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All Caribbean Cruises with Windstar Cruises in December 2025

  • 2026
  • 2027
December 2025
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January 2027 February 2027 March 2027
5 cruises
sold out
Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Martinique
Bridgetown Itinerary Caribbean
External from $4,928
price per person Taxes included
Wind Spirit | Dec. 28, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Mayreau,
7. Fort de france,
8. Bridgetown
sold out
Aruba, Netherlands Antilles, Grenada, Saint Vincent and the Grenadines, Barbados
Oranjestad Itinerary Caribbean
External from $5,974
price per person Taxes included
Wind Spirit | Dec. 20, 2025
Duration: 8 nights
Departure from: Oranjestad Landing: Bridgetown
Itinerary:
1. Oranjestad,
2. Willemstad,
3. Kralendijk,
4. navigation,
5. Saint George,
6. Saint George,
7. Mayreau,
8. Bequia,
9. Bridgetown
sold out
Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $7,030
price per person Taxes included
Wind Surf | Dec. 28, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. navigation,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $8,321
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | Dec. 21, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
sold out
Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy, British Virgin Islands, Virgin Islands
Philipsburg Itinerary Caribbean
External from $14,364
price per person Taxes included
Wind Surf | Dec. 21, 2025
Duration: 14 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg,
9. navigation,
10. Tortola Island,
11. Tortola Island,
12. Jost Van Dyke,
13. Jost Van Dyke,
14. Virgin Gorda,
15. Gustavia,
16. Philipsburg
5 cruises