Windstar Cruises from Caribbean: Departures November 2026 $2,108

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

Suite from $4,514
price per person Taxes included

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Star Pride | 22 Nov 2026

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 $4,627
price per person Taxes included

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Star Pride | 29 Nov 2026

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: Barbados, Martinique, Saint Lucia, Saint Vincent and the Grenadines, Grenada

Suite from $5,702
price per person Taxes included

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Star Legend | 27 Nov 2026

Duration: 7 nights

Departure from: Bridgetown Landing: Bridgetown

Itinerary:

1. Bridgetown,

2. Fort de france,

3. Rodney Bay,

4. Rodney Bay,

5. Castries,

6. Pitons,

7. Mayreau,

8. Saint George,

9. Bequia,

10. Bridgetown

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

Suite from $6,447
price per person Taxes included

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Star Pride | 15 Nov 2026

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, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin

Suite from $8,037
price per person Taxes included

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Star Pride | 8 Nov 2026

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, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin

Suite from $8,519
price per person Taxes included

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Star Pride | 15 Nov 2026

Duration: 14 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,

9. navigation,

10. Saint George,

11. Bequia,

12. Mayreau,

13. Les Saintes,

14. Marigot,

15. Saint Johns

Caribbean: Barbados, Martinique, Saint Lucia, Saint Vincent and the Grenadines, Grenada, Trinidad and Tobago, Netherlands Antilles, Aruba

Suite from $8,527
price per person Taxes included

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Star Legend | 27 Nov 2026

Duration: 15 nights

Departure from: Bridgetown Landing: Oranjestad

Itinerary:

1. Bridgetown,

2. Fort de france,

3. Rodney Bay,

4. Rodney Bay,

5. Castries,

6. Pitons,

7. Mayreau,

8. Saint George,

9. Bequia,

10. Bridgetown,

11. Rodney Bay,

12. Pitons,

13. Scarborough,

14. Bequia,

15. Mayreau,

16. Saint George,

17. navigation,

18. Willemstad,

19. Oranjestad

Caribbean: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands

Suite from $8,566
price per person Taxes included

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Star Pride | 22 Nov 2026

Duration: 14 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,

9. St. John ,

10. Gustavia,

11. Basseterre,

12. Philipsburg,

13. Jost Van Dyke,

14. Virgin Gorda,

15. Saint Johns

Caribbean: Antigua and Barbuda, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands, Grenada, Saint Vincent and the Grenadines, France, Saint Martin

Suite from $10,163
price per person Taxes included

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Star Pride | 29 Nov 2026

Duration: 14 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,

9. navigation,

10. Saint George,

11. Bequia,

12. Mayreau,

13. Deshaies,

14. Marigot,

15. Saint Johns

Caribbean: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands

Suite from $12,511
price per person Taxes included

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Star Pride | 8 Nov 2026

Duration: 14 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,

9. St. John ,

10. Basseterre,

11. Gustavia,

12. Philipsburg,

13. Jost Van Dyke,

14. Virgin Gorda,

15. Saint Johns

All Caribbean Cruises with Windstar Cruises in November 2026