Bucket-List Cruise Adventures

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Filtering North America ×Holland America ×Regent × Clear all
Showing 36 of 49 sailings
Holland America · ZuiderdamOne-way
North America 7 nights Jun 20 – Jun 27, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $889
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Holland America · ZuiderdamRound-trip
North America 7 nights Jul 4 – Jul 11, 2026 from Boston, Massachusetts
Boston, Massachusetts · Saint John, New Brunswick · Norfolk, Virginia · New York, New York · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourManhattan Helicopter Tour
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from $1,479
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Holland America · VolendamOne-way
North America 10 nights Aug 22 – Sep 1, 2026 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Eastport, Maine, United States · … · Montreal, Quebec10 ports
Boston, Massachusetts · Eastport, Maine, United States · Halifax, Nova Scotia · St. Johns, Newfoundland · St. Anthony, Newfoundland · Corner Brook, Newfoundland · Havre St. Pierre, Quebec · Baie-Commeau, Quebec · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
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from $1,999
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Holland America · ZuiderdamOne-way
North America 7 nights Aug 22 – Aug 29, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,159
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Regent · Seven Seas SplendorOne-way
Australia & South Pacific 11 nights Sep 6 – Sep 17, 2026 from New York, New York to Montreal, Quebec
New York, New York · Willis Island · … · Montreal, Quebec12 ports
New York, New York · Willis Island · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Willis Island · Gaspe, Quebec · Baie-Commeau, Quebec · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourZodiac Circumnavigation of Willis IslandPeggy's Cove & LunenburgBridgeClimb Sydney
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from $14,780
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Holland America · VolendamOne-way
North America 7 nights Sep 12 – Sep 19, 2026 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Quebec City, Quebec · … · Boston, Massachusetts7 ports
Montreal, Quebec · Quebec City, Quebec · Cap-Aux-Meules, Canada · Halifax, Nova Scotia · Saint John, New Brunswick · Eastport, Maine, United States · Boston, Massachusetts
★ Bucket-list Peggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,179
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Holland America · ZuiderdamOne-way
North America 7 nights Sep 12 – Sep 19, 2026 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Charlottetown, Prince Edward Island · … · Boston, Massachusetts6 ports
Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,189
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Regent · Seven Seas SplendorOne-way
Australia & South Pacific 11 nights Sep 17 – Sep 28, 2026 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Quebec City, Quebec · … · Boston, Massachusetts11 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Havre St. Pierre, Quebec · Willis Island · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list Zodiac Circumnavigation of Willis IslandBridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $13,199
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Holland America · VolendamOne-way
North America 7 nights Sep 19 – Sep 26, 2026 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Eastport, Maine, United States · … · Montreal, Quebec7 ports
Boston, Massachusetts · Eastport, Maine, United States · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,349
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Holland America · ZuiderdamOne-way
North America 7 nights Sep 19 – Sep 26, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,369
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Holland America · VolendamOne-way
North America 12 nights Sep 26 – Oct 8, 2026 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York10 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts · Oak Bluffs, Massachusetts · New York, New York
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston TourManhattan Helicopter Tour
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from $1,529
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Holland America · ZuiderdamOne-way
North America 7 nights Sep 26 – Oct 3, 2026 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts6 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Cap-Aux-Meules, Canada · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston Tour
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from $1,409
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Regent · Seven Seas SplendorOne-way
Australia & South Pacific 11 nights Sep 28 – Oct 9, 2026 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Portland, Maine · … · Montreal, Quebec12 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Willis Island · Gaspe, Quebec · Sept-Iles, Canada · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb SydneyZodiac Circumnavigation of Willis Island
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from $11,899
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Holland America · ZuiderdamRound-trip
North America 7 nights Oct 3 – Oct 10, 2026 from Boston, Massachusetts
Boston, Massachusetts · Eastport, Maine, United States · … · Boston, Massachusetts7 ports
Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,429
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Regent · Seven Seas SplendorOne-way
