Star Pride schedule from Boston
- Boston departures
- 6
- Passengers
- 312
- From
- $4,477
- Itineraries
- 10 to 25 nights
Ship figures from Windstar Cruises, fleet specifications, checked 2026-11-03.
Star Pride is a Windstar Cruises ship with 6 departures from the Port of Boston in the period we track, from Thu, Sep 16, 2027 to Thu, Sep 14, 2028. Windstar lists her at 312 guests. She was built in 1988, and Windstar has sailed her since 2014.
From Boston she sails 10- to 25-night trips to Canada and New England and the Caribbean.
The lowest starting fare on her schedule is $4,477 per person as of November 3, 2026, for the Fri, Oct 22, 2027 sailing.
Planning a trip? See our Canada and New England guide and Caribbean guide.
Schedule coverage: published through 2028-09-14.
Itineraries Star Pride runs from Boston
All routes| Itinerary | Nights | Departures | From |
|---|---|---|---|
| 17-Night Caribbean Calls at Hamilton (Bermuda) · St. George's (Bermuda) · Hamilton (Bermuda) · St. George's (Bermuda) · Gustavia (St. Barts) · Virgin Gorda (British Virgin Islands) · San Juan (Puerto Rico) · St. John (U.S. Virgin Islands) · Basseterre (St. Kitts) · Gustavia (St. Barts) · Philipsburg (St. Maarten) · Jost Van Dyke (British Virgin Islands) · Virgin Gorda (British Virgin Islands) Ends in San Juan (Puerto Rico) Next on Fri, Oct 22, 2027 | 17 | 1 | $6,040$355 a night |
| 10-Night Caribbean Calls at Hamilton (Bermuda) · St. George's (Bermuda) · Gustavia (St. Barts) · Virgin Gorda (British Virgin Islands) Ends in San Juan (Puerto Rico) Next on Fri, Oct 22, 2027 | 10 | 1 | $4,477$448 a night |
| 25-Night Canada Calls at Portland (Maine) · Bar Harbor (Maine) · Halifax (Nova Scotia) · Charlottetown (Prince Edward Island) · Gaspé (Quebec) · Quebec City (Quebec) · Montreal (Quebec) · Tadoussac (Quebec) · Saguenay (Quebec) · Cap-aux-Meules (Quebec) · Saint-Pierre (Saint-Pierre and Miquelon) · St. John's (Newfoundland) · St. Anthony (Newfoundland) · Red Bay (Labrador) · Bonne Bay (Newfoundland) · Havre-Saint-Pierre (Quebec) · Quebec City (Quebec) Ends in Montreal (Quebec) Next on Thu, Sep 16, 2027 | 25 | 2 | $12,666$507 a night |
| 11-Night Canada Calls at Portland (Maine) · Bar Harbor (Maine) · Halifax (Nova Scotia) · Charlottetown (Prince Edward Island) · Gaspé (Quebec) · Quebec City (Quebec) Ends in Montreal (Quebec) Next on Thu, Sep 16, 2027 | 11 | 2 | $6,091$554 a night |
Starting fares per person, for the cheapest cabin listed, with taxes and port fees included, checked . Fares change often, so check the current price before you book.
Every departure by date
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| Departs | Nights | Itinerary & ports | From |
|---|---|---|---|
Thu, Sep 16, 2027 ends Mon, Sep 27, 2027 | 11 | 11-Night Canada Calls at Portland (Maine) · Bar Harbor (Maine) · Halifax (Nova Scotia) · Charlottetown (Prince Edward Island) · Gaspé (Quebec) · Quebec City (Quebec) Ends in Montreal (Quebec) | |
Thu, Sep 16, 2027 ends Mon, Oct 11, 2027 | 25 | 25-Night Canada Calls at Portland (Maine) · Bar Harbor (Maine) · Halifax (Nova Scotia) · Charlottetown (Prince Edward Island) · Gaspé (Quebec) · Quebec City (Quebec) · Montreal (Quebec) · Tadoussac (Quebec) · Saguenay (Quebec) · Cap-aux-Meules (Quebec) · Saint-Pierre (Saint-Pierre and Miquelon) · St. John's (Newfoundland) · St. Anthony (Newfoundland) · Red Bay (Labrador) · Bonne Bay (Newfoundland) · Havre-Saint-Pierre (Quebec) · Quebec City (Quebec) Ends in Montreal (Quebec) | |
Fri, Oct 22, 2027 ends Mon, Nov 1, 2027 | 10 | 10-Night Caribbean Calls at Hamilton (Bermuda) · St. George's (Bermuda) · Gustavia (St. Barts) · Virgin Gorda (British Virgin Islands) Ends in San Juan (Puerto Rico) | Lowest fare shown |
