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 Princess ×Virgin Voyages ×Visits Saint John × Clear all
Showing 22 of 22 sailings
Princess · Sapphire PrincessOne-way
North America 10 nights Sep 3 – Sep 13, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +3 more
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from $1,344
Book This Cruise@ Cruisebound
Princess · Sapphire PrincessOne-way
North America 10 nights Sep 13 – Sep 23, 2026 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts7 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Green Gables House & Anne of Green Gables Island E…BridgeClimb SydneyPeggy's Cove & Lunenburg +2 more
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from $1,137
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Virgin Voyages · Valiant LadyRound-trip
North America Sep 19, 2026 from Brooklyn, NY
Brooklyn, NY · Gloucester, Massachusetts · … · Brooklyn, NY6 ports
Brooklyn, NY · Gloucester, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Brooklyn, NY
★ Bucket-list Portland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $1,779
Book This Cruise@ Cruisebound
Princess · Sapphire PrincessOne-way
North America 10 nights Sep 23 – Oct 3, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +3 more
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from $1,229
Book This Cruise@ Cruisebound
Princess · Majestic PrincessRound-trip
North America 7 nights Oct 3 – Oct 10, 2026 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York6 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourReversing Falls & Fundy Tidal Bore +1 more
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from $1,388
Book This Cruise@ Cruisebound
Princess · Sapphire PrincessOne-way
North America 10 nights Oct 3 – Oct 13, 2026 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts8 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Portland, Maine · Boston, Massachusetts
★ Bucket-list Old Québec Private Walking Tour with Expert Local…Green Gables House & Anne of Green Gables Island E…BridgeClimb SydneyPeggy's Cove & Lunenburg +3 more
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from $1,421
Book This Cruise@ Cruisebound
Princess · Majestic PrincessRound-trip
North America 7 nights Oct 10 – Oct 17, 2026 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $1,404
Book This Cruise@ Cruisebound
Princess · Sapphire PrincessOne-way
North America 10 nights Oct 13 – Oct 23, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +3 more
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from $1,074
Book This Cruise@ Cruisebound
Princess · Majestic PrincessRound-trip
North America 7 nights Oct 17 – Oct 24, 2026 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $1,418
Book This Cruise@ Cruisebound
Princess · Majestic PrincessRound-trip
North America 7 nights Oct 24 – Oct 31, 2026 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $1,187
Book This Cruise@ Cruisebound
Princess · Majestic PrincessRound-trip
North America 7 nights Oct 31 – Nov 7, 2026 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $1,145
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
North America 7 nights Aug 21 – Aug 28, 2027 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 $829
Book This Cruise@ Cruisebound
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 TourReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $700
Book This Cruise@ Cruisebound
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 TourReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $727
Book This Cruise@ Cruisebound
Princess · Caribbean PrincessOne-way
North America 10 nights Sep 7 – Sep 17, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +3 more
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from $1,200
Book This Cruise@ Cruisebound
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 TourReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
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from $727
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
North America 7 nights Sep 18 – Sep 25, 2027 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $889
Book This Cruise@ Cruisebound
Princess · Caribbean PrincessOne-way
North America 10 nights Sep 28 – Oct 8, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +3 more
View →
from $1,199
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
North America 7 nights Oct 2 – Oct 9, 2027 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
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from $1,449
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
North America 7 nights Oct 16 – Oct 23, 2027 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
View →
from $769
Book This Cruise@ Cruisebound
Princess · Caribbean PrincessOne-way
North America 10 nights Oct 19 – Oct 29, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec8 ports
Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +3 more
View →
from $1,199
Book This Cruise@ Cruisebound
Princess · Regal PrincessRound-trip
North America 7 nights Oct 30 – Nov 6, 2027 from New York, New York
New York, New York · Newport, Rhode Island · … · New York, New York7 ports
New York, New York · Newport, Rhode Island · Boston, Massachusetts · Portland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourThe BreakersPrivate Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse… +2 more
View →
from $806
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