Caribbean: United States, Grenada, Antigua and Barbuda

Suite from $4,485
price per person Taxes included

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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 George,

5. Saint George,

6. navigation,

7. navigation,

8. Saint Johns

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

Suite from $4,921
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

Suite from $4,921
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

Suite from $4,513
price per person Taxes included

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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

Suite from $5,291
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

Suite from $4,862
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, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin

Suite from $4,862
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 George,

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

Suite from $4,921
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

Suite from $4,921
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, Grenada, Netherlands Antilles, Aruba, Spain, Panama

External from $7,101
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 George,

5. navigation,

6. Kralendijk,

7. Willemstad,

8. Oranjestad,

9. navigation,

10. Cartagena ,

11. navigation,

12. Colon

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

External from $8,580
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 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 $4,862
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, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin

Suite from $4,862
price per person Taxes included

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 George,

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

Suite from $5,106
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

Suite from $4,921
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

External from $3,790
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

External from $4,529
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

External from $4,346
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

External from $4,716
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

External from $4,561
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: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $4,930
price per person Taxes included

See the cruise Book

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, Grenada, Saint Vincent and the Grenadines, Barbados

External from $5,964
price per person Taxes included

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 George,

6. Saint George,

7. Mayreau,

8. Bequia,

9. Bridgetown

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

External from $6,010
price per person Taxes included

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

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

External from $5,086
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

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

External from $5,391
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

External from $6,500
price per person Taxes included

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

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

External from $6,409
price per person Taxes included

See the cruise Book

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

External from $5,115
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

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

External from $5,380
price per person Taxes included

See the cruise Book

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

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

External from $4,825
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

All Caribbean Cruises with Windstar Cruises