Caribbean: United States, Antigua and Barbuda

from $4,522
price per person Taxes included

4 reservations in 72 hours

See the cruise Book

Star Pride | 19 Oct 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

from $4,962
price per person Taxes included

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Star Pride | 26 Oct 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

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

from $4,962
price per person Taxes included

Star Pride | 26 Oct 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

from $5,335
price per person Taxes included

5 reservations in 72 hours

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Star Pride | 2 Nov 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

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

from $5,335
price per person Taxes included

Star Pride | 2 Nov 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

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

from $4,903
price per person Taxes included

Star Pride | 9 Nov 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

from $4,903
price per person Taxes included

See the cruise Book

Star Pride | 9 Nov 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

from $4,962
price per person Taxes included

See the cruise Book

Star Pride | 16 Nov 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

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

from $4,962
price per person Taxes included

Star Pride | 16 Nov 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

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

from $7,160
price per person Taxes included

Wind Spirit | 18 Nov 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

from $7,906
price per person Taxes included

See the cruise Book

Wind Spirit | 18 Nov 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

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

from $4,903
price per person Taxes included

Star Pride | 23 Nov 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

from $4,903
price per person Taxes included

1 booking in 72 hours

See the cruise Book

Star Pride | 23 Nov 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 Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands

from $4,962
price per person Taxes included

See the cruise Book

Star Pride | 30 Nov 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

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

from $4,962
price per person Taxes included

Star Pride | 30 Nov 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

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

from $3,821
price per person Taxes included

Wind Surf | 2 Dec 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

from $4,008
price per person Taxes included

See the cruise Book

Wind Surf | 2 Dec 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

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

from $4,382
price per person Taxes included

Wind Surf | 7 Dec 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

from $4,382
price per person Taxes included

See the cruise Book

Wind Surf | 7 Dec 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

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

from $4,599
price per person Taxes included

Wind Surf | 14 Dec 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

from $5,454
price per person Taxes included

4 reservations in 72 hours

See the cruise Book

Wind Spirit | 20 Dec 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

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

from $5,128
price per person Taxes included

Wind Surf | 21 Dec 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

from $5,501
price per person Taxes included

4 reservations in 72 hours

See the cruise Book

Wind Surf | 21 Dec 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

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

from $5,436
price per person Taxes included

Wind Spirit | 28 Dec 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

from $5,809
price per person Taxes included

1 booking in 72 hours

See the cruise Book

Wind Spirit | 28 Dec 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

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

from $5,158
price per person Taxes included

Wind Surf | 28 Dec 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

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

from $4,865
price per person Taxes included

Wind Surf | 4 Jan 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

Caribbean: Barbados, Saint Vincent and the Grenadines, Dominica, Martinique, France, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy, British Virgin Islands, Sint Maarten

from $6,375
price per person Taxes included

See the cruise Book

Wind Spirit | 4 Jan 2026

Duration: 10 nights

Departure from: Bridgetown Landing: Philipsburg

Itinerary:

1. Bridgetown,

2. Mayreau,

3. Roseau,

4. Fort de france,

5. Deshaies,

6. Basseterre,

7. Saint Johns,

8. navigation,

9. Gustavia,

10. Tortola Island,

11. Philipsburg

Caribbean: Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Saint Vincent and the Grenadines, Barbados

from $4,914
price per person Taxes included

See the cruise Book

Wind Surf | 11 Jan 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Bridgetown

Itinerary:

1. Philipsburg,

2. Basseterre,

3. Gustavia,

4. Saint Johns,

5. Les Saintes,

6. Mayreau,

7. Kingstown,

8. Bridgetown

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

from $4,914
price per person Taxes included

Wind Surf | 11 Jan 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Bridgetown

Itinerary:

1. Philipsburg,

2. Basseterre,

3. Gustavia,

4. St. John ,

5. Les Saintes,

6. Pigeon Island,

7. Kingstown,

8. Bridgetown

All Caribbean Cruises with Windstar Cruises

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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