2027 Cruise Calendar

Every Major Cruise Leaving Boston in 2027

My full, continually reviewed calendar of every commercial cruise currently published as departing from Boston, Massachusetts in 2027.

Jump to the full calendar

This schedule was last reviewed on July 21, 2026. Cruise lines can add, cancel, or change sailings, so dates and itineraries should always be confirmed before making travel arrangements.

The overview

Boston Cruises 2027: Every Ship and Sailing Leaving Boston

Looking for a cruise you can take from Boston in 2027? This is the complete list of currently published commercial cruises scheduled to begin in Boston, Massachusetts.

You do not have to fly to Florida or New York to take a great cruise. In 2027, travelers can sail directly from Boston to Bermuda, the Canadian Maritimes, Quebec, coastal New England, and New York. The options range from Norwegian Cruise Line’s weekly seven-night cruises aboard Norwegian Breakaway to smaller coastal voyages with American Cruise Lines and destination-focused Canada and New England itineraries with Holland America Line.

At a Glance: Cruises Leaving Boston in 2027

Currently published Boston departures include:

  • Norwegian Cruise Line: Bermuda and Canada and New England
  • Holland America Line: Montreal, Quebec City, Canada and New England
  • American Cruise Lines: Cape Cod, coastal New England, New York and Grand New England voyages
Most large-ship cruises depart from Flynn Cruiseport Boston in the Seaport. Small coastal ships may use a different Boston-area dock, which will be confirmed in each passenger’s final cruise documents.

The biggest schedule

Every Norwegian Cruise Line Sailing From Boston in 2027

Norwegian Cruise Line has the largest 2027 Boston cruise schedule currently available. Norwegian Breakaway is scheduled to operate weekly seven-night round-trip cruises from April through October. Most spring and summer departures visit Bermuda, while late-August through mid-October sailings focus on Canada and New England.

Norwegian Breakaway: Bermuda Cruises

Departure dateLengthShipItineraryEnds in
April 18, 20277 nightsNorwegian BreakawayBermudaBoston
April 25, 20277 nightsNorwegian BreakawayBermudaBoston
May 2, 20277 nightsNorwegian BreakawayBermudaBoston
May 9, 20277 nightsNorwegian BreakawayBermudaBoston
May 16, 20277 nightsNorwegian BreakawayBermudaBoston
May 23, 20277 nightsNorwegian BreakawayBermudaBoston
May 30, 20277 nightsNorwegian BreakawayBermudaBoston
June 6, 20277 nightsNorwegian BreakawayBermudaBoston
June 13, 20277 nightsNorwegian BreakawayBermudaBoston
June 20, 20277 nightsNorwegian BreakawayBermudaBoston
June 27, 20277 nightsNorwegian BreakawayBermudaBoston
July 4, 20277 nightsNorwegian BreakawayBermudaBoston
July 11, 20277 nightsNorwegian BreakawayBermudaBoston
July 18, 20277 nightsNorwegian BreakawayBermudaBoston
July 25, 20277 nightsNorwegian BreakawayBermudaBoston
August 1, 20277 nightsNorwegian BreakawayBermudaBoston
August 8, 20277 nightsNorwegian BreakawayBermudaBoston
August 15, 20277 nightsNorwegian BreakawayBermudaBoston
August 22, 20277 nightsNorwegian BreakawayBermudaBoston
October 24, 20277 nightsNorwegian BreakawayBermudaBoston
October 31, 20277 nightsNorwegian BreakawayBermudaBoston

Norwegian’s Bermuda itineraries generally include an extended stay at Royal Naval Dockyard. Some departures may also include an additional port, such as Halifax, depending on the specific sailing. Because the itinerary details are not identical on every date, travelers should compare the full port schedule rather than assuming every seven-night Bermuda cruise follows the same route.

Norwegian Breakaway: Canada and New England Cruises

Departure dateLengthShipItineraryEnds in
August 29, 20277 nightsNorwegian BreakawayCanada & New EnglandBoston
September 5, 20277 nightsNorwegian BreakawayCanada & New EnglandBoston
September 12, 20277 nightsNorwegian BreakawayCanada & New EnglandBoston
September 19, 20277 nightsNorwegian BreakawayCanada & New EnglandBoston
September 26, 20277 nightsNorwegian BreakawayCanada & New EnglandBoston
October 3, 20277 nightsNorwegian BreakawayCanada & New EnglandBoston
October 10, 20277 nightsNorwegian BreakawayCanada & New EnglandBoston
October 17, 20277 nightsNorwegian BreakawayCanada & New EnglandBoston

Ports vary by departure, but published itineraries include combinations of Portland, Eastport, Saint John, Halifax and Sydney. These cruises are especially popular during the fall foliage season. September and October sailings can sell quickly, particularly in balcony cabins and accommodations that hold three or four guests.

