Bucket-List Cruise Adventures
Pick your sailing — we plan the whole adventure
142 sailings across 23 cruise lines, each one priced and planned end to end: the ports it calls at, the one unmissable thing to do at each, and the flights and nights either side.
A balcony averages about $166 a night on Carnival and about $414 on Disney, per person with taxes in — what a night costs on every line.
Leaving within three weeks?
Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.
Showing 36 of 142 sailings
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Vision of the Seas
Balcony: above average 19% over usual↑ 8% balcony, 35d
Caribbean 7 nights Nov 1 – Nov 8, 2026
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
10-night Caribbean from San JuanRound-trip
Viking Ocean · Viking Sea
Balcony: typical fare in the usual range
Caribbean 10 nights Nov 5 – Nov 15, 2026
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Rhapsody of the Seas
Balcony: low fare 20% under usualAll grades open↓ 37% inside, 36d
Caribbean 7 nights Nov 7 – Nov 14, 2026
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Vision of the Seas
Balcony: typical fare in the usual range↑ 20% balcony, 32d
Caribbean 7 nights Nov 8 – Nov 15, 2026
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Rhapsody of the Seas
Balcony: low fare 15% under usual↑ 20% inside, 38d
Caribbean 7 nights Nov 14 – Nov 21, 2026
San Juan, Puerto Rico · Philipsburg, St. Maarten · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Explora Journeys · EXPLORA III
Suite: typical fare in the usual range
Caribbean 7 nights Nov 15, 2026
San Juan, Puerto Rico · Road Bay, Anguilla · … · San Juan, Puerto Rico12 ports
San Juan, Puerto Rico · Road Bay, Anguilla · St. John's, Antigua · Frederikstad, St. Croix · Ain Sokhna, Egypt · Puerto Plata, Dominican Republic · Miami, Florida · Saint John/cruz Bay · St. John's, Antigua · Terre-de-haut, Guadeloupe · Philipsburg, St. Maarten · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Vision of the Seas
Balcony: low fare 34% under usualAll grades open↓ 19% balcony, 28d
Caribbean 7 nights Nov 15 – Nov 22, 2026
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
10-night Caribbean from San JuanRound-trip
Viking Ocean · Viking Sea
Balcony: typical fare in the usual range
Caribbean 10 nights Nov 15 – Nov 25, 2026
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Rhapsody of the Seas
Balcony: low fare 12% under usualAll grades open↑ 10% balcony, 38d
Caribbean 7 nights Nov 21 – Nov 28, 2026
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Vision of the Seas
Balcony: low fare 29% under usual↓ 23% balcony, 34d
Caribbean 7 nights Nov 22 – Nov 29, 2026
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
10-night Caribbean from San JuanRound-trip
Viking Ocean · Viking Sea
Balcony: typical fare in the usual range
Caribbean 10 nights Nov 25 – Dec 5, 2026
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Rhapsody of the Seas
Balcony: low fare 31% under usualAll grades open↑ 22% balcony, 37d
Caribbean 7 nights Nov 28 – Dec 5, 2026
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
10-night Bahamas from MiamiRound-trip
Regent · Seven Seas Grandeur
Bahamas 10 nights Nov 29 – Dec 9, 2026
Miami, Florida · Willis Island · … · Miami, Florida10 ports
Miami, Florida · Willis Island · San Juan, Puerto Rico · Gustavia, St. Barts · Philipsburg, St. Maarten · Frederikstad, St. Croix · La Romana, Dominican Republic · Willis Island · Nassau, Bahamas · Miami, Florida
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Vision of the Seas
Balcony: low fare 33% under usualAll grades open↑ 29% balcony, 24d
Caribbean 7 nights Nov 29 – Dec 6, 2026
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
10-night Caribbean from MiamiRound-trip
Virgin · Brilliant Lady
Balcony: low fare 38% under usualAll grades open↓ 21% inside, 37d
Caribbean 10 nights Nov 30, 2026
Miami, Florida · St. Maarten, Netherlands Antilles · … · Miami, Florida8 ports
Miami, Florida · St. Maarten, Netherlands Antilles · Road Town, Tortola, B.V.I. · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Bimini, Bahamas · Miami, Florida
10-night Caribbean from MiamiRound-trip
Oceania · Oceania Allura
Balcony: low fare 42% under usual↓ 37% balcony, 38d
Caribbean 10 nights Dec 2 – Dec 12, 2026
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida7 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Gustavia, St. Barts · Philipsburg, St. Maarten · Frederikstad, St. Croix · Tortola, B.V.I. · Miami, Florida
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Rhapsody of the Seas
Balcony: above average 6% over usualAll grades open↑ 48% balcony, 36d
Caribbean 7 nights Dec 5 – Dec 12, 2026
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
10-night Caribbean from San JuanRound-trip
Viking Ocean · Viking Sea
Balcony: typical fare in the usual range
Caribbean 10 nights Dec 5 – Dec 15, 2026
