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 ×Celebrity ×Visits Saint John × Clear all
Showing 23 of 23 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 JewelRound-trip
Bermuda 9 nights Aug 27 – Sep 5, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Saint John, New Brunswick · Halifax, Nova Scotia · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $774
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Norwegian · Norwegian EscapeRound-trip
North America 7 nights Aug 29 – Sep 5, 2026 from New York, New York
New York, New York · Boston, Massachusetts · … · New York, New York6 ports
New York, New York · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal Bore +1 more
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from $956
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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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Celebrity · Celebrity SilhouetteRound-trip
North America 12 nights Sep 5 – Sep 17, 2026 from Boston, Massachusetts
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts9 ports
Boston, Massachusetts · Rockland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +4 more
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from $3,432
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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
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Norwegian · Norwegian EscapeRound-trip
North America 7 nights Sep 12 – Sep 19, 2026 from New York, New York
New York, New York · Halifax, Nova Scotia · … · New York, New York7 ports
New York, New York · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts · Portland, Maine · Newport, Rhode Island · New York, New York
★ Bucket-list Manhattan Helicopter TourPeggy's Cove & LunenburgReversing Falls & Fundy Tidal BorePrivate Luxury Boston Tour +2 more
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from $935
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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 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
Book This Cruise@ Cruisebound
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
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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
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Aug 29 – Sep 5, 2027 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BoreBridgeClimb Sydney +1 more
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from $853
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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…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $816
Book This Cruise@ Cruisebound
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 TourReversing Falls & Fundy Tidal BorePeggy's Cove & LunenburgBridgeClimb Sydney +3 more
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from $1,212
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 12 – Sep 19, 2027 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BoreBridgeClimb Sydney +1 more
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from $824
Book This Cruise@ Cruisebound
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 TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $816
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 TourReversing Falls & Fundy Tidal BorePeggy's Cove & LunenburgPortland Head Light & Casco Bay Scenic Lighthouse…
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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 TourReversing Falls & Fundy Tidal BorePeggy's Cove & LunenburgBridgeClimb Sydney +3 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 TourPeggy's Cove & LunenburgBridgeClimb SydneyReversing Falls & Fundy Tidal Bore
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from $824
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Oct 10 – Oct 17, 2027 from Boston, Massachusetts
Boston, Massachusetts · Saint John, New Brunswick · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Saint John, New Brunswick · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourReversing Falls & Fundy Tidal BoreBridgeClimb SydneyPeggy's Cove & Lunenburg +1 more
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from $816
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 TourReversing Falls & Fundy Tidal BorePeggy's Cove & LunenburgPortland Head Light & Casco Bay Scenic Lighthouse…
View →
from $816
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
North America 11 nights Oct 19 – Oct 30, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Boston, Massachusetts · … · Philadelphia, Pennsylvania9 ports
Philadelphia, Pennsylvania · Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Portland, Maine · Philadelphia, Pennsylvania
★ Bucket-list Private Luxury Boston TourReversing Falls & Fundy Tidal BorePeggy's Cove & LunenburgBridgeClimb Sydney +2 more
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from $1,459
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