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
Cruise level tap one or more Luxury Premium Contemporary River
+ 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 ×Oceania ×Viking Ocean × Clear all
Showing 22 of 22 sailings
Viking Ocean · Viking NeptuneOne-way
Europe 14 nights Jun 20 – Jul 4, 2026 from Reykjavik, Iceland to Boston, Massachusetts
Reykjavik, Iceland · Heimaey, Iceland · … · Boston, Massachusetts15 ports
Reykjavik, Iceland · Heimaey, Iceland · Djupivogur, Iceland · Seydisfjordur, Iceland · Akureyri, Iceland · Isafjord, Iceland · Sail the Atlantic Ocean · Nanortalik, Greenland · Qaqortoq, Greenland · Sail the Labrador Sea · LAnse Aux Meadows, Newfoundland · Sail the Gulf of St. Lawrence · Halifax, Nova Scotia · Sail the Atlantic Ocean · Boston, Massachusetts
★ Bucket-list Inside the VolcanoDynjandi WaterfallPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $10,499
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Viking Ocean · Viking NeptuneOne-way
North America 14 nights Jul 4 – Jul 18, 2026 from Boston, Massachusetts to Reykjavik, Iceland
Boston, Massachusetts · Sail the Atlantic Ocean · … · Reykjavik, Iceland15 ports
Boston, Massachusetts · Sail the Atlantic Ocean · Halifax, Nova Scotia · Sail the Gulf of St. Lawrence · LAnse Aux Meadows, Newfoundland · Sail the Labrador Sea · Qaqortoq, Greenland · Nanortalik, Greenland · Sail the Atlantic Ocean · Isafjord, Iceland · Akureyri, Iceland · Seydisfjordur, Iceland · Djupivogur, Iceland · Heimaey, Iceland · Reykjavik, Iceland
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgDynjandi WaterfallInside the Volcano
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from $10,499
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Viking Ocean · Viking MarsOne-way
North America 12 nights Aug 31 – Sep 12, 2026 from New York, New York to Montreal, Quebec
New York, New York · Boston, Massachusetts · … · Montreal, Quebec10 ports
New York, New York · Boston, Massachusetts · Sail the Nova Scotia Coast · Halifax, Nova Scotia · Sail the Gulf of St. Lawrence · Gaspe, Quebec · Sail the Gulf of St. Lawrence · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourPeggy's Cove & Lunenburg
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from $8,299
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Viking Ocean · Viking MarsOne-way
North America 12 nights Sep 12 – Sep 24, 2026 from Montreal, Quebec to Brooklyn, NY
Montreal, Quebec · Quebec City, Quebec · … · Brooklyn, NY10 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Sail the Gulf of St. Lawrence · Gaspe, Quebec · Sail the Gulf of St. Lawrence · Halifax, Nova Scotia · Sail the Nova Scotia Coast · Boston, Massachusetts · Brooklyn, NY
★ Bucket-list Peggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $9,999
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Oceania · Oceania VistaOne-way
North America 11 nights Sep 14 – Sep 25, 2026 from New York, New York to Montreal, Quebec
New York, New York · Halifax, Nova Scotia · … · Montreal, Quebec9 ports
New York, New York · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Gaspe, Quebec · Baie-Commeau, Quebec · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $5,480
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Viking Ocean · Viking MarsOne-way
North America 12 nights Sep 24 – Oct 6, 2026 from Brooklyn, NY to Montreal, Quebec
Brooklyn, NY · Boston, Massachusetts · … · Montreal, Quebec10 ports
Brooklyn, NY · Boston, Massachusetts · Sail the Nova Scotia Coast · Halifax, Nova Scotia · Sail the Gulf of St. Lawrence · Gaspe, Quebec · Sail the Gulf of St. Lawrence · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
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from $10,099
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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 BridgeClimb SydneyManhattan Helicopter Tour
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from $7,349
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Oceania · Oceania VistaOne-way
Europe 11 nights Oct 6 – Oct 17, 2026 from New York, New York to Montreal, Quebec
New York, New York · Newport, Rhode Island · … · Montreal, Quebec11 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Bay of Fundy, Canada · Halifax, Nova Scotia · Sydney, Nova Scotia · Corner Brook, Newfoundland · Kiel Canal, Germany · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $6,460
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Viking Ocean · Viking MarsOne-way
North America 14 nights Oct 6 – Oct 20, 2026 from Montreal, Quebec to Fort Lauderdale (Port Everglades), Florida
Montreal, Quebec · Quebec City, Quebec · … · Fort Lauderdale (Port Everglades), Florida13 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Sail the Gulf of St. Lawrence · Charlottetown, Prince Edward Island · Scenic Sailing: St. Lawrence Seaway · Sail the Nova Scotia Coast · Saint John, New Brunswick · Eastport, Maine, United States · Portland, Maine · Newport, Rhode Island · Sail the Atlantic Ocean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live Show
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from $9,099
