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
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+ 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
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Filtering North America ×Norwegian ×Round trip × Clear all
Showing 36 of 50 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
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from $610
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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
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from $764
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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
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from $801
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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
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from $826
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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
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from $1,113
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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
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from $883
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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
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from $1,088
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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
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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
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from $867
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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
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from $823
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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
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from $838
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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
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from $838
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
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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
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
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from $690
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
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from $797
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
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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
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
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from $693
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 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
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights May 16 – May 23, 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 23 – May 30, 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 30 – Jun 6, 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 $923
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jun 6 – Jun 13, 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 $1,209
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jun 13 – Jun 20, 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 $975
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jun 20 – Jun 27, 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 $1,027
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jun 27 – Jul 4, 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 $1,339
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jul 4 – Jul 11, 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 $1,071
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jul 11 – Jul 18, 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 $1,034
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jul 18 – Jul 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 $1,259
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Jul 25 – Aug 1, 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 $1,259
Book This Cruise@ Cruisebound
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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