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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Showing 35 of 35 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
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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
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Norwegian · Norwegian EscapeRound-trip
North America 7 nights Sep 5 – Sep 12, 2026 from New York, New York
New York, New York · Sydney, Nova Scotia · … · New York, New York7 ports
New York, New York · Sydney, Nova Scotia · Halifax, Nova Scotia · Portland, Maine · Boston, Massachusetts · Newport, Rhode Island · New York, New York
★ Bucket-list Manhattan Helicopter TourBridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
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from $915
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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
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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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
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from $1,349
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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
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Norwegian · Norwegian EscapeRound-trip
North America 7 nights Sep 19 – Sep 26, 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 · Sydney, Nova Scotia · Halifax, Nova Scotia · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourBridgeClimb SydneyPeggy's Cove & Lunenburg
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from $935
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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 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
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Royal Caribbean · Anthem of the SeasRound-trip
Australia & South Pacific 8 nights Dec 11 – Dec 19, 2026 from Sydney, Australia
Sydney, Australia · Noumea, New Caledonia · Port Vila, Vanuatu · Mystery Island Vanuatu · Sydney, Australia
★ Bucket-list BridgeClimb SydneyAmédée Island Day TripLelepa IslandClear Kayak & Snorkel
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from $1,093
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Royal Caribbean · Anthem of the SeasRound-trip
Australia & South Pacific 8 nights Jan 24 – Feb 1, 2027 from Sydney, Australia
Sydney, Australia · Cairns, Australia · Airlie Beach · Sydney, Australia
★ Bucket-list BridgeClimb SydneyOuter Great Barrier Reef
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from $919
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Princess · Royal PrincessRound-trip
Australia & South Pacific 8 nights Jan 30 – Feb 7, 2027 from Sydney, Australia
Sydney, Australia · Hobart, Australia · … · Sydney, Australia6 ports
Sydney, Australia · Hobart, Australia · Port Arthur, Australia · Melbourne, Australia · Eden, Australia · Sydney, Australia
★ Bucket-list BridgeClimb Sydney
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from $995
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Royal Caribbean · Anthem of the SeasRound-trip
Australia & South Pacific 8 nights Feb 21 – Mar 1, 2027 from Sydney, Australia
Sydney, Australia · Noumea, New Caledonia · Port Vila, Vanuatu · Mystery Island Vanuatu · Sydney, Australia
★ Bucket-list BridgeClimb SydneyAmédée Island Day TripLelepa IslandClear Kayak & Snorkel
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from $1,162
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Princess · Royal PrincessRound-trip
Australia & South Pacific 6 nights Mar 19 – Mar 25, 2027 from Sydney, Australia
Sydney, Australia · Eden, Australia · Hobart, Australia · Port Arthur, Australia · Sydney, Australia
★ Bucket-list BridgeClimb Sydney
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from $927
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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 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
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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 TourBridgeClimb SydneyPeggy's Cove & Lunenburg
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from $853
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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
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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
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from $1,709
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 TourBridgeClimb SydneyPeggy's Cove & Lunenburg
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from $824
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
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 Sydney
View →
from $824
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
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 TourBridgeClimb SydneyPeggy's Cove & Lunenburg
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from $816
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Princess · Royal PrincessOne-way
Australia & South Pacific 7 nights Oct 16 – Oct 23, 2027 from Auckland, New Zealand to Sydney, Australia
Auckland, New Zealand · Napier, New Zealand · Wellington, New Zealand · Sydney, Australia
★ Bucket-list Waiheke Island Private Wine TourBridgeClimb Sydney
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from $1,647
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Princess · Royal PrincessRound-trip
Australia & South Pacific 7 nights Oct 23 – Oct 30, 2027 from Sydney, Australia
Sydney, Australia · Hobart, Australia · Port Arthur, Australia · Melbourne, Australia · Sydney, Australia
★ Bucket-list BridgeClimb Sydney
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from $1,259
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Celebrity · Celebrity SolsticeRound-trip
Australia & South Pacific 8 nights Nov 2 – Nov 10, 2027 from Sydney, Australia
Sydney, Australia · Hobart, Australia · Adelaide, Australia · Melbourne, Australia · Sydney, Australia
★ Bucket-list BridgeClimb Sydney
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from $1,302
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Princess · Royal PrincessRound-trip
Australia & South Pacific 7 nights Nov 28 – Dec 5, 2027 from Sydney, Australia
Sydney, Australia · Hobart, Australia · Port Arthur, Australia · Melbourne, Australia · Sydney, Australia
★ Bucket-list BridgeClimb Sydney
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from $1,229
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Norwegian · Norwegian SpiritRound-trip
Australia & South Pacific 8 nights Dec 12 – Dec 20, 2027 from Sydney, Australia
Sydney, Australia · Newcastle, Australia · … · Sydney, Australia6 ports
Sydney, Australia · Newcastle, Australia · Eden, Australia · Melbourne, Australia · Burnie, Tasmania · Sydney, Australia
★ Bucket-list BridgeClimb Sydney
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from $1,256
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Celebrity · Celebrity EdgeRound-trip
Australia & South Pacific 6 nights Jan 25 – Jan 31, 2028 from Sydney, Australia
Sydney, Australia · Hobart, Australia · Melbourne, Australia · Sydney, Australia
★ Bucket-list BridgeClimb Sydney
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from $1,030
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Princess · Grand PrincessOne-way
Australia & South Pacific 6 nights Mar 2 – Mar 8, 2028 from Sydney, Australia to Adelaide, Australia
Sydney, Australia · Eden, Australia · Melbourne, Australia · Adelaide, Australia
★ Bucket-list BridgeClimb Sydney
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from $749
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