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40 Results

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A vibrant panoramic view of Castries, St. Lucia, with colorful buildings nestled along the harbor and lush green hills in the background under a blue sky with white clouds.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

14-night Caribbean: Aruba & Curacao Cruise From Boston, Massachusetts

Boston
St. Thomas (Charlotte Amalie)
Castries
St. George's
Willemstad
+4 more

Aboard

Norwegian Breakaway

From

Boston, Massachusetts

1 Sailing

Nov 8, 2026

1 Sailing

Nov 8, 2026

Published prices from

$869

per person*

taxes & fees included

An aerial view of the Royal Naval Dockyard in Bermuda, with a cruise ship docked at the pier, surrounded by a historic stone fortress, buildings, and the turquoise waters of the Atlantic Ocean.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

7-night Bermuda Round-Trip Boston Cruise: Halifax & Bermuda From Boston, Massachusetts

Boston
Halifax (Nova Scotia)
Royal Naval Dockyard

Aboard

Norwegian Breakaway

From

Boston, Massachusetts

11 Sailings

Apr 25 - Oct 31, 2027

11 Sailings

Apr 25 - Oct 31, 2027

Published prices from

$699

per person*

taxes & fees included

A vibrant orange and red sunset over the tranquil harbor in Sydney, Nova Scotia, with the setting sun reflecting on the water.
Up to 50% off + up to $800 Onboard Credit*
Holland America logo

7-night Canada & New England Cruise: Maine, Maritimes & Montreal From Boston, Massachusetts

Boston
Eastport
Halifax (Nova Scotia)
Sydney (Nova Scotia)
Charlottetown
+4 more

Aboard

Volendam

From

Boston, Massachusetts

2 Sailings

Jun 19 - Sep 25, 2027

2 Sailings

Jun 19 - Sep 25, 2027

Published prices from

$1,619

per person*

taxes & fees included

An aerial view of the Biosphere, a large geodesic dome, on an island in the St. Lawrence River in Quebec, Canada, surrounded by lush green and autumn-colored trees and several bridges.
Up to 50% off + up to $800 Onboard Credit*
Holland America logo

14-night Canada & New England Cruise: Maritimes & Montreal Collectors From Boston, Massachusetts

Boston
Eastport
Halifax (Nova Scotia)
Sydney (Nova Scotia)
Charlottetown
+5 more

Aboard

Volendam

From

Boston, Massachusetts

2 Sailings

Jun 19 - Jul 3, 2027

2 Sailings

Jun 19 - Jul 3, 2027

Published prices from

$3,459

per person*

taxes & fees included

An aerial view of the Biosphere, a large geodesic dome, on an island in the St. Lawrence River in Quebec, Canada, surrounded by lush green and autumn-colored trees and several bridges.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Holland America logo

7-night Canada & New England Cruise: Maaine, Maritimes & Montreal From Boston, Massachusetts

Boston
Portland
Halifax (Nova Scotia)
Sydney (Nova Scotia)
Charlottetown
+4 more

Aboard

Volendam

From

Boston, Massachusetts

1 Sailing

Jul 3, 2027

1 Sailing

Jul 3, 2027

Published prices from

$1,849

per person*

taxes & fees included

Kinderdijk windmills lining a canal in the Netherlands, Rotterdam.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Holland America logo

17-night Voyage of the Vikings Cruise From Boston, Massachusetts

Boston
Portland
Sydney (Nova Scotia)
Corner Brook
Red Bay
+9 more

Aboard

Volendam

From

Boston, Massachusetts

1 Sailing

Jul 17, 2027

1 Sailing

Jul 17, 2027

A vibrant close-up of a puffin, with its colorful orange beak and feet, standing on a grassy cliff overlooking the bright blue ocean.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Holland America logo

35-night Legendary Voyage Of The Vikings From Boston, Massachusetts

Boston
Portland
Sydney (Nova Scotia)
Corner Brook
Red Bay
+19 more

Aboard

Volendam

From

Boston, Massachusetts

1 Sailing

Jul 17, 2027

1 Sailing

Jul 17, 2027

Published prices from

$9,454

per person*

taxes & fees included

An aerial view of the rocky coastline of St. John's, Newfoundland, with a long, brown rocky point with abandoned buildings and a lighthouse on a lush green cliff, jutting out into the deep blue sea.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Holland America logo

11-night New England, New France & Newfoundland Cruise: Corner Brook From Boston, Massachusetts

