All Caribbean Cruises with Windstar Cruises
- 2025
- 2026
- 2027
January 2026
February 2026
March 2026
April 2026
May 2026
June 2026
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December 2026
101 cruises

Suite
from $4,051
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

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

External
from $4,099
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 $4,701
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 $4,701
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 $4,899
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, British Virgin Islands, Virgin Islands, Saint Barthelemy

External
from $4,933
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, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy

External
from $4,933
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, British Virgin Islands, Virgin Islands, Saint Barthelemy

External
from $4,933
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 $5,031
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. Tobago Cays,
3. Pigeon Island,
4. Pigeon Island,
5. Castries,
6. Pitons,
7. Mayreau,
8. Bequia,
9. Bridgetown

Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Dominica, Sri Lanka, Barbados

External
from $5,039
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. St. John ,
5. Les Saintes,
6. Roseau,
7. Pigeon Island,
8. Bridgetown

Suite
from $5,059
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 $5,059
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 $5,059
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

External
from $5,101
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Les Saintes,
4. Mayreau,
5. Roseau,
6. Basseterre,
7. Gustavia,
8. Philipsburg

External
from $5,101
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, Sri Lanka, Guadeloupe, Saint Barthelemy, Saint Kitts and Nevis

External
from $5,101
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Pigeon Island,
5. Les Saintes,
6. Gustavia,
7. Basseterre,
8. Philipsburg

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

External
from $5,119
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

Suite
from $5,123
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

Suite
from $5,123
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 $5,123
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

External
from $5,133
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 $5,133
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Tortola Island,
4. Jost Van Dyke,
5. Jost Van Dyke,
6. Virgin Gorda,
7. Gustavia,
8. navigation,
9. Philipsburg

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

External
from $5,219
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

Barbados, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, Grenada

External
from $5,231
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. Pigeon Island,
3. Pigeon Island,
4. Castries,
5. Pitons,
6. Kingstown,
7. Mayreau,
8. Saint George,
9. Bequia,
10. Bridgetown

Barbados, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, Grenada

External
from $5,231
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. Pigeon Island,
3. Pigeon Island,
4. Castries,
5. Pitons,
6. Kingstown,
7. Mayreau,
8. Saint George,
9. Bequia,
10. Bridgetown

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

External
from $5,231
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Fort de france,
7. Pigeon Island,
8. Bridgetown

Sint Maarten, United States, Dominica, Sri Lanka, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

External
from $5,233
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Pigeon Island,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg

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

Suite
from $5,259
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

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

Suite
from $5,259
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

Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Sri Lanka, Saint Vincent and the Grenadines, Barbados

External
from $5,271
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. St. John ,
5. Les Saintes,
6. Pigeon Island,
7. Kingstown,
8. Bridgetown
101 cruises