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 · 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 Norwegian ×Regent ×Visits Bar Harbor × Clear all
Showing 16 of 16 sailings
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Aug 23 – Aug 30, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Peggy's Cove & Lunenburg +1 more
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from $838
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Aug 30 – Sep 6, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Saint John, New Brunswick · 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…Reversing Falls & Fundy Tidal Bore +1 more
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from $838
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Norwegian · Norwegian JewelOne-way
North America 11 nights Sep 5 – Sep 16, 2026 from Philadelphia, Pennsylvania to Quebec City, Quebec
Philadelphia, Pennsylvania · Boston, Massachusetts · … · Quebec City, Quebec9 ports
Philadelphia, Pennsylvania · Boston, Massachusetts · Bar Harbor, Maine · 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 TourPrivate Acadia National Park Van Tour with Expert…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +4 more
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from $1,071
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 6 – Sep 13, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Peggy's Cove & Lunenburg +1 more
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from $731
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 13 – Sep 20, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Saint John, New Brunswick · 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…Reversing Falls & Fundy Tidal Bore +1 more
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from $690
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Norwegian · Norwegian JewelOne-way
North America 10 nights Sep 16 – Sep 26, 2026 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 · Bar Harbor, Maine · 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 $1,043
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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…Peggy's Cove & Lunenburg
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from $690
Book This Cruise@ Cruisebound
Norwegian · Norwegian JewelOne-way
North America 11 nights Sep 26 – Oct 7, 2026 from Philadelphia, Pennsylvania to Quebec City, Quebec
Philadelphia, Pennsylvania · Portland, Maine · … · Quebec City, Quebec9 ports
Philadelphia, Pennsylvania · Portland, Maine · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · La Baie, Canada · Quebec City, Quebec
★ Bucket-list Portland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +4 more
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from $1,090
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 27 – Oct 4, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Saint John, New Brunswick · 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…Reversing Falls & Fundy Tidal Bore +1 more
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from $989
Book This Cruise@ Cruisebound
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…Peggy's Cove & Lunenburg
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from $797
Book This Cruise@ Cruisebound
Norwegian · Norwegian JewelOne-way
North America 10 nights Oct 7 – Oct 17, 2026 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 · Bar Harbor, Maine · 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 $1,206
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Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Oct 11 – Oct 18, 2026 from Boston, Massachusetts
Boston, Massachusetts · Newport, Rhode Island · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Newport, Rhode Island · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourThe BreakersPrivate Acadia National Park Van Tour with Expert…Reversing Falls & Fundy Tidal Bore +1 more
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from $957
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Regent · Seven Seas GrandeurOne-way
Australia & South Pacific 11 nights Sep 10 – Sep 21, 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 · Willis Island · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Bar Harbor, Maine · Portland, Maine · Willis Island · New York, New York
★ 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 +4 more
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from $10,799
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Regent · Seven Seas GrandeurOne-way
Australia & South Pacific 11 nights Sep 21 – Oct 2, 2027 from New York, New York to Montreal, Quebec
New York, New York · Willis Island · … · Montreal, Quebec11 ports
New York, New York · Willis Island · Boston, Massachusetts · Bar Harbor, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Willis Island · Sept-Iles, Canada · Saguenay Fjord, Canada · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourZodiac Circumnavigation of Willis IslandPrivate Luxury Boston TourPrivate Acadia National Park Van Tour with Expert… +3 more
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from $11,099
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Regent · Seven Seas GrandeurOne-way
Australia & South Pacific 11 nights Oct 13 – Oct 24, 2027 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Bar Harbor, Maine · … · Montreal, Quebec12 ports
Boston, Massachusetts · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Willis Island · Gaspe, Quebec · Willis Island · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPrivate Acadia National Park Van Tour with Expert…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +5 more
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from $13,249
Book This Cruise@ Cruisebound
Regent · Seven Seas GrandeurOne-way
Australia & South Pacific 11 nights Oct 24 – Nov 4, 2027 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 · Sept-Iles, Canada · Willis Island · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Bar Harbor, Maine · Boston, Massachusetts · Willis Island · New York, New York
★ 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 +4 more
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from $10,949
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