Caribbean cruises from Boston: one-way voyages south in the fall

Boston has no Caribbean round trips and no Bahamas cruises on this schedule. What it has is a few one-way voyages each fall, when ships head south from New England for the winter.

This schedule has 6 of them, from 8 November 2026 to 20 October 2028. On 3 November 2026 fares ran from $839 to $6,040 per person, for the cheapest cabin listed with two sharing, taxes and port fees included. Every one ends in another port, so the flight home is part of the trip. The table at the end of this guide lists them all.

Are there cruises from Boston to the Bahamas?

Not on this schedule. None of the sailings we track from Boston calls in the Bahamas, round trip or one way. The fall voyages south call at islands such as Aruba, Curaçao, St. Thomas and Tortola instead. For a Bahamas cruise you would have to start from another East Coast port, such as New York or Baltimore.

Are there winter Caribbean cruises from Boston?

No. Nothing on this schedule leaves Boston between mid-November and mid-April, so there are no winter Caribbean round trips from here. The Caribbean voyages all leave in October or November, at the end of the Boston season, and finish in Florida, Louisiana or Puerto Rico.

Our Boston cruise season guide shows what leaves in each month. If you want a round trip from Boston that heads south, the 7-night Bermuda cruises are the only ones on this schedule.

What is a repositioning cruise?

Norwegian Cruise Line describes a repositioning cruise as one that happens when a ship moves from one region to another to match seasonal travel demand. It says these trips are usually one way between two ports and often take place in spring or fall. Every Caribbean sailing from Boston on this schedule fits that description.

The pattern shows in the dates. Celebrity Silhouette sails Canada round trips from Boston in September and October 2027, then leaves for Fort Lauderdale on 16 October 2027. Jewel of the Seas does the same in 2028 and leaves for Fort Lauderdale on 20 October 2028. Windstar's Star Pride sails to Montreal in September 2027 and leaves Boston for San Juan on 22 October 2027.

Norwegian also says repositioning cruises tend to have more sea days and often cost less per night. On these voyages Celebrity Silhouette spends four days at sea before Aruba, and Norwegian Breakaway three before St. Thomas. On 3 November 2026 the lowest fare per night on the Caribbean voyages was $60, against $97 on the Bermuda weeks.

Which Caribbean cruises leave Boston?

Norwegian, Celebrity, Windstar and Royal Caribbean sail them, each one way to Fort Lauderdale, San Juan or New Orleans, in October or November. Star Pride and Jewel of the Seas also stop in Bermuda on the way. These are the voyages on this schedule, with the ports they list.

Ship	Leaves	Nights	Ends	Ports of call	Lowest fare on 3 November 2026
Norwegian Breakaway	8 November 2026	14	New Orleans	St. Thomas, St. Lucia, Grenada, Curaçao, Aruba, Grand Cayman	$839
Celebrity Silhouette	16 October 2027	10	Fort Lauderdale	Aruba, Curaçao, Bonaire	$913
Celebrity Summit	20 October 2027	9	San Juan	Puerto Plata, Samana, St. Thomas, St. John's in Antigua, Tortola	$904
Star Pride	22 October 2027	10	San Juan	Hamilton and St. George's in Bermuda, St. Barts, Virgin Gorda	$4,477
Star Pride	22 October 2027	17	San Juan	The 10-night ports, then St. John, St. Kitts, St. Barts, St. Maarten, Jost Van Dyke and Virgin Gorda	$6,040
Jewel of the Seas	20 October 2028	10	Fort Lauderdale	Royal Naval Dockyard in Bermuda, Aruba, Curaçao	$954

Star Pride's 17-night trip is the 10-night trip with an extra week from San Juan round the islands and back to San Juan. Both Star Pride voyages spend a night in Hamilton and a night in St. George's, and Jewel of the Seas spends a night at the Royal Naval Dockyard. Our Bermuda guide explains getting around from there.

The Jewel of the Seas sailing is listed by only one of the two sources we check, and the schedule marks it, so confirm the date with Royal Caribbean before you book.

Why do Boston to Fort Lauderdale cruises call at Aruba and Curaçao?

The likely reason is the coastwise law. The regulation that applies it lets a ship not qualified for U.S. coastwise trade carry you from one U.S. port to another only if the voyage reaches a distant foreign port. It puts Aruba, Bonaire and Curaçao outside the nearby group, which covers Bermuda, the Bahamas and the rest of the West Indies.

On a voyage that only reaches nearby foreign ports, the regulation counts getting off at a U.S. port other than the one where you boarded as a violation. Every voyage on this schedule that ends in Fort Lauderdale or New Orleans calls at Aruba and Curaçao, which meets that condition.

San Juan is different. The same regulation makes an exception for carrying passengers between Puerto Rico and other U.S. ports, so the Celebrity Summit and Star Pride voyages to San Juan do not need to call at Aruba, Bonaire or Curaçao.

How do you get home from a Caribbean cruise from Boston?

You fly home from where the ship ends, in Fort Lauderdale, San Juan or New Orleans. All three are in the United States, so the flight is domestic. The ships arrive early, but Celebrity says passengers normally leave the ship between about 8am and 10am, and that a very early morning flight is usually impractical.

The itineraries on sale give these arrival times. Fort Lauderdale and New Orleans are due at 7am. In San Juan, Celebrity Summit is due at 5am and Star Pride at 7am. Celebrity says it gives you the earliest reasonable flight time when you book, and other lines set their own advice.

A one-way also changes how you start the trip. You will not come back to Boston by sea, so leaving a car in cruise parking makes little sense. Plan on a drop-off, or see our guides to getting from Logan Airport to the cruise port and hotels near the port.

Do you need a passport for a Caribbean cruise from Boston?

These voyages end at a different U.S. port, so they are not closed-loop cruises in the sense U.S. Customs and Border Protection uses, which means coming back to the same U.S. port on the same ship. For the San Juan voyages, CBP says a traveler coming from Puerto Rico who also visited places outside U.S. territory must present a passport.

Every San Juan voyage here calls at foreign islands first, in the Dominican Republic, Antigua, the British Virgin Islands, Bermuda or St. Barts. CBP also says the countries a ship visits may ask for a passport. Our cruise documents guide explains which documents work for which trip.

How much is a Caribbean cruise from Boston?

On 3 November 2026 fares ran from $839 to $6,040 per person, for the cheapest cabin listed with two sharing, taxes and port fees included. The lowest rate per night was $60. Add a one-way flight home from Florida, Louisiana or Puerto Rico, which the cruise fare does not cover.

The fare for each ship is in the table above, and the Caribbean destination page lists the same voyages. For low fares on every route from Boston, see cheap cruises from Boston.