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 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
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Showing 20 of 20 sailings
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 TourCampobello IslandPeggy's Cove & LunenburgCape St. Mary's Ecological Reserve +6 more
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from $1,999
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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 Notre-Dame BasilicaOld Québec Private Walking Tour with Expert Local…Archipelago FlavoursPeggy's Cove & Lunenburg +3 more
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from $1,179
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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 TourCampobello IslandPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
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from $1,349
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 20 – Sep 27, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Eastport, Maine, United States · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Campobello Island +1 more
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from $690
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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 TourCampobello IslandReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +2 more
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from $1,429
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Oct 4 – Oct 11, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Eastport, Maine, United States · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Campobello Island +1 more
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from $797
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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 Notre-Dame BasilicaOld Québec Private Walking Tour with Expert Local…Saguenay Fjord Whale-WatchGreen Gables House & Anne of Green Gables Island E… +8 more
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from $9,099
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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 Notre-Dame BasilicaOld Québec Private Walking Tour with Expert Local…Daniel-Johnson DamZodiac Circumnavigation of Willis Island +6 more
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from $11,399
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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 TourCampobello IslandPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
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from $1,609
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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 TourCampobello IslandPeggy's Cove & LunenburgCape St. Mary's Ecological Reserve +6 more
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from $2,839
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 5 – Sep 12, 2027 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Campobello IslandReversing Falls & Fundy Tidal Bore +1 more
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from $816
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Norwegian · Norwegian PearlOne-way
North America 11 nights Sep 7 – Sep 18, 2027 from Philadelphia, Pennsylvania to Quebec City, Quebec
Philadelphia, Pennsylvania · Boston, Massachusetts · … · Quebec City, Quebec9 ports
Philadelphia, Pennsylvania · Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · La Baie, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourCampobello IslandReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +4 more
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from $1,212
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Holland America · VolendamRound-trip
North America 7 nights Sep 18 – Sep 25, 2027 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 TourCampobello IslandReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +2 more
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from $1,709
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Norwegian · Norwegian PearlOne-way
North America 10 nights Sep 18 – Sep 28, 2027 from Quebec City, Quebec to Philadelphia, Pennsylvania
Quebec City, Quebec · La Baie, Canada · … · Philadelphia, Pennsylvania9 ports
Quebec City, Quebec · La Baie, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Eastport, Maine, United States · Portland, Maine · Boston, Massachusetts · Philadelphia, Pennsylvania
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Saguenay Fjord Zodiac Whale-Watching with NaturalistGreen Gables House & Anne of Green Gables Island E…BridgeClimb Sydney +4 more
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from $1,171
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 19 – Sep 26, 2027 from Boston, Massachusetts
Boston, Massachusetts · Eastport, Maine, United States · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Eastport, Maine, United States · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourCampobello IslandPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal Bore +1 more
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from $816
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Holland America · VolendamOne-way
North America 7 nights Sep 25 – Oct 2, 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 TourCampobello IslandPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
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from $1,709
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 26 – Oct 3, 2027 from Boston, Massachusetts
Boston, Massachusetts · Eastport, Maine, United States · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourCampobello IslandReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +1 more
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from $816
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlOne-way
North America 11 nights Sep 28 – Oct 9, 2027 from Philadelphia, Pennsylvania to Quebec City, Quebec
Philadelphia, Pennsylvania · Boston, Massachusetts · … · Quebec City, Quebec9 ports
Philadelphia, Pennsylvania · Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · La Baie, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourCampobello IslandReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +4 more
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from $1,609
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Oct 3 – Oct 10, 2027 from Boston, Massachusetts
Boston, Massachusetts · Eastport, Maine, United States · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Eastport, Maine, United States · Halifax, Nova Scotia · Sydney, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourCampobello IslandPeggy's Cove & LunenburgBridgeClimb Sydney +1 more
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from $824
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Oct 17 – Oct 24, 2027 from Boston, Massachusetts
Boston, Massachusetts · Eastport, Maine, United States · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourCampobello IslandReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +1 more
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from $816
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