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
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Where to? tap as many as you like 1 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
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+ pick specific cruise lines · 2 selected
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 North America ×Princess ×Azamara × Clear all
Showing 23 of 23 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 VolcanoDynjandi Waterfall
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from $5,949
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Princess · Sapphire PrincessRepositioning
Northern Europe 15 nights Aug 19 – Sep 3, 2026 from Copenhagen, Denmark to Boston, Massachusetts
Copenhagen, Denmark · Lerwick, Shetland Islands · … · Boston, Massachusetts9 ports
Copenhagen, Denmark · Lerwick, Shetland Islands · Stornoway, Scotland · Belfast, Northern Ireland · Liverpool, England · Cobh (Cork), Ireland · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Copenhagen Walking Tour with a Local ExpertGiant's Causeway Private Luxury Day Tour from Belf…BridgeClimb SydneyPeggy's Cove & Lunenburg +1 more
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from $1,455
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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 Inside the Volcano
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from $5,769
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Princess · Sapphire PrincessOne-way
North America 10 nights Sep 3 – Sep 13, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,344
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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 Volcano
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from $3,759
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Princess · Sapphire PrincessOne-way
North America 10 nights Sep 13 – Sep 23, 2026 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts7 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,137
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Princess · Sapphire PrincessOne-way
North America 10 nights Sep 23 – Oct 3, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,229
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Azamara · Azamara JourneyOne-way
North America 12 nights Sep 25 – Oct 7, 2026 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York13 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Lunenburg, Nova Scotia · Saint John, New Brunswick · Portland, Maine · Cape Cod, Massachusetts · Boston, Massachusetts · Marthas Vineyard, Massachusetts · New York, New York
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston TourManhattan Helicopter Tour
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from $3,649
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Princess · Sapphire PrincessOne-way
North America 10 nights Oct 3 – Oct 13, 2026 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts8 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Portland, Maine · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,421
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Princess · Sapphire PrincessOne-way
North America 10 nights Oct 13 – Oct 23, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,074
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Princess · Sapphire PrincessOne-way
Bahamas 14 nights Oct 23 – Nov 6, 2026 from Quebec City, Quebec to Fort Lauderdale (Port Everglades), Florida
Quebec City, Quebec · Saguenay Fjord, Canada · … · Fort Lauderdale (Port Everglades), Florida10 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts · Newport, Rhode Island · New York, New York · Nassau, Bahamas · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston TourManhattan Helicopter Tour +2 more
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from $1,345
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Princess · Caribbean PrincessRepositioning
Northern Europe 28 nights Aug 10 – Sep 7, 2027 from Copenhagen, Denmark to Boston, Massachusetts
Copenhagen, Denmark · Visby, Sweden · … · Boston, Massachusetts20 ports
Copenhagen, Denmark · Visby, Sweden · Stockholm, Sweden · Helsinki, Finland · Tallinn, Estonia · Riga, Latvia · Klaipeda, Lithuania · Gdansk, Poland · Oslo, Norway · Skagen, Denmark · Copenhagen, Denmark · Gothenburg, Sweden · Runavik, Faroe Islands · Seydisfjordur, Iceland · Akureyri, Iceland · Isafjord, Iceland · Reykjavik, Iceland · St. Johns, Newfoundland · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Copenhagen Walking Tour with a Local ExpertVasa MuseumPrivate Half-Day Tallinn Old Town & City Sightseei…Private Oslo Highlights & Hidden Gems with a Local… +4 more
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from $5,263
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Princess · Caribbean PrincessRepositioning
Northern Europe 16 nights Aug 22 – Sep 7, 2027 from Copenhagen, Denmark to Boston, Massachusetts
Copenhagen, Denmark · Gothenburg, Sweden · … · Boston, Massachusetts10 ports
Copenhagen, Denmark · Gothenburg, Sweden · Runavik, Faroe Islands · Seydisfjordur, Iceland · Akureyri, Iceland · Isafjord, Iceland · Reykjavik, Iceland · St. Johns, Newfoundland · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Copenhagen Walking Tour with a Local ExpertDynjandi WaterfallInside the VolcanoPeggy's Cove & Lunenburg +1 more
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from $1,759
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Princess · Caribbean PrincessOne-way
North America 10 nights Sep 7 – Sep 17, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,200
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Azamara · Azamara QuestOne-way
North America 12 nights Sep 10 – Sep 22, 2027 from New York, New York to Montreal, Quebec
New York, New York · Cape Cod, Massachusetts · … · Montreal, Quebec14 ports
New York, New York · Cape Cod, Massachusetts · Marthas Vineyard, Massachusetts · Boston, Massachusetts · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Cap-Aux-Meules, Canada · Gaspe, Quebec · Sept-Iles, Canada · Cruise Saguenay River · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourPeggy's Cove & Lunenburg
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from $5,019
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Princess · Caribbean PrincessOne-way
North America 11 nights Sep 17 – Sep 28, 2027 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts8 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Corner Brook, Newfoundland · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,126
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Azamara · Azamara QuestOne-way
North America 12 nights Sep 22 – Oct 4, 2027 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Troisrivieres, Canada · … · Boston, Massachusetts12 ports
Montreal, Quebec · Troisrivieres, Canada · Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Gaspe, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Portland, Maine · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $4,699
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Princess · Caribbean PrincessOne-way
North America 10 nights Sep 28 – Oct 8, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,199
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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 TourPeggy's Cove & Lunenburg
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from $4,789
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Princess · Caribbean PrincessOne-way
North America 11 nights Oct 8 – Oct 19, 2027 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts8 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Corner Brook, Newfoundland · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,204
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Azamara · Azamara QuestOne-way
North America 12 nights Oct 16 – Oct 28, 2027 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York13 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Baie-Commeau, Quebec · Gaspe, Quebec · Halifax, Nova Scotia · Lunenburg, Nova Scotia · Saint John, New Brunswick · Portland, Maine · Cape Cod, Massachusetts · Boston, Massachusetts · Newport, Rhode Island · New York, New York
★ Bucket-list Peggy's Cove & LunenburgPrivate Luxury Boston TourManhattan Helicopter Tour
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from $6,559
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Princess · Caribbean PrincessOne-way
North America 10 nights Oct 19 – Oct 29, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,199
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Princess · Caribbean PrincessOne-way
North America 13 nights Oct 29 – Nov 11, 2027 from Quebec City, Quebec to Fort Lauderdale (Port Everglades), Florida
Quebec City, Quebec · Saguenay Fjord, Canada · … · Fort Lauderdale (Port Everglades), Florida10 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts · Newport, Rhode Island · New York, New York · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston TourManhattan Helicopter Tour +1 more
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from $1,339
Book This Cruise@ Cruisebound

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