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All Caribbean Cruises with Windstar Cruises

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79 cruises
sold out

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

Philipsburg Itinerary Caribbean
from $5,258
price per person Taxes included
Wind Surf | Mar. 22, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
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
sold out

Barbados, Sri Lanka, Saint Lucia, Martinique, Saint Vincent and the Grenadines, Antigua and Barbuda

Bridgetown Itinerary Caribbean
from $3,407
price per person Taxes included
Star Pride | Mar. 29, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Pigeon Island,
3. Pigeon Island,
4. Castries,
5. Pitons,
6. Fort de france,
7. Mayreau,
8. Saint Johns,
9. Bequia,
10. Bridgetown
sold out

Barbados, Sri Lanka, Saint Lucia, Martinique, Saint Vincent and the Grenadines, Antigua and Barbuda

Bridgetown Itinerary Caribbean
from $4,246
price per person Taxes included
Star Pride | Mar. 29, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Pigeon Island,
3. Pigeon Island,
4. Castries,
5. Pitons,
6. Fort de france,
7. Mayreau,
8. Saint Johns,
9. Bequia,
10. Bridgetown

Caribbean: United States, Antigua and Barbuda

New York Itinerary Caribbean
from $3,904
price per person Taxes included
1 booking in 72 hours
Star Pride | Oct. 19, 2025
Duration: 7 nights
Departure from: New York Landing: Saint Johns
Itinerary:
1. New York,
2. navigation,
3. navigation,
4. Saint Johns,
5. Saint Johns,
6. navigation,
7. navigation,
8. Saint Johns

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

Saint Johns Itinerary Caribbean
from $4,284
price per person Taxes included
Star Pride | Oct. 26, 2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
sold out

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

Saint Johns Itinerary Caribbean
from $4,284
price per person Taxes included
Star Pride | Oct. 26, 2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns

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

Saint Johns Itinerary Caribbean
from $4,606
price per person Taxes included
Star Pride | Nov. 2, 2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
sold out

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

Saint Johns Itinerary Caribbean
from $4,606
price per person Taxes included
Star Pride | Nov. 2, 2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
sold out

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

San Juan Itinerary Caribbean
from $4,233
price per person Taxes included
Star Pride | Nov. 9, 2025
Duration: 7 nights
Departure from: San Juan Landing: San Juan
Itinerary:
1. San Juan,
2. navigation,
3. Saint George,
4. Bequia,
5. Pigeon Island,
6. Les Saintes,
7. Marigot,
8. San Juan

Caribbean: Antigua and Barbuda, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin

Saint Johns Itinerary Caribbean
from $4,233
price per person Taxes included
Star Pride | Nov. 9, 2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint Johns,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns

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

Saint Johns Itinerary Caribbean
from $4,284
price per person Taxes included
Star Pride | Nov. 16, 2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
sold out

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

Saint Johns Itinerary Caribbean
from $4,284
price per person Taxes included
Star Pride | Nov. 16, 2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
sold out

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

Bridgetown Itinerary Caribbean
from $6,182
price per person Taxes included
Wind Spirit | Nov. 18, 2025
Duration: 11 nights
Departure from: Bridgetown Landing: Colon
Itinerary:
1. Bridgetown,
2. Bequia,
3. Mayreau,
4. Saint Johns,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad,
9. navigation,
10. Cartagena ,
11. navigation,
12. Colon

Caribbean: Barbados, Saint Vincent and the Grenadines, Antigua and Barbuda, Netherlands Antilles, Aruba, Spain, Panama

Bridgetown Itinerary Caribbean
from $6,825
price per person Taxes included
Wind Spirit | Nov. 18, 2025
Duration: 11 nights
Departure from: Bridgetown Landing: Colon
Itinerary:
1. Bridgetown,
2. Bequia,
3. Mayreau,
4. Saint Johns,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad,
9. navigation,
10. Cartagena ,
11. navigation,
12. Colon
sold out

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

San Juan Itinerary Caribbean
from $4,233
price per person Taxes included
Star Pride | Nov. 23, 2025
Duration: 7 nights
Departure from: San Juan Landing: San Juan
Itinerary:
1. San Juan,
2. navigation,
3. Saint George,
4. Bequia,
5. Pigeon Island,
6. Les Saintes,
7. Marigot,
8. San Juan

Caribbean: Antigua and Barbuda, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin

Saint Johns Itinerary Caribbean
from $4,233
price per person Taxes included
Star Pride | Nov. 23, 2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint Johns,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns
sold out

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

Saint Johns Itinerary Caribbean
from $4,284
price per person Taxes included
Star Pride | Nov. 30, 2025
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, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands

Saint Johns Itinerary Caribbean
from $4,284
price per person Taxes included
1 booking in 72 hours
Star Pride | Nov. 30, 2025
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
sold out

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

Philipsburg Itinerary Caribbean
from $3,299
price per person Taxes included
Wind Surf | Dec. 2, 2025
Duration: 5 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Jost Van Dyke,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Gustavia,
7. Philipsburg

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

Philipsburg Itinerary Caribbean
from $3,460
price per person Taxes included
1 booking in 72 hours
Wind Surf | Dec. 2, 2025
Duration: 5 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Jost Van Dyke,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Gustavia,
7. Philipsburg

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

Philipsburg Itinerary Caribbean
from $3,784
price per person Taxes included
1 booking in 72 hours
Wind Surf | Dec. 7, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
sold out

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

Philipsburg Itinerary Caribbean
from $3,784
price per person Taxes included
Wind Surf | Dec. 7, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
sold out

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

Philipsburg Itinerary Caribbean
from $3,970
price per person Taxes included
Wind Surf | Dec. 14, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
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

Caribbean: Aruba, Netherlands Antilles, Antigua and Barbuda, Saint Vincent and the Grenadines, Barbados

Oranjestad Itinerary Caribbean
from $4,709
price per person Taxes included
Wind Spirit | Dec. 20, 2025
Duration: 8 nights
Departure from: Oranjestad Landing: Bridgetown
Itinerary:
1. Oranjestad,
2. Willemstad,
3. Kralendijk,
4. navigation,
5. Saint Johns,
6. Saint Johns,
7. Mayreau,
8. Bequia,
9. Bridgetown
sold out

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

Philipsburg Itinerary Caribbean
from $4,427
price per person Taxes included
Wind Surf | Dec. 21, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg

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

Philipsburg Itinerary Caribbean
from $4,749
price per person Taxes included
5 reservations in 72 hours
Wind Surf | Dec. 21, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
sold out

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

Philipsburg Itinerary Caribbean
from $4,453
price per person Taxes included
Wind Surf | Dec. 28, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
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
sold out

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

Bridgetown Itinerary Caribbean
from $4,693
price per person Taxes included
Wind Spirit | Dec. 28, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Pigeon Island,
7. Fort de france,
8. Bridgetown

Caribbean: Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Martinique

Bridgetown Itinerary Caribbean
from $5,015
price per person Taxes included
Wind Spirit | Dec. 28, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Mayreau,
7. Fort de france,
8. Bridgetown
sold out

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

Philipsburg Itinerary Caribbean
from $4,200
price per person Taxes included
Wind Surf | Jan. 4, 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
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
79 cruises