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
8-night Caribbean from MiamiRound-trip
Virgin · Resilient Lady
Balcony: low fare 32% under usualAll grades open↑ 8% balcony, 38d
Caribbean 8 nights Dec 5, 2026
Miami, Florida · St. Croix, U.S. Virgin Islands · … · Miami, Florida6 ports
Miami, Florida · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Bimini, Bahamas · Miami, Florida
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Vision of the Seas
Balcony: typical fare in the usual rangeAll grades open↑ 18% balcony, 16d
Caribbean 7 nights Dec 6 – Dec 13, 2026
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Rhapsody of the Seas
Balcony: low fare 19% under usualAll grades open↓ 33% suite, 37d
Caribbean 7 nights Dec 12 – Dec 19, 2026
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Vision of the Seas
Balcony: typical fare in the usual range↑ 39% balcony, 14d
Caribbean 7 nights Dec 13 – Dec 20, 2026
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Rhapsody of the Seas
Balcony: low fare 17% under usualAll grades open↓ 16% balcony, 37d
Caribbean 7 nights Dec 19 – Dec 26, 2026
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Vision of the Seas
Balcony: typical fare in the usual range↓ 28% suite, 36d
Caribbean 7 nights Dec 20 – Dec 27, 2026
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Roseau, Dominica · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Vision of the Seas
Balcony: above average 125% over usualAll grades open↑ 42% balcony, 36d
Caribbean 7 nights Dec 27 – Jan 3, 2027
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · St. John's, Antigua · Roseau, Dominica · Philipsburg, St. Maarten · San Juan, Puerto Rico
8-night Bridgetown to San JuanOne-way
Azamara · Azamara Journey
Balcony: typical fare in the usual range↓ 9% balcony, 29d
Caribbean 8 nights Dec 28 – Jan 5, 2027
Bridgetown, Barbados · Port of Oranjestad, Aruba, Caribbean · … · San Juan, Puerto Rico7 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
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Rhapsody of the Seas
Balcony: typical fare in the usual rangeAll grades open↑ 40% balcony, 37d
Caribbean 7 nights Jan 2 – Jan 9, 2027
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Vision of the Seas
Balcony: low fare 17% under usualAll grades open↑ 9% balcony, 37d
Caribbean 7 nights Jan 3 – Jan 10, 2027
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Roseau, Dominica · St. Croix, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
10-night Caribbean from San JuanRound-trip
Viking Ocean · Viking Sea
Balcony: typical fare in the usual range
Caribbean 10 nights Jan 5 – Jan 15, 2027
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Rhapsody of the Seas
Balcony: above average 11% over usualAll grades open↑ 8% balcony, 36d
Caribbean 7 nights Jan 9 – Jan 16, 2027
San Juan, Puerto Rico · St. Croix, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Vision of the Seas
Balcony: typical fare in the usual range↑ 15% balcony, 32d
Caribbean 7 nights Jan 10 – Jan 17, 2027
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
10-night Bahamas from MiamiRound-trip
Virgin · Brilliant Lady
Balcony: low fare 29% under usualAll grades open↑ 7% balcony, 37d
Bahamas 10 nights Jan 11, 2027
Miami, Florida · St. Maarten, Netherlands Antilles · … · Miami, Florida8 ports
Miami, Florida · St. Maarten, Netherlands Antilles · Road Town, Tortola, B.V.I. · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Bimini, Bahamas · Miami, Florida
10-night Caribbean from San JuanRound-trip
Viking Ocean · Viking Sea
Balcony: above average 53% over usual
Caribbean 10 nights Jan 15 – Jan 25, 2027
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · St. John's, Antigua · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
14-night Caribbean from GalvestonRound-trip
Carnival · Carnival Dream
Balcony: typical fare in the usual range
Caribbean 14 nights Jan 16, 2027
Galveston, Texas · Key West, Florida · … · Galveston, Texas10 ports
Galveston, Texas · Key West, Florida · Grand Turk, Turks and Caicos · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Croix, U.S. Virgin Islands · Ocho Rios, Jamaica · Galveston, Texas
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Rhapsody of the Seas
Balcony: typical fare in the usual rangeAll grades open↓ 14% suite, 37d
Caribbean 7 nights Jan 16 – Jan 23, 2027
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. Croix, U.S. Virgin Islands · Philipsburg, St. Maarten · St. John's, Antigua · Roseau, Dominica · San Juan, Puerto Rico
7-night Caribbean from San JuanRound-trip
Royal Caribbean · Rhapsody of the Seas
Balcony: typical fare in the usual rangeAll grades open↑ 12% inside, 37d
Caribbean 7 nights Jan 23 – Jan 30, 2027
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Croix, U.S. Virgin Islands · San Juan, Puerto Rico
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.