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 1 selected · clear 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 Caribbean ×One-way ×3–5 nights × Clear all
Showing 9 of 9 sailings
Norwegian · Norwegian PrimaOne-way
Caribbean 3 nights Nov 12 – Nov 15, 2026 from Port Canaveral, Florida to San Juan, Puerto Rico
Port Canaveral, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico
★ Bucket-list Kennedy Space Center Visitor ComplexThe full 27 jumps at the Damajagua WaterfallsWalk El Morro & Old San Juan's City Walls
View →
from $447
Book This Cruise@ Cruisebound
Costa · Costa FascinosaOne-way
Caribbean 4 nights Dec 23 – Dec 27, 2026 from Pointe-a-Pitre, Guadeloupe to La Romana, Dominican Republic
Pointe-a-Pitre, Guadeloupe · Guadeloupe Bay · … · La Romana, Dominican Republic6 ports
Pointe-a-Pitre, Guadeloupe · Guadeloupe Bay · Antigua, Antigua & Barbuda · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic
★ Bucket-list Death in Paradise Filming Locations & Botanical Ga…Mt. Liamuiga Volcano Crater HikeNorman IslandSaona Island Private Speedboat & Natural Pool Day
View →
from $723
Book This Cruise@ Cruisebound
Princess · Crown PrincessOne-way
Caribbean 5 nights Jan 3 – Jan 8, 2027 from San Juan, Puerto Rico to Bridgetown, Barbados
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · Bridgetown, Barbados6 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Dominica, Caribbean · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Mt. Liamuiga Volcano Crater HikeGrenada Private Taxi Tour +1 more
View →
from $474
Book This Cruise@ Cruisebound
MSC Cruises · MSC OperaOne-way
Caribbean 3 nights Mar 12 – Mar 15, 2027 from Fort-de-France, Martinique to La Romana, Dominican Republic
Fort-de-France, Martinique · St. John's, Antigua · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic
★ Bucket-list Mount Pelée & Saint-PierrePrivate Half-Day Island Adventure & Trunk Bay BeachNorman IslandSaona Island Private Speedboat & Natural Pool Day
View →
from $299
Book This Cruise@ Cruisebound
Disney · Disney DreamOne-way
Caribbean 4 nights Apr 12 – Apr 16, 2027 from Fort Lauderdale (Port Everglades), Florida to San Juan, Puerto Rico
Fort Lauderdale (Port Everglades), Florida · Castaway Cay, Bahamas · Disney Lookout Cay · San Juan, Puerto Rico
★ Bucket-list Everglades Airboat Skim + Gator Boys Live ShowAbaco Backcountry Fishing AdventurePrivate Historical & Cultural SUV Tour of EleutheraWalk El Morro & Old San Juan's City Walls
View →
from $1,256
Book This Cruise@ Cruisebound
Disney · Disney DreamOne-way
Bahamas 4 nights Apr 23 – Apr 27, 2027 from San Juan, Puerto Rico to Port Canaveral, Florida
San Juan, Puerto Rico · Disney Lookout Cay · Castaway Cay, Bahamas · Port Canaveral, Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Historical & Cultural SUV Tour of EleutheraAbaco Backcountry Fishing AdventureKennedy Space Center Visitor Complex
View →
from $1,509
Book This Cruise@ Cruisebound
MSC Cruises · MSC OperaOne-way
Caribbean 4 nights Nov 11 – Nov 15, 2027 from Bridgetown, Barbados to La Romana, Dominican Republic
Bridgetown, Barbados · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Norman Island +1 more
View →
from $709
Book This Cruise@ Cruisebound
MSC Cruises · MSC OperaOne-way
Caribbean 3 nights Nov 12 – Nov 15, 2027 from Fort-de-France, Martinique to La Romana, Dominican Republic
Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · Road Town, Tortola, B.V.I. · La Romana, Dominican Republic
★ Bucket-list Mount Pelée & Saint-PierreDeath in Paradise Filming Locations & Botanical Ga…Norman IslandSaona Island Private Speedboat & Natural Pool Day
View →
from $209
Book This Cruise@ Cruisebound
Celebrity · Celebrity SummitOne-way
Caribbean 4 nights Jan 2 – Jan 6, 2028 from San Juan, Puerto Rico to Fort Lauderdale (Port Everglades), Florida
San Juan, Puerto Rico · Philipsburg, St. Maarten · Fort Lauderdale (Port Everglades), Florida
★ Bucket-list Walk El Morro & Old San Juan's City WallsRandom Wind 'Paradise Day Sail'Everglades Airboat Skim + Gator Boys Live Show
View →
from $506
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