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All Caribbean Cruises with Windstar Cruises in November 2026

  • 2027
  • 2028
October 2026 November 2026 December 2026
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January 2028 February 2028 March 2028
11 cruises
Caribbean: Barbados, Martinique, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, Grenada
Bridgetown Itinerary Caribbean
Suite from $3,751
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
Saint Johns Itinerary Caribbean
Suite from $4,880
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
Saint Johns Itinerary Caribbean
Suite from $4,992
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, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin
Saint Johns Itinerary Caribbean
Suite from $5,321
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, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from $5,868
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, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from $8,391
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: 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
Saint Johns Itinerary Caribbean
Suite from $8,391
price per person Taxes included
See the cruise Book
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: Barbados, Martinique, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, Grenada, Trinidad and Tobago, Netherlands Antilles, Aruba
Bridgetown Itinerary Caribbean
Suite from $8,827
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
Saint Johns Itinerary Caribbean
Suite from $9,379
price per person Taxes included
See the cruise Book
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, Spain, Panama
Bridgetown Itinerary Caribbean
External from $9,440
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 ,
10. navigation,
11. San Blas Island,
12. Colon
11 cruises