Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

When are you free? — only cruises that fit entirely inside your dates
My result then click any cruise row to open it
Where to? tap as many as you like 2 selected · clear Caribbean Mediterranean Alaska Bahamas Mexico Northern Europe Hawaii Bermuda Europe Asia Australia & South Pacific Panama Canal South America North America Pacific Middle East Africa
Trip tap one or more Round-trip One-way Repositioning
Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights
Cruise level tap one or more Luxury Premium Contemporary River
+ pick specific cruise lines
Luxury Azamara Oceania Regent Seabourn Viking Ocean River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
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Filtering Alaska ×North America ×Visits St. Pierre × Clear all
Showing 19 of 19 sailings
Azamara · Azamara JourneyOne-way
North America 18 nights Aug 8 – Aug 26, 2026 from Reykjavik, Iceland to Montreal, Quebec
Reykjavik, Iceland · Reyjanes, Iceland · … · Montreal, Quebec13 ports
Reykjavik, Iceland · Reyjanes, Iceland · Grundarfjordur, Iceland · Isafjord, Iceland · Prince Christian Sund, Greenland · Nanortalik, Greenland · Paamiut (Frederickshaab), Greenland · Nuuk, Greenland · St. Johns, Newfoundland · St. Pierre, St. Pierre and Miquelon · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Inside the VolcanoBlue Lagoon Premium Entry with Mask, Drink & Trans…Dynjandi WaterfallPrins Christian Sund +6 more
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from $5,949
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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 & LunenburgCape St. Mary's Ecological ReserveOld Québec Private Walking Tour with Expert Local…
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from $1,999
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Azamara · Azamara JourneyRepositioning
North America 16 nights Aug 26 – Sep 11, 2026 from Montreal, Quebec to Reykjavik, Iceland
Montreal, Quebec · Quebec City, Quebec · … · Reykjavik, Iceland10 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Havre St. Pierre, Quebec · Nuuk, Greenland · Paamiut (Frederickshaab), Greenland · Qaqortoq, Greenland · Prince Christian Sund, Greenland · Grundarfjordur, Iceland · Reykjavik, Iceland
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Nuuk Icefjord Private Boat ExpeditionKuannersooq FjordPrins Christian Sund +1 more
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from $5,769
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Azamara · Azamara JourneyOne-way
North America 14 nights Sep 11 – Sep 25, 2026 from Reykjavik, Iceland to Montreal, Quebec
Reykjavik, Iceland · Prince Christian Sund, Greenland · … · Montreal, Quebec9 ports
Reykjavik, Iceland · Prince Christian Sund, Greenland · Qaqortoq, Greenland · Nanortalik, Greenland · St. Johns, Newfoundland · St. Pierre, St. Pierre and Miquelon · Charlottetown, Prince Edward Island · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Inside the VolcanoPrins Christian SundTasermiut Fjord Full-Day Boat ExpeditionCape St. Mary's Ecological Reserve +3 more
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from $3,759
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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 Old Québec Private Walking Tour with Expert Local…Zodiac Circumnavigation of Willis IslandGreen Gables House & Anne of Green Gables Island E…BridgeClimb Sydney +3 more
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from $13,199
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Oceania · Oceania VistaOne-way
North America 11 nights Sep 25 – Oct 6, 2026 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York10 ports
Montreal, Quebec · Quebec City, Quebec · Baie-Commeau, Quebec · Sept-Iles, Canada · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · Sydney, Nova Scotia · Bay of Fundy, Canada · Portland, Maine · New York, New York
★ Bucket-list Old Québec Private Walking Tour with Expert Local…BridgeClimb SydneyPortland Head Light & Casco Bay Scenic Lighthouse…Manhattan Helicopter Tour
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from $7,349
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Seabourn · Seabourn OvationRound-trip
North America 12 nights Sep 25 – Oct 7, 2026 from Montreal, Quebec
Montreal, Quebec · Havre St. Pierre, Quebec · … · Montreal, Quebec9 ports
Montreal, Quebec · Havre St. Pierre, Quebec · LAnse Aux Meadows, Newfoundland · St. Johns, Newfoundland · St Pierre et Miquelon · Cap-Aux-Meules, Canada · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Cape St. Mary's Ecological ReserveOld Québec Private Walking Tour with Expert Local…
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from $9,859
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Oceania · Oceania VistaOne-way
North America 11 nights Oct 17 – Oct 28, 2026 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 · Baie-Commeau, Quebec · Sept-Iles, Canada · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · Sydney, Nova Scotia · Halifax, Nova Scotia · Bay of Fundy, Canada · New York, New York
★ Bucket-list Old Québec Private Walking Tour with Expert Local…BridgeClimb SydneyPeggy's Cove & LunenburgManhattan Helicopter Tour
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from $4,830
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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
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Green Gables House & Anne of Green Gables Island E…Cape St. Mary's Ecological ReserveÎle aux Marins