Fri, Oct 22, 2027 ends Mon, Nov 8, 2027 | 17 | 17-Night Caribbean Calls at Hamilton (Bermuda) · St. George's (Bermuda) · Hamilton (Bermuda) · St. George's (Bermuda) · Gustavia (St. Barts) · Virgin Gorda (British Virgin Islands) · San Juan (Puerto Rico) · St. John (U.S. Virgin Islands) · Basseterre (St. Kitts) · Gustavia (St. Barts) · Philipsburg (St. Maarten) · Jost Van Dyke (British Virgin Islands) · Virgin Gorda (British Virgin Islands) Ends in San Juan (Puerto Rico) | |
Thu, Sep 14, 2028 ends Mon, Sep 25, 2028 | 11 | 11-Night Canada Calls at Portland (Maine) · Bar Harbor (Maine) · Halifax (Nova Scotia) · Charlottetown (Prince Edward Island) · Gaspé (Quebec) · Quebec City (Quebec) Ends in Montreal (Quebec) | |
Thu, Sep 14, 2028 ends Mon, Oct 9, 2028 | 25 | 25-Night Canada Calls at Portland (Maine) · Bar Harbor (Maine) · Halifax (Nova Scotia) · Charlottetown (Prince Edward Island) · Gaspé (Quebec) · Quebec City (Quebec) · Montreal (Quebec) · Tadoussac (Quebec) · Saguenay (Quebec) · Cap-aux-Meules (Quebec) · Saint-Pierre (Saint-Pierre and Miquelon) · St. John's (Newfoundland) · St. Anthony (Newfoundland) · Red Bay (Labrador) · Bonne Bay (Newfoundland) · Havre-Saint-Pierre (Quebec) · Quebec City (Quebec) Ends in Montreal (Quebec) |
- SEP16
Thursday · 11 nights
11-Night Canada
Calls at Portland (Maine) · Bar Harbor (Maine) · Halifax (Nova Scotia) · Charlottetown (Prince Edward Island) · Gaspé (Quebec) · Quebec City (Quebec)
Ends in Montreal (Quebec)
Ends Mon, Sep 27, 2027 in Montreal
- SEP16
Thursday · 25 nights
25-Night Canada
Calls at Portland (Maine) · Bar Harbor (Maine) · Halifax (Nova Scotia) · Charlottetown (Prince Edward Island) · Gaspé (Quebec) · Quebec City (Quebec) · Montreal (Quebec) · Tadoussac (Quebec) · Saguenay (Quebec) · Cap-aux-Meules (Quebec) · Saint-Pierre (Saint-Pierre and Miquelon) · St. John's (Newfoundland) · St. Anthony (Newfoundland) · Red Bay (Labrador) · Bonne Bay (Newfoundland) · Havre-Saint-Pierre (Quebec) · Quebec City (Quebec)
Ends in Montreal (Quebec)
Ends Mon, Oct 11, 2027 in Montreal
- OCT22
Friday · 10 nights
10-Night Caribbean
Calls at Hamilton (Bermuda) · St. George's (Bermuda) · Gustavia (St. Barts) · Virgin Gorda (British Virgin Islands)
Ends in San Juan (Puerto Rico)
Ends Mon, Nov 1, 2027 in San Juan
Lowest fare shown
- OCT22
Friday · 17 nights
17-Night Caribbean
Calls at Hamilton (Bermuda) · St. George's (Bermuda) · Hamilton (Bermuda) · St. George's (Bermuda) · Gustavia (St. Barts) · Virgin Gorda (British Virgin Islands) · San Juan (Puerto Rico) · St. John (U.S. Virgin Islands) · Basseterre (St. Kitts) · Gustavia (St. Barts) · Philipsburg (St. Maarten) · Jost Van Dyke (British Virgin Islands) · Virgin Gorda (British Virgin Islands)
Ends in San Juan (Puerto Rico)
Ends Mon, Nov 8, 2027 in San Juan
- SEP14
Thursday · 11 nights
11-Night Canada
Calls at Portland (Maine) · Bar Harbor (Maine) · Halifax (Nova Scotia) · Charlottetown (Prince Edward Island) · Gaspé (Quebec) · Quebec City (Quebec)
Ends in Montreal (Quebec)
Ends Mon, Sep 25, 2028 in Montreal
- SEP14
Thursday · 25 nights
25-Night Canada
Calls at Portland (Maine) · Bar Harbor (Maine) · Halifax (Nova Scotia) · Charlottetown (Prince Edward Island) · Gaspé (Quebec) · Quebec City (Quebec) · Montreal (Quebec) · Tadoussac (Quebec) · Saguenay (Quebec) · Cap-aux-Meules (Quebec) · Saint-Pierre (Saint-Pierre and Miquelon) · St. John's (Newfoundland) · St. Anthony (Newfoundland) · Red Bay (Labrador) · Bonne Bay (Newfoundland) · Havre-Saint-Pierre (Quebec) · Quebec City (Quebec)
Ends in Montreal (Quebec)
Ends Mon, Oct 9, 2028 in Montreal
