Bucket-List Cruise Adventures

Cruises from Philadelphia, Pennsylvania

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
My result then click any cruise row to open it
Where to? tap as many as you like 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
Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights
Cruise level tap one or more Luxury Premium Contemporary River
+ pick specific cruise lines
Luxury Azamara Explora Journeys Oceania Regent Seabourn Silversea Viking Ocean Windstar River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
Must visit a specific port
Reset
Filtering From Philadelphia, Pennsylvania × Clear all
Showing 36 of 82 sailings
Norwegian · Norwegian JewelOne-way
North America 11 nights Sep 26 – Oct 7, 2026 from Philadelphia, Pennsylvania to Quebec City, Quebec
Philadelphia, Pennsylvania · Portland, Maine · … · Quebec City, Quebec9 ports
Philadelphia, Pennsylvania · Portland, Maine · Bar Harbor, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · La Baie, Canada · Quebec City, Quebec
★ Bucket-list Portland Head Light & Casco Bay Scenic Lighthouse…Private Acadia National Park Van Tour with Expert…Reversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +4 more
View →
from $949
Book This Cruise@ Cruisebound
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
View →
from $649
Book This Cruise@ Cruisebound
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
View →
from $649
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Nov 28 – Dec 8, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Tortola, B.V.I. · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Jost Van DykePrivate Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City WallsThe full 27 jumps at the Damajagua Waterfalls
View →
from $749
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Dec 8 – Dec 18, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philadelphia, Pennsylvania
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van Dyke
View →
from $709
Book This Cruise@ Cruisebound
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
View →
from $919
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 11 nights Dec 23 – Jan 3, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Random Wind 'Paradise Day Sail'Private Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van DykeWalk El Morro & Old San Juan's City Walls +1 more
View →
from $1,369
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Jan 3 – Jan 13, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · Philadelphia, Pennsylvania
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsJost Van DykePrivate Catamaran Sail & Snorkel at Honeymoon Beac…
View →
from $669
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Jan 13 – Jan 23, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · St. Thomas, U.S. Virgin Islands · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Private Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van DykeWalk El Morro & Old San Juan's City WallsThe full 27 jumps at the Damajagua Waterfalls
View →
from $699
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Jan 23 – Feb 2, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Tortola, B.V.I. · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Jost Van DykePrivate Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City WallsThe full 27 jumps at the Damajagua Waterfalls
View →
from $789
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Feb 2 – Feb 12, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philadelphia, Pennsylvania
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van Dyke
View →
from $859
Book This Cruise@ Cruisebound
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
View →
from $919
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Feb 20 – Mar 2, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Tortola, B.V.I. · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Jost Van DykePrivate Catamaran Sail & Snorkel at Honeymoon Beac…Walk El Morro & Old San Juan's City WallsThe full 27 jumps at the Damajagua Waterfalls
View →
from $939
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Mar 2 – Mar 12, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philadelphia, Pennsylvania
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Jost Van Dyke
View →
from $939
Book This Cruise@ Cruisebound
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
View →
from $919
Book This Cruise@ Cruisebound
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
View →
from $959
Book This Cruise@ Cruisebound
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
View →
from $1,349
Book This Cruise@ Cruisebound
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
View →
from $919
Book This Cruise@ Cruisebound
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
View →
from $869
Book This Cruise@ Cruisebound
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
View →
from $919
Book This Cruise@ Cruisebound
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
View →
from $949
Book This Cruise@ Cruisebound
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
View →
from $949
Book This Cruise@ Cruisebound
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
View →
from $879
Book This Cruise@ Cruisebound
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
View →
from $879
Book This Cruise@ Cruisebound
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
View →
from $929
Book This Cruise@ Cruisebound
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
View →
from $899
Book This Cruise@ Cruisebound
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
View →
from $929
Book This Cruise@ Cruisebound
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
View →
from $969
Book This Cruise@ Cruisebound
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
View →
from $1,069
Book This Cruise@ Cruisebound
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
View →
from $1,079
Book This Cruise@ Cruisebound
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
View →
from $1,089
Book This Cruise@ Cruisebound
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
View →
from $1,089
Book This Cruise@ Cruisebound
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
View →
from $1,059
Book This Cruise@ Cruisebound
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
View →
from $1,039
Book This Cruise@ Cruisebound
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
View →
from $1,009
Book This Cruise@ Cruisebound
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
View →
from $1,009
Book This Cruise@ Cruisebound
Load more 46 more

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.

23 lines
aboard
MSC Cruises Royal Caribbean Carnival Viking River Norwegian AmaWaterways Costa Princess Celebrity Avalon Disney Viking Ocean Holland America Silversea Oceania Virgin Regent Explora Journeys Cunard Azamara Windstar Seabourn Virgin Voyages