Australia & South Pacific 11 nights Oct 9 – Oct 20, 2026 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York12 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Willis Island · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Eastport, Maine, United States · Willis Island · New York, New York
★ Bucket-list Zodiac Circumnavigation of Willis IslandBridgeClimb SydneyPeggy's Cove & LunenburgManhattan Helicopter Tour
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from $11,399
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Holland America · ZuiderdamOne-way
North America 7 nights Oct 10 – Oct 17, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,399
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Holland America · ZuiderdamOne-way
North America 14 nights Oct 17 – Oct 31, 2026 from Quebec City, Quebec to Miami, Florida
Quebec City, Quebec · Saguenay Fjord, Canada · … · Miami, Florida10 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts · Norfolk, Virginia · Miami, Florida
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston TourStar Island & Millionaire's Row Skyline Cruise on…
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from $1,139
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Regent · Seven Seas SplendorOne-way
Australia & South Pacific 10 nights Oct 20 – Oct 30, 2026 from New York, New York to Montreal, Quebec
New York, New York · Willis Island · … · Montreal, Quebec11 ports
New York, New York · Willis Island · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Willis Island · Baie-Commeau, Quebec · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourZodiac Circumnavigation of Willis IslandPeggy's Cove & LunenburgBridgeClimb Sydney
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from $12,450
Book This Cruise@ Cruisebound
Regent · Seven Seas SplendorOne-way
Australia & South Pacific 16 nights Oct 30 – Nov 15, 2026 from Montreal, Quebec to Miami, Florida
Montreal, Quebec · Quebec City, Quebec · … · Miami, Florida14 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Willis Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Willis Island · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · San Juan, Puerto Rico · Willis Island · Miami, Florida
★ Bucket-list Zodiac Circumnavigation of Willis IslandBridgeClimb SydneyPeggy's Cove & LunenburgRandom Wind 'Paradise Day Sail' +5 more
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from $11,950
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Holland America · VolendamOne-way
North America 14 nights May 15 – May 29, 2027 from Fort Lauderdale (Port Everglades), Florida to Montreal, Quebec
Fort Lauderdale (Port Everglades), Florida · Norfolk, Virginia · … · Montreal, Quebec9 ports
Fort Lauderdale (Port Everglades), Florida · Norfolk, Virginia · Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $2,059
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Holland America · VolendamOne-way
North America 10 nights May 29 – Jun 8, 2027 from Montreal, Quebec
Montreal, Quebec · Quebec City, Quebec · … · Montreal, Quebec7 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · St. Johns, Newfoundland · St. Pierre, St. Pierre and Miquelon · Montreal, Quebec
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from $2,999
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Holland America · VolendamOne-way
North America 11 nights Jun 8 – Jun 19, 2027 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Quebec City, Quebec · … · Boston, Massachusetts10 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · St. Anthony, Newfoundland · St. Johns, Newfoundland · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Peggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $2,874
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Holland America · VolendamOne-way
North America 7 nights Jun 19 – Jun 26, 2027 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Eastport, Maine, United States · … · Montreal, Quebec7 ports
Boston, Massachusetts · Eastport, Maine, United States · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,609
Book This Cruise@ Cruisebound
Holland America · VolendamRound-trip
North America 14 nights Jun 26 – Jul 10, 2027 from Montreal, Quebec
Montreal, Quebec · Quebec City, Quebec · … · Montreal, Quebec13 ports
Montreal, Quebec · Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $3,369
Book This Cruise@ Cruisebound
Holland America · VolendamRound-trip
North America 14 nights Jul 3 – Jul 17, 2027 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts13 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec · Montreal, Quebec · Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $3,454
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Holland America · VolendamOne-way
North America 7 nights Jul 10 – Jul 17, 2027 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Quebec City, Quebec · … · Boston, Massachusetts7 ports
Montreal, Quebec · Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,654
Book This Cruise@ Cruisebound
Holland America · VolendamRound-trip
Northern Europe 35 nights Jul 17 – Aug 21, 2027 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts21 ports
Boston, Massachusetts · Portland, Maine · Sydney, Nova Scotia · Corner Brook, Newfoundland · Red Bay, Canada · Paamiut (Frederickshaab), Greenland · Nanortalik, Greenland · Isafjord, Iceland · Akureyri, Iceland · Eidfjord, Norway · Rotterdam, The Netherlands · Cobh (Cork), Ireland · Dun Laoghaire, Dublin, Ireland · Belfast, Northern Ireland · Reykjavik, Iceland · Grundarfjordur, Iceland · Qaqortoq, Greenland · St. Anthony, Newfoundland · St. Johns, Newfoundland · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourBridgeClimb SydneyDynjandi WaterfallAll-Inclusive Private Windmill Tour to Kinderdijk… +3 more