What Norwegian Breakaway Is Best For

Norwegian Breakaway is generally the best fit for travelers who want:

  • A casual, flexible cruise experience
  • Plenty of restaurants and entertainment
  • A ship with activities for adults, teens and children
  • A seven-night round-trip itinerary
  • A cruise that does not require a flight
  • More departure dates from which to choose

It is also one of the easiest Boston options for families and multigenerational groups because of the number of weekly sailings and variety of cabin categories.

Destination focused

Every Holland America Line Sailing From Boston in 2027

Holland America’s Boston schedule is much smaller than Norwegian’s, but its itineraries place more emphasis on the destination. These cruises are particularly appealing to travelers who want a quieter ship, a traditional cruise experience and more time exploring Canada and New England.

Volendam Departures

Departure dateLengthShipItineraryEnds in
June 19, 20277 nightsVolendamBoston to MontrealMontreal
June 19, 202714 nightsVolendamRound-trip Canada and New EnglandBoston

The 14-night voyage combines the Boston-to-Montreal sailing with the ship’s return journey to Boston. It is one physical departure from Boston, but it can be booked as either a seven-night one-way cruise or a longer round-trip itinerary.

Zuiderdam Departures

Departure dateLengthShipItineraryEnds in
September 4, 20277 nightsZuiderdamBoston to Quebec CityQuebec City
September 4, 202714 nightsZuiderdamRound-trip Canada and New EnglandBoston
September 18, 20277 nightsZuiderdamRound-trip Canada and New EnglandBoston
September 25, 20277 nightsZuiderdamBoston to Quebec CityQuebec City
September 25, 202714 nightsZuiderdamRound-trip Canada and New EnglandBoston
October 9, 20277 nightsZuiderdamBoston to Quebec CityQuebec City

As with Volendam, some Holland America departures can be purchased either as a seven-night segment or as part of a longer combined itinerary. Ports vary by date and may include destinations such as Bar Harbor, Portland, Halifax, Sydney, Charlottetown, Saguenay and Quebec City.

What Holland America Is Best For

Holland America is generally a good choice for travelers who prioritize:

  • Destination-focused itineraries
  • A quieter onboard atmosphere
  • Traditional cruise service
  • Live music and enrichment
  • Scenic cruising
  • One-way itineraries that include Montreal or Quebec City

These sailings tend to attract more adults than families with young children, although children are permitted onboard.

Small-ship coastal

Every American Cruise Lines Sailing From Boston in 2027

American Cruise Lines operates small-ship coastal cruises rather than traditional large ocean cruises. Its ships generally carry roughly 90 to 130 guests and visit smaller New England ports that cannot accommodate ships the size of Norwegian Breakaway or Zuiderdam. The experience is quieter, more inclusive and considerably more expensive than a mainstream cruise.

American Cruise Lines publishes some of its schedule as cruise-and-land packages. The displayed trip length can therefore include a hotel night or other land-based component in addition to the nights spent aboard the ship.

Cape Codder Cruises

The Cape Codder is a round-trip Boston itinerary visiting coastal Massachusetts destinations. Depending on the departure, ports may include Gloucester, Plymouth, Martha’s Vineyard, Falmouth, New Bedford and Provincetown. Currently published 2027 departures include:

Departure datePublished trip lengthItineraryEnds in
May 11, 20279 days / 8 nightsCape CodderBoston
May 18, 20279 days / 8 nightsCape CodderBoston
May 25, 20279 days / 8 nightsCape CodderBoston
July 30, 20279 days / 8 nightsCape CodderBoston
August 6, 20279 days / 8 nightsCape CodderBoston
August 13, 20279 days / 8 nightsCape CodderBoston
August 20, 20279 days / 8 nightsCape CodderBoston
August 27, 20279 days / 8 nightsCape CodderBoston

The July 30 departure is expected to be the inaugural cruise of American Navigator, a new Patriot-class coastal ship.