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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 BridgeClimb SydneyPeggy's Cove & LunenburgManhattan Helicopter Tour
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from $4,830
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Oceania · Oceania VistaOne-way
Middle East 11 nights Sep 7 – Sep 18, 2027 from New York, New York to Montreal, Quebec
New York, New York · Newport, Rhode Island · … · Montreal, Quebec10 ports
New York, New York · Newport, Rhode Island · Portland, Maine · Bay of Fundy, Canada · Halifax, Nova Scotia · Sydney, Nova Scotia · Suez Canal, Egypt · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $5,949
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Viking Ocean · Viking MarsOne-way
North America 12 nights Sep 16 – Sep 28, 2027 from New York, New York to Montreal, Quebec
New York, New York · Boston, Massachusetts · … · Montreal, Quebec10 ports
New York, New York · Boston, Massachusetts · Sail the Nova Scotia Coast · Halifax, Nova Scotia · Sail the Gulf of St. Lawrence · Gaspe, Quebec · Scenic Sailing: St. Lawrence Seaway · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourPeggy's Cove & Lunenburg
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from $8,299
Book This Cruise@ Cruisebound
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 & LunenburgPrivate Luxury Boston Tour
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from $6,649
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Oceania · Oceania SirenaOne-way
North America 12 nights Sep 19 – Oct 1, 2027 from New York, New York to Montreal, Quebec
New York, New York · Newport, Rhode Island · … · Montreal, Quebec12 ports
New York, New York · Newport, Rhode Island · Portland, Maine · Bay of Fundy, Canada · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Gaspe, Quebec · Sept-Iles, Canada · Baie-Commeau, Quebec · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $5,449
Book This Cruise@ Cruisebound
Viking Ocean · Viking MarsOne-way
North America 12 nights Sep 28 – Oct 10, 2027 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 · Scenic Sailing: St. Lawrence Seaway · Gaspe, Quebec · Sail the Gulf of St. Lawrence · Halifax, Nova Scotia · Sail the Nova Scotia Coast · Boston, Massachusetts · New York, New York
★ Bucket-list Peggy's Cove & LunenburgPrivate Luxury Boston TourManhattan Helicopter Tour
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from $8,199
Book This Cruise@ Cruisebound
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $6,199
Book This Cruise@ Cruisebound
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 BridgeClimb SydneyPeggy's Cove & LunenburgManhattan Helicopter Tour
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from $5,199
Book This Cruise@ Cruisebound
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 BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of BermudaSwim With the Wild Exuma Pigs +1 more
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from $7,349
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Viking Ocean · Viking MarsOne-way
North America 12 nights Oct 10 – Oct 22, 2027 from New York, New York to Montreal, Quebec
New York, New York · Boston, Massachusetts · … · Montreal, Quebec10 ports
New York, New York · Boston, Massachusetts · Sail the Nova Scotia Coast · Halifax, Nova Scotia · Sail the Gulf of St. Lawrence · Gaspe, Quebec · Scenic Sailing: St. Lawrence Seaway · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourPeggy's Cove & Lunenburg
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from $7,999
Book This Cruise@ Cruisebound
Oceania · Oceania SirenaOne-way
Mediterranean 12 nights Oct 13 – Oct 25, 2027 from New York, New York to Montreal, Quebec
New York, New York · Suez Canal, Egypt · … · Montreal, Quebec13 ports
New York, New York · Suez Canal, Egypt · Boston, Massachusetts · Portland, Maine · Bay of Fundy, Canada · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Gaspe, Quebec · Sept-Iles, Canada · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $4,999
Book This Cruise@ Cruisebound
Viking Ocean · Viking MarsOne-way
North America 14 nights Oct 22 – Nov 5, 2027 from Montreal, Quebec to Fort Lauderdale (Port Everglades), Florida
Montreal, Quebec · Quebec City, Quebec · … · Fort Lauderdale (Port Everglades), Florida13 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Scenic Sailing: St. Lawrence Seaway · Charlottetown, Prince Edward Island · Sail the Gulf of St. Lawrence · Sail the Nova Scotia Coast · Saint John, New Brunswick · Bar Harbor, Maine · Portland, Maine · Newport, Rhode Island · Sail the Atlantic Ocean · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Everglades Airboat Skim + Gator Boys Live Show
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from $8,299
Book This Cruise@ Cruisebound
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 BridgeClimb SydneyPeggy's Cove & LunenburgManhattan Helicopter TourJost Van Dyke +7 more
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from $8,749
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.

19 lines
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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