All Caribbean Cruises with Windstar Cruises in January 2026
- 2025
- 2026
- 2027
January 2026
February 2026
March 2026
April 2026
May 2026
June 2026
July 2026
August 2026
September 2026
October 2026
November 2026
December 2026
13 cruises
External from $5,331
price per person Taxes included
price per person Taxes included
Book Online 
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. Saint Johns,
5. Les Saintes,
6. Roseau,
7. Mayreau,
8. Bridgetown
Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
External from $6,030
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Saint Johns,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
External from $6,359
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Saint Johns,
3. Tortola Island,
4. Virgin Gorda,
5. Tortola Island,
6. Tortola Island,
7. Jost Van Dyke,
8. Gustavia,
9. Philipsburg
Barbados, Saint Vincent and the Grenadines, Dominica, Martinique, United States, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy, British Virgin Islands, Sint Maarten
External from $7,002
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. Mayreau,
3. Roseau,
4. Fort de france,
5. Charlestown,
6. Basseterre,
7. Saint Johns,
8. navigation,
9. Gustavia,
10. Tortola Island,
11. Philipsburg
External from $7,288
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. Bequia,
3. Mayreau,
4. Soufriere,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad
External from $8,438
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. Fort de france,
3. Castries,
4. Pigeon Island,
5. Pigeon Island,
6. Bequia,
7. Mayreau,
8. Saint George,
9. Bridgetown
Sint Maarten, Saint Kitts and Nevis, Dominica, Saint Lucia, Martinique, Guadeloupe, United States, British Virgin Islands, Virgin Islands, Saint Barthelemy
External from $8,786
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Roseau,
4. Castries,
5. Fort de france,
6. Les Saintes,
7. Charlestown,
8. Virgin Gorda,
9. Jost Van Dyke,
10. Gustavia,
11. Philipsburg
Suite from $11,384
price per person Taxes included
price per person Taxes included
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
Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Barbados
External from $12,598
price per person Taxes included
price per person Taxes included
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,
10. Basseterre,
11. Gustavia,
12. Saint Johns,
13. Les Saintes,
14. Roseau,
15. Mayreau,
16. Bridgetown
External from $12,794
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. Bequia,
3. Mayreau,
4. Soufriere,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad,
9. navigation,
10. Cartagena De Indias,
11. Cartagena De Indias,
12. San Blas Island,
13. navigation,
14. Bocas del Toro,
15. Colon,
16. Colon
13 cruises
