Enjoy Cruises from Boston

The Ultimate Guide to Cruises from Boston

by Gillian Birch - updated July 30, 2020

Boston is essentially a summer cruise port (and if you’ve ever visited “Beantown” in January, you’ll understand why!) Cruises from Boston usually start in April and run until early November when cruise ships reposition further south for subtropical Caribbean cruises during the winter months.

Located in South Boston’s historic Seaport District, Flynn Cruiseport is the hub for the gleaming mega cruise ships that carry over 300,000 passengers on luxury cruises every year.

Destinations and ports of call on Boston cruises offer a diversity of attractions.

Whether you’re into photography, watersports, historic homes and gardens, wildlife or great seafood, these cruises from Boston have something for everyone. 

Cruises from Boston in 2020 will head to Canada, New England, Bermuda and further afield.

Scoot down the article and read about each port of call in detail before booking your next cruise from Boston. You’ll be surprised where cruises can take you!

Guide to Cruises from Boston Contents

Related read: The Ultimate Guide to Transatlantic and Repositioning Cruises

A white cruise with tourists is sailing on the ocean.
A white cruise with tourists is sailing on the ocean.

Flynn Cruiseport Boston’s Prime Location

Boston Harbor is just three miles southeast of the historic city, known as America’s “Cradle of Liberty”.

Located on the northern edge of Massachusetts Bay, the harbor and cruise port are conveniently just a stone’s throw from Boston Logan (BOS) International Airport.

Cruisers flying into Boston Airport are just a 10-minute taxi ride from the cruise port.

If you’re traveling to the port from the city, MBTA Silver Line Rapid Transit Service (bus) stops one block from the cruise terminal. 

If you’re driving to Flynn Cruiseport in Boston, it is easy to reach from the east-west I-90 and the north-south I-95 and I-93.

Boston Cruiseport and Skyline.
Boston Cruiseport and Skyline.

Boston Cruise Parking

If you’re arriving in Boston by car, you will need to park your car somewhere secure for the duration of your cruise.

You will also need a transfer from your vehicle to the cruise terminal, along with your luggage.

The easiest place to leave your car is at the official port garage as it is conveniently close to the cruise terminals, but it is not cheap.

The address is: South Boston Waterfront Transportation Center, 1 World Trade Center Ave, Boston.

If you book prepaid cruise parking in advance, it is $21 per day.

If you arrive without prebooking, it is $30 per day.

This includes a complimentary shuttle service to and from the ship.  

Another option is to book a Park and Cruise package at one of the hotels in Boston.

If you are planning to stay the night before or after your cruise, a Park and Cruise package is often the best value deal.

All-inclusive packages offer a night’s stay for two in a double room, parking for the duration of your cruise and transport to and from the ship.

Check out the options and book your hotel and parking well ahead of your cruise departure to get the best deals. Prices are provided when you make your booking.

The Hampton Inn Revere is four miles from Boston Flynn Cruiseport.

 It includes overnight accommodation and free parking for up to 10 days.

In addition, they charge $10 per person for the transfer to the cruise port.

Alternatively, the DoubleTree by Hilton Boston Bayside is three miles from the cruise port.

The package includes free parking for 14 days and transport to and from the cruise port for two guests. 

Cruise terminal and liner on parking.
Cruise terminal and liner on parking.

Must-See Attractions Around Boston’s Cruiseport

It’s smart to arrive in Boston the day before your cruise departure just in case there are any problems that might cause you to miss your cruise, such as flight delays, bad weather conditions or vehicle breakdowns. 

Once in Boston you can fill your time seeing some of the historic sights and attractions close to Flynn Cruiseport.

Check out the historic Fish Pier – a great place to sample the freshest seafood that Boston is known for. New England Clam Chowder is a must along with gourmet seafood dishes. 

100 years anni fish pier market place in Boston.
100 years anni fish pier market place in Boston.

Still on a foodie theme, you’ll find coffee shops, bars and pubs on every street corner in Boston.

It’s a great place to sample craft beers in a friendly, welcoming atmosphere.

Walk the Freedom Trail, a 2.5 mile red brick line that connects most of the historic locations relating to Boston’s history.

It starts in Boston Common, a peaceful park in the city centre and visits 16 Revolutionary War sites, churches, houses and graveyards.

Freedom Trail, Boston, a path connecting historic sites in the city.
Freedom Trail, Boston, a path connecting historic sites in the city.

Visit Faneuil Hall Marketplace, site of many speeches during the struggle for US Independence. It’s a beautiful building with food and market stalls inside.

