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
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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
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Showing 36 of 57 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
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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
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
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from $745
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Celebrity · Celebrity XcelRepositioning
Bermuda 16 nights Oct 23 – Nov 8, 2026 from Barcelona, Spain to Miami, Florida
Barcelona, Spain · Cartagena, Spain · … · Miami, Florida8 ports
Barcelona, Spain · Cartagena, Spain · Malaga, Spain · Gibraltar, British Territory · Seville, Spain · Funchal, Madeira, Portugal · Royal Naval Dockyard, Bermuda · Miami, Florida
★ Bucket-list Sagrada FamiliaThe Roman Theatre of Cartagena with the Rafael Mon…Granada & the AlhambraUpper Rock Nature Reserve +3 more
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from $2,823
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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
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Celebrity · Celebrity AscentRepositioning
Bermuda 14 nights Oct 30 – Nov 13, 2026 from Civitavecchia (Rome), Italy to Fort Lauderdale (Port Everglades), Florida
Civitavecchia (Rome), Italy · Cagliari, Sardinia, Italy · … · Fort Lauderdale (Port Everglades), Florida6 ports
Civitavecchia (Rome), Italy · Cagliari, Sardinia, Italy · Malaga, Spain · Funchal, Madeira, Portugal · Royal Naval Dockyard, Bermuda · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DaySu Nuraxi di BaruminiGranada & the AlhambraPico do Arieiro to Pico Ruivo +2 more
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from $1,440
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Royal Caribbean · Explorer of the SeasRepositioning
Mediterranean 13 nights Oct 31 – Nov 13, 2026 from Barcelona, Spain to Port Canaveral, Florida
Barcelona, Spain · Palma de Mallorca, Spain · … · Port Canaveral, Florida6 ports
Barcelona, Spain · Palma de Mallorca, Spain · Cartagena, Spain · Ponta Delgada, Azores, Portugal · Royal Naval Dockyard, Bermuda · Port Canaveral, Florida
★ Bucket-list Sagrada FamiliaLa Seu Cathedral + Rooftop Terraces ClimbThe Roman Theatre of Cartagena with the Rafael Mon…Private Island Wrap-Around Van Tour of Bermuda +1 more
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from $1,032
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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
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from $707
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Regent · Seven Seas GrandeurOne-way
Bermuda 21 nights Nov 1 – Nov 22, 2026 from Piraeus (Athens), Greece to Miami, Florida
Piraeus (Athens), Greece · Mykonos, Greece · … · Miami, Florida16 ports
Piraeus (Athens), Greece · Mykonos, Greece · Katakolon (Olympia), Greece · Willis Island · Valletta, Malta · Messina, Sicily, Italy · Naples, Italy · Civitavecchia (Rome), Italy · Willis Island · Palma de Mallorca, Spain · Willis Island · Funchal, Madeira, Portugal · Willis Island · Royal Naval Dockyard, Bermuda · Willis Island · Miami, Florida
★ Bucket-list The Acropolis & Parthenon, Guided Skip-the-LineDelosAncient OlympiaZodiac Circumnavigation of Willis Island +8 more
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from $14,205
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Royal Caribbean · Brilliance of the SeasRepositioning
Mediterranean 14 nights Nov 2 – Nov 16, 2026 from Barcelona, Spain to Fort Lauderdale (Port Everglades), Florida
Barcelona, Spain · Valencia, Spain · … · Fort Lauderdale (Port Everglades), Florida7 ports
Barcelona, Spain · Valencia, Spain · Cartagena, Spain · Malaga, Spain · Ponta Delgada, Azores, Portugal · Royal Naval Dockyard, Bermuda · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Sagrada FamiliaOceanograficThe Roman Theatre of Cartagena with the Rafael Mon…Granada & the Alhambra +2 more
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from $1,870
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Regent · Seven Seas GrandeurOne-way
Bermuda 21 nights Nov 8 – Nov 29, 2026 from Civitavecchia (Rome), Italy to Miami, Florida
Civitavecchia (Rome), Italy · Willis Island · … · Miami, Florida16 ports
Civitavecchia (Rome), Italy · Willis Island · Palma de Mallorca, Spain · Willis Island · Funchal, Madeira, Portugal · Willis Island · Royal Naval Dockyard, Bermuda · Willis Island · Miami, Florida · Willis Island · Roatan, Honduras · Santo Tomas de Castilla, Guatemala · Harvest Caye, Belize · Costa Maya, Mexico · Willis Island · Miami, Florida
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayZodiac Circumnavigation of Willis IslandLa Seu Cathedral + Rooftop Terraces ClimbPico do Arieiro to Pico Ruivo +5 more
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from $14,399
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Celebrity · Celebrity EclipseRepositioning
