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 1 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
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 · 1 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
Must visit a specific port
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Filtering North America ×Holland America ×6–8 nights × Clear all
Showing 20 of 20 sailings
Holland America · ZuiderdamOne-way
North America 7 nights Jun 20 – Jun 27, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $889
Book This Cruise@ Cruisebound
Holland America · ZuiderdamRound-trip
North America 7 nights Jul 4 – Jul 11, 2026 from Boston, Massachusetts
Boston, Massachusetts · Saint John, New Brunswick · Norfolk, Virginia · New York, New York · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourManhattan Helicopter Tour
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from $1,479
Book This Cruise@ Cruisebound
Holland America · ZuiderdamOne-way
North America 7 nights Aug 22 – Aug 29, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,159
Book This Cruise@ Cruisebound
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 Peggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,179
Book This Cruise@ Cruisebound
Holland America · ZuiderdamOne-way
North America 7 nights Sep 12 – Sep 19, 2026 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Charlottetown, Prince Edward Island · … · Boston, Massachusetts6 ports
Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,189
Book This Cruise@ Cruisebound
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,349
Book This Cruise@ Cruisebound
Holland America · ZuiderdamOne-way
North America 7 nights Sep 19 – Sep 26, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,369
Book This Cruise@ Cruisebound
Holland America · ZuiderdamOne-way
North America 7 nights Sep 26 – Oct 3, 2026 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Saguenay Fjord, Canada · … · Boston, Massachusetts6 ports
Quebec City, Quebec · Saguenay Fjord, Canada · Cap-Aux-Meules, Canada · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston Tour
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from $1,409
Book This Cruise@ Cruisebound
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,429
Book This Cruise@ Cruisebound
Holland America · ZuiderdamOne-way
North America 7 nights Oct 10 – Oct 17, 2026 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,399
Book This Cruise@ Cruisebound
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,609
Book This Cruise@ Cruisebound
Holland America · VolendamOne-way
North America 7 nights Jul 10 – Jul 17, 2027 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Quebec City, Quebec · … · Boston, Massachusetts7 ports
Montreal, Quebec · Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,654
Book This Cruise@ Cruisebound
Holland America · ZuiderdamOne-way
North America 7 nights Sep 4 – Sep 11, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $1,709
Book This Cruise@ Cruisebound
Holland America · VolendamOne-way
North America 7 nights Sep 11 – Sep 18, 2027 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Quebec City, Quebec · … · Boston, Massachusetts7 ports
Montreal, Quebec · Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $1,689
Book This Cruise@ Cruisebound
Holland America · ZuiderdamOne-way
North America 7 nights Sep 11 – Sep 18, 2027 from Quebec City, Quebec to Boston, Massachusetts
Quebec City, Quebec · Charlottetown, Prince Edward Island · … · Boston, Massachusetts6 ports
Quebec City, Quebec · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
View →
from $1,709
Book This Cruise@ Cruisebound
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $1,709
Book This Cruise@ Cruisebound
Holland America · ZuiderdamRound-trip
North America 7 nights Sep 18 – Sep 25, 2027 from Boston, Massachusetts
Boston, Massachusetts · Saint John, New Brunswick · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $1,804
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $1,709
Book This Cruise@ Cruisebound
Holland America · ZuiderdamOne-way
North America 7 nights Sep 25 – Oct 2, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $1,784
Book This Cruise@ Cruisebound
Holland America · ZuiderdamOne-way
North America 7 nights Oct 9 – Oct 16, 2027 from Boston, Massachusetts to Quebec City, Quebec
Boston, Massachusetts · Portland, Maine · … · Quebec City, Quebec6 ports
Boston, Massachusetts · Portland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $1,784
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