Griffin’s Wharf is another historic museum and site of the restored Tea Party clipper ships. 

Visit Harvard University, America’s oldest college and admire the architecture in this legendary complex.

Other Boston attractions include the Museum of Fine Arts, Fenway Park (home to the legendary Boston Red Sox), and the huge New England Aquarium. 

People in front of New England Aquarium in Boston, Massachusetts, USA.
People in front of New England Aquarium in Boston, Massachusetts, USA.

Cruise Lines Using Boston as Home Port

There are four major cruise lines using Boston Flynn Cruiseport:

Royal Caribbean International cruise ship docked in Boston.
Royal Caribbean International cruise ship docked in Boston.

There are also some smaller vessels that use Boston as their home port for their 2020 cruise itineraries. These include:

Cruise Itineraries Sailing from Boston

Take your pick from the following cruises from Boston (note that some companies might change these itineraries as years go on, this is current as of 2020).

They include locally inspired activities and foods such as lobster rolls, British High Tea, scenic natural beauty and top golf courses.

During your cruise, keep your eyes peeled for water spouts denoting the presence of migratory Humpback and Wright’s Whales!  

Top deck of cruise ship with golf course.
Top deck of cruise ship with golf course.

Norwegian Gem

5-day Bermuda cruises

This mini cruise includes two days in Bermuda (Royal Naval Dockyard) and two Sea Days to relax and appreciate the ship’s amenities while sailing the Atlantic Ocean.

Check out what Bermuda has to offer including exclusive shopping and Bermuda rum!

Two Cruise Ships at Bermuda Dockyard.
Two Cruise Ships at Bermuda Dockyard.

7-day Bermuda cruises

Enjoy three days in Bermuda (Royal Naval Dockyard) and three Sea Days to relax and appreciate the ship’s amenities while sailing the Atlantic Ocean.

7-day Canada and New England

Hug the coastline of New England ticking off the landmark lighthouses.

This itinerary has ports of call at Halifax, Nova Scotia; Bar Harbor, Maine; Portland, Maine; Martha’s Vineyard; Newport, Rhode Island (check out those fabulous mansions!) and back to Boston.

7-day Canada and New England (Fall Color)

Taking in the resplendent fall colors and possibility of whale-watching, this glorious cruise from Boston heads to Bar Harbor, Maine; Halifax, Nova Scotia; Cape Breton Island, Nova Scotia; Charlottetown, Prince Edward Island (PEI) and Saguenay, Quebec.  

7-day Canada and New England

A third 7-day cruise itinerary from Boston takes in three ports in Canada and two in Maine.

These include Charlottetown (Birthplace of Canada and inspiration for the classic Anne of Green Gables), Sydney, Cape Breton Island; Halifax, Nova Scotia, Portland, Maine and Bar Harbor, Maine with shore excursions to Acadia National Park.

Cruise docked at the Canada Place cruise ship terminal in downtown.
Cruise docked at the Canada Place cruise ship terminal in downtown.

Holland America Zaandam

View of the Lower Town of the Old City with the MS MS Zaandam docked at the Old Port. Quebec City is a very popular cruise ship destination.
View of the Lower Town of the Old City with the MS MS Zaandam docked at the Old Port. Quebec City is a very popular cruise ship destination.

7-day Canada and New England Discovery

From Boston, visit Bar Harbor, Maine; Halifax, Nova Scotia; Sydney, Cape Breton Island; Charlottetown, PEI, delightful Quebec City and Montreal, Quebec. 

7-day Historic Coasts

On limited dates in August, the Zaandam will sail to Portland, Maine; Saint John, New Brunswick; Halifax and Sydney in Nova Scotia; Bar Harbor, Maine and back to Boston. 

14-day Canada and New England Discovery

Ports of call on this back-to-back cruise include Bar Harbor, Maine; Halifax, Nova Scotia; Sydney, Nova Scotia; Charlottetown, PEI; Quebec City; Montreal and then back in reverse to Boston

Holland America Rotterdam

10-day Newfoundland and New England

Ports of call on this voyage of discovery include Bar Harbor, Maine; Halifax, Nova Scotia; St Johns, Newfoundland; St Anthony, Newfoundland; Corner Brook, Newfoundland and a trio of ports in Quebec – Havre St Pierre, Quebec City and Montreal.

17-day Greenland, Newfoundland and New England

This fantastic itinerary sails from Boston to Sydney, Nova Scotia; Charlottetown, PEI; Corner Brook, Newