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All Caribbean Cruises with Windstar Cruises in December 2026

  • 2027
  • 2028
October 2026 November 2026 December 2026
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January 2028 February 2028 March 2028
14 cruises
Caribbean: Barbados, Saint Lucia, Trinidad and Tobago, Saint Vincent and the Grenadines, Grenada, Netherlands Antilles, Aruba
Bridgetown Itinerary Caribbean
Suite from $4,533
price per person Taxes included
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Star Legend | Dec. 4, 2026
Duration: 8 nights
Departure from: Bridgetown Landing: Oranjestad
Itinerary:
1. Bridgetown,
2. Rodney Bay,
3. Pitons,
4. Scarborough,
5. Bequia,
6. Mayreau,
7. Saint George,
8. Willemstad,
9. Oranjestad
Caribbean: Antigua and Barbuda, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from $5,258
price per person Taxes included
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Star Pride | Dec. 13, 2026
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Gustavia,
4. Basseterre,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Caribbean: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, France, Saint Martin
Saint Johns Itinerary Caribbean
Suite from $5,726
price per person Taxes included
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Star Pride | Dec. 6, 2026
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. Saint George,
3. Bequia,
4. Mayreau,
5. Deshaies,
6. Marigot,
7. Saint Johns
Caribbean: Antigua and Barbuda, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from $5,837
price per person Taxes included
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Star Pride | Dec. 27, 2026
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Gustavia,
4. Basseterre,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Caribbean: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, France, Saint Martin
Saint Johns Itinerary Caribbean
Suite from $6,363
price per person Taxes included
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Star Pride | Dec. 20, 2026
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. Saint George,
3. Bequia,
4. Mayreau,
5. Deshaies,
6. Marigot,
7. Saint Johns
Caribbean: Sint Maarten, Saint Barthelemy, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
Suite External from $6,455
price per person Taxes included
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Wind Surf | Dec. 26, 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Gustavia,
3. Charlestown,
4. Roseau,
5. Mayreau,
6. Les Saintes,
7. Basseterre,
8. Philipsburg
Caribbean: Sint Maarten, Saint Barthelemy, British Virgin Islands, Virgin Islands
Philipsburg Itinerary Caribbean
Suite External from $7,003
price per person Taxes included
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Wind Surf | Dec. 19, 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Gustavia,
3. navigation,
4. Tortola Island,
5. Tortola Island,
6. Jost Van Dyke,
7. Jost Van Dyke,
8. Virgin Gorda,
9. Philipsburg
Caribbean: Barbados, Saint Lucia, Trinidad and Tobago, Saint Vincent and the Grenadines, Grenada, Netherlands Antilles, Aruba, Spain, Panama
Bridgetown Itinerary Caribbean
Suite from $8,573
price per person Taxes included
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Star Legend | Dec. 4, 2026
Duration: 16 nights
Departure from: Bridgetown Landing: Balboa
Itinerary:
1. Bridgetown,
2. Rodney Bay,
3. Pitons,
4. Scarborough,
5. Bequia,
6. Mayreau,
7. Saint George,
8. Willemstad,
9. Oranjestad,
10. Cartagena ,
11. Cartagena ,
12. Bocas del Toro,
13. San Blas Island,
14. navigation,
15. Balboa
Caribbean: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, France, Saint Martin, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from $9,999
price per person Taxes included
See the cruise Book
Star Pride | Dec. 6, 2026
Duration: 14 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. Saint George,
3. Bequia,
4. Mayreau,
5. Deshaies,
6. Marigot,
7. Saint Johns,
8. St. John ,
9. Gustavia,
10. Basseterre,
11. Philipsburg,
12. Jost Van Dyke,
13. Virgin Gorda,
14. Saint Johns
Caribbean: Antigua and Barbuda, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands, Grenada, Saint Vincent and the Grenadines, France, Saint Martin
Saint Johns Itinerary Caribbean
Suite from $10,578
price per person Taxes included
See the cruise Book
Star Pride | Dec. 13, 2026
Duration: 14 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Gustavia,
4. Basseterre,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns,
9. Saint George,
10. Bequia,
11. Mayreau,
12. Deshaies,
13. Marigot,
14. Saint Johns
14 cruises