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All Caribbean Cruises with Windstar Cruises in January 2026

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6 cruises

Caribbean: Sint Maarten, Antigua and Barbuda, United Kingdom, British Virgin Islands, Virgin Islands, Saint Barthelemy

Sint Maarten Itinerary Caribbean
from $4,615.65
price per person Taxes included
16 reservations in 36 hours
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Wind Surf | 4/01/2026
Duration: 7 nights
Departure from: Sint Maarten Landing: Sint Maarten
Itinerary:
1. Sint Maarten,
2. Falmouth Harbour,
3. Anguilla,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Sint Maarten

Caribbean: Sint Maarten, Saint Kitts and Nevis, Montserrat, Saint Barthelemy, France, Dominica, Sri Lanka, Barbados

Sint Maarten Itinerary Caribbean
from $4,615.65
price per person Taxes included
18 reservations in 36 hours
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Wind Surf | 11/01/2026
Duration: 7 nights
Departure from: Sint Maarten Landing: Bridgetown
Itinerary:
1. Sint Maarten,
2. Basseterre,
3. Little Bay,
4. Gustavia,
5. Deshaies,
6. Roseau,
7. Pigeon Island,
8. Bridgetown

Caribbean: Sint Maarten, Saint Kitts and Nevis, Dominica, Saint Lucia, Saint Vincent and the Grenadines, Grenada, Martinique, Guadeloupe, Saint Barthelemy

Sint Maarten Itinerary Caribbean
from $6,462.65
price per person Taxes included
19 reservations in 36 hours
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Wind Spirit | 14/01/2026
Duration: 10 nights
Departure from: Sint Maarten Landing: Sint Maarten
Itinerary:
1. Sint Maarten,
2. Basseterre,
3. Roseau,
4. Castries,
5. Bequia,
6. Saint George,
7. Mayreau,
8. Fort de france,
9. Les Saintes,
10. Gustavia,
11. Sint Maarten

Caribbean: Barbados, Martinique, Saint Lucia, Sri Lanka, Saint Vincent and the Grenadines, Grenada

Bridgetown Itinerary Caribbean
from $4,615.65
price per person Taxes included
15 reservations in 48 hours
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Wind Surf | 18/01/2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Fort de france,
3. Castries,
4. Pigeon Island,
5. Pigeon Island,
6. Bequia,
7. Mayreau,
8. Saint George,
9. Bridgetown

Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy, United Kingdom, Antigua and Barbuda

Sint Maarten Itinerary Caribbean
from $4,615.65
price per person Taxes included
19 reservations in 36 hours
See the cruise
Wind Spirit | 24/01/2026
Duration: 7 nights
Departure from: Sint Maarten Landing: Sint Maarten
Itinerary:
1. Sint Maarten,
2. Tortola Island,
3. Jost Van Dyke,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Gustavia,
7. Anguilla,
8. Falmouth Harbour,
9. Sint Maarten

Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy, United Kingdom, Antigua and Barbuda

Sint Maarten Itinerary Caribbean
from $4,615.65
price per person Taxes included
21 reservations in 36 hours
See the cruise
Wind Spirit | 31/01/2026
Duration: 7 nights
Departure from: Sint Maarten Landing: Sint Maarten
Itinerary:
1. Sint Maarten,
2. Tortola Island,
3. Jost Van Dyke,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Gustavia,
7. Anguilla,
8. Falmouth Harbour,
9. Sint Maarten
6 cruises