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 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 Visits Eastport ×6–8 nights ×13+ nights × Clear all
Showing 17 of 17 sailings
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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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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Princess · Regal PrincessRound-trip
North America 7 nights Aug 28 – Sep 4, 2027 from New York, New York
New York, New York · Boston, Massachusetts · … · New York, New York6 ports
New York, New York · Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourCampobello IslandReversing Falls & Fundy Tidal Bore +1 more
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from $700
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Princess · Regal PrincessRound-trip
North America 7 nights Sep 4 – Sep 11, 2027 from New York, New York
New York, New York · Boston, Massachusetts · … · New York, New York6 ports
New York, New York · Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourCampobello IslandReversing Falls & Fundy Tidal Bore +1 more
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from $727
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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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Princess · Regal PrincessRound-trip
North America 7 nights Sep 11 – Sep 18, 2027 from New York, New York
New York, New York · Boston, Massachusetts · … · New York, New York6 ports
New York, New York · Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourCampobello IslandReversing Falls & Fundy Tidal Bore +1 more
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from $727
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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 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
Book This Cruise@ Cruisebound
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
Book This Cruise@ Cruisebound
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 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
Book This Cruise@ Cruisebound
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.

19 lines
aboard
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