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 · 1 selected
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 clear
Reset
Filtering Oceania ×Visits Guadeloupe ×Round trip × Clear all
Showing 5 of 5 sailings
Oceania · Oceania VistaRound-trip
Caribbean 12 nights Nov 25 – Dec 7, 2026 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida9 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Fort-de-France, Martinique · Pointe-a-Pitre, Guadeloupe · St. John's, Antigua · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterRandom Wind 'Paradise Day Sail'Private Open-Top Mini Moke Island Tour of St. Barts +4 more
View →
from $3,360
Book This Cruise@ Cruisebound
Oceania · Oceania AlluraRound-trip
Caribbean 13 nights Jan 7 – Jan 20, 2027 from Miami, Florida
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · … · Miami, Florida9 ports
Miami, Florida · Georgetown, Grand Cayman, Cayman Islands · Falmouth, Jamaica · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Castries, St. Lucia · Pointe-a-Pitre, Guadeloupe · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Stingray City SandbarBlue Hole & Secret FallsAruba +4 more
View →
from $7,099
Book This Cruise@ Cruisebound
Oceania · Oceania SirenaRound-trip
Caribbean 12 nights Nov 28 – Dec 10, 2027 from Miami, Florida
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · … · Miami, Florida9 ports
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Castries, St. Lucia · Pointe-a-Pitre, Guadeloupe · Philipsburg, St. Maarten · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Klein Bonaire +4 more
View →
from $3,399
Book This Cruise@ Cruisebound
Oceania · Oceania SonataRound-trip
Caribbean 13 nights Dec 6 – Dec 19, 2027 from Miami, Florida
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · … · Miami, Florida10 ports
Miami, Florida · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Castries, St. Lucia · Pointe-a-Pitre, Guadeloupe · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Klein Bonaire +5 more
View →
from $6,399
Book This Cruise@ Cruisebound
Oceania · Oceania SonataRound-trip
Caribbean 10 nights Feb 2 – Feb 12, 2028 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida7 ports
Miami, Florida · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Pointe-a-Pitre, Guadeloupe · Tortola, B.V.I. · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsPrivate Full-Day Boat CharterMt. Liamuiga Volcano Crater Hike +2 more
View →
from $4,799
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