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 2 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 clear
Reset
Filtering Africa ×Bahamas ×Visits Port of Charlestown × Clear all
Showing 24 of 24 sailings
MSC Cruises · MSC PoesiaRound-trip
Caribbean 21 nights Nov 1 – Nov 22, 2026 from Miami, Florida
Miami, Florida · Ocho Rios, Jamaica · … · Miami, Florida15 ports
Miami, Florida · Ocho Rios, Jamaica · Cartagena, Colombia · Colon, Panama · Puerto Limon, Costa Rica · Roatan, Honduras · Belize City, Belize · Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Blue HoleThe Roman Theatre of Cartagena with the Rafael Mon…Panama Canal Full Transit +8 more
View →
from $2,225
Book This Cruise@ Cruisebound
MSC Cruises · MSC PoesiaRound-trip
Caribbean 10 nights Nov 12 – Nov 22, 2026 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida8 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Charlestown, Nevis, St. Kitts and Nevis · Philipsburg, St. Maarten · St. John's, Antigua · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Private Full-Day Boat CharterPrivate Island TourRandom Wind 'Paradise Day Sail' +3 more
View →
from $818
Book This Cruise@ Cruisebound
MSC Cruises · MSC MeravigliaRound-trip
Bahamas 14 nights Nov 15 – Nov 29, 2026 from Miami, Florida
Miami, Florida · Grand Turk, Turks and Caicos · … · Miami, Florida10 ports
Miami, Florida · Grand Turk, Turks and Caicos · Ocean Cay, Bahamas · Nassau, Bahamas · Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelShipwreck Snorkel SafariSwim With the Wild Exuma Pigs +4 more
View →
from $1,306
Book This Cruise@ Cruisebound
MSC Cruises · MSC MeravigliaRound-trip
Bahamas 14 nights Nov 21 – Dec 5, 2026 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · … · Miami, Florida10 ports
Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida · Grand Turk, Turks and Caicos · Ocean Cay, Bahamas · Nassau, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Island TourPrivate Full-Day Boat Charter +4 more
View →
from $1,216
Book This Cruise@ Cruisebound
MSC Cruises · MSC MeravigliaRound-trip
Bahamas 14 nights Nov 29 – Dec 13, 2026 from Miami, Florida
Miami, Florida · Grand Turk, Turks and Caicos · … · Miami, Florida10 ports
Miami, Florida · Grand Turk, Turks and Caicos · Ocean Cay, Bahamas · Nassau, Bahamas · Miami, Florida · San Juan, Puerto Rico · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelShipwreck Snorkel SafariSwim With the Wild Exuma Pigs +4 more
View →
from $1,096
Book This Cruise@ Cruisebound
MSC Cruises · MSC MeravigliaRound-trip
Caribbean 14 nights Dec 5 – Dec 19, 2026 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida10 ports
Miami, Florida · San Juan, Puerto Rico · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida · Grand Turk, Turks and Caicos · Ocean Cay, Bahamas · Nassau, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Walk El Morro & Old San Juan's City WallsPrivate Island TourPrivate Full-Day Boat Charter +4 more
View →
from $1,116
Book This Cruise@ Cruisebound
MSC Cruises · MSC MeravigliaRound-trip
Bahamas 14 nights Dec 13 – Dec 27, 2026 from Miami, Florida
Miami, Florida · Grand Turk, Turks and Caicos · … · Miami, Florida10 ports
Miami, Florida · Grand Turk, Turks and Caicos · Ocean Cay, Bahamas · Nassau, Bahamas · Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelShipwreck Snorkel SafariSwim With the Wild Exuma Pigs +4 more
View →
from $1,496
Book This Cruise@ Cruisebound
MSC Cruises · MSC MeravigliaRound-trip
Caribbean 14 nights Dec 19 – Jan 2, 2027 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · … · Miami, Florida10 ports
Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida · Grand Turk, Turks and Caicos · Ocean Cay, Bahamas · Nassau, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Island TourPrivate Full-Day Boat Charter +4 more
