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 74 of 74 sailings
Norwegian · Norwegian EscapeRound-trip
Caribbean 10 nights Aug 19 – Aug 29, 2026 from New York, New York
New York, New York · San Juan, Puerto Rico · … · New York, New York7 ports
New York, New York · San Juan, Puerto Rico · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Puerto Plata, Dominican Republic · New York, New York
Royal Caribbean · Vision of the SeasOne-way
Caribbean 10 nights Oct 22 – Nov 1, 2026 from Baltimore, Maryland to San Juan, Puerto Rico
Baltimore, Maryland · Grand Turk, Turks and Caicos · … · San Juan, Puerto Rico8 ports
Baltimore, Maryland · Grand Turk, Turks and Caicos · Philipsburg, St. Maarten · Roseau, Dominica · Fort-de-France, Martinique · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
Azamara · Azamara JourneyOne-way
Bermuda 9 nights Oct 29 – Nov 7, 2026 from New York, New York to San Juan, Puerto Rico
New York, New York · Hamilton, Bermuda · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · 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
Celebrity · Celebrity ConstellationRound-trip
Caribbean 11 nights Nov 17 – Nov 28, 2026 from San Juan, Puerto Rico
San Juan, Puerto Rico · Tortola, B.V.I. · … · San Juan, Puerto Rico10 ports
San Juan, Puerto Rico · Tortola, B.V.I. · St. John's, Antigua · Castries, St. Lucia · St. Georges, Grenada, West Indies · Bridgetown, Barbados · Port of Kingstown, St. Vincent & the Grenadines · Fort-de-France, Martinique · Roseau, Dominica · San Juan, Puerto Rico
Cunard · Queen Mary 2Round-trip
Caribbean 11 nights Nov 17 – Nov 28, 2026 from New York, New York
New York, New York · St. Thomas, U.S. Virgin Islands · … · New York, New York6 ports
New York, New York · St. Thomas, U.S. Virgin Islands · Road Town, Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · New York, New York
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
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
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Nov 28 – Dec 8, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Tortola, B.V.I. · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
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
Oceania · Oceania AlluraRound-trip
Caribbean 10 nights Dec 2 – Dec 12, 2026 from Miami, Florida
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
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Dec 8 – Dec 18, 2026 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philadelphia, Pennsylvania
Oceania · Oceania MarinaRound-trip
Caribbean 12 nights Dec 10 – Dec 22, 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 · Gustavia, St. Barts · St. John's, Antigua · Fort-de-France, Martinique · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Tortola, B.V.I. · Miami, Florida
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
Celebrity · Celebrity EclipseRound-trip
Caribbean 10 nights Dec 12 – Dec 22, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Tortola, B.V.I. · … · Fort Lauderdale (Port Everglades), Florida7 ports
Fort Lauderdale (Port Everglades), Florida · Tortola, B.V.I. · St. John's, Antigua · Bridgetown, Barbados · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort Lauderdale (Port Everglades), Florida
Oceania · Oceania AlluraRound-trip
Caribbean 9 nights Dec 12 – Dec 21, 2026 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida6 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Tortola, B.V.I. · Miami, Florida
Regent · Seven Seas GrandeurRound-trip
Caribbean 10 nights Dec 19 – Dec 29, 2026 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida9 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Roseau, Dominica · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Willis Island · Miami, Florida
Norwegian · Norwegian GetawayRound-trip
Caribbean 9 nights Dec 22 – Dec 31, 2026 from Port Canaveral, Florida
Port Canaveral, Florida · Puerto Plata, Dominican Republic · … · Port Canaveral, Florida8 ports
Port Canaveral, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Great Stirrup Cay, Bahamas · Port Canaveral, Florida
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 JewelRound-trip
Bahamas 12 nights Dec 23 – Jan 4, 2027 from Miami, Florida
Miami, Florida · Great Stirrup Cay, Bahamas · … · Miami, Florida10 ports
Miami, Florida · Great Stirrup Cay, Bahamas · Cabo Rojo, Dominican Republic · Port of Oranjestad, Aruba, Caribbean · Willemstad, Curacao · Philipsburg, St. Maarten · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · Puerto Plata, Dominican Republic · Miami, Florida
Norwegian · Norwegian PearlRound-trip
Caribbean 11 nights Dec 23 – Jan 3, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
Oceania · Oceania AlluraRound-trip
Caribbean 10 nights Dec 28 – Jan 7, 2027 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida7 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Miami, Florida
