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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Filtering Mediterranean ×North America ×Visits Bermuda × Clear all
Showing 36 of 66 sailings
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 +4 more
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from $2,823
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Holland America · OosterdamRepositioning
Mediterranean 25 nights Oct 24 – Nov 18, 2026 from Piraeus (Athens), Greece to Fort Lauderdale (Port Everglades), Florida
Piraeus (Athens), Greece · Katakolon (Olympia), Greece · … · Fort Lauderdale (Port Everglades), Florida15 ports
Piraeus (Athens), Greece · Katakolon (Olympia), Greece · Sarande, Albania · Valletta, Malta · Messina, Sicily, Italy · Naples, Italy · Civitavecchia (Rome), Italy · Ajaccio, Corsica, France · Villefranche, France · Barcelona, Spain · Cartagena, Spain · Malaga, Spain · Gibraltar, British Territory · Kings Wharf, Bermuda · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list The Acropolis & Parthenon, Guided Skip-the-LineAncient OlympiaButrint UNESCO RuinsSt John's Co-Cathedral & the Caravaggio masterpieces +11 more
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from $3,519
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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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Regent · Seven Seas MarinerOne-way
Mediterranean 14 nights Oct 26 – Nov 9, 2026 from Barcelona, Spain to Miami, Florida
Barcelona, Spain · Willis Island · … · Miami, Florida9 ports
Barcelona, Spain · Willis Island · Malaga, Spain · Willis Island · Funchal, Madeira, Portugal · Willis Island · Hamilton, Bermuda · Willis Island · Miami, Florida
★ Bucket-list Sagrada FamiliaZodiac Circumnavigation of Willis IslandGranada & the AlhambraPico do Arieiro to Pico Ruivo +2 more
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from $8,599
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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…Sete Cidades Twin Lakes +2 more
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from $1,032
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Carnival · Carnival LegendRepositioning
Mediterranean Nov 1, 2026 from Civitavecchia (Rome), Italy to Tampa, Florida
Civitavecchia (Rome), Italy · Cartagena, Spain · … · Tampa, Florida6 ports
Civitavecchia (Rome), Italy · Cartagena, Spain · Malaga, Spain · Gibraltar, British Territory · Bermuda · Tampa, Florida
★ Bucket-list Vatican, Sistine Chapel & Colosseum in One DayThe Roman Theatre of Cartagena with the Rafael Mon…Granada & the AlhambraUpper Rock Nature Reserve +2 more
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from $737
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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 +3 more
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from $1,870
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Holland America · OosterdamRepositioning
Mediterranean 14 nights Nov 4 – Nov 18, 2026 from Barcelona, Spain to Fort Lauderdale (Port Everglades), Florida
Barcelona, Spain · Cartagena, Spain · … · Fort Lauderdale (Port Everglades), Florida6 ports
Barcelona, Spain · Cartagena, Spain · Malaga, Spain · Gibraltar, British Territory · Kings Wharf, Bermuda · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Sagrada FamiliaThe Roman Theatre of Cartagena with the Rafael Mon…Granada & the AlhambraUpper Rock Nature Reserve +2 more
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from $869
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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 +6 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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Azamara · Azamara JourneyRepositioning
Bermuda 12 nights Mar 29 – Apr 10, 2027 from Miami, Florida to Lisbon, Portugal
Miami, Florida · Hamilton, Bermuda · Horta, Azores, Portugal · Lisbon, Portugal
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Rising Son CatamaranPico Mountain Private Climb with Round-Trip Ferry…Sintra
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from $2,007
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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 BermudaSete Cidades Twin LakesRoyal Alcázar of Seville +5 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 BermudaSete Cidades Twin Lakes +6 more
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from $15,699
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Princess · Enchanted PrincessRepositioning
Mediterranean 15 nights Apr 16 – May 1, 2027 from Fort Lauderdale (Port Everglades), Florida to Civitavecchia (Rome), Italy
Fort Lauderdale (Port Everglades), Florida · West End, Bermuda · … · Civitavecchia (Rome), Italy7 ports
Fort Lauderdale (Port Everglades), Florida · West End, Bermuda · Azores Islands, Portugal · Gibraltar, British Territory · Cartagena, Spain · Ajaccio, Corsica, France · Civitavecchia (Rome), Italy
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowPrivate Half-Day Snorkel & Reef Exploration, West…Private Sete Cidades Twin Lakes & Crater Rim DriveUpper Rock Nature Reserve +3 more
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from $909
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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 BermudaSete Cidades Twin LakesGranada & the Alhambra +2 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 Mountain Private Climb with Round-Trip Ferry… +5 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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Carnival · Carnival MiracleRepositioning
Bermuda May 6, 2027 from Galveston, Texas to Lisbon, Portugal
Galveston, Texas · Bermuda · Ponta Delgada, Azores, Portugal · Funchal, Madeira, Portugal · Lisbon, Portugal
★ Bucket-list Moody GardensRestless Native CatamaranSete Cidades Twin LakesPico do Arieiro to Pico Ruivo +1 more
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from $821
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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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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