Boston
Eastport
Halifax (Nova Scotia)
St. John's
St. Anthony
+8 more

Aboard

Volendam

From

Boston, Massachusetts

1 Sailing

Aug 21, 2027

1 Sailing

Aug 21, 2027

Published prices from

$2,809

per person*

taxes & fees included

A picturesque view of the Reversing Falls Rapids in Saint John, New Brunswick, with a bridge crossing the water and the city's skyline in the background, as seen from a grassy park with a bench.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

7-night Canada & New England: Eastport & Halifax Cruise From Boston, Massachusetts

Boston
Portland
Saint John (Bay of Fundy)
Sydney (Nova Scotia)
Halifax (Nova Scotia)

Aboard

Norwegian Breakaway

From

Boston, Massachusetts

2 Sailings

Aug 29 - Sep 19, 2027

2 Sailings

Aug 29 - Sep 19, 2027

Published prices from

$869

per person*

taxes & fees included

Historic Halifax waterfront buildings.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

11-night Boston,Maine & Canada Cruise From Boston, Massachusetts

Boston
Rockland
Halifax (Nova Scotia)
Sydney (Nova Scotia)
Quebec City
+3 more

Aboard

Celebrity Silhouette

From

Boston, Massachusetts

4 Sailings

Sep 2 - Oct 5, 2027

4 Sailings

Sep 2 - Oct 5, 2027

Published prices from

$1,941

per person*

taxes & fees included

Historic Château Frontenac hotel in Quebec City.
Up to 50% off + up to $800 Onboard Credit*
Holland America logo

7-night Canada & New England Cruise: Unesco Sites & Quebecois Nights From Boston, Massachusetts

Boston
Portland
Halifax (Nova Scotia)
Sydney (Nova Scotia)
Charlottetown
+3 more

Aboard

Zuiderdam

From

Boston, Massachusetts

3 Sailings

Sep 4 - Oct 9, 2027

3 Sailings

Sep 4 - Oct 9, 2027

Published prices from

$1,349

per person*

taxes & fees included

Historic Halifax waterfront buildings.
Up to 50% off + up to $800 Onboard Credit*
Holland America logo

14-night Canada & New England Cruise: Unesco Sites & Nights Collector From Boston, Massachusetts

Boston
Portland
Halifax (Nova Scotia)
Sydney (Nova Scotia)
Charlottetown
+3 more

Aboard

Zuiderdam

From

Boston, Massachusetts

2 Sailings

Sep 4 - Sep 25, 2027

2 Sailings

Sep 4 - Sep 25, 2027

Published prices from

$2,644

per person*

taxes & fees included

Historic Halifax waterfront buildings.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

7-night Canada & New England Round-Trip Boston Cruise: Eastport & Halifax From Boston, Massachusetts

Boston
Portland
Eastport
Saint John (Bay of Fundy)
Halifax (Nova Scotia)

Aboard

Norwegian Breakaway

From

Boston, Massachusetts

6 Sailings

Sep 5 - Oct 17, 2027

6 Sailings

Sep 5 - Oct 17, 2027

Published prices from

$869

per person*

taxes & fees included

Historic Château Frontenac hotel in Quebec City.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

15-night Maple Explorer Cruisetour #2C From Boston, Massachusetts

Boston
Portland
Saint John (Bay of Fundy)
Halifax (Nova Scotia)
Sydney (Nova Scotia)
+8 more

Aboard

Caribbean Princess

From

Boston, Massachusetts

2 Sailings

Sep 7 - Sep 28, 2027

2 Sailings

Sep 7 - Sep 28, 2027

A beautiful autumn landscape in Saguenay with a river flowing under a bridge, surrounded by hillsides adorned with houses and vibrant yellow, orange, and red fall foliage.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

10-night Classic Canada & New England Cruise From Boston, Massachusetts

Boston
Portland
Saint John (Bay of Fundy)
Halifax (Nova Scotia)
Sydney (Nova Scotia)
+4 more

Aboard

Caribbean Princess

From

Boston, Massachusetts

3 Sailings

Sep 7 - Oct 19, 2027

3 Sailings

Sep 7 - Oct 19, 2027

Historic Halifax waterfront buildings.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

25-night Star Collector: Autumn In Newfoundland And New England Cruise From Boston, Massachusetts

Boston
Portland
Bar Harbor
Halifax (Nova Scotia)
Charlottetown
+13 more

Aboard

Star Pride

From

Boston, Massachusetts

2 Sailings

Sep 16, 2027 - Sep 14, 2028

2 Sailings

Sep 16, 2027 - Sep 14, 2028

Published prices from

$11,582

per person*

taxes & fees included

Historic Acorn Street in Boston.
Up to 50% off + up to $800 Onboard Credit*
Holland America logo