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Jan 3 – Jan 13, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · Philadelphia, Pennsylvania
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
Norwegian · Norwegian EscapeRound-trip
Caribbean 9 nights Jan 6 – Jan 15, 2027 from Port Canaveral, Florida
Port Canaveral, Florida · Puerto Plata, Dominican Republic · … · Port Canaveral, Florida8 ports
Port Canaveral, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Great Stirrup Cay, Bahamas · Port Canaveral, Florida
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Jan 13 – Jan 23, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · St. Thomas, U.S. Virgin Islands · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Jan 23 – Feb 2, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Tortola, B.V.I. · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
Oceania · Oceania AlluraRound-trip
Caribbean 9 nights Jan 27 – Feb 5, 2027 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida6 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · 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 PearlRound-trip
Caribbean 10 nights Feb 2 – Feb 12, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philadelphia, Pennsylvania
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Feb 20 – Mar 2, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Tortola, B.V.I. · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
Oceania · Oceania MarinaRound-trip
Caribbean 10 nights Feb 23 – Mar 5, 2027 from Miami, Florida
Miami, Florida · San Juan, Puerto Rico · … · Miami, Florida8 ports
Miami, Florida · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Tortola, B.V.I. · Puerto Plata, Dominican Republic · Great Stirrup Cay, Bahamas · Miami, Florida
Holland America · EurodamRound-trip
Bahamas 10 nights Feb 27 – Mar 9, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Half Moon Cay (Little San Salvador Island), Bahamas · … · Fort Lauderdale (Port Everglades), Florida8 ports
Fort Lauderdale (Port Everglades), Florida · Half Moon Cay (Little San Salvador Island), Bahamas · San Juan, Puerto Rico · Road Town, Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort Lauderdale (Port Everglades), Florida
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
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Mar 2 – Mar 12, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philadelphia, Pennsylvania
Regent · Seven Seas PrestigeRound-trip
Caribbean 12 nights Mar 5 – Mar 17, 2027 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida11 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · Pointe-a-Pitre, Guadeloupe · Tortola, B.V.I. · Willis Island · Miami, Florida
Royal Caribbean · Rhapsody of the SeasOne-way
Caribbean 10 nights Mar 6 – Mar 16, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Tortola, B.V.I. · … · Miami, Florida9 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Philipsburg, St. Maarten · St. John's, Antigua · Bridgetown, Barbados · Castries, St. Lucia · Roseau, Dominica · St. Croix, U.S. Virgin Islands · Miami, Florida
Oceania · Oceania AlluraRound-trip
Caribbean 10 nights Mar 11 – Mar 21, 2027 from Miami, Florida
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · … · Miami, Florida7 ports
Miami, Florida · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Miami, Florida
Regent · Seven Seas PrestigeOne-way
Caribbean 10 nights Mar 20 – Mar 30, 2027 from Miami, Florida to San Juan, Puerto Rico
Miami, Florida · Willis Island · … · San Juan, Puerto Rico10 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Roseau, Dominica · Bridgetown, Barbados · Castries, St. Lucia · Fort-de-France, Martinique · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
Oceania · Oceania AlluraRound-trip
Caribbean 10 nights Mar 21 – Mar 31, 2027 from Miami, Florida
Miami, Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Miami, Florida7 ports
Miami, Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · Gustavia, St. Barts · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Miami, Florida
Norwegian · Norwegian PearlRound-trip
Bermuda 11 nights Mar 28 – Apr 8, 2027 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · … · Philadelphia, Pennsylvania7 ports
Philadelphia, Pennsylvania · Royal Naval Dockyard, Bermuda · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
Regent · Seven Seas PrestigeOne-way
Bahamas 10 nights Mar 30 – Apr 9, 2027 from San Juan, Puerto Rico to Miami, Florida
San Juan, Puerto Rico · Tortola, B.V.I. · … · Miami, Florida11 ports
San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Gustavia, St. Barts · Philipsburg, St. Maarten · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · La Romana, Dominican Republic · Willis Island · Nassau, Bahamas · Miami, Florida
Celebrity · Celebrity SummitRepositioning
Caribbean 9 nights Oct 20 – Oct 29, 2027 from Boston, Massachusetts to San Juan, Puerto Rico
Boston, Massachusetts · Puerto Plata, Dominican Republic · … · San Juan, Puerto Rico7 ports
