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 North America ×Northern Europe ×Visits Royal Naval Dockyard × Clear all
Showing 36 of 40 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
Celebrity · Celebrity ApexRepositioning
Northern Europe Oct 18, 2026 from Southampton, England to Orlando, Florida
Southampton, England · Vigo, Spain · … · Orlando, Florida6 ports
Southampton, England · Vigo, Spain · Lisbon, Portugal · Ponta Delgada, Azores, Portugal · Royal Naval Dockyard, Bermuda · Orlando, Florida
★ Bucket-list Stand Inside Stonehenge & See the Original 1215 Ma…SintraPrivate Island Wrap-Around Van Tour of Bermuda
View →
from $1,401
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
View →
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
Oceania · Oceania InsigniaRepositioning
Bermuda 25 nights Apr 9 – May 4, 2027 from Miami, Florida to Southampton, England
Miami, Florida · Royal Naval Dockyard, Bermuda · … · Southampton, England15 ports
Miami, Florida · Royal Naval Dockyard, Bermuda · Santa Cruz de La Palma, Spain · Arrecife, Lanzarote, Canary Islands · Santa Cruz de Tenerife, Canary Islands · Funchal, Madeira, Portugal · Lisbon, Portugal · Leixoes (Oporto), Portugal · La Coruna, Spain · Bilbao, Spain · St. Jean de Luz, France · Bordeaux, France · Saint Malo, France · St. Peter Port (Guernsey), England · Southampton, England
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Island Wrap-Around Van Tour of BermudaTajogaite VolcanoTimanfaya Volcanic Park +5 more
View →
from $6,199
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
Celebrity · Celebrity ApexRepositioning
Bermuda Apr 24, 2027 from Orlando, Florida to Southampton, England
Orlando, Florida · Royal Naval Dockyard, Bermuda · Ponta Delgada, Azores, Portugal · Lisbon, Portugal · Southampton, England
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaSintraStand Inside Stonehenge & See the Original 1215 Ma…
View →
from $1,197
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
Royal Caribbean · Freedom of the SeasRepositioning
Northern Europe 12 nights Apr 27 – May 9, 2027 from Miami, Florida to Southampton, England
Miami, Florida · Royal Naval Dockyard, Bermuda · Ponta Delgada, Azores, Portugal · Southampton, England
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Island Wrap-Around Van Tour of BermudaStand Inside Stonehenge & See the Original 1215 Ma…
View →
from $638
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
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Aug 1 – Aug 8, 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 $1,239
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Aug 8 – Aug 15, 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 $1,239
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Aug 15 – Aug 22, 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 $1,229
Book This Cruise@ Cruisebound
Norwegian · Norwegian BreakawayRound-trip
Bermuda 7 nights Aug 22 – Aug 29, 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 $960
Book This Cruise@ Cruisebound
Load more 4 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