Port of Boston schedule

Cruises from Boston in October 2027

14 cruises leave Boston in October 2027. Seven lines run them, using eight ships. The ships are Azamara Quest, Caribbean Princess, Celebrity Silhouette, Celebrity Summit, Norwegian Breakaway, Seven Seas Grandeur, Star Pride, and Zuiderdam.

Trips run from 7 to 17 nights. They head to Canada and New England, the Caribbean, and Bermuda.

Norwegian Breakaway on Sun, Oct 3, 2027 has the lowest starting fare this month, $889 per person as of November 3, 2026. We build this list from the sailings on sale through Cruisebound, check each one against CruiseTimetables, and take the ports from that sailing's own page. Sailings whose ports we couldn't confirm are left out.

Departures: 14
Ships: 8
Length: 7 to 17 nights
From: $889

Schedule last updated 2026-11-03 · 14 departures listed · Dates can change. Verify with the cruise line before booking.

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Cruises departing the Port of Boston in October 2027
Departs	Ship	Line	Nights	Itinerary & ports	From
Sun, Oct 3, 2027 back Sun, Oct 10, 2027	Norwegian Breakaway	Norwegian Cruise Line	7	7-Night Canada and New England Calls at Eastport (Maine) · Halifax (Nova Scotia) · Sydney (Nova Scotia) · Saint John (New Brunswick)	from $889 $127 a night · per person interior, as of 2026-11-03 Lowest fare shown
Mon, Oct 4, 2027 ends Sat, Oct 16, 2027	Azamara Quest	Azamara	12	12-Night New England Calls at Portland (Maine) · Rockland (Maine) · Saint John (New Brunswick) · Halifax (Nova Scotia) · Charlottetown (Prince Edward Island) · Baie-Comeau (Quebec) · Saguenay (Quebec) · Quebec City (Quebec) · Trois-Rivieres (Quebec) Ends in Montreal (Quebec)	from $4,789 $399 a night · per person interior, as of 2026-11-03
Tue, Oct 5, 2027 back Sat, Oct 16, 2027	Celebrity Silhouette	Celebrity Cruises	11	11-Night Boston, Maine & Canada Calls at Portland (Maine) · Rockland (Maine) · Halifax (Nova Scotia) · Sydney (Nova Scotia) · Quebec City (Quebec) · Charlottetown (Prince Edward Island)	from $2,027 $184 a night · per person interior, as of 2026-11-03
Sat, Oct 9, 2027 ends Sat, Oct 16, 2027	Zuiderdam	Holland America Line	7	7-Night Canada and New England Calls at Portland (Maine) · Halifax (Nova Scotia) · Sydney (Nova Scotia) · Charlottetown (Prince Edward Island) Ends in Quebec City (Quebec)	from $1,804 $258 a night · per person interior, as of 2026-11-03
Sun, Oct 10, 2027 back Sun, Oct 17, 2027	Norwegian Breakaway	Norwegian Cruise Line	7	7-Night Canada and New England Calls at Saint John (New Brunswick) · Sydney (Nova Scotia) · Halifax (Nova Scotia) · Portland (Maine)	from $889 $127 a night · per person interior, as of 2026-11-03
Wed, Oct 13, 2027 ends Sun, Oct 24, 2027	Seven Seas Grandeur	Regent Seven Seas Cruises	11	11-Night Canada and New England Calls at Bar Harbor (Maine) · Saint John (New Brunswick) · Halifax (Nova Scotia) · Sydney (Nova Scotia) · Charlottetown (Prince Edward Island) · Gaspé (Quebec) · Saguenay (Quebec) · Quebec City (Quebec) Ends in Montreal (Quebec)	from $13,849 $1,259 a night · per person suite, as of 2026-11-03
Sat, Oct 16, 2027 ends Tue, Oct 26, 2027	Celebrity Silhouette	Celebrity Cruises	10	10-Night Boston To Fort Lauderdale Calls at Aruba · Curaçao · Bonaire Ends in Fort Lauderdale (Florida)	from $913 $91 a night · per person interior, as of 2026-11-03
Sun, Oct 17, 2027 back Sun, Oct 24, 2027	Norwegian Breakaway	Norwegian Cruise Line	7	7-Night Canada and New England Calls at Eastport (Maine) · Saint John (New Brunswick) · Halifax (Nova Scotia) · Portland (Maine)	from $889 $127 a night · per person interior, as of 2026-11-03
Tue, Oct 19, 2027 ends Fri, Oct 29, 2027	Caribbean Princess	Princess Cruises	10	10-Night Canada and New England Calls at Portland (Maine) · Saint John (New Brunswick) · Halifax (Nova Scotia) · Sydney (Nova Scotia) · Charlottetown (Prince Edward Island) · Saguenay (Quebec) Ends in Quebec City (Quebec)	from $949 $95 a night · per person interior, as of 2026-11-03
Wed, Oct 20, 2027 ends Fri, Oct 29, 2027	Celebrity Summit	Celebrity Cruises	9	9-Night Boston To San Juan Calls at Puerto Plata (Dominican Republic) · Samana (Dominican Republic) · St. Thomas (U.S. Virgin Islands) · St. John's (Antigua) · Tortola (British Virgin Islands) Ends in San Juan (Puerto Rico)	from $904 $100 a night · per person interior, as of 2026-11-03
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Fri, Oct 22, 2027 ends Mon, Nov 1, 2027	Star Pride	Windstar Cruises	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
Fri, Oct 22, 2027 ends Mon, Nov 8, 2027	Star Pride	Windstar Cruises	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
Sun, Oct 24, 2027 back Sun, Oct 31, 2027	Norwegian Breakaway	Norwegian Cruise Line	7	7-Night Bermuda Calls at Halifax (Nova Scotia) · Royal Naval Dockyard (Bermuda)	from $979 $140 a night · per person interior, as of 2026-11-03
Sun, Oct 31, 2027 back Sun, Nov 7, 2027	Norwegian Breakaway	Norwegian Cruise Line	7	7-Night Bermuda Calls at Halifax (Nova Scotia) · Royal Naval Dockyard (Bermuda)	from $889 $127 a night · per person interior, as of 2026-11-03

