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.
Showing 36 of 84 sailings
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
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
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Nov 9 – Nov 21, 2026 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
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
Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Nov 15 – Nov 22, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
Virgin Voyages · Brilliant LadyRound-trip
Bahamas Nov 15, 2026 from Miami, Florida
Miami, Florida · St. Maarten, Netherlands Antilles · … · Miami, Florida7 ports
Miami, Florida · St. Maarten, Netherlands Antilles · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Bimini, Bahamas · Miami, Florida
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
Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Nov 22 – Nov 29, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
Norwegian · Norwegian GemRound-trip
Caribbean 12 nights Nov 28 – Dec 10, 2026 from Tampa, Florida
Tampa, Florida · San Juan, Puerto Rico · … · Tampa, Florida9 ports
Tampa, Florida · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Falmouth, Jamaica · Georgetown, Grand Cayman, Cayman Islands · Tampa, Florida
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
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Nov 29 – Dec 11, 2026 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · New York, New York
Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Nov 29 – Dec 6, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
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
Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Dec 6 – Dec 13, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Philipsburg, St. Maarten · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Philipsburg, St. Maarten · St. Lucia, Caribbean · Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · San Juan, Puerto Rico
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Dec 11 – Dec 23, 2026 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
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
Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Dec 13 – Dec 20, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Philipsburg, St. Maarten · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
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
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Dec 23 – Jan 4, 2027 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philipsburg, St. Maarten · New York, New York
Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Dec 27 – Jan 3, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Philipsburg, St. Maarten · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · San Juan, Puerto Rico
Virgin Voyages · Brilliant LadyRound-trip
Bahamas Dec 28, 2026 from Miami, Florida
Miami, Florida · St. Maarten, Netherlands Antilles · … · Miami, Florida7 ports
Miami, Florida · St. Maarten, Netherlands Antilles · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Road Town, Tortola, B.V.I. · St. John's, Antigua · Bimini, Bahamas · Miami, Florida
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Jan 4 – Jan 16, 2027 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
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
Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Jan 10 – Jan 17, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · Bridgetown, Barbados · St. Lucia, Caribbean · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
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
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
Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Jan 24 – Jan 31, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
Virgin Voyages · Brilliant LadyRound-trip
Bahamas Jan 25, 2027 from Miami, Florida
Miami, Florida · St. Maarten, Netherlands Antilles · … · Miami, Florida7 ports
Miami, Florida · St. Maarten, Netherlands Antilles · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Bimini, Bahamas · Miami, Florida
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Feb 1 – Feb 13, 2027 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · New York, New York
Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Feb 7 – Feb 14, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Philipsburg, St. Maarten · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · San Juan, Puerto Rico
Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Feb 14 – Feb 21, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Bridgetown, Barbados · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
Norwegian · Norwegian PrimaRound-trip
Caribbean 7 nights Feb 21 – Feb 28, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico8 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. Lucia, Caribbean · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
Virgin Voyages · Brilliant LadyRound-trip
Caribbean Feb 22, 2027 from Miami, Florida
Miami, Florida · St. Maarten, Netherlands Antilles · … · Miami, Florida7 ports
Miami, Florida · St. Maarten, Netherlands Antilles · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Bimini, Bahamas · Miami, Florida
Virgin Voyages · Valiant LadyRound-trip
Caribbean Feb 27, 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
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Mar 1 – Mar 13, 2027 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York8 ports
New York, New York · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
Virgin Voyages · Valiant LadyRound-trip
Caribbean Mar 13, 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
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.