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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 TRY 89,343.25
price per person Taxes included
16 reservations in 36 hours
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Wind Surf | Jan 4, 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 TRY 89,343.25
price per person Taxes included
18 reservations in 36 hours
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Wind Surf | Jan 11, 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 TRY 125,094.85
price per person Taxes included
19 reservations in 36 hours
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Wind Spirit | Jan 14, 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 TRY 89,343.25
price per person Taxes included
15 reservations in 48 hours
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Wind Surf | Jan 18, 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 TRY 89,343.25
price per person Taxes included
19 reservations in 36 hours
See the cruise
Wind Spirit | Jan 24, 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 TRY 89,343.25
price per person Taxes included
21 reservations in 36 hours
See the cruise
Wind Spirit | Jan 31, 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