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 146 sailings
Celebrity · Celebrity BeyondRound-trip
Caribbean Jun 21, 2026 from Miami, Florida
Miami, Florida · Perfect Day at CocoCay · San Juan, Puerto Rico · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida
Celebrity · Celebrity BeyondRound-trip
Caribbean Jul 19, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida
Celebrity · Celebrity BeyondRound-trip
Caribbean Aug 16, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida
Celebrity · Celebrity BeyondRound-trip
Caribbean Sep 13, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida
Celebrity · Celebrity BeyondRound-trip
Caribbean Oct 11, 2026 from Miami, Florida
Miami, Florida · Puerto Plata, Dominican Republic · Tortola, B.V.I. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Miami, Florida
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Nov 7 – Nov 14, 2026 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Orlando, Florida
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
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
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Nov 21 – Nov 28, 2026 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Orlando, Florida
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
Celebrity · Celebrity EclipseRound-trip
Caribbean Nov 24, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · St. John's, Antigua · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · St. John's, Antigua · Castries, St. Lucia · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Fort Lauderdale (Port Everglades), Florida
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Nov 28 – Dec 5, 2026 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. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · 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
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
Celebrity · Celebrity EclipseRound-trip
Caribbean 9 nights Dec 3 – Dec 12, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Fort Lauderdale (Port Everglades), Florida6 ports
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Roseau, Dominica · St. John's, Antigua · Fort Lauderdale (Port Everglades), Florida
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Dec 5 – Dec 12, 2026 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Orlando, Florida
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
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Dec 12 – Dec 19, 2026 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. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · St. Georges, Grenada, West Indies · San Juan, Puerto Rico
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
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
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Dec 19 – Dec 26, 2026 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Orlando, Florida
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Dec 19 – Dec 26, 2026 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. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
Celebrity · Celebrity BeyondRound-trip
Caribbean 7 nights Dec 20 – Dec 27, 2026 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · San Juan, Puerto Rico · Perfect Day at CocoCay · Fort Lauderdale (Port Everglades), Florida
Celebrity · Celebrity EclipseRound-trip
Caribbean 12 nights Dec 22 – Jan 3, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · … · Fort Lauderdale (Port Everglades), Florida8 ports
Fort Lauderdale (Port Everglades), Florida · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Castries, St. Lucia · Bridgetown, Barbados · Willemstad, Curacao · Kralendijk, Bonaire, Dutch Antilles · Port of Oranjestad, Aruba, Caribbean · Fort Lauderdale (Port Everglades), 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
Celebrity · Celebrity AscentRound-trip
Caribbean 11 nights Dec 24 – Jan 4, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Philipsburg, St. Maarten · … · Fort Lauderdale (Port Everglades), Florida8 ports
Fort Lauderdale (Port Everglades), Florida · Philipsburg, St. Maarten · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort Lauderdale (Port Everglades), Florida
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
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Jan 2 – Jan 9, 2027 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Orlando, Florida
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Jan 2 – Jan 9, 2027 from San Juan, Puerto Rico
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 · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
Celebrity · Celebrity BeyondRound-trip
Caribbean 7 nights Jan 3 – Jan 10, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort Lauderdale (Port Everglades), Florida
Celebrity · Celebrity AscentRound-trip
Caribbean 11 nights Jan 4 – Jan 15, 2027 from Fort Lauderdale (Port Everglades), Florida
Fort Lauderdale (Port Everglades), Florida · Philipsburg, St. Maarten · … · Fort Lauderdale (Port Everglades), Florida8 ports
Fort Lauderdale (Port Everglades), Florida · Philipsburg, St. Maarten · St. John's, Antigua · Castries, St. Lucia · Bridgetown, Barbados · Roseau, Dominica · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Fort Lauderdale (Port Everglades), 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
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
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Jan 16 – Jan 23, 2027 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Orlando, 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.