Get FREE Price Alerts

Subscribe to our weekly cruise deals email and enjoy FREE price change alerts and updates for this cruise and others like it.

We promise to protect your privacy and personal data. You can review our privacy policy here.

Modify Your Choices
Vacation Type


Filters
Destination
- Any Destination
Travel Dates
Narrow Date Range
Departure Port
- Boston, MA
Cruise Length
- All Durations
Cruise Line
- All Cruise Lines
Cruise Ships
- All Cruise Ships

Cruises from Boston in October 2025


Sailings per page
19 Matched Sailings
Departing
Itinerary and Ship
Length
Save to
Favorites
Priced from

Oct 26, 2025

(Sunday)

7 Night Canada Cruise

Brilliance of the Seas
Royal Caribbean Cruises
4.0 based on 352 ratings
Starts: Boston, Massachusetts
Ends: Boston, Massachusetts
Ports of Call:
Boston, Portland, St John, Halifax, Sydney, Boston
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$547

per person
(double occupancy)
Learn More

Oct 12, 2025

(Sunday)

7 Night Canada Cruise

Brilliance of the Seas
Royal Caribbean Cruises
4.0 based on 352 ratings
Starts: Boston, Massachusetts
Ends: Boston, Massachusetts
Ports of Call:
Boston, St John, Halifax, Sydney, Portland, Boston
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$587

per person
(double occupancy)
Learn More

Oct 05, 2025

(Sunday)

7 Night Canada Cruise

Brilliance of the Seas
Royal Caribbean Cruises
4.0 based on 352 ratings
Starts: Boston, Massachusetts
Ends: Boston, Massachusetts
Ports of Call:
Boston, Portland, St John, Halifax, Sydney, Boston
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
Retail Price $733
Save $102
Lowest from

$599

per person
(double occupancy)
Learn More

Oct 19, 2025

(Sunday)

7 Night Canada Cruise

Brilliance of the Seas
Royal Caribbean Cruises
4.0 based on 352 ratings
Starts: Boston, Massachusetts
Ends: Boston, Massachusetts
Ports of Call:
Boston, Halifax, Sydney, Charlottetown, St John, Boston
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
Retail Price $819
Save $207
Lowest from

$612

per person
(double occupancy)
Learn More

Oct 10, 2025

(Friday)

10 Night Boston to Fort Lauderdale Cruise

Celebrity Silhouette
Celebrity Cruises
4.4 based on 370 ratings
Starts: Boston, Massachusetts
Ends: Fort Lauderdale, Florida
Ports of Call:
Boston, Willemstad (Curacao), Bonaire, Oranjestad, Fort Lauderdale
Special Promotions

10 Nights


Add to Favorites
Compare Favorites
Lowest from

$750

per person
(double occupancy)
Learn More

Oct 03, 2025

(Friday)

7 Night Canada and New England Cruise

Norwegian Gem
Norwegian Cruise Line
3.9 based on 389 ratings
Starts: Boston, Massachusetts
Ends: Quebec City, Canada
Ports of Call:
Boston, Bar Harbor, Halifax, Sydney, Charlottetown, La Baie, Quebec City

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$799

per person
(double occupancy)
Learn More

Oct 24, 2025

(Friday)

7 Night Bermuda and Maine Cruise

Norwegian Gem
Norwegian Cruise Line
3.9 based on 389 ratings
Starts: Boston, Massachusetts
Ends: Boston, Massachusetts
Ports of Call:
Boston, Bar Harbor, Royal Naval Dockyard (West End), Boston

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$819

per person
(double occupancy)
Learn More

Oct 17, 2025

(Friday)

7 Night Canada and New England Portland and Bar Harbor Cruise

Norwegian Gem
Norwegian Cruise Line
3.9 based on 389 ratings
Starts: Boston, Massachusetts
Ends: Boston, Massachusetts
Ports of Call:
Boston, Charlottetown, Sydney, Halifax, Portland, Bar Harbor, Boston

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$819

per person
(double occupancy)
Learn More

Oct 09, 2025

(Thursday)

10 Night Classic Canada and New England Cruise

Majestic Princess
Princess Cruises
4.1 based on 51 ratings
Starts: Boston, Massachusetts
Ends: Quebec City, Canada
Ports of Call:
Boston, Portland, St John, Halifax, Sydney, Charlottetown, Saguenay Quebec Canada, Quebec City

10 Nights


Add to Favorites
Compare Favorites
Lowest from

$898

per person
(double occupancy)
Learn More

Oct 04, 2025

(Saturday)

7 Night Canada and New England UNESCO Sites and Quebecois Nights Cruise

Zuiderdam
Holland America Line
4.0 based on 247 ratings
Starts: Boston, Massachusetts
Ends: Quebec City, Canada
Ports of Call:
Boston, Rockland, Halifax, Sydney, Charlottetown, Cruising the Gulf of St Lawrence...