7-night Canada & New England Circle Cruise: New Brunswick From Boston, Massachusetts

Boston
Eastport
Saint John (Bay of Fundy)
Halifax (Nova Scotia)
Sydney (Nova Scotia)
+2 more

Aboard

Volendam

From

Boston, Massachusetts

1 Sailing

Sep 18, 2027

1 Sailing

Sep 18, 2027

Published prices from

$1,269

per person*

taxes & fees included

Historic Acorn Street in Boston.
Up to 50% off + up to $800 Onboard Credit*
Holland America logo

7-night Canada & New England Circle Cruise: New Brunswick From Boston, Massachusetts

Boston
Saint John (Bay of Fundy)
Halifax (Nova Scotia)
Sydney (Nova Scotia)
Portland

Aboard

Zuiderdam

From

Boston, Massachusetts

1 Sailing

Sep 18, 2027

1 Sailing

Sep 18, 2027

Published prices from

$1,449

per person*

taxes & fees included

Historic Acorn Street in Boston.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

11-night Northeastern Charm in Fall Voyage From Boston, Massachusetts

Boston
Portland
Saint John (Bay of Fundy)
Halifax (Nova Scotia)
Sydney (Nova Scotia)
+7 more

Aboard

Vista

From

Boston, Massachusetts

1 Sailing

Sep 29, 2027

1 Sailing

Sep 29, 2027

Published prices from

$7,699

per person*

taxes & fees included

A stunning autumn landscape in Havre-Saint-Pierre, Quebec, with a lake reflecting a forest of trees in various shades of green, yellow, and orange, with a wooden pier in the foreground.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Azamara logo

12-night Canada & New England Intensive Voyage: Portland, Saguenay & Montreal From Boston, Massachusetts

Boston
Portland
Rockland
Saint John (Bay of Fundy)
Halifax (Nova Scotia)
+9 more

Aboard

Azamara Quest

From

Boston, Massachusetts

1 Sailing

Oct 4, 2027

1 Sailing

Oct 4, 2027

Published prices from

$4,789

per person*

taxes & fees included

A wide shot of the Government House, a large white mansion with a Greek Revival facade and a prominent portico, surrounded by a green lawn and tall trees in Charlottetown.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

11-night Leaves & Lobsters Cruise From Boston, Massachusetts

Boston
Bar Harbor
Saint John (Bay of Fundy)
Halifax (Nova Scotia)
Sydney (Nova Scotia)
+7 more

Aboard

Seven Seas Grandeur

From

Boston, Massachusetts

1 Sailing

Oct 13, 2027

1 Sailing

Oct 13, 2027

Published prices from

$14,449

per person*

taxes & fees included

Historic Château Frontenac hotel in Quebec City.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

15-night Maple Explorer Cruisetour #2D From Boston, Massachusetts

Boston
Portland
Saint John (Bay of Fundy)
Halifax (Nova Scotia)
Sydney (Nova Scotia)
+8 more

Aboard

Caribbean Princess

From

Boston, Massachusetts

1 Sailing

Oct 19, 2027

1 Sailing

Oct 19, 2027

A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

9-night Boston to San Juan Cruise From Boston, Massachusetts

Boston
Puerto Plata
Samaná
St. Thomas (Charlotte Amalie)
St. John's
+3 more

Aboard

Celebrity Summit

From

Boston, Massachusetts

1 Sailing

Oct 20, 2027

1 Sailing

Oct 20, 2027

Published prices from

$1,138

per person*

taxes & fees included

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

17-night Star Collector Cruise: Bermuda & Caribbean Island Explorer From Boston, Massachusetts

Boston
Hamilton
St. George's
Gustavia
Virgin Gorda
+6 more

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Oct 22, 2027

1 Sailing

Oct 22, 2027

Published prices from

$5,705

per person*

taxes & fees included

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

10-night Bermuda Bliss Cruise From Boston, Massachusetts

Boston
Hamilton
St. George's
Gustavia
Virgin Gorda
+2 more

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Oct 22, 2027

1 Sailing

Oct 22, 2027

Published prices from

$3,954

per person*

taxes & fees included

    • Showing results 1 - 24 of 40

*Rates and offers are per person, in US Dollars, based on double occupancy, capacity controlled, subject to availability and confirmation, and may change without notice. Government taxes and fees are included. Rates and offers are available for select dates and categories only. Additional restrictions may apply. Call 1-800-377-9383 for full terms and conditions.