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 · 2 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
Reset
Filtering Caribbean ×Disney ×Virgin Voyages × Clear all
Showing 36 of 84 sailings
Virgin Voyages · Valiant LadyOne-way
Bermuda Oct 19, 2026 from Brooklyn, NY to San Juan, Puerto Rico
Brooklyn, NY · Kings Wharf, Bermuda · … · San Juan, Puerto Rico7 ports
Brooklyn, NY · Kings Wharf, Bermuda · Bimini, Bahamas · St. Croix, U.S. Virgin Islands · St. Maarten, Netherlands Antilles · Road Town, Tortola, B.V.I. · San Juan, Puerto Rico
★ Bucket-list Swim with Wild Dolphins at Honeymoon HarbourBuck Island ReefMaho BeachNorman Island +1 more
View →
from $1,443
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Oct 31, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Willemstad, Curacao · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Full-Day Curaçao Island Tour with Local Ex…ArubaMount Pelée & Saint-Pierre +1 more
View →
from $1,253
Book This Cruise@ Cruisebound
Disney · Disney MagicRepositioning
Mediterranean 14 nights Nov 6 – Nov 20, 2026 from San Diego, California to Galveston, Texas
San Diego, California · Cabo San Lucas, Mexico · … · Galveston, Texas7 ports
San Diego, California · Cabo San Lucas, Mexico · Puerto Vallarta, Mexico · Panama City, Panama · Cartagena, Spain · Georgetown, Grand Cayman, Cayman Islands · Galveston, Texas
★ Bucket-list San Diego ZooEl Arco & Lover's BeachHidden Beach at Marietas IslandsThe Roman Theatre of Cartagena with the Rafael Mon… +2 more
View →
from $2,967
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Nov 7, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
View →
from $1,755
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Nov 14, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · St. John's, Antigua · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsNorman IslandPrivate Half-Day Island Adventure & Trunk Bay BeachCosol Tours +1 more
View →
from $1,153
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Caribbean 5 nights Nov 20 – Nov 25, 2026 from Galveston, Texas
Galveston, Texas · Cozumel, Mexico · Progreso, Mexico · Galveston, Texas
★ Bucket-list Moody GardensEl Cielo + Palancar + Columbia 3-Stop SnorkelChichén Itzá
View →
from $1,680
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Nov 20, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Willemstad, Curacao · Port of Oranjestad, Aruba, Caribbean · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Private Full-Day Curaçao Island Tour with Local Ex…Aruba +2 more
View →
from $1,437
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Mexico 4 nights Nov 25 – Nov 29, 2026 from Galveston, Texas
Galveston, Texas · Progreso, Mexico · Galveston, Texas
★ Bucket-list Moody GardensChichén Itzá
View →
from $1,557
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Nov 28, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsPrivate Catamaran Sail & Snorkel at Honeymoon Beac…Norman IslandMt. Liamuiga Volcano Crater Hike +2 more
View →
from $1,273
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Caribbean 5 nights Nov 29 – Dec 4, 2026 from Galveston, Texas
Galveston, Texas · Cozumel, Mexico · Progreso, Mexico · Galveston, Texas
★ Bucket-list Moody GardensEl Cielo + Palancar + Columbia 3-Stop SnorkelChichén Itzá
View →
from $1,300
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Mexico 5 nights Dec 4 – Dec 9, 2026 from Galveston, Texas
Galveston, Texas · Cozumel, Mexico · Progreso, Mexico · Galveston, Texas
★ Bucket-list Moody GardensEl Cielo + Palancar + Columbia 3-Stop SnorkelChichén Itzá
View →
from $1,300
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Dec 5, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Mount Pelée & Saint-Pierre +1 more
View →
from $1,253
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Mexico 4 nights Dec 9 – Dec 13, 2026 from Galveston, Texas
Galveston, Texas · Progreso, Mexico · Galveston, Texas
★ Bucket-list Moody GardensChichén Itzá
View →
from $1,177
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Dec 12, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
View →
from $1,335
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Mexico 4 nights Dec 13 – Dec 17, 2026 from Galveston, Texas
Galveston, Texas · Progreso, Mexico · Galveston, Texas
★ Bucket-list Moody GardensChichén Itzá
View →
from $1,109
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Mexico 5 nights Dec 17 – Dec 22, 2026 from Galveston, Texas
Galveston, Texas · Cozumel, Mexico · Progreso, Mexico · Galveston, Texas
★ Bucket-list Moody GardensEl Cielo + Palancar + Columbia 3-Stop SnorkelChichén Itzá
View →
from $1,715
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Dec 19, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort-de-France, Martinique · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMt. Liamuiga Volcano Crater HikeMount Pelée & Saint-PierreAruba +1 more
View →
from $1,183
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Mexico 5 nights Dec 22 – Dec 27, 2026 from Galveston, Texas
Galveston, Texas · Progreso, Mexico · Galveston, Texas
★ Bucket-list Moody GardensChichén Itzá
View →
from $1,987
