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

All Caribbean Cruises with Windstar Cruises in December 2026

  • 2025
  • 2027
December 2025
January 2026 February 2026 March 2026 April 2026 May 2026 June 2026 July 2026 August 2026 September 2026 October 2026 November 2026 December 2026
January 2027 February 2027 March 2027
14 cruises
Caribbean: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin
Saint Johns Itinerary Caribbean
Suite from $6,259
price per person Taxes included
See the cruise Book Online Book Online
Star Pride | 6/12/2026
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Les Saintes,
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 $6,323
price per person Taxes included
See the cruise Book Online Book Online
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: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin
Saint Johns Itinerary Caribbean
Suite from $6,658
price per person Taxes included
See the cruise Book Online Book Online
Star Pride | 20/12/2026
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns
Caribbean: Sint Maarten, Saint Barthelemy, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
External from $6,700
price per person Taxes included
See the cruise Book Online Book Online
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: Sint Maarten, Saint Barthelemy, British Virgin Islands, Virgin Islands
Philipsburg Itinerary Caribbean
External from $6,732
price per person Taxes included
See the cruise Book Online Book Online
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, Netherlands Antilles, Aruba
Bridgetown Itinerary Caribbean
Suite from $7,036
price per person Taxes included
See the cruise Book Online Book Online
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. navigation,
8. Kralendijk,
9. Willemstad,
10. Oranjestad
Caribbean: Antigua and Barbuda, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from $8,522
price per person Taxes included
See the cruise Book Online Book Online
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, Guadeloupe, Saint Martin, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from $9,984
price per person Taxes included
See the cruise Book Online Book Online
Star Pride | 6/12/2026
Duration: 14 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns,
9. St. John ,
10. Gustavia,
11. Basseterre,
12. Philipsburg,
13. Jost Van Dyke,
14. Virgin Gorda,
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 $10,036
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 26/12/2026
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: Antigua and Barbuda, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin
Saint Johns Itinerary Caribbean
Suite from $10,384
price per person Taxes included
See the cruise Book Online Book Online
Star Pride | 13/12/2026
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. navigation,
10. Saint George,
11. Bequia,
12. Mayreau,
13. Les Saintes,
14. Marigot,
15. Saint Johns
14 cruises