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 From Philadelphia, Pennsylvania ×3–5 nights ×6–8 nights × Clear all
Showing 36 of 47 sailings
Norwegian · Norwegian JewelRound-trip
Bermuda 7 nights Jun 18 – Jun 25, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Charleston, South Carolina · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaPrivate Historic Charleston
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from $640
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Norwegian · Norwegian JewelRound-trip
Bermuda 7 nights Jun 25 – Jul 2, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Charleston, South Carolina · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaPrivate Historic Charleston
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from $949
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Norwegian · Norwegian JewelRound-trip
Bermuda 7 nights Jul 2 – Jul 9, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Halifax, Nova Scotia · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaPeggy's Cove & Lunenburg
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from $692
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Norwegian · Norwegian JewelRound-trip
Bermuda 7 nights Jul 9 – Jul 16, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Halifax, Nova Scotia · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaPeggy's Cove & Lunenburg
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from $692
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Norwegian · Norwegian JewelRound-trip
Bermuda 7 nights Jul 16 – Jul 23, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Halifax, Nova Scotia · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaPeggy's Cove & Lunenburg
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from $711
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Norwegian · Norwegian JewelRound-trip
Bermuda 7 nights Jul 23 – Jul 30, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Halifax, Nova Scotia · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaPeggy's Cove & Lunenburg
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from $711
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Norwegian · Norwegian JewelRound-trip
Bermuda 7 nights Jul 30 – Aug 6, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Halifax, Nova Scotia · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaPeggy's Cove & Lunenburg
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from $705
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Norwegian · Norwegian JewelRound-trip
Bermuda 7 nights Aug 6 – Aug 13, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Halifax, Nova Scotia · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaPeggy's Cove & Lunenburg
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from $744
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Norwegian · Norwegian JewelRound-trip
Bermuda 7 nights Aug 13 – Aug 20, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Halifax, Nova Scotia · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaPeggy's Cove & Lunenburg
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from $737
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Norwegian · Norwegian JewelRound-trip
Bermuda 7 nights Aug 20 – Aug 27, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Halifax, Nova Scotia · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaPeggy's Cove & Lunenburg
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from $692
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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 $799
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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 $799
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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 $782
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Norwegian · Norwegian PearlRound-trip
Bahamas 8 nights Feb 12 – Feb 20, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Nassau, Bahamas · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Nassau, Bahamas · Grand Bahama Island · Port Canaveral, Florida · Jacksonville, Florida · Philadelphia, Pennsylvania
★ Bucket-list Swim With the Wild Exuma PigsUNEXSOKennedy Space Center Visitor ComplexAmelia Island Guided Kayak Tour of Lofton Creek
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from $830
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Norwegian · Norwegian PearlRound-trip
Bahamas 8 nights Mar 12 – Mar 20, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Nassau, Bahamas · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Nassau, Bahamas · Great Stirrup Cay, Bahamas · Port Canaveral, Florida · Jacksonville, Florida · Philadelphia, Pennsylvania
★ Bucket-list Swim With the Wild Exuma PigsSilver Cove Private VillaKennedy Space Center Visitor ComplexAmelia Island Guided Kayak Tour of Lofton Creek
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from $999
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Norwegian · Norwegian PearlRound-trip
Bahamas 8 nights Mar 20 – Mar 28, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Norfolk, Virginia · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Norfolk, Virginia · Port Canaveral, Florida · Grand Bahama Island · Great Stirrup Cay, Bahamas · Philadelphia, Pennsylvania
★ Bucket-list Battleship WisconsinKennedy Space Center Visitor ComplexUNEXSOSilver Cove Private Villa
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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 $808
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Apr 15 – Apr 22, 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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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Apr 22 – Apr 29, 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 $999
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Apr 29 – May 6, 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 $852
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights May 6 – May 13, 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 $852
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights May 13 – May 20, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Boston, Massachusetts · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaPrivate Luxury Boston Tour
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from $1,089
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights May 20 – May 27, 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 $941
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights May 27 – Jun 3, 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 $1,169
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Jun 3 – Jun 10, 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 $956
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Jun 10 – Jun 17, 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 $971
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Jun 17 – Jun 24, 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 $993
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Jun 24 – Jul 1, 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 $1,249
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Jul 1 – Jul 8, 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 $1,279
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Jul 8 – Jul 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 $1,269
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Jul 15 – Jul 22, 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 $1,259
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Jul 22 – Jul 29, 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 $996
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Jul 29 – Aug 5, 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 $1,010
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Aug 5 – Aug 12, 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 $1,229
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Aug 12 – Aug 19, 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 $1,209
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Norwegian · Norwegian PearlRound-trip
Bermuda 7 nights Aug 19 – Aug 26, 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 $1,209
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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