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.

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 Oceania Regent Seabourn Viking Ocean River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
Must visit a specific port
Reset
Filtering From Philadelphia, Pennsylvania ×Round trip ×9–12 nights × Clear all
Showing 21 of 21 sailings
Norwegian · Norwegian JewelRound-trip
Bermuda 9 nights Aug 27 – Sep 5, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Saint John, New Brunswick · Halifax, Nova Scotia · Philadelphia, Pennsylvania
★ Bucket-list Private Island Wrap-Around Van Tour of BermudaReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg
View →
from $774
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 $846
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 $755
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 $1,199
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 $685
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 $714
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 $737
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 $734
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 $869
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 $864
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 $1,279
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
North America 11 nights Oct 19 – Oct 30, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Boston, Massachusetts · … · Philadelphia, Pennsylvania9 ports
Philadelphia, Pennsylvania · Boston, Massachusetts · Eastport, Maine, United States · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Portland, Maine · Philadelphia, Pennsylvania
★ Bucket-list Private Luxury Boston TourCampobello IslandReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +3 more
View →
from $1,459
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 11 nights Nov 27 – Dec 8, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. John's, Antigua · St. Lucia, Caribbean · Philipsburg, St. Maarten · Philadelphia, Pennsylvania
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsPrivate Half-Day Island Adventure & Trunk Bay BeachGros Piton Summit Hike +1 more
View →
from $927
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Dec 13 – Dec 23, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. John's, Antigua · Philipsburg, St. Maarten · Philadelphia, Pennsylvania
★ Bucket-list The full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City WallsPrivate Half-Day Island Adventure & Trunk Bay BeachRandom Wind 'Paradise Day Sail'
View →
from $858
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 11 nights Dec 23 – Jan 3, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Lucia, Caribbean · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Mt. Liamuiga Volcano Crater HikeGros Piton Summit HikePrivate Half-Day Island Adventure & Trunk Bay BeachWalk El Morro & Old San Juan's City Walls +1 more
View →
from $1,516
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 12 nights Jan 3 – Jan 15, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · … · Philadelphia, Pennsylvania8 ports
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · Bridgetown, Barbados · St. Lucia, Caribbean · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Random Wind 'Paradise Day Sail'Swim with wild green sea turtles + two shipwrecks…Gros Piton Summit HikePrivate Half-Day Island Adventure & Trunk Bay Beach +2 more
View →
from $885
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 12 nights Jan 15 – Jan 27, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · … · Philadelphia, Pennsylvania8 ports
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · St. Lucia, Caribbean · Bridgetown, Barbados · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Random Wind 'Paradise Day Sail'Gros Piton Summit HikeSwim with wild green sea turtles + two shipwrecks…Private Half-Day Island Adventure & Trunk Bay Beach +2 more
View →
from $885
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 11 nights Jan 27 – Feb 7, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · St. John's, Antigua · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · St. John's, Antigua · St. Lucia, Caribbean · Philipsburg, St. Maarten · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Private Half-Day Island Adventure & Trunk Bay BeachGros Piton Summit HikeRandom Wind 'Paradise Day Sail'Walk El Morro & Old San Juan's City Walls +1 more
View →
from $831
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 11 nights Feb 7 – Feb 18, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · St. Lucia, Caribbean · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
★ Bucket-list Random Wind 'Paradise Day Sail'Gros Piton Summit HikePrivate Half-Day Island Adventure & Trunk Bay BeachWalk El Morro & Old San Juan's City Walls +1 more
View →
from $831
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Feb 26 – Mar 7, 2028 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 $1,059
Book This Cruise@ Cruisebound
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Mar 7 – Mar 17, 2028 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 $907
Book This Cruise@ Cruisebound

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