OCT
3
Sunday · 7 nights
7-Night Canada and New England
Norwegian Breakaway · Norwegian Cruise Line
Calls at Eastport (Maine) · Halifax (Nova Scotia) · Sydney (Nova Scotia) · Saint John (New Brunswick)
Returns Sun, Oct 10, 2027
Lowest fare shown
from $889 $127 a night · per person
interior, as of 2026-11-03
OCT
4
Monday · 12 nights
12-Night New England
Azamara Quest · Azamara
Calls at Portland (Maine) · Rockland (Maine) · Saint John (New Brunswick) · Halifax (Nova Scotia) · Charlottetown (Prince Edward Island) · Baie-Comeau (Quebec) · Saguenay (Quebec) · Quebec City (Quebec) · Trois-Rivieres (Quebec)
Ends in Montreal (Quebec)
Ends Sat, Oct 16, 2027 in Montreal
from $4,789 $399 a night · per person
interior, as of 2026-11-03
OCT
5
Tuesday · 11 nights
11-Night Boston, Maine & Canada
Celebrity Silhouette · Celebrity Cruises
Calls at Portland (Maine) · Rockland (Maine) · Halifax (Nova Scotia) · Sydney (Nova Scotia) · Quebec City (Quebec) · Charlottetown (Prince Edward Island)
Returns Sat, Oct 16, 2027
from $2,027 $184 a night · per person
interior, as of 2026-11-03
OCT
9
Saturday · 7 nights
7-Night Canada and New England
Zuiderdam · Holland America Line
Calls at Portland (Maine) · Halifax (Nova Scotia) · Sydney (Nova Scotia) · Charlottetown (Prince Edward Island)
Ends in Quebec City (Quebec)
Ends Sat, Oct 16, 2027 in Quebec City
from $1,804 $258 a night · per person
interior, as of 2026-11-03
OCT
10
Sunday · 7 nights
7-Night Canada and New England
Norwegian Breakaway · Norwegian Cruise Line
Calls at Saint John (New Brunswick) · Sydney (Nova Scotia) · Halifax (Nova Scotia) · Portland (Maine)
Returns Sun, Oct 17, 2027
from $889 $127 a night · per person
interior, as of 2026-11-03
OCT
13
Wednesday · 11 nights
11-Night Canada and New England
Seven Seas Grandeur · Regent Seven Seas Cruises
Calls at Bar Harbor (Maine) · Saint John (New Brunswick) · Halifax (Nova Scotia) · Sydney (Nova Scotia) · Charlottetown (Prince Edward Island) · Gaspé (Quebec) · Saguenay (Quebec) · Quebec City (Quebec)
Ends in Montreal (Quebec)
Ends Sun, Oct 24, 2027 in Montreal
from $13,849 $1,259 a night · per person
suite, as of 2026-11-03
OCT
16
Saturday · 10 nights
10-Night Boston To Fort Lauderdale
Celebrity Silhouette · Celebrity Cruises
Calls at Aruba · Curaçao · Bonaire
Ends in Fort Lauderdale (Florida)
Ends Tue, Oct 26, 2027 in Fort Lauderdale
from $913 $91 a night · per person
interior, as of 2026-11-03
OCT
17
Sunday · 7 nights
7-Night Canada and New England
Norwegian Breakaway · Norwegian Cruise Line
Calls at Eastport (Maine) · Saint John (New Brunswick) · Halifax (Nova Scotia) · Portland (Maine)
Returns Sun, Oct 24, 2027
from $889 $127 a night · per person
