Bucket-List Cruise Adventures

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Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

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Showing 36 of 60 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 SunOne-way
Bermuda 13 nights Oct 24 – Nov 6, 2026 from New York, New York to Miami, Florida
New York, New York · Royal Naval Dockyard, Bermuda · … · Miami, Florida10 ports
New York, New York · Royal Naval Dockyard, Bermuda · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Cabo Rojo, Dominican Republic · Great Stirrup Cay, Bahamas · Miami, Florida
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of BermudaWalk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac… +5 more
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from $1,257
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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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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
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from $6,199
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Regent · Seven Seas PrestigeOne-way
Bermuda 14 nights Apr 9 – Apr 23, 2027 from Miami, Florida to New York, New York
Miami, Florida · Willis Island · … · New York, New York13 ports
Miami, Florida · Willis Island · Oranjestad, Sint Eustatius · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Castries, St. Lucia · Gustavia, St. Barts · San Juan, Puerto Rico · Willis Island · Royal Naval Dockyard, Bermuda · Willis Island · New York, New York
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Zodiac Circumnavigation of Willis IslandThe Natural PoolPrivate Full-Day Curaçao Island Tour with Local Ex… +6 more
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from $10,199
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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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Celebrity · Celebrity EclipseRepositioning
Bermuda Apr 23, 2027 from Fort Lauderdale (Port Everglades), Florida to Amsterdam, The Netherlands
Fort Lauderdale (Port Everglades), Florida · Royal Naval Dockyard, Bermuda · Ponta Delgada, Azores, Portugal · Lisbon, Portugal · Amsterdam, The Netherlands
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Island Wrap-Around Van Tour of BermudaSintraWalk Into the Secret Annex - Anne Frank House
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from $1,072
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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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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…
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from $638
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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
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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
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from $864
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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
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from $864
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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
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from $1,209
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