View →
from $1,906
Book This Cruise@ Cruisebound
MSC Cruises · MSC MeravigliaRound-trip
Bahamas 14 nights Dec 27 – Jan 10, 2027 from Miami, Florida
Miami, Florida · Grand Turk, Turks and Caicos · … · Miami, Florida10 ports
Miami, Florida · Grand Turk, Turks and Caicos · Ocean Cay, Bahamas · Nassau, Bahamas · Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelShipwreck Snorkel SafariSwim With the Wild Exuma Pigs +4 more
View →
from $1,586
Book This Cruise@ Cruisebound
Azamara · Azamara JourneyOne-way
Caribbean 17 nights Dec 28 – Jan 14, 2027 from Bridgetown, Barbados to Miami, Florida
Bridgetown, Barbados · Port of Oranjestad, Aruba, Caribbean · … · Miami, Florida14 ports
Bridgetown, Barbados · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Castries, St. Lucia · Port of Charlestown, Nevis, St. Kitts and Nevis · Frederikstad, St. Croix · San Juan, Puerto Rico · Virgin Gorda, British Virgin Islands · Gustavia, St. Barts · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · Miami, Florida
★ Bucket-list Swim with wild green sea turtles + two shipwrecks…ArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Cosol Tours +8 more
View →
from $7,329
Book This Cruise@ Cruisebound
MSC Cruises · MSC MeravigliaRound-trip
Caribbean 14 nights Jan 2 – Jan 16, 2027 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · … · Miami, Florida10 ports
Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida · Grand Turk, Turks and Caicos · Ocean Cay, Bahamas · Nassau, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Island TourPrivate Full-Day Boat Charter +4 more
View →
from $1,016
Book This Cruise@ Cruisebound
Azamara · Azamara JourneyOne-way
Caribbean 11 nights Jan 14 – Jan 25, 2027 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · Saint John, New Brunswick · … · Bridgetown, Barbados10 ports
Miami, Florida · Saint John, New Brunswick · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · St. John's, Antigua · Saint- Pierre · Port Elizabeth, Saint Vincent · St. Georges, Grenada, West Indies · Bridgetown, Barbados
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Reversing Falls & Fundy Tidal BorePrivate Full-Day Boat CharterRandom Wind 'Paradise Day Sail' +5 more
View →
from $3,116
Book This Cruise@ Cruisebound
MSC Cruises · MSC MeravigliaRound-trip
Bahamas 14 nights Feb 7 – Feb 21, 2027 from Miami, Florida
Miami, Florida · Grand Turk, Turks and Caicos · … · Miami, Florida10 ports
Miami, Florida · Grand Turk, Turks and Caicos · Ocean Cay, Bahamas · Nassau, Bahamas · Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelShipwreck Snorkel SafariSwim With the Wild Exuma Pigs +4 more
View →
from $1,196
Book This Cruise@ Cruisebound
MSC Cruises · MSC MeravigliaRound-trip
Caribbean 8 nights Feb 13 – Feb 21, 2027 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · … · Miami, Florida6 ports
Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Island TourPrivate Full-Day Boat Charter +1 more
View →
from $648
Book This Cruise@ Cruisebound
MSC Cruises · MSC MeravigliaRound-trip
Caribbean 14 nights Mar 21 – Apr 4, 2027 from Miami, Florida
Miami, Florida · Grand Turk, Turks and Caicos · … · Miami, Florida10 ports
Miami, Florida · Grand Turk, Turks and Caicos · Ocean Cay, Bahamas · Nassau, Bahamas · Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Gibbs Cay Private Stingray Swim & Reef SnorkelShipwreck Snorkel SafariSwim With the Wild Exuma Pigs +4 more
View →
from $1,376
Book This Cruise@ Cruisebound
MSC Cruises · MSC MeravigliaRound-trip
Caribbean 8 nights Mar 27 – Apr 4, 2027 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · … · Miami, Florida6 ports
Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Island TourPrivate Full-Day Boat Charter +1 more
View →
from $747
Book This Cruise@ Cruisebound
MSC Cruises · MSC SeashoreRound-trip
