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 · 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
Must visit a specific port
Reset
Filtering North America ×Seabourn ×Norwegian × Clear all
Showing 36 of 72 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
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
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 12 – Jul 19, 2026 from Boston, Massachusetts
Boston, Massachusetts · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPrivate Island Wrap-Around Van Tour of Bermuda
View →
from $1,113
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 Jul 26 – Aug 2, 2026 from Boston, Massachusetts
Boston, Massachusetts · Royal Naval Dockyard, Bermuda · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPrivate Island Wrap-Around Van Tour of Bermuda
View →
from $1,088
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
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
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
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
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
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
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
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Sep 20 – Sep 27, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Eastport, Maine, United States · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
View →
from $690
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationRound-trip
North America 12 nights Sep 25 – Oct 7, 2026 from Montreal, Quebec
Montreal, Quebec · Havre St. Pierre, Quebec · … · Montreal, Quebec9 ports
Montreal, Quebec · Havre St. Pierre, Quebec · LAnse Aux Meadows, Newfoundland · St. Johns, Newfoundland · St Pierre et Miquelon · Cap-Aux-Meules, Canada · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
View →
from $9,859
Book This Cruise@ Cruisebound
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 Peggy's Cove & LunenburgBridgeClimb Sydney
View →
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 TourPeggy's Cove & Lunenburg
View →
from $989
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
North America 7 nights Oct 4 – Oct 11, 2026 from Boston, Massachusetts
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Portland, Maine · Bar Harbor, Maine · Eastport, Maine, United States · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPeggy's Cove & Lunenburg
View →
from $797
Book This Cruise@ Cruisebound
Norwegian · Norwegian JewelOne-way
North America 10 nights Oct 7 – Oct 17, 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 $1,206
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
North America 12 nights Oct 7 – Oct 19, 2026 from Montreal, Quebec to New York, New York
Montreal, Quebec · Quebec City, Quebec · … · New York, New York10 ports
Montreal, Quebec · Quebec City, Quebec · Saguenay Fjord, Canada · Charlottetown, Prince Edward Island · Halifax, Nova Scotia · Portland, Maine · Transit The Cape Cod Canal · Boston, Massachusetts · Newport, Rhode Island · New York, New York
★ Bucket-list Peggy's Cove & LunenburgPrivate Luxury Boston TourManhattan Helicopter Tour
View →
from $8,924
Book This Cruise@ Cruisebound
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 TourPeggy's Cove & Lunenburg
View →
from $957
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Oct 18 – Oct 25, 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 $745
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
North America 12 nights Oct 19 – Oct 31, 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 $6,204
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Oct 25 – Nov 1, 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 $693
Book This Cruise@ Cruisebound
Seabourn · Seabourn OvationOne-way
North America 13 nights Oct 31 – Nov 13, 2026 from Montreal, Quebec to Miami, Florida
Montreal, Quebec · Quebec City, Quebec · … · Miami, Florida7 ports
Montreal, Quebec · Quebec City, Quebec · Gaspe, Quebec · Halifax, Nova Scotia · Boston, Massachusetts · Norfolk, Virginia · Miami, Florida
★ Bucket-list Peggy's Cove & LunenburgPrivate Luxury Boston TourStar Island & Millionaire's Row Skyline Cruise on…
View →
from $4,797
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Nov 1 – Nov 8, 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 $707
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRepositioning
Caribbean 14 nights Nov 8 – Nov 22, 2026 from Boston, Massachusetts to New Orleans, Louisiana
Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · … · New Orleans, Louisiana8 ports
Boston, Massachusetts · St. Thomas, U.S. Virgin Islands · St. Lucia, Caribbean · St. Georges, Grenada, West Indies · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Georgetown, Grand Cayman, Cayman Islands · New Orleans, Louisiana
★ Bucket-list Private Luxury Boston TourPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Grenada Private Taxi TourPrivate Full-Day Curaçao Island Tour with Local Ex… +3 more
View →
from $970
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRepositioning
Caribbean 14 nights Apr 4 – Apr 18, 2027 from New Orleans, Louisiana to Boston, Massachusetts
New Orleans, Louisiana · Georgetown, Grand Cayman, Cayman Islands · … · Boston, Massachusetts9 ports
New Orleans, Louisiana · Georgetown, Grand Cayman, Cayman Islands · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · St. Lucia, Caribbean · Tortola, B.V.I. · Boston, Massachusetts
★ Bucket-list Steamboat NatchezStingray City SandbarArubaPrivate Full-Day Curaçao Island Tour with Local Ex… +4 more
View →
from $1,726
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Apr 18 – Apr 25, 2027 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 $849
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Apr 25 – May 2, 2027 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 $849
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights May 2 – May 9, 2027 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 $864
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights May 9 – May 16, 2027 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 $849
Book This Cruise@ Cruisebound
Load more 36 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