Guadeloupe, Dominica, Grenada, Saint Vincent and the Grenadines, Saint Martin, Saint Lucia, Barbados

Saint Johns Itinerary Caribbean
from $3,284
price per person Taxes included
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: Barbados, Saint Vincent and the Grenadines, Grenada, Martinique, Saint Martin

Bridgetown Itinerary Caribbean
from $3,284
price per person Taxes included
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

Philipsburg Itinerary Caribbean
from $3,860
price per person Taxes included
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

Bridgetown Itinerary Caribbean
from $3,284
price per person Taxes included
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

Philipsburg Itinerary Caribbean
from $3,965
price per person Taxes included
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

Bridgetown Itinerary Caribbean
from $3,284
price per person Taxes included
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

Philipsburg Itinerary Caribbean
from $3,860
price per person Taxes included
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

Bridgetown Itinerary Caribbean
from $3,284
price per person Taxes included
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

Philipsburg Itinerary Caribbean
from $3,860
price per person Taxes included
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

Bridgetown Itinerary Caribbean
from $3,284
price per person Taxes included
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

Philipsburg Itinerary Caribbean
from $3,860
price per person Taxes included
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

Bridgetown Itinerary Caribbean
from $3,284
price per person Taxes included
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

Philipsburg Itinerary Caribbean
from $3,860
price per person Taxes included
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

Bridgetown Itinerary Caribbean
from $3,284
price per person Taxes included
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

Philipsburg Itinerary Caribbean
from $3,860
price per person Taxes included
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

Bridgetown Itinerary Caribbean
from $3,284
price per person Taxes included
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

Saint Johns Itinerary Caribbean
from $3,860
price per person Taxes included
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
18 cruises