Caribbean 15 nights Nov 5 – Nov 20, 2027 from Miami, Florida
Miami, Florida · Ocean Cay, Bahamas · … · Miami, Florida11 ports
Miami, Florida · Ocean Cay, Bahamas · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida · Ocean Cay, Bahamas · Puerto Plata, Dominican Republic · Nassau, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Shipwreck Snorkel SafariRandom Wind 'Paradise Day Sail'Private Island Tour +4 more
View →
from $1,389
Book This Cruise@ Cruisebound
MSC Cruises · MSC SeashoreRound-trip
Bahamas 14 nights Dec 12 – Dec 26, 2027 from Miami, Florida
Miami, Florida · Ocean Cay, Bahamas · … · Miami, Florida10 ports
Miami, Florida · Ocean Cay, Bahamas · Puerto Plata, Dominican Republic · Nassau, Bahamas · Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Shipwreck Snorkel SafariThe full 27 jumps at the Damajagua WaterfallsSwim With the Wild Exuma Pigs +3 more
View →
from $1,568
Book This Cruise@ Cruisebound
MSC Cruises · MSC SeashoreRound-trip
Bahamas 15 nights Dec 18 – Jan 2, 2028 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · … · Miami, Florida11 ports
Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Puerto Plata, Dominican Republic · Miami, Florida · Grand Turk, Turks and Caicos · Puerto Plata, Dominican Republic · Ocean Cay, Bahamas · Nassau, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Island TourPrivate Full-Day Boat Charter +4 more
View →
from $2,181
Book This Cruise@ Cruisebound
MSC Cruises · MSC SeashoreRound-trip
Caribbean 14 nights Jan 15 – Jan 29, 2028 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · … · Miami, Florida10 ports
Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Puerto Plata, Dominican Republic · Miami, Florida · Puerto Plata, Dominican Republic · Ocean Cay, Bahamas · Nassau, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Island TourPrivate Full-Day Boat Charter +3 more
View →
from $2,218
Book This Cruise@ Cruisebound
MSC Cruises · MSC SeashoreRound-trip
Bahamas 14 nights Jan 23 – Feb 6, 2028 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida10 ports
Miami, Florida · Puerto Plata, Dominican Republic · Ocean Cay, Bahamas · Nassau, Bahamas · Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…The full 27 jumps at the Damajagua WaterfallsShipwreck Snorkel SafariSwim With the Wild Exuma Pigs +3 more
View →
from $1,608
Book This Cruise@ Cruisebound
MSC Cruises · MSC SeashoreRound-trip
Caribbean 8 nights Jan 29 – Feb 6, 2028 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · … · Miami, Florida6 ports
Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Puerto Plata, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Island TourPrivate Full-Day Boat Charter +1 more
View →
from $728
Book This Cruise@ Cruisebound
MSC Cruises · MSC SeashoreRound-trip
Bahamas 14 nights Feb 12 – Feb 26, 2028 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · … · Miami, Florida10 ports
Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Puerto Plata, Dominican Republic · Miami, Florida · Puerto Plata, Dominican Republic · Ocean Cay, Bahamas · Nassau, Bahamas · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Island TourPrivate Full-Day Boat Charter +3 more
View →
from $1,378
Book This Cruise@ Cruisebound
MSC Cruises · MSC SeashoreRound-trip
Caribbean 8 nights Mar 11 – Mar 19, 2028 from Miami, Florida
Miami, Florida · Philipsburg, St. Maarten · … · Miami, Florida6 ports
Miami, Florida · Philipsburg, St. Maarten · Port of Charlestown, Nevis, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Amber Cove, Dominican Republic · Miami, Florida
★ Bucket-list Star Island & Millionaire's Row Skyline Cruise on…Random Wind 'Paradise Day Sail'Private Island TourPrivate Full-Day Boat Charter +1 more
View →
from $848
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