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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 Old Québec Private Walking Tour with Expert Local…Cape St. Mary's Ecological ReservePeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $2,874
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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 & LunenburgCape St. Mary's Ecological ReserveOld Québec Private Walking Tour with Expert Local…
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from $2,839
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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
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Green Gables House & Anne of Green Gables Island E…Cape St. Mary's Ecological ReserveÎle aux Marins
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from $3,039
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Oceania · Oceania VistaOne-way
North America 11 nights Sep 18 – Sep 29, 2027 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts10 ports
Montreal, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Sept-Iles, Canada · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · Halifax, Nova Scotia · Bay of Fundy, Canada · Portland, Maine · Boston, Massachusetts
★ Bucket-list Peggy's Cove & LunenburgPortland Head Light & Casco Bay Scenic Lighthouse…Private Luxury Boston Tour
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from $6,649
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Seabourn · Seabourn QuestRound-trip
North America 12 nights Sep 25 – Oct 7, 2027 from Montreal, Quebec
Montreal, Quebec · Havre St. Pierre, Quebec · … · Montreal, Quebec9 ports
Montreal, Quebec · Havre St. Pierre, Quebec · LAnse Aux Meadows, Newfoundland · St. Johns, Newfoundland · St Pierre et Miquelon · Cap-Aux-Meules, Canada · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Cape St. Mary's Ecological ReserveOld Québec Private Walking Tour with Expert Local…
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from $6,884
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Oceania · Oceania VistaOne-way
North America 11 nights Sep 29 – Oct 10, 2027 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Portland, Maine · … · Montreal, Quebec11 ports
Boston, Massachusetts · Portland, Maine · Bay of Fundy, Canada · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Havre St. Pierre, Quebec · Sept-Iles, Canada · Baie-Commeau, Quebec · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Peggy's Cove & LunenburgBridgeClimb Sydney +2 more
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from $6,199
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Oceania · Oceania SirenaOne-way
North America 12 nights Oct 1 – Oct 13, 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 · Baie-Commeau, Quebec · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · Sydney, Nova Scotia · Halifax, Nova Scotia · Bay of Fundy, Canada · Portland, Maine · New York, New York
★ Bucket-list Old Québec Private Walking Tour with Expert Local…BridgeClimb SydneyPeggy's Cove & LunenburgPortland Head Light & Casco Bay Scenic Lighthouse… +1 more
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from $5,199
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Azamara · Azamara QuestOne-way
North America 12 nights Oct 4 – Oct 16, 2027 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Portland, Maine · … · Montreal, Quebec12 ports
Boston, Massachusetts · Portland, Maine · Rockland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Corner Brook, Newfoundland · Havre St. Pierre, Quebec · Sept-Iles, Canada · Saguenay Fjord, Canada · Quebec City, Quebec · Troisrivieres, Canada · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Luxury Camden Sailing Experience on Penobscot BayReversing Falls & Fundy Tidal Bore +2 more
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from $4,789
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Oceania · Oceania VistaOne-way
Bermuda 14 nights Oct 10 – Oct 24, 2027 from Montreal, Quebec to Miami, Florida
Montreal, Quebec · Quebec City, Quebec · … · Miami, Florida12 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · Sydney, Nova Scotia · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Suez Canal, Egypt · Nassau, Bahamas · Miami, Florida
★ Bucket-list Old Québec Private Walking Tour with Expert Local…BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda +2 more
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from $7,349
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Oceania · Oceania SirenaRepositioning
Caribbean 27 nights Oct 25 – Nov 21, 2027 from Montreal, Quebec to Miami, Florida
Montreal, Quebec · Quebec City, Quebec · … · Miami, Florida21 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Havre St. Pierre, Quebec · Corner Brook, Newfoundland · Sydney, Nova Scotia · Halifax, Nova Scotia · Bay of Fundy, Canada · Portland, Maine · New York, New York · Tortola, B.V.I. · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Kralendijk, Bonaire, Dutch Antilles · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Ocho Rios, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Suez Canal, Egypt · Miami, Florida
★ Bucket-list Old Québec Private Walking Tour with Expert Local…BridgeClimb SydneyPeggy's Cove & LunenburgPortland Head Light & Casco Bay Scenic Lighthouse… +9 more
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from $8,749
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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