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.

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Showing 36 of 260 sailings
Norwegian · Norwegian AquaRound-trip
Bermuda 5 nights Sep 18 – Sep 23, 2026 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $789
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Royal Caribbean · Vision of the SeasRound-trip
Bermuda 5 nights Sep 19 – Sep 24, 2026 from Baltimore, Maryland
Baltimore, Maryland · Royal Naval Dockyard, Bermuda · Baltimore, Maryland
★ Bucket-list National AquariumPrivate Island Wrap-Around Van Tour of Bermuda
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from $782
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Norwegian · Norwegian AquaRound-trip
Bermuda 5 nights Sep 23 – Sep 28, 2026 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $769
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Royal Caribbean · Independence of the SeasRound-trip
Bermuda 5 nights Sep 26 – Oct 1, 2026 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Royal Naval Dockyard, Bermuda · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandPrivate Island Wrap-Around Van Tour of Bermuda
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from $2,766
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Norwegian · Norwegian AquaRound-trip
Bermuda 5 nights Sep 28 – Oct 3, 2026 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $729
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Norwegian · Norwegian AquaRound-trip
Bermuda 5 nights Oct 3 – Oct 8, 2026 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $749
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Royal Caribbean · Vision of the SeasRound-trip
Bermuda 5 nights Oct 3 – Oct 8, 2026 from Baltimore, Maryland
Baltimore, Maryland · Royal Naval Dockyard, Bermuda · Baltimore, Maryland
★ Bucket-list National AquariumPrivate Island Wrap-Around Van Tour of Bermuda
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from $1,865
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Norwegian · Norwegian AquaRound-trip
Bermuda 5 nights Oct 8 – Oct 13, 2026 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $639
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Royal Caribbean · Independence of the SeasRound-trip
Bermuda 5 nights Oct 10 – Oct 15, 2026 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Royal Naval Dockyard, Bermuda · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandPrivate Island Wrap-Around Van Tour of Bermuda
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from $1,835
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Royal Caribbean · Vision of the SeasRound-trip
Bermuda 5 nights Oct 17 – Oct 22, 2026 from Baltimore, Maryland
Baltimore, Maryland · Royal Naval Dockyard, Bermuda · Baltimore, Maryland
★ Bucket-list National AquariumPrivate Island Wrap-Around Van Tour of Bermuda
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from $2,972
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Celebrity · Celebrity ApexRepositioning
Northern Europe 13 nights 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…Cíes IslandsSintraSete Cidades Twin Lakes +1 more
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from $3,287
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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 $689
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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 $2,603
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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… +6 more
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from $979
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Royal Caribbean · Independence of the SeasRound-trip
Bermuda 5 nights Oct 24 – Oct 29, 2026 from Cape Liberty (Bayonne), New Jersey
Cape Liberty (Bayonne), New Jersey · Royal Naval Dockyard, Bermuda · Cape Liberty (Bayonne), New Jersey
★ Bucket-list Statue of Liberty & Ellis IslandPrivate Island Wrap-Around Van Tour of Bermuda
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from $1,081
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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 $619
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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 $15,954
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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 $8,646
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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 $579
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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 $16,649
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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 $1,162
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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 $1,363
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Nov 14 – Nov 21, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of Bermuda
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from $649
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Nov 21 – Nov 28, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of Bermuda
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from $649
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Silversea · Silver RayOne-way
Bermuda 13 nights Nov 28 – Dec 11, 2026 from Lisbon, Portugal to Miami, Florida
Lisbon, Portugal · Gibraltar, British Territory · Royal Naval Dockyard, Bermuda · Miami, Florida
★ Bucket-list SintraUpper Rock Nature ReservePrivate Island Wrap-Around Van Tour of BermudaStar Island & Millionaire's Row Skyline Cruise on…
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from $8,800
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Norwegian · Norwegian PearlRound-trip
Bermuda 5 nights Dec 18 – Dec 23, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of Bermuda
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from $919
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Silversea · Silver RayOne-way
Bermuda 14 nights Mar 10 – Mar 24, 2027 from Miami, Florida to Lisbon, Portugal
Miami, Florida · Royal Naval Dockyard, Bermuda · Funchal, Madeira, Portugal · Lisbon, Portugal
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Island Wrap-Around Van Tour of BermudaPico do Arieiro to Pico RuivoSintra
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from $7,900
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Norwegian · Norwegian BlissRound-trip
Bermuda 7 nights Mar 21 – Mar 28, 2027 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $1,099
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Silversea · Silver NovaOne-way
Bermuda 14 nights Mar 23 – Apr 6, 2027 from Miami, Florida to Lisbon, Portugal
Miami, Florida · Royal Naval Dockyard, Bermuda · Funchal, Madeira, Portugal · Lisbon, Portugal
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Island Wrap-Around Van Tour of BermudaPico do Arieiro to Pico RuivoSintra
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from $8,200
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Norwegian · Norwegian BlissRound-trip
Bermuda 7 nights Mar 28 – Apr 4, 2027 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $1,039
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Norwegian · Norwegian PearlRound-trip
Bermuda 11 nights Mar 28 – Apr 8, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaJost Van DykePrivate Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City Walls +1 more
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from $1,349
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Oceania · Oceania AlluraOne-way
Bermuda 23 nights Mar 31 – Apr 23, 2027 from Miami, Florida to Civitavecchia (Rome), Italy
Miami, Florida · Royal Naval Dockyard, Bermuda · … · Civitavecchia (Rome), Italy16 ports
Miami, Florida · Royal Naval Dockyard, Bermuda · Ponta Delgada, Azores, Portugal · Seville, Spain · Gibraltar, British Territory · Motril, Spain · Cartagena, Spain · Valencia, Spain · Barcelona, Spain · Palamos, Spain · Sete, France · St. Tropez, France · Portofino, Italy · Florence, Italy · Portoferraio (elba Island) · Civitavecchia (Rome), Italy
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Island Wrap-Around Van Tour of BermudaSete Cidades Twin LakesRoyal Alcázar of Seville +12 more
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from $10,249
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Norwegian · Norwegian BlissRound-trip
Bermuda 5 nights Apr 4 – Apr 9, 2027 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $829
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Norwegian · Norwegian LunaRound-trip
Bermuda 4 nights Apr 6 – Apr 10, 2027 from New York, New York
New York, New York · Royal Naval Dockyard, Bermuda · New York, New York
★ Bucket-list Manhattan Helicopter TourPrivate Island Wrap-Around Van Tour of Bermuda
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from $869
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Apr 8 – Apr 15, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Norfolk, Virginia · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaBattleship Wisconsin
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from $919
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