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 41 sailings
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
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
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
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
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
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 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 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 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
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Jan 16 – Jan 23, 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 ApexRound-trip
Caribbean 7 nights Jan 30 – Feb 6, 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 30 – Feb 6, 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. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
Celebrity · Celebrity ConstellationRound-trip
Caribbean 7 nights Feb 6 – Feb 13, 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 · St. John's, Antigua · Roseau, Dominica · Castries, St. Lucia · St. Georges, Grenada, West Indies · San Juan, Puerto Rico
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Feb 13 – Feb 20, 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 Feb 13 – Feb 20, 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. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Feb 27 – Mar 6, 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 Feb 27 – Mar 6, 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. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Mar 13 – Mar 20, 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 Mar 13 – Mar 20, 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 ConstellationRound-trip
Caribbean 7 nights Mar 20 – Mar 27, 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 · St. John's, Antigua · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Mar 27 – Apr 3, 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 Mar 27 – Apr 3, 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. · Port of Basseterre, St. Kitts, St. Kitts and Nevis · Roseau, Dominica · Castries, St. Lucia · Bridgetown, Barbados · San Juan, Puerto Rico
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Apr 10 – Apr 17, 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 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
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Oct 30 – Nov 6, 2027 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Orlando, Florida
Celebrity · Celebrity SummitRound-trip
Caribbean 7 nights Nov 7 – Nov 14, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Roseau, Dominica · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Roseau, Dominica · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Nov 13 – Nov 20, 2027 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Orlando, Florida
Celebrity · Celebrity SummitRound-trip
Caribbean 7 nights Nov 21 – Nov 28, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Roseau, Dominica · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Roseau, Dominica · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Nov 27 – Dec 4, 2027 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Orlando, Florida
Celebrity · Celebrity SummitRound-trip
Caribbean 7 nights Dec 5 – Dec 12, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Roseau, Dominica · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Roseau, Dominica · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
Celebrity · Celebrity SummitRound-trip
Caribbean 7 nights Dec 19 – Dec 26, 2027 from San Juan, Puerto Rico
San Juan, Puerto Rico · Roseau, Dominica · … · San Juan, Puerto Rico7 ports
San Juan, Puerto Rico · Roseau, Dominica · Bridgetown, Barbados · Castries, St. Lucia · St. John's, Antigua · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · San Juan, Puerto Rico
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Jan 8 – Jan 15, 2028 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · Orlando, Florida
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Jan 22 – Jan 29, 2028 from Orlando, Florida
Orlando, Florida · Philipsburg, St. Maarten · San Juan, Puerto Rico · Puerto Plata, Dominican Republic · Orlando, Florida
Celebrity · Celebrity ApexRound-trip
Caribbean 7 nights Feb 5 – Feb 12, 2028 from Orlando, Florida
Orlando, Florida · Puerto Plata, Dominican Republic · Charlotte Amalie, St. Thomas, U.S. Virgin Islands · Philipsburg, St. Maarten · 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.