interior, as of 2026-11-03
OCT
19
Tuesday · 10 nights
10-Night Canada and New England
Caribbean Princess · Princess Cruises
Calls at Portland (Maine) · Saint John (New Brunswick) · Halifax (Nova Scotia) · Sydney (Nova Scotia) · Charlottetown (Prince Edward Island) · Saguenay (Quebec)
Ends in Quebec City (Quebec)
Ends Fri, Oct 29, 2027 in Quebec City
from $949 $95 a night · per person
interior, as of 2026-11-03
OCT
20
Wednesday · 9 nights
9-Night Boston To San Juan
Celebrity Summit · Celebrity Cruises
Calls at Puerto Plata (Dominican Republic) · Samana (Dominican Republic) · St. Thomas (U.S. Virgin Islands) · St. John's (Antigua) · Tortola (British Virgin Islands)
Ends in San Juan (Puerto Rico)
Ends Fri, Oct 29, 2027 in San Juan
from $904 $100 a night · per person
interior, as of 2026-11-03
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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
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
OCT
24
Sunday · 7 nights
7-Night Bermuda
Norwegian Breakaway · Norwegian Cruise Line
Calls at Halifax (Nova Scotia) · Royal Naval Dockyard (Bermuda)
Returns Sun, Oct 31, 2027
from $979 $140 a night · per person
interior, as of 2026-11-03
OCT
31
Sunday · 7 nights
7-Night Bermuda
Norwegian Breakaway · Norwegian Cruise Line
Calls at Halifax (Nova Scotia) · Royal Naval Dockyard (Bermuda)
Returns Sun, Nov 7, 2027
from $889 $127 a night · per person
interior, as of 2026-11-03

Our guide to the Boston cruise season covers which months ships sail from Boston, what goes where in each, and fall foliage sailings.

Narrow down October 2027

Ships this month

Lines this month

Where they go

Cruising from Boston in October 2027

How many cruises leave Boston in October 2027?

14 cruises leave Boston in October 2027, on 8 ships from 7 lines: Norwegian Cruise Line, Celebrity Cruises, Windstar Cruises, Azamara, Holland America Line, Regent Seven Seas Cruises, and Princess Cruises.

What is the cheapest cruise from Boston in October 2027?

The lowest starting fare we have on record is $889 per person for the 7-night Norwegian Breakaway sailing departing Sun, Oct 3, 2027. The average starting fare across the month is about $2,878 per person.

Which ships sail from Boston in October 2027?

8 ships sail from Boston in October 2027: Norwegian Breakaway (5), Celebrity Silhouette (2), Star Pride (2), Azamara Quest (1), Zuiderdam (1), Seven Seas Grandeur (1), Caribbean Princess (1), Celebrity Summit (1). The number beside each ship is its departures that month.

How long are the October 2027 sailings?

They run from 7 to 17 nights. The most common length is 7 nights, with 6 sailings.