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 calendarThis 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
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 date | Length | Ship | Itinerary | Ends in |
|---|---|---|---|---|
| April 18, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| April 25, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| May 2, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| May 9, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| May 16, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| May 23, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| May 30, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| June 6, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| June 13, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| June 20, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| June 27, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| July 4, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| July 11, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| July 18, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| July 25, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| August 1, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| August 8, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| August 15, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| August 22, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| October 24, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
| October 31, 2027 | 7 nights | Norwegian Breakaway | Bermuda | Boston |
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 date | Length | Ship | Itinerary | Ends in |
|---|---|---|---|---|
| August 29, 2027 | 7 nights | Norwegian Breakaway | Canada & New England | Boston |
| September 5, 2027 | 7 nights | Norwegian Breakaway | Canada & New England | Boston |
| September 12, 2027 | 7 nights | Norwegian Breakaway | Canada & New England | Boston |
| September 19, 2027 | 7 nights | Norwegian Breakaway | Canada & New England | Boston |
| September 26, 2027 | 7 nights | Norwegian Breakaway | Canada & New England | Boston |
| October 3, 2027 | 7 nights | Norwegian Breakaway | Canada & New England | Boston |
| October 10, 2027 | 7 nights | Norwegian Breakaway | Canada & New England | Boston |
| October 17, 2027 | 7 nights | Norwegian Breakaway | Canada & New England | Boston |
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 date | Length | Ship | Itinerary | Ends in |
|---|---|---|---|---|
| June 19, 2027 | 7 nights | Volendam | Boston to Montreal | Montreal |
| June 19, 2027 | 14 nights | Volendam | Round-trip Canada and New England | Boston |
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 date | Length | Ship | Itinerary | Ends in |
|---|---|---|---|---|
| September 4, 2027 | 7 nights | Zuiderdam | Boston to Quebec City | Quebec City |
| September 4, 2027 | 14 nights | Zuiderdam | Round-trip Canada and New England | Boston |
| September 18, 2027 | 7 nights | Zuiderdam | Round-trip Canada and New England | Boston |
| September 25, 2027 | 7 nights | Zuiderdam | Boston to Quebec City | Quebec City |
| September 25, 2027 | 14 nights | Zuiderdam | Round-trip Canada and New England | Boston |
| October 9, 2027 | 7 nights | Zuiderdam | Boston to Quebec City | Quebec 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.
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 date | Published trip length | Itinerary | Ends in |
|---|---|---|---|
| May 11, 2027 | 9 days / 8 nights | Cape Codder | Boston |
| May 18, 2027 | 9 days / 8 nights | Cape Codder | Boston |
| May 25, 2027 | 9 days / 8 nights | Cape Codder | Boston |
| July 30, 2027 | 9 days / 8 nights | Cape Codder | Boston |
| August 6, 2027 | 9 days / 8 nights | Cape Codder | Boston |
| August 13, 2027 | 9 days / 8 nights | Cape Codder | Boston |
| August 20, 2027 | 9 days / 8 nights | Cape Codder | Boston |
| August 27, 2027 | 9 days / 8 nights | Cape Codder | Boston |
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 date | Published trip length | Itinerary | Ends in |
|---|---|---|---|
| June 4, 2027 | 16 days / 15 nights | Grand New England | Boston |
| August 14, 2027 | 15-night cruise-and-land program | Grand New England | Boston |
| August 28, 2027 | 15-night cruise-and-land program | Grand New England | Boston |
| September 11, 2027 | 15-night cruise-and-land program | Grand New England | Boston |
| September 25, 2027 | 15-night cruise-and-land program | Grand New England | Boston |
| October 9, 2027 | 15-night cruise-and-land program | Grand New England | Boston |
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 date | Published trip length | Itinerary | Ends in |
|---|---|---|---|
| May 21, 2027 | 9 days / 8 nights | Boston to New York | New 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
| Date | Cruise line | Ship | Itinerary |
|---|---|---|---|
| April 18 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| April 25 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
May 2027
| Date | Cruise line | Ship | Itinerary |
|---|---|---|---|
| May 2 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| May 9 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| May 11 | American Cruise Lines | Varies by departure | Cape Codder |
| May 16 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| May 18 | American Cruise Lines | Varies by departure | Cape Codder |
| May 21 | American Cruise Lines | Varies by departure | Northeast Harbors to New York |
| May 23 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| May 25 | American Cruise Lines | Varies by departure | Cape Codder |
| May 30 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
June 2027
| Date | Cruise line | Ship | Itinerary |
|---|---|---|---|
| June 4 | American Cruise Lines | Varies by departure | Grand New England |
| June 6 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| June 13 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| June 19 | Holland America Line | Volendam | 7-night Boston to Montreal or 14-night round trip |
| June 20 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| June 27 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
July 2027
| Date | Cruise line | Ship | Itinerary |
|---|---|---|---|
| July 4 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| July 11 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| July 18 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| July 25 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| July 30 | American Cruise Lines | American Navigator | Cape Codder |
August 2027
| Date | Cruise line | Ship | Itinerary |
|---|---|---|---|
| August 1 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| August 6 | American Cruise Lines | American Navigator | Cape Codder |
| August 8 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| August 13 | American Cruise Lines | American Navigator | Cape Codder |
| August 14 | American Cruise Lines | American Pioneer | Grand New England program |
| August 15 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| August 20 | American Cruise Lines | American Navigator | Cape Codder |
| August 22 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| August 27 | American Cruise Lines | American Navigator | Cape Codder |
| August 28 | American Cruise Lines | American Pioneer | Grand New England program |
| August 29 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Canada and New England |
September 2027
| Date | Cruise line | Ship | Itinerary |
|---|---|---|---|
| September 4 | Holland America Line | Zuiderdam | 7-night to Quebec City or 14-night round trip |
| September 5 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Canada and New England |
| September 11 | American Cruise Lines | American Pioneer | Grand New England program |
| September 12 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Canada and New England |
| September 18 | Holland America Line | Zuiderdam | 7-night round-trip Canada and New England |
| September 19 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Canada and New England |
| September 25 | Holland America Line | Zuiderdam | 7-night to Quebec City or 14-night round trip |
| September 25 | American Cruise Lines | American Pioneer | Grand New England program |
| September 26 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Canada and New England |
October 2027
| Date | Cruise line | Ship | Itinerary |
|---|---|---|---|
| October 3 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Canada and New England |
| October 9 | Holland America Line | Zuiderdam | 7-night Boston to Quebec City |
| October 9 | American Cruise Lines | American Pioneer | Grand New England program |
| October 10 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Canada and New England |
| October 17 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Canada and New England |
| October 24 | Norwegian Cruise Line | Norwegian Breakaway | 7-night Bermuda |
| October 31 | Norwegian Cruise Line | Norwegian Breakaway | 7-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.
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.
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.
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?+
Are there cruises from Boston to Bermuda in 2027?+
Are there fall foliage cruises from Boston?+
Can I cruise from Boston to Quebec City or Montreal?+
Are there round-trip cruises from Boston?+
Does Royal Caribbean sail from Boston in 2027?+
Does Celebrity Cruises sail from Boston in 2027?+
Do Princess or Cunard have Boston departures in 2027?+
Are these all the ships visiting Boston in 2027?+
Where do cruises leave from in Boston?+
When should I book a 2027 Boston cruise?+
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 GuideSchedule 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.