Cruise line

Windstar cruises from Boston

Windstar Cruises has 6 departures from the Port of Boston in the period we cover, on one ship: Star Pride.

They run from 10 to 25 nights and go to Canada and New England and the Caribbean.

The cheapest Windstar Cruises sailing we list is Star Pride on Fri, Oct 22, 2027, from $4,477 per person as of November 3, 2026.

Windstar Cruises can move ships and change routes, and the fares here are starting prices rather than quotes. Confirm both with the line.

Star Pride 6

Schedule last updated 2026-11-03 · 6 departures listed · Dates can change. Verify with the cruise line before booking.

What Windstar Cruises runs from Boston

All routes

The 6 departures below run 4 different routes, cheapest per night first.

Distinct itineraries available, cheapest per night first
Itinerary	Ship	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	Star Pride	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	Star Pride	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	Star Pride	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	Star Pride	11	2	$6,091$554 a night

Starting fares per person, for the cheapest cabin listed, with taxes and port fees included, checked 2026-11-03. Fares change often, so check the current price before you book.

All Windstar Cruises routes from Boston

All routes

25-Night Canada from Boston on Star Pride 11-Night Canada from Boston on Star Pride

What Windstar Cruises is advertising

Promotions Cruisebound lists for Windstar Cruises, confirmed on 2026-11-03. These are the advertiser's terms, not ours, and whether one applies to a particular Boston sailing depends on the cabin, the date and how many of you are travelling. The fares in the table on this page are what we recorded ourselves and do not include any of this.

Complimentary All-Inclusive Experienceends 2026-11-18Check terms →Reduced Single Supplement: 120% vs. Standard 175%listed on 2026-11-03, no end date givenCheck terms →

Discounts that depend on who you are rather than what you book, for military, first responders, residents of qualifying states and guests over 55, are claimed with the cruise line itself. They are not part of the above, and a booking site cannot apply them for you.

See Windstar Cruises sailings from Boston on Cruisebound. We may earn a commission if you book through the links in this section, at no cost to you, and it does not change which sailings this site lists or how they are ordered.

Every departure by date

We may earn a commission if you book through these buttons, at no cost to you.

Windstar Cruises sailings from the Port of Boston
Departs	Ship	Nights	Itinerary & ports	From
Thu, Sep 16, 2027 ends Mon, Sep 27, 2027	Star Pride	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)	from $9,886 $899 a night · per person ocean view, as of 2026-11-03
Thu, Sep 16, 2027 ends Mon, Oct 11, 2027	Star Pride	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)	from $20,791 $832 a night · per person ocean view, as of 2026-11-03
Fri, Oct 22, 2027 ends Mon, Nov 1, 2027	Star Pride	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)	from $4,477 $448 a night · per person ocean view, as of 2026-11-03 Lowest fare shown
Fri, Oct 22, 2027 ends Mon, Nov 8, 2027	Star Pride	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)	from $6,040 $355 a night · per person ocean view, as of 2026-11-03
Thu, Sep 14, 2028 ends Mon, Sep 25, 2028	Star Pride	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)	from $6,091 $554 a night · per person ocean view, as of 2026-11-03
Thu, Sep 14, 2028 ends Mon, Oct 9, 2028	Star Pride	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)	from $12,666 $507 a night · per person ocean view, as of 2026-11-03

SEP
16
Thursday · 11 nights
11-Night Canada
Star Pride · Windstar Cruises
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
from $9,886 $899 a night · per person
ocean view, as of 2026-11-03
SEP
16
Thursday · 25 nights
25-Night Canada
Star Pride · Windstar Cruises
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
from $20,791 $832 a night · per person
ocean view, as of 2026-11-03
OCT
22
Friday · 10 nights
10-Night Caribbean
Star Pride · Windstar Cruises
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
from $4,477 $448 a night · per person
ocean view, as of 2026-11-03
OCT
22
Friday · 17 nights
17-Night Caribbean
Star Pride · Windstar Cruises
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
from $6,040 $355 a night · per person
ocean view, as of 2026-11-03
SEP
14
Thursday · 11 nights
11-Night Canada
Star Pride · Windstar Cruises
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
from $6,091 $554 a night · per person
ocean view, as of 2026-11-03
SEP
14
Thursday · 25 nights
25-Night Canada
Star Pride · Windstar Cruises
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
from $12,666 $507 a night · per person
ocean view, as of 2026-11-03

Windstar Cruises by month

September 2027 2 October 2027 2 September 2028 2

Where these sailings go

Canada and New England 4 Caribbean and Florida 2

Cruise line website: Windstar Cruises. Confirm dates and fares there before you book.

Windstar from Boston: questions

Which Windstar ships sail from Boston?

Only Star Pride, with 6 departures from Boston between September 2027 and September 2028 in the schedule we track.

How much is a Windstar cruise from Boston?

The lowest starting fare we recorded is $4,477 per person, for the cheapest cabin listed, with taxes and port fees included, on the 10-night sailing of Fri, Oct 22, 2027, about $448 a night. We checked it on November 3, 2026. Fares change daily, so check the current price before you book.

How long are Windstar cruises from Boston?

Windstar cruises from Boston run from 10 to 25 nights. The most common length is 11 nights, with 2 of the 6 departures.

Where do Windstar cruises leave from in Boston?

Cruises that start in Boston, Windstar's among them, board at Flynn Cruiseport Boston, the city's cruise terminal at 1 Black Falcon Avenue in South Boston. Your cruise documents confirm it for each sailing. Our guide to Flynn Cruiseport Boston has directions, parking and drop-off.