Boston, Massachusetts · Puerto Plata, Dominican Republic · Samana, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Tortola, B.V.I. · San Juan, Puerto Rico
Norwegian · Norwegian PrimaOne-way
Caribbean 10 nights Nov 3 – Nov 13, 2027 from New York, New York to San Juan, Puerto Rico
New York, New York · Royal Naval Dockyard, Bermuda · … · San Juan, Puerto Rico9 ports
New York, New York · Royal Naval Dockyard, Bermuda · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Bridgetown, Barbados · St. John's, Antigua · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Nov 8 – Nov 20, 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 BlissRound-trip
Caribbean 12 nights Nov 28 – Dec 10, 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 · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · New York, New York
Regent · Seven Seas GrandeurRound-trip
Caribbean 10 nights Nov 28 – Dec 8, 2027 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida10 ports
Miami, Florida · Willis Island · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Gustavia, St. Barts · Tortola, B.V.I. · Willis Island · Miami, Florida
Norwegian · Norwegian DawnRound-trip
Bahamas 10 nights Nov 29 – Dec 9, 2027 from Jacksonville, Florida
Jacksonville, Florida · Grand Bahama Island · … · Jacksonville, Florida8 ports
Jacksonville, Florida · Grand Bahama Island · Nassau, Bahamas · Puerto Plata, Dominican Republic · Samana, Dominican Republic · Tortola, B.V.I. · San Juan, Puerto Rico · Jacksonville, Florida
Regent · Seven Seas PrestigeRound-trip
Caribbean 11 nights Dec 7 – Dec 18, 2027 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida10 ports
Miami, Florida · Willis Island · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · St. John's, Antigua · Castries, St. Lucia · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Willis Island · Miami, Florida
Norwegian · Norwegian DawnRound-trip
Bahamas 9 nights Dec 9 – Dec 18, 2027 from Jacksonville, Florida
Jacksonville, Florida · Grand Bahama Island · … · Jacksonville, Florida7 ports
Jacksonville, Florida · Grand Bahama Island · Great Stirrup Cay, Bahamas · San Juan, Puerto Rico · Tortola, B.V.I. · Puerto Plata, Dominican Republic · Jacksonville, Florida
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Dec 10 – Dec 22, 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 · Tortola, B.V.I. · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. Thomas, U.S. Virgin Islands · New York, New York
Norwegian · Norwegian EpicRound-trip
Caribbean 10 nights Dec 10 – Dec 20, 2027 from Port Canaveral, Florida
Port Canaveral, Florida · Puerto Plata, Dominican Republic · … · Port Canaveral, Florida9 ports
Port Canaveral, Florida · Puerto Plata, Dominican Republic · 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 · Great Stirrup Cay, Bahamas · Port Canaveral, Florida
Oceania · Oceania SirenaRound-trip
Bahamas 12 nights Dec 10 – Dec 22, 2027 from Miami, Florida
Miami, Florida · Nassau, Bahamas · … · Miami, Florida10 ports
Miami, Florida · Nassau, Bahamas · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Gustavia, St. Barts · Tortola, B.V.I. · Miami, Florida
Regent · Seven Seas PrestigeRound-trip
Caribbean 10 nights Dec 18 – Dec 28, 2027 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida10 ports
Miami, Florida · Willis Island · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · St. John's, Antigua · Tortola, B.V.I. · Willis Island · Miami, Florida
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Dec 22 – Jan 3, 2028 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 · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · New York, New York
Oceania · Oceania MarinaRound-trip
Caribbean 10 nights Dec 27 – Jan 6, 2028 from Miami, Florida
Miami, Florida · Nassau, Bahamas · … · Miami, Florida9 ports
Miami, Florida · Nassau, Bahamas · San Juan, Puerto Rico · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Gustavia, St. Barts · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Puerto Plata, Dominican Republic · Miami, Florida
Norwegian · Norwegian DawnRound-trip
Caribbean 12 nights Jan 2 – Jan 14, 2028 from Jacksonville, Florida
Jacksonville, Florida · Great Stirrup Cay, Bahamas · … · Jacksonville, Florida10 ports
Jacksonville, Florida · Great Stirrup Cay, Bahamas · Grand Bahama Island · Puerto Plata, Dominican Republic · Samana, Dominican Republic · Tortola, B.V.I. · St. John's, Antigua · Philipsburg, St. Maarten · San Juan, Puerto Rico · Jacksonville, Florida
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Jan 3 – Jan 15, 2028 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 · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · New York, New York
Regent · Seven Seas GrandeurOne-way
Caribbean 10 nights Jan 5 – Jan 15, 2028 from Miami, Florida to Bridgetown, Barbados
Miami, Florida · Willis Island · … · Bridgetown, Barbados10 ports
