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 2 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
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 clear
Reset
Filtering Alaska ×North America ×Visits Halifax × Clear all
Showing 36 of 159 sailings
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jun 14 – Jun 21, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
View →
from $610
Book This Cruise@ Cruisebound
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
View →
from $889
Book This Cruise@ Cruisebound
Viking Ocean · Viking NeptuneOne-way
Europe 14 nights Jun 20 – Jul 4, 2026 from Reykjavik, Iceland to Boston, Massachusetts
Reykjavik, Iceland · Heimaey, Iceland · … · Boston, Massachusetts15 ports
Reykjavik, Iceland · Heimaey, Iceland · Djupivogur, Iceland · Seydisfjordur, Iceland · Akureyri, Iceland · Isafjord, Iceland · Sail the Atlantic Ocean · Nanortalik, Greenland · Qaqortoq, Greenland · Sail the Labrador Sea · LAnse Aux Meadows, Newfoundland · Sail the Gulf of St. Lawrence · Halifax, Nova Scotia · Sail the Atlantic Ocean · Boston, Massachusetts
★ Bucket-list Inside the VolcanoDynjandi WaterfallPeggy's Cove & LunenburgPrivate Luxury Boston Tour
View →
from $10,499
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jun 21 – Jun 28, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
View →
from $764
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jun 28 – Jul 5, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
View →
from $801
Book This Cruise@ Cruisebound
Viking Ocean · Viking NeptuneOne-way
North America 14 nights Jul 4 – Jul 18, 2026 from Boston, Massachusetts to Reykjavik, Iceland
Boston, Massachusetts · Sail the Atlantic Ocean · … · Reykjavik, Iceland15 ports
Boston, Massachusetts · Sail the Atlantic Ocean · Halifax, Nova Scotia · Sail the Gulf of St. Lawrence · LAnse Aux Meadows, Newfoundland · Sail the Labrador Sea · Qaqortoq, Greenland · Nanortalik, Greenland · Sail the Atlantic Ocean · Isafjord, Iceland · Akureyri, Iceland · Seydisfjordur, Iceland · Djupivogur, Iceland · Heimaey, Iceland · Reykjavik, Iceland
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgDynjandi WaterfallInside the Volcano
View →
from $10,499
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jul 5 – Jul 12, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
View →
from $826
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jul 19 – Jul 26, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
View →
from $883
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Aug 2 – Aug 9, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
View →
from $842
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Aug 9 – Aug 16, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
View →
from $867
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Aug 16 – Aug 23, 2026 from Boston, Massachusetts
Boston, Massachusetts · Halifax, Nova Scotia · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgPrivate Island Wrap-Around Van Tour of Bermuda
View →
from $823
Book This Cruise@ Cruisebound
Princess · Sapphire PrincessRepositioning
Northern Europe 15 nights Aug 19 – Sep 3, 2026 from Copenhagen, Denmark to Boston, Massachusetts
Copenhagen, Denmark · Lerwick, Shetland Islands · … · Boston, Massachusetts9 ports
Copenhagen, Denmark · Lerwick, Shetland Islands · Stornoway, Scotland · Belfast, Northern Ireland · Liverpool, England · Cobh (Cork), Ireland · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Copenhagen Walking Tour with a Local ExpertGiant's Causeway Private Luxury Day Tour from Belf…BridgeClimb SydneyPeggy's Cove & Lunenburg +1 more
View →
from $1,455
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteOne-way
Europe 14 nights Aug 22 – Sep 5, 2026 from Reykjavik, Iceland to Boston, Massachusetts
Reykjavik, Iceland · Isafjord, Iceland · … · Boston, Massachusetts9 ports
Reykjavik, Iceland · Isafjord, Iceland · Akureyri, Iceland · Prins Christian Sund(cruise) · Qaqortoq, Greenland · St. Johns, Newfoundland · Halifax, Nova Scotia · Sydney, Nova Scotia · Boston, Massachusetts
★ Bucket-list Inside the VolcanoDynjandi WaterfallPeggy's Cove & LunenburgBridgeClimb Sydney +1 more
View →
from $1,787
Book This Cruise@ Cruisebound
Holland America · VolendamOne-way
North America 10 nights Aug 22 – Sep 1, 2026 from Boston, Massachusetts to Montreal, Quebec
Boston, Massachusetts · Eastport, Maine, United States · … · Montreal, Quebec10 ports
Boston, Massachusetts · Eastport, Maine, United States · Halifax, Nova Scotia · St. Johns, Newfoundland · St. Anthony, Newfoundland · Corner Brook, Newfoundland · Havre St. Pierre, Quebec · Baie-Commeau, Quebec · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
View →
from $1,999
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
View →
from $1,159
Book This Cruise@ Cruisebound
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 TourPeggy's Cove & Lunenburg
View →
from $838
Book This Cruise@ Cruisebound
Seabourn · Seabourn VentureRepositioning
Alaska 37 nights Aug 29 – Oct 5, 2026 from Anchorage, Alaska to Halifax, Nova Scotia
Anchorage, Alaska · Nome, Alaska · … · Halifax, Nova Scotia26 ports
