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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: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, France, Saint Martin
Saint Johns Itinerary Caribbean
Suite from $4,060
price per person Taxes included
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Star Pride | 20 Dec 2026
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Deshaies,
7. Marigot,
8. 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 $4,114
price per person Taxes included
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Star Pride | 13 Dec 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: Barbados, Saint Lucia, Trinidad and Tobago, Saint Vincent and the Grenadines, Grenada, Netherlands Antilles, Aruba
Bridgetown Itinerary Caribbean
Suite from $4,546
price per person Taxes included
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Star Legend | 4 Dec 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. navigation,
9. Willemstad,
10. Oranjestad
Caribbean: Sint Maarten, Saint Barthelemy, British Virgin Islands, Virgin Islands
Philipsburg Itinerary Caribbean
External from $4,947
price per person Taxes included
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Wind Surf | 19 Dec 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: Sint Maarten, Saint Barthelemy, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
External from $5,804
price per person Taxes included
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Wind Surf | 26 Dec 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: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, France, Saint Martin
Saint Johns Itinerary Caribbean
Suite from $6,122
price per person Taxes included
See the cruise Book
Star Pride | 6 Dec 2026
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Deshaies,
7. Marigot,
8. 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 $6,471
price per person Taxes included
See the cruise Book
Star Pride | 27 Dec 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, 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 $7,722
price per person Taxes included
See the cruise Book
Star Pride | 13 Dec 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. navigation,
10. Saint George,
11. Bequia,
12. Mayreau,
13. Deshaies,
14. Marigot,
15. Saint Johns
Caribbean: Sint Maarten, Saint Barthelemy, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, British Virgin Islands, Virgin Islands
Philipsburg Itinerary Caribbean
External from $9,418
price per person Taxes included
See the cruise Book
Wind Surf | 26 Dec 2026
Duration: 14 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Gustavia,
3. Charlestown,
4. Roseau,
5. Mayreau,
6. Les Saintes,
7. Basseterre,
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
Caribbean: Sint Maarten, Saint Barthelemy, British Virgin Islands, Virgin Islands, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
External from $9,600
price per person Taxes included
See the cruise Book
Wind Surf | 19 Dec 2026
Duration: 14 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,
10. Gustavia,
11. Charlestown,
12. Roseau,
13. Mayreau,
14. Les Saintes,
15. Basseterre,
16. Philipsburg
14 cruises