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Dec 26, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Fort-de-France, Martinique · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachMount Pelée & Saint-PierreSwim with wild green sea turtles + two shipwrecks… +2 more
View →
from $2,039
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Bahamas 7 nights Dec 27 – Jan 3, 2027 from Galveston, Texas
Galveston, Texas · Nassau, Bahamas · Castaway Cay, Bahamas · Galveston, Texas
★ Bucket-list Moody GardensSwim With the Wild Exuma PigsAbaco Backcountry Fishing Adventure
View →
from $2,944
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Jan 2, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsNorman IslandSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
View →
from $1,213
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Mexico 4 nights Jan 3 – Jan 7, 2027 from Galveston, Texas
Galveston, Texas · Progreso, Mexico · Galveston, Texas
★ Bucket-list Moody GardensChichén Itzá
View →
from $1,054
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Mexico 4 nights Jan 7 – Jan 11, 2027 from Galveston, Texas
Galveston, Texas · Progreso, Mexico · Galveston, Texas
★ Bucket-list Moody GardensChichén Itzá
View →
from $870
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Jan 9, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Mount Pelée & Saint-Pierre +1 more
View →
from $1,190
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Mexico 4 nights Jan 11 – Jan 15, 2027 from Galveston, Texas
Galveston, Texas · Progreso, Mexico · Galveston, Texas
★ Bucket-list Moody GardensChichén Itzá
View →
from $854
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Mexico 5 nights Jan 15 – Jan 20, 2027 from Galveston, Texas
Galveston, Texas · Cozumel, Mexico · Progreso, Mexico · Galveston, Texas
★ Bucket-list Moody GardensEl Cielo + Palancar + Columbia 3-Stop SnorkelChichén Itzá
View →
from $1,161
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Jan 16, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Maarten, Netherlands Antilles · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsMaho BeachSwim with wild green sea turtles + two shipwrecks…Cosol Tours +2 more
View →
from $1,271
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Mexico 4 nights Jan 20 – Jan 24, 2027 from Galveston, Texas
Galveston, Texas · Progreso, Mexico · Galveston, Texas
★ Bucket-list Moody GardensChichén Itzá
View →
from $866
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Jan 23, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Castries, St. Lucia · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsNorman IslandMt. Liamuiga Volcano Crater HikePrivate Half-Day Island Adventure & Trunk Bay Beach +1 more
View →
from $1,127
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Bahamas 7 nights Jan 24 – Jan 31, 2027 from Galveston, Texas
Galveston, Texas · Nassau, Bahamas · Castaway Cay, Bahamas · Galveston, Texas
★ Bucket-list Moody GardensSwim With the Wild Exuma PigsAbaco Backcountry Fishing Adventure
View →
from $1,573
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Jan 29, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Fort-de-France, Martinique · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Klein Bonaire +2 more
View →
from $1,519
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Bahamas 7 nights Jan 31 – Feb 7, 2027 from Galveston, Texas
Galveston, Texas · Nassau, Bahamas · Castaway Cay, Bahamas · Galveston, Texas
★ Bucket-list Moody GardensSwim With the Wild Exuma PigsAbaco Backcountry Fishing Adventure
View →
from $1,580
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Feb 6, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico6 ports
San Juan, Puerto Rico · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · St. John's, Antigua · St. Maarten, Netherlands Antilles · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsArubaPrivate Full-Day Curaçao Island Tour with Local Ex…Private Half-Day Island Adventure & Trunk Bay Beach +1 more
View →
from $1,063
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Mexico 5 nights Feb 7 – Feb 12, 2027 from Galveston, Texas
Galveston, Texas · Cozumel, Mexico · Progreso, Mexico · Galveston, Texas
★ Bucket-list Moody GardensEl Cielo + Palancar + Columbia 3-Stop SnorkelChichén Itzá
View →
from $1,146
Book This Cruise@ Cruisebound
Disney · Disney MagicRound-trip
Caribbean 5 nights Feb 12 – Feb 17, 2027 from Galveston, Texas
Galveston, Texas · Cozumel, Mexico · Progreso, Mexico · Galveston, Texas
★ Bucket-list Moody GardensEl Cielo + Palancar + Columbia 3-Stop SnorkelChichén Itzá
View →
from $1,236
Book This Cruise@ Cruisebound
Virgin Voyages · Valiant LadyRound-trip
Caribbean Feb 13, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Samana, Dominican Republic · Grand Turk, Turks and Caicos · Cabo Rojo, Dominican Republic · San Juan, Puerto Rico
★ Bucket-list Walk El Morro & Old San Juan's City WallsGibbs Cay Private Stingray Swim & Reef Snorkel
View →
from $1,966
Book This Cruise@ Cruisebound
Load more 48 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.

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