All Caribbean Cruises with Windstar Cruises
- 2025
- 2026
- 2027
January 2026
February 2026
March 2026
April 2026
May 2026
June 2026
July 2026
August 2026
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October 2026
November 2026
December 2026
85 cruises

Suite
from $4,789
price per person Taxes included
price per person Taxes included
Itinerary:
1. New York,
2. navigation,
3. navigation,
4. Saint George,
5. Saint George,
6. navigation,
7. navigation,
8. Saint Johns

Suite
from $5,255
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns

Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands

Suite
from $5,255
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns

Suite
from $5,650
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns

Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands

Suite
from $5,650
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns

Puerto Rico, Grenada, Saint Vincent and the Grenadines, Sri Lanka, Guadeloupe, Saint Martin

Suite
from $5,192
price per person Taxes included
price per person Taxes included
Itinerary:
1. San Juan,
2. navigation,
3. Saint George,
4. Bequia,
5. Pigeon Island,
6. Les Saintes,
7. Marigot,
8. San Juan

Suite
from $5,192
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns

Suite
from $5,255
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns

Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands

Suite
from $5,255
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns

Barbados, Saint Vincent and the Grenadines, Grenada, Netherlands Antilles, Aruba, Spain, Panama

External
from $7,583
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. Bequia,
3. Mayreau,
4. Saint George,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad,
9. navigation,
10. Cartagena ,
11. navigation,
12. Colon

External
from $8,373
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. Bequia,
3. Mayreau,
4. Saint George,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad,
9. navigation,
10. Cartagena ,
11. navigation,
12. Colon

Puerto Rico, Grenada, Saint Vincent and the Grenadines, Sri Lanka, Guadeloupe, Saint Martin

Suite
from $5,192
price per person Taxes included
price per person Taxes included
Itinerary:
1. San Juan,
2. navigation,
3. Saint George,
4. Bequia,
5. Pigeon Island,
6. Les Saintes,
7. Marigot,
8. San Juan

Suite
from $5,192
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns

Suite
from $5,453
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. St. John ,
3. Gustavia,
4. Basseterre,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns

Antigua and Barbuda, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands

Suite
from $5,255
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. St. John ,
3. Gustavia,
4. Basseterre,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns

Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

External
from $4,047
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Jost Van Dyke,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Gustavia,
7. Philipsburg

External
from $4,245
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Jost Van Dyke,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Gustavia,
7. Philipsburg

Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

External
from $4,641
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg

External
from $5,036
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg

Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

External
from $4,870
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

External
from $5,265
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

External
from $5,974
price per person Taxes included
price per person Taxes included
Itinerary:
1. Oranjestad,
2. Willemstad,
3. Kralendijk,
4. navigation,
5. Saint George,
6. Saint George,
7. Mayreau,
8. Bequia,
9. Bridgetown

External
from $6,023
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg

Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

External
from $5,431
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg

Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Sri Lanka, Martinique

External
from $5,757
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Pigeon Island,
7. Fort de france,
8. Bridgetown

External
from $6,349
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Mayreau,
7. Fort de france,
8. Bridgetown

External
from $6,252
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

External
from $5,463
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

External
from $5,350
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

External
from $5,153
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
85 cruises