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$1,043

per person
(double occupancy)
Learn More

Oct 18, 2025

(Saturday)

11 Night Boston Sights Warm Caribbean Nights Cruise

Star Pride
Windstar Cruises
Starts: Boston, Massachusetts
Ends: San Juan, Puerto Rico
Ports of Call:
Boston, Hamilton, St George, Gustavia St. Barts, Basseterre, Virgin Gorda, San Juan

11 Nights


Add to Favorites
Compare Favorites
Lowest from

$2,999

per person
(double occupancy)
Learn More

Oct 27, 2025

(Monday)

16 Night Island Inspiration Cruise

Insignia
Oceania Cruises
4.4 based on 14 ratings
Starts: Boston, Massachusetts
Ends: Miami, Florida
Ports of Call:
Boston, Newport, Hamilton, St George, Gustavia St. Barts, St John's, Castries, Bridgetown...

16 Nights


Add to Favorites
Compare Favorites
Lowest from

$3,499

per person
(double occupancy)
Learn More

Oct 05, 2025

(Sunday)

11 Night Canadian Connoisseur Cruise

Insignia
Oceania Cruises
4.4 based on 14 ratings
Starts: Boston, Massachusetts
Ends: Montreal, Canada
Ports of Call:
Boston, Bar Harbor, St John, Halifax, Sydney, Corner Brook, Havre Saint Pierre, Sept-Iles...

11 Nights


Add to Favorites
Compare Favorites
Lowest from

$5,299

per person
(double occupancy)
Learn More

Oct 27, 2025

(Monday)

41 Night Caribbean and Amazon Icons Cruise

Insignia
Oceania Cruises
4.4 based on 14 ratings
Starts: Boston, Massachusetts
Ends: Miami, Florida
Ports of Call:
Boston, Newport, Hamilton, St George, Gustavia St. Barts, St John's, Castries, Bridgetown...

41 Nights


Add to Favorites
Compare Favorites
Lowest from

$8,999

per person
(double occupancy)
Learn More

Oct 15, 2025

(Wednesday)

10 Night A Musical Cruise in Nova Scotia and the East Coast of the United States Cruise

Le Champlain
Ponant Cruises
Starts: Boston, Massachusetts
Ends: Boston, Massachusetts
Ports of Call:
Boston, Halifax, Eastport, Portland, Provincetown, Cruising Cape Cod, Newport, New York, Boston

10 Nights


Add to Favorites
Compare Favorites
Lowest from

$9,370

per person
(double occupancy)
Learn More

Oct 18, 2025

(Saturday)

21 Night Eastern Caribbean San Juan and Antilles Cruise

Zuiderdam
Holland America Line
4.0 based on 247 ratings
Starts: Boston, Massachusetts
Ends: Miami, Florida
Ports of Call:
Boston, San Juan, Charlotte Amalie (St Thomas), Philipsburg (St. Maarten), Castries, Bridgetown...

21 Nights


Add to Favorites
Compare Favorites

Pricing On
Request

Learn More

Oct 18, 2025

(Saturday)

14 Night Eastern Caribbean San Juan and Antilles Cruise

Zuiderdam
Holland America Line
4.0 based on 247 ratings
Starts: Boston, Massachusetts
Ends: Miami, Florida
Ports of Call:
Boston, San Juan, Charlotte Amalie (St Thomas), Philipsburg (St. Maarten), Castries, Bridgetown...
Special Promotions

14 Nights


Add to Favorites
Compare Favorites

Pricing On
Request

Learn More

Oct 05, 2025

(Sunday)

14 Night Grand New England Cruise

American Glory
American Cruise Lines
Starts: Boston, Massachusetts
Ends: Boston, Massachusetts
Ports of Call:
Boston, Portland, Bath, Boothbay Harbor, Bar Harbor, Bangor, Rockland, Portsmouth, Gloucester...

14 Nights


Add to Favorites
Compare Favorites

Pricing On
Request

Learn More

Oct 11, 2025

(Saturday)

11 Night Fall Foliage Journey Boston to Montreal Cruise

Seven Seas Splendor
Regent Seven Seas Cruises
5.0 based on 7 ratings
Starts: Boston, Massachusetts
Ends: Montreal, Canada
Ports of Call:
Boston, Bar Harbor, St John, Cruising the Atlantic Ocean, Sydney, Corner Brook, Havre Saint Pierre...

11 Nights


Add to Favorites
Compare Favorites

Pricing On
Request

Learn More



Overlay Title