Grand New England Cruises

The Grand New England itinerary is a longer round-trip voyage from Boston. It combines ports along the Maine coast with destinations elsewhere in New England. Currently published Boston departures include:

Departure datePublished trip lengthItineraryEnds in
June 4, 202716 days / 15 nightsGrand New EnglandBoston
August 14, 202715-night cruise-and-land programGrand New EnglandBoston
August 28, 202715-night cruise-and-land programGrand New EnglandBoston
September 11, 202715-night cruise-and-land programGrand New EnglandBoston
September 25, 202715-night cruise-and-land programGrand New EnglandBoston
October 9, 202715-night cruise-and-land programGrand New EnglandBoston

American Cruise Lines uses both cruise-only and cruise-and-land descriptions for these programs. Confirm the exact embarkation date, included hotel nights and number of nights aboard the ship before comparing one departure with another.

Northeast Harbors Cruise

Departure datePublished trip lengthItineraryEnds in
May 21, 20279 days / 8 nightsBoston to New YorkNew York City

This one-way coastal itinerary connects Boston and New York while visiting smaller ports along the New England coast.

What American Cruise Lines Is Best For

American Cruise Lines is best suited to travelers who want:

  • A small ship with fewer than 150 passengers
  • Domestic coastal cruising
  • Smaller ports and locally focused excursions
  • A slower, quieter experience
  • Spacious accommodations
  • More inclusions than a typical mainstream cruise
  • An itinerary that does not require international travel

It is not directly comparable to Norwegian, Royal Caribbean or Celebrity. The ships, pricing, onboard experience and target traveler are very different.

Month by month

Complete 2027 Boston Cruise Calendar

This chronological calendar makes it easier to see every currently published departure together.

April 2027

DateCruise lineShipItinerary
April 18Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
April 25Norwegian Cruise LineNorwegian Breakaway7-night Bermuda

May 2027

DateCruise lineShipItinerary
May 2Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
May 9Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
May 11American Cruise LinesVaries by departureCape Codder
May 16Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
May 18American Cruise LinesVaries by departureCape Codder
May 21American Cruise LinesVaries by departureNortheast Harbors to New York
May 23Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
May 25American Cruise LinesVaries by departureCape Codder
May 30Norwegian Cruise LineNorwegian Breakaway7-night Bermuda

June 2027

DateCruise lineShipItinerary
June 4American Cruise LinesVaries by departureGrand New England
June 6Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
June 13Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
June 19Holland America LineVolendam7-night Boston to Montreal or 14-night round trip
June 20Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
June 27Norwegian Cruise LineNorwegian Breakaway7-night Bermuda

July 2027

DateCruise lineShipItinerary
July 4Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
July 11Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
July 18Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
July 25Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
July 30American Cruise LinesAmerican NavigatorCape Codder

August 2027

DateCruise lineShipItinerary
August 1Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
August 6American Cruise LinesAmerican NavigatorCape Codder
August 8Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
August 13American Cruise LinesAmerican NavigatorCape Codder
August 14American Cruise LinesAmerican PioneerGrand New England program
August 15Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
August 20American Cruise LinesAmerican NavigatorCape Codder
August 22Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
August 27American Cruise LinesAmerican NavigatorCape Codder
August 28American Cruise LinesAmerican PioneerGrand New England program
August 29Norwegian Cruise LineNorwegian Breakaway7-night Canada and New England

September 2027

DateCruise lineShipItinerary
September 4Holland America LineZuiderdam7-night to Quebec City or 14-night round trip
September 5Norwegian Cruise LineNorwegian Breakaway7-night Canada and New England
September 11American Cruise LinesAmerican PioneerGrand New England program
September 12Norwegian Cruise LineNorwegian Breakaway7-night Canada and New England
September 18Holland America LineZuiderdam7-night round-trip Canada and New England
September 19Norwegian Cruise LineNorwegian Breakaway7-night Canada and New England
September 25Holland America LineZuiderdam7-night to Quebec City or 14-night round trip
September 25American Cruise LinesAmerican PioneerGrand New England program
September 26Norwegian Cruise LineNorwegian Breakaway7-night Canada and New England

October 2027

DateCruise lineShipItinerary
October 3Norwegian Cruise LineNorwegian Breakaway7-night Canada and New England
October 9Holland America LineZuiderdam7-night Boston to Quebec City
October 9American Cruise LinesAmerican PioneerGrand New England program
October 10Norwegian Cruise LineNorwegian Breakaway7-night Canada and New England
October 17Norwegian Cruise LineNorwegian Breakaway7-night Canada and New England
October 24Norwegian Cruise LineNorwegian Breakaway7-night Bermuda
October 31Norwegian Cruise LineNorwegian Breakaway7-night Bermuda

Match the ship to your trip

Which Boston Cruise Should You Choose?

The best cruise depends on much more than the departure date.

