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Itineraries and cruises Windstar Cruises departing from Boston

  • 2027
September 2026 October 2026 November 2026 December 2026
January 2027 February 2027 March 2027 April 2027 May 2027 June 2027 July 2027 August 2027
7 cruises
Caribbean: United States, Bermuda, Grenada, Antigua and Barbuda
Boston Itinerary Caribbean
Suite from $5,110
price per person Taxes included
See the cruise Book
Star Pride | Oct. 20, 2026
Duration: 8 nights
Departure from: Boston Landing: Saint Johns
Itinerary:
1. Boston,
2. navigation,
3. navigation,
4. Hamilton,
5. Hamilton,
6. Saint George,
7. Saint George,
8. navigation,
9. navigation,
10. Saint Johns
Caribbean: United States, Bermuda, Grenada, Saint Barthelemy, British Virgin Islands, Antigua and Barbuda
Boston Itinerary Caribbean
Suite from $6,710
price per person Taxes included
See the cruise Book
Star Pride | Oct. 22, 2027
Duration: 10 nights
Departure from: Boston Landing: Saint Johns
Itinerary:
1. Boston,
2. navigation,
3. navigation,
4. Hamilton,
5. Hamilton,
6. Saint George,
7. Saint George,
8. navigation,
9. navigation,
10. Gustavia,
11. Virgin Gorda,
12. Saint Johns
Caribbean: United States, Bermuda, Grenada, Saint Barthelemy, British Virgin Islands, Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Sint Maarten
Boston Itinerary Caribbean
Suite from $8,654
price per person Taxes included
See the cruise Book
Star Pride | Oct. 22, 2027
Duration: 17 nights
Departure from: Boston Landing: Saint Johns
Itinerary:
1. Boston,
2. navigation,
3. navigation,
4. Hamilton,
5. Hamilton,
6. Saint George,
7. Saint George,
8. navigation,
9. navigation,
10. Gustavia,
11. Virgin Gorda,
12. Saint Johns,
13. St. John ,
14. Basseterre,
15. Gustavia,
16. Philipsburg,
17. Jost Van Dyke,
18. Virgin Gorda,
19. Saint Johns
North America: United States, United Kingdom, Canada
Boston Itinerary North America
Suite from $12,715
price per person Taxes included
See the cruise Book
Star Pride | Sep. 14, 2026
Duration: 11 nights
Departure from: Boston Landing: Montreal
Itinerary:
1. Boston,
2. Rockland,
3. Portland (GB),
4. navigation,
5. Halifax,
6. Sydney,
7. cap-aux-meules,
8. navigation,
9. navigation,
10. Quebec City,
11. Quebec City,
12. navigation,
13. Montreal
North America: United States, United Kingdom, Canada
Boston Itinerary North America
Suite from $13,082
price per person Taxes included
See the cruise Book
Star Pride | Sep. 16, 2027
Duration: 11 nights
Departure from: Boston Landing: Montreal
Itinerary:
1. Boston,
2. Portland (GB),
3. Halifax,
4. Halifax,
5. navigation,
6. Charlottetown,
7. Charlottetown,
8. navigation,
9. navigation,
10. Quebec City,
11. Quebec City,
12. navigation,
13. Montreal
sold out
United States, United Kingdom, Canada, France, Antigua and Barbuda, Chile
Boston Itinerary North America
Suite from $25,830
price per person Taxes included
Star Pride | Sep. 14, 2026
Duration: 25 nights
Departure from: Boston Landing: Montreal
Itinerary:
1. Boston,
2. Rockland,
3. Portland (GB),
4. navigation,
5. Halifax,
6. Sydney,
7. cap-aux-meules,
8. navigation,
9. navigation,
10. Quebec City,
11. Quebec City,
12. navigation,
13. Montreal,
14. Quebec City,
15. Baie-Comeau,
16. navigation,
17. cap-aux-meules,
18. St. Pierre Miquelon,
19. Saint Johns,
20. Saint Johns,
21. San Antonio,
22. Red Bay,
23. navigation,
24. Le Havre,
25. navigation,
26. navigation,
27. Trois-Rivières,
28. Montreal
North America: United States, United Kingdom, Canada, France, Antigua and Barbuda, Chile
Boston Itinerary North America
Suite from $29,709
price per person Taxes included
See the cruise Book
Star Pride | Sep. 16, 2027
Duration: 25 nights
Departure from: Boston Landing: Montreal
Itinerary:
1. Boston,
2. Portland (GB),
3. Halifax,
4. Halifax,
5. navigation,
6. Charlottetown,
7. Charlottetown,
8. navigation,
9. navigation,
10. Quebec City,
11. Quebec City,
12. navigation,
13. Montreal,
14. Tadoussac,
15. navigation,
16. navigation,
17. cap-aux-meules,
18. St. Pierre Miquelon,
19. Saint Johns,
20. Saint Johns,
21. San Antonio,
22. Red Bay,
23. navigation,
24. Le Havre,
25. navigation,
26. Quebec City,
27. navigation,
28. Montreal
7 cruises