Anchorage, Alaska · Nome, Alaska · Herschel Island, Yukon, Canada · Northwest Passage Experience · Cambridge Bay, Nunavut, Canada · Northwest Passage Experience · DUNDAS HARBOUR, Nunavut, Canada · Croker Bay, Nunavut, Canada · Pond Inlet, Nunavut, Canada · Ilulissat, Greenland · Sisimiut Holsteinsborg, Greenland · Nuuk, Greenland · Kangerlussuaq, Greenland · Pangnirtung, Nunavut, Canada · Monumental Island, Canada · Lady Franklin Island, Nunavut, Canada · Lower Savage Islands, Nunavut, Canada · Resolution Island, Nunavut, Canada · Nachvak Fiord, Torngat Mts, Labrador, Canada · Saglek Fjord, Labrador, Canada · Hebron, Labrador, Canada · Nain, Canada · Indian Harbour, Labrador, Canada · Battle Harbour, Canada · LAnse Aux Meadows, Newfoundland · Halifax, Nova Scotia
★ Bucket-list Peggy's Cove & Lunenburg
View →
from $36,469
Book This Cruise@ Cruisebound
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 TourPeggy's Cove & Lunenburg
View →
from $838
Book This Cruise@ Cruisebound
Viking Ocean · Viking MarsOne-way
North America 12 nights Aug 31 – Sep 12, 2026 from New York, New York to Montreal, Quebec
New York, New York · Boston, Massachusetts · … · Montreal, Quebec10 ports
New York, New York · Boston, Massachusetts · Sail the Nova Scotia Coast · Halifax, Nova Scotia · Sail the Gulf of St. Lawrence · Gaspe, Quebec · Sail the Gulf of St. Lawrence · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourPeggy's Cove & Lunenburg
View →
from $8,299
Book This Cruise@ Cruisebound
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $1,344
Book This Cruise@ Cruisebound
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $3,432
Book This Cruise@ Cruisebound
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 TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $1,071
Book This Cruise@ Cruisebound
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 TourPeggy's Cove & Lunenburg
View →
from $731
Book This Cruise@ Cruisebound
Regent · Seven Seas SplendorOne-way
Australia & South Pacific 11 nights Sep 6 – Sep 17, 2026 from New York, New York to Montreal, Quebec
New York, New York · Willis Island · … · Montreal, Quebec12 ports
New York, New York · Willis Island · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Willis Island · Gaspe, Quebec · Baie-Commeau, Quebec · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourZodiac Circumnavigation of Willis IslandPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $14,780
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
View →
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
View →
from $1,189
Book This Cruise@ Cruisebound
Viking Ocean · Viking MarsOne-way
North America 12 nights Sep 12 – Sep 24, 2026 from Montreal, Quebec to Brooklyn, NY
Montreal, Quebec · Quebec City, Quebec · … · Brooklyn, NY10 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Sail the Gulf of St. Lawrence · Gaspe, Quebec · Sail the Gulf of St. Lawrence · Halifax, Nova Scotia · Sail the Nova Scotia Coast · Boston, Massachusetts · Brooklyn, NY
★ Bucket-list Peggy's Cove & LunenburgPrivate Luxury Boston Tour
View →
from $9,999
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 TourPeggy's Cove & Lunenburg
View →
from $690
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 BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
View →
from $1,137
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
North America 12 nights Sep 13 – Sep 25, 2026 from New York, New York to Montreal, Quebec
New York, New York · Newport, Rhode Island · … · Montreal, Quebec10 ports
New York, New York · Newport, Rhode Island · Transit The Cape Cod Canal · Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourPeggy's Cove & Lunenburg
View →
from $7,649
Book This Cruise@ Cruisebound
Oceania · Oceania VistaOne-way
North America 11 nights Sep 14 – Sep 25, 2026 from New York, New York to Montreal, Quebec
New York, New York · Halifax, Nova Scotia · … · Montreal, Quebec9 ports
New York, New York · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Gaspe, Quebec · Baie-Commeau, Quebec · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $5,480
Book This Cruise@ Cruisebound
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 BridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
View →
from $1,043
Book This Cruise@ Cruisebound
Celebrity · Celebrity SilhouetteRound-trip
North America 11 nights Sep 17 – Sep 28, 2026 from Boston, Massachusetts
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & LunenburgBridgeClimb Sydney
View →
from $2,052
Book This Cruise@ Cruisebound
Regent · Seven Seas SplendorOne-way
Australia & South Pacific 11 nights Sep 17 – Sep 28, 2026 from Montreal, Quebec to Boston, Massachusetts
Montreal, Quebec · Quebec City, Quebec · … · Boston, Massachusetts11 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Sept-Iles, Canada · Havre St. Pierre, Quebec · Willis Island · Charlottetown, Prince Edward Island · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list Zodiac Circumnavigation of Willis IslandBridgeClimb SydneyPeggy's Cove & LunenburgPrivate Luxury Boston Tour
View →
from $13,199
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
View →
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
View →
from $1,369
Book This Cruise@ Cruisebound
Load more 123 more

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