Choose if you want big-ship variety

Norwegian Breakaway

You want a traditional large cruise ship with entertainment, multiple restaurants, nightlife, family activities and a relatively wide range of prices. For most first-time cruisers, families and groups, Norwegian will be the most practical place to begin the comparison.

Choose if the destination comes first

Holland America

You care more about the ports, scenery and onboard atmosphere than waterslides or high-energy entertainment. Holland America’s one-way Quebec and Montreal itineraries are especially appealing when the journey itself is the priority.

Choose if you prefer small ships

American Cruise Lines

You want a small, quiet ship and are willing to pay considerably more for a coastal experience with fewer passengers and more inclusions. This is the most specialized option and is generally best for travelers who already know they prefer small ships.

Questions

Frequently Asked Questions About Cruises From Boston in 2027

Which cruise line has the most Boston departures in 2027?+
Norwegian Cruise Line has the most currently published departures. Norwegian Breakaway is scheduled to sail from Boston almost every Sunday from April 18 through October 31, 2027.
Are there cruises from Boston to Bermuda in 2027?+
Yes. Norwegian Breakaway has numerous seven-night Bermuda cruises scheduled from April through August, followed by two additional departures on October 24 and October 31.
Are there fall foliage cruises from Boston?+
Yes. Norwegian and Holland America both offer Canada and New England cruises during September and October. The timing of peak foliage varies from year to year and by location. A cruise marketed for fall foliage cannot guarantee that every port will be at peak color during a particular week.
Can I cruise from Boston to Quebec City or Montreal?+
Yes. Holland America offers one-way cruises from Boston to Quebec City and Montreal, along with select round-trip combinations. Because these are not closed-loop cruises, passport and transportation requirements are different from those of a round-trip Boston sailing.
Are there round-trip cruises from Boston?+
Yes. Most Norwegian departures are round trip. Holland America also has select round-trip Canada and New England options, and American Cruise Lines offers several round-trip coastal itineraries.
Does Royal Caribbean sail from Boston in 2027?+
Royal Caribbean operates cruises from Boston in some seasons, but I could not verify a currently published Royal Caribbean cruise beginning in Boston during 2027 as of July 21, 2026. A general cruises-from-Boston page on a cruise line’s website does not necessarily mean that line has a bookable departure during the specific year being researched.
Does Celebrity Cruises sail from Boston in 2027?+
Celebrity has sailed from Boston in previous seasons, but I could not verify a currently published Celebrity cruise beginning in Boston in 2027 as of July 21, 2026.
Do Princess or Cunard have Boston departures in 2027?+
Neither line currently shows a verified 2027 cruise beginning in Boston. Both may visit Boston as a port of call, but visiting the city is not the same as departing from it.
Are these all the ships visiting Boston in 2027?+
No. This page covers cruises that begin in Boston, not every ship that visits the port. Many cruise lines call at Boston during Canada and New England itineraries without allowing passengers to begin their cruise here.
Where do cruises leave from in Boston?+
Most large cruise ships use Flynn Cruiseport Boston, also known by many locals as the Black Falcon Cruise Terminal, in Boston’s Seaport District. Small coastal ships may depart from another nearby dock. The exact embarkation location will appear in your cruise documents.
When should I book a 2027 Boston cruise?+
Book early when you need a cabin for three or four people, connecting cabins, an accessible stateroom, a suite, a specific deck or location, a school-vacation-week sailing, a fall foliage itinerary, or a lower-cost solo cabin. Waiting may still work for two adults who are flexible about the ship, date and cabin location, but the most limited accommodations often disappear first.

Work with Celeste

Planning a Cruise From Boston?

A long list of dates is helpful, but choosing the right sailing means looking at the ship, ports, time in each destination, cabin options and total vacation cost. As a Boston based travel advisor, I help clients compare the cruises leaving from Boston and narrow the choices to the two or three that genuinely fit their priorities. When you book with me, I also monitor eligible reservations for price drops and request a reprice when the cruise line’s rules allow it. You still receive the cruise line’s promotions and loyalty benefits, plus someone helping with the details before, during and after your trip.

Find My 2027 Boston Cruise Get the Free Boston Cruise Guide

Schedule and Accuracy Note

This page lists commercial overnight cruises currently published as departing from Boston in 2027. It does not include ships that only visit Boston, cruises that end in Boston but begin elsewhere, ferries, sightseeing boats, private charters or single-day harbor cruises.

Flynn Cruiseport Boston had not yet released its complete official 2027 port calendar when this page was reviewed on July 21, 2026. The schedule will be updated as cruise lines release additional departures and the port publishes its official calendar. Cruise dates, ships, ports and itineraries remain subject to change.