Windstar Cruises from Caribbean: Departures November 2026 $2,426

Caribbean: Barbados, Martinique, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, Grenada

Suite from $4,511
price per person Taxes included

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Star Legend | Nov. 27, 2026

Duration: 7 nights

Departure from: Bridgetown Landing: Bridgetown

Itinerary:

1. Bridgetown,

2. Fort de france,

3. Pigeon Island,

4. Pigeon Island,

5. Castries,

6. Pitons,

7. Mayreau,

8. Saint George,

9. Bequia,

10. Bridgetown

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

Suite from $4,550
price per person Taxes included

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Star Pride | Nov. 29, 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: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin

Suite from $4,827
price per person Taxes included

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Star Pride | Nov. 8, 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, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin

Suite from $4,827
price per person Taxes included

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Star Pride | Nov. 22, 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

Suite from $4,880
price per person Taxes included

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Star Pride | Nov. 15, 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, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin

Suite from $7,237
price per person Taxes included

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Star Pride | Nov. 29, 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. Les Saintes,

14. Marigot,

15. Saint Johns

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 $7,567
price per person Taxes included

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Star Pride | Nov. 22, 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: Barbados, Martinique, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, Grenada, Trinidad and Tobago, Netherlands Antilles, Aruba

Suite from $7,674
price per person Taxes included

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Star Legend | Nov. 27, 2026

Duration: 15 nights

Departure from: Bridgetown Landing: Oranjestad

Itinerary:

1. Bridgetown,

2. Fort de france,

3. Pigeon Island,

4. Pigeon Island,

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. navigation,

17. Kralendijk,

18. Willemstad,

19. Oranjestad

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 $7,732
price per person Taxes included

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Star Pride | Nov. 15, 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, Saint Vincent and the Grenadines, Grenada, Netherlands Antilles, Aruba, Colombia, Panama

External from $7,957
price per person Taxes included

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Wind Star | Nov. 24, 2026

Duration: 11 nights

Departure from: Bridgetown Landing: Colon

Itinerary:

1. Bridgetown,

2. Bequia,

3. Saint George,

4. navigation,

5. Kralendijk,

6. Willemstad,

7. Oranjestad,

8. navigation,

9. Cartagena De Indias,

10. navigation,

11. San Blas Island,

12. Colon

All Caribbean Cruises with Windstar Cruises in November 2026