Mediterranean 14 nights Nov 10 – Nov 24, 2026 from Barcelona, Spain to Fort Lauderdale (Port Everglades), Florida
Barcelona, Spain · Palma de Mallorca, Spain · … · Fort Lauderdale (Port Everglades), Florida7 ports
Barcelona, Spain · Palma de Mallorca, Spain · Cartagena, Spain · Malaga, Spain · Gibraltar, British Territory · Royal Naval Dockyard, Bermuda · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Sagrada FamiliaLa Seu Cathedral + Rooftop Terraces ClimbThe Roman Theatre of Cartagena with the Rafael Mon…Granada & the Alhambra +3 more
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from $1,056
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Oceania · Oceania AlluraRepositioning
Bermuda 16 nights Mar 31 – Apr 16, 2027 from Miami, Florida to Barcelona, Spain
Miami, Florida · Royal Naval Dockyard, Bermuda · … · Barcelona, Spain9 ports
Miami, Florida · Royal Naval Dockyard, Bermuda · Ponta Delgada, Azores, Portugal · Seville, Spain · Gibraltar, British Territory · Motril, Spain · Cartagena, Spain · Valencia, Spain · Barcelona, Spain
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Island Wrap-Around Van Tour of BermudaUpper Rock Nature ReserveThe Roman Theatre of Cartagena with the Rafael Mon… +2 more
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from $5,149
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Regent · Seven Seas GrandeurOne-way
Bermuda 24 nights Apr 14 – May 8, 2027 from Miami, Florida to Lisbon, Portugal
Miami, Florida · Willis Island · … · Lisbon, Portugal15 ports
Miami, Florida · Willis Island · Royal Naval Dockyard, Bermuda · Willis Island · Ponta Delgada, Azores, Portugal · Willis Island · Malaga, Spain · Cadiz (Seville), Spain · Lisbon, Portugal · Willis Island · Santander, Spain · Bordeaux, France · Bilbao, Spain · Willis Island · Lisbon, Portugal
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandPrivate Island Wrap-Around Van Tour of BermudaGranada & the Alhambra +3 more
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from $15,699
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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
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from $849
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Celebrity · Celebrity AscentRepositioning
Mediterranean 14 nights Apr 19 – May 3, 2027 from Fort Lauderdale (Port Everglades), Florida to Civitavecchia (Rome), Italy
Fort Lauderdale (Port Everglades), Florida · Royal Naval Dockyard, Bermuda · … · Civitavecchia (Rome), Italy6 ports
Fort Lauderdale (Port Everglades), Florida · Royal Naval Dockyard, Bermuda · Ponta Delgada, Azores, Portugal · Malaga, Spain · Cartagena, Spain · Civitavecchia (Rome), Italy
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Island Wrap-Around Van Tour of BermudaGranada & the AlhambraThe Roman Theatre of Cartagena with the Rafael Mon… +1 more
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from $1,124
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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
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from $849
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Regent · Seven Seas PrestigeOne-way
Caribbean 14 nights Apr 27 – May 11, 2027 from New York, New York to Barcelona, Spain
New York, New York · Willis Island · … · Barcelona, Spain12 ports
New York, New York · Willis Island · Royal Naval Dockyard, Bermuda · Willis Island · Horta, Azores, Portugal · Willis Island · Funchal, Madeira, Portugal · Willis Island · Malaga, Spain · Cartagena, Colombia · Valencia, Spain · Barcelona, Spain
★ Bucket-list Manhattan Helicopter TourZodiac Circumnavigation of Willis IslandPrivate Island Wrap-Around Van Tour of BermudaPico do Arieiro to Pico Ruivo +4 more
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from $10,549
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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
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from $864
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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
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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
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from $923
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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
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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
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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
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from $1,027
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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
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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
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from $1,071
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.

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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