home › Windstar Cruises › All Caribbean Cruises with Windstar Cruises in December 2026›December 2026

All Caribbean Cruises with Windstar Cruises in December 2026

  • 2027
  • 2028
November 2026 December 2026
January 2027 February 2027 March 2027 April 2027 May 2027 June 2027 July 2027 August 2027 September 2027 October 2027 November 2027 December 2027
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 $5,002
price per person Taxes included
See the cruise Book
Star Pride | 6/12/2026
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, British Virgin Islands, Virgin Islands
Philipsburg Itinerary Caribbean
Suite External from $5,514
price per person Taxes included
See the cruise Book
Wind Surf | 19/12/2026
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
Bridgetown Itinerary Caribbean
Suite from $5,684
price per person Taxes included
See the cruise Book
Star Legend | 4/12/2026
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 $6,085
price per person Taxes included
See the cruise Book
Star Pride | 13/12/2026
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: Sint Maarten, Saint Barthelemy, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
Suite External from $6,788
price per person Taxes included
See the cruise Book
Wind Surf | 26/12/2026
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, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from $6,811
price per person Taxes included
See the cruise Book
Star Pride | 27/12/2026
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 $7,035
price per person Taxes included
See the cruise Book
Star Pride | 20/12/2026
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, 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 $10,070
price per person Taxes included
See the cruise Book
Star Pride | 6/12/2026
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: Barbados, Saint Lucia, Trinidad and Tobago, Saint Vincent and the Grenadines, Grenada, Netherlands Antilles, Aruba, Spain, Panama
Bridgetown Itinerary Caribbean
Suite from $10,750
price per person Taxes included
See the cruise Book
Star Legend | 4/12/2026
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, 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 $11,231
price per person Taxes included
See the cruise Book
Star Pride | 27/12/2026
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