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from $9,214
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Holland America · VolendamOne-way
Northern Europe 18 nights Aug 3 – Aug 21, 2027 from Rotterdam, The Netherlands to Boston, Massachusetts
Rotterdam, The Netherlands · Cobh (Cork), Ireland · … · Boston, Massachusetts11 ports
Rotterdam, The Netherlands · Cobh (Cork), Ireland · Dun Laoghaire, Dublin, Ireland · Belfast, Northern Ireland · Reykjavik, Iceland · Grundarfjordur, Iceland · Qaqortoq, Greenland · St. Anthony, Newfoundland · St. Johns, Newfoundland · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list All-Inclusive Private Windmill Tour to Kinderdijk…Giant's Causeway Private Luxury Day Tour from Belf…Inside the VolcanoPeggy's Cove & Lunenburg +1 more
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from $4,684
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Holland America · ZuiderdamOne-way
Northern Europe 28 nights Aug 7 – Sep 4, 2027 from Amsterdam, The Netherlands to Boston, Massachusetts
Amsterdam, The Netherlands · Aarhus, Denmark · … · Boston, Massachusetts20 ports
Amsterdam, The Netherlands · Aarhus, Denmark · Warnemunde, Germany · Ronne, Denmark · Copenhagen, Denmark · Amsterdam, The Netherlands · Lerwick, Shetland Islands · Seydisfjordur, Iceland · Akureyri, Iceland · Husavik, Iceland · Isafjord, Iceland · Grundarfjordur, Iceland · Reykjavik, Iceland · Nanortalik, Greenland · Qaqortoq, Greenland · St. Anthony, Newfoundland · St. Johns, Newfoundland · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Walk Into the Secret Annex - Anne Frank HouseBerlin Private Full-Day Shore Excursion from Warne…Private Copenhagen Walking Tour with a Local ExpertDynjandi Waterfall +3 more
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from $5,354
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Holland America · ZuiderdamOne-way
Northern Europe 21 nights Aug 14 – Sep 4, 2027 from Amsterdam, The Netherlands to Boston, Massachusetts
Amsterdam, The Netherlands · Lerwick, Shetland Islands · … · Boston, Massachusetts15 ports
Amsterdam, The Netherlands · Lerwick, Shetland Islands · Seydisfjordur, Iceland · Akureyri, Iceland · Husavik, Iceland · Isafjord, Iceland · Grundarfjordur, Iceland · Reykjavik, Iceland · Nanortalik, Greenland · Qaqortoq, Greenland · St. Anthony, Newfoundland · St. Johns, Newfoundland · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Walk Into the Secret Annex - Anne Frank HouseDynjandi WaterfallInside the VolcanoPeggy's Cove & Lunenburg +1 more
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from $4,264
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Holland America · VolendamOne-way
North America 11 nights Aug 21 – Sep 1, 2027 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Eastport, Maine, United States · … · Montreal, Quebec11 ports
Boston, Massachusetts · Eastport, Maine, United States · Halifax, Nova Scotia · St. Johns, Newfoundland · St. Anthony, Newfoundland · Corner Brook, Newfoundland · Havre St. Pierre, Quebec · Baie-Commeau, Quebec · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
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from $2,839
Book This Cruise@ Cruisebound
Regent · Seven Seas GrandeurOne-way
Northern Europe 14 nights Aug 27 – Sep 10, 2027 from Southampton, England to Montreal, Quebec
Southampton, England · Fowey, Cornwall, England · … · Montreal, Quebec11 ports
Southampton, England · Fowey, Cornwall, England · Cobh (Cork), Ireland · Liverpool, England · Dun Laoghaire, Dublin, Ireland · Willis Island · St. Johns, Newfoundland · Willis Island · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…Zodiac Circumnavigation of Willis Island
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from $9,249
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Holland America · VolendamRound-trip
North America 10 nights Sep 1 – Sep 11, 2027 from Montreal, Quebec
Montreal, Quebec · Quebec City, Quebec · … · Montreal, Quebec7 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · St. Johns, Newfoundland · St. Pierre, St. Pierre and Miquelon · Montreal, Quebec
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from $3,039
Book This Cruise@ Cruisebound
Holland America · ZuiderdamOne-way
North America 7 nights Sep 4 – Sep 11, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $1,709
Book This Cruise@ Cruisebound
Regent · Seven Seas GrandeurOne-way
Australia & South Pacific 11 nights Sep 10 – Sep 21, 2027 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York11 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Willis Island · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Bar Harbor, Maine · Portland, Maine · Willis Island · New York, New York
★ Bucket-list Zodiac Circumnavigation of Willis IslandBridgeClimb SydneyPeggy's Cove & LunenburgManhattan Helicopter Tour
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from $10,799
Book This Cruise@ Cruisebound
Holland America · VolendamOne-way
North America 7 nights Sep 11 – Sep 18, 2027 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Quebec City, Quebec · … · Boston, Massachusetts7 ports
Montreal, Quebec · Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
View →
from $1,689
Book This Cruise@ Cruisebound
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Itineraries from the Cruisebound catalog + our enrichment; schedules cross-checked against official port authorities. Booking via Cruisebound and CruiseDirect — we may earn a commission, at no extra cost to you.

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MSC Cruises Royal Caribbean Carnival Viking River Costa Norwegian AmaWaterways Princess Celebrity Viking Ocean Avalon Disney Holland America Oceania Virgin Voyages Regent Cunard Seabourn Azamara