Miami, Florida · Willis Island · Tortola, B.V.I. · Gustavia, St. Barts · Philipsburg, St. Maarten · Pointe-a-Pitre, Guadeloupe · Roseau, Dominica · Fort-de-France, Martinique · Castries, St. Lucia · Bridgetown, Barbados
Regent · Seven Seas PrestigeRound-trip
Caribbean 10 nights Jan 7 – Jan 17, 2028 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida9 ports
Miami, Florida · Willis Island · Philipsburg, St. Maarten · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Gustavia, St. Barts · Tortola, B.V.I. · Willis Island · Miami, Florida
Norwegian · Norwegian BlissRound-trip
Caribbean 11 nights Jan 15 – Jan 26, 2028 from New York, New York
New York, New York · Puerto Plata, Dominican Republic · … · New York, New York7 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. · St. Thomas, U.S. Virgin Islands · New York, New York
Regent · Seven Seas PrestigeRound-trip
Caribbean 10 nights Jan 17 – Jan 27, 2028 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida10 ports
Miami, Florida · Willis Island · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Philipsburg, St. Maarten · Gustavia, St. Barts · St. John's, Antigua · Tortola, B.V.I. · Willis Island · Miami, Florida
Norwegian · Norwegian DawnRound-trip
Caribbean 10 nights Jan 18 – Jan 28, 2028 from Jacksonville, Florida
Jacksonville, Florida · Grand Bahama Island · … · Jacksonville, Florida8 ports
Jacksonville, Florida · Grand Bahama Island · Puerto Plata, Dominican Republic · Samana, Dominican Republic · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · San Juan, Puerto Rico · Jacksonville, Florida
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Jan 26 – Feb 7, 2028 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 · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · New York, New York
Norwegian · Norwegian DawnRound-trip
Caribbean 10 nights Jan 28 – Feb 7, 2028 from Jacksonville, Florida
Jacksonville, Florida · Grand Bahama Island · … · Jacksonville, Florida8 ports
Jacksonville, Florida · Grand Bahama Island · Great Stirrup Cay, Bahamas · Samana, Dominican Republic · Puerto Plata, Dominican Republic · Tortola, B.V.I. · San Juan, Puerto Rico · Jacksonville, Florida
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
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Feb 7 – Feb 19, 2028 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 · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
Norwegian · Norwegian DawnRound-trip
Caribbean 10 nights Feb 7 – Feb 17, 2028 from Jacksonville, Florida
Jacksonville, Florida · Grand Bahama Island · … · Jacksonville, Florida8 ports
Jacksonville, Florida · Grand Bahama Island · Great Stirrup Cay, Bahamas · Puerto Plata, Dominican Republic · Samana, Dominican Republic · Tortola, B.V.I. · San Juan, Puerto Rico · Jacksonville, Florida
Oceania · Oceania SonataRound-trip
Caribbean 11 nights Feb 19 – Mar 1, 2028 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · … · Miami, Florida9 ports
Miami, Florida · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · St. John's, Antigua · Philipsburg, St. Maarten · Tortola, B.V.I. · Miami, Florida
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Feb 26 – Mar 7, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Tortola, B.V.I. · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Tortola, B.V.I. · St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Philadelphia, Pennsylvania
Norwegian · Norwegian BlissRound-trip
Caribbean 12 nights Mar 6 – Mar 18, 2028 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 · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Philipsburg, St. Maarten · St. Thomas, U.S. Virgin Islands · New York, New York
Norwegian · Norwegian PearlRound-trip
Caribbean 10 nights Mar 7 – Mar 17, 2028 from Philadelphia, Pennsylvania
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · … · Philadelphia, Pennsylvania6 ports
Philadelphia, Pennsylvania · Puerto Plata, Dominican Republic · San Juan, Puerto Rico · St. Thomas, U.S. Virgin Islands · Tortola, B.V.I. · Philadelphia, Pennsylvania
Azamara · Azamara QuestOne-way
Caribbean 9 nights Mar 13 – Mar 22, 2028 from Bridgetown, Barbados to Miami, Florida
Bridgetown, Barbados · St. Georges, Grenada, West Indies · … · Miami, Florida8 ports
Bridgetown, Barbados · St. Georges, Grenada, West Indies · Castries, St. Lucia · Saint- Pierre · Roseau, Dominica · Philipsburg, St. Maarten · Road Town, Tortola, B.V.I. · Miami, Florida
Regent · Seven Seas GrandeurRound-trip
Caribbean 12 nights Mar 20 – Apr 1, 2028 from Miami, Florida
Miami, Florida · Willis Island · … · Miami, Florida12 ports
Miami, Florida · Willis Island · Puerto Plata, Dominican Republic · Cayo Levantado, Dominican Republic · San Juan, Puerto Rico · Gustavia, St. Barts · Roseau, Dominica · Pointe-a-Pitre, Guadeloupe · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Tortola, B.V.I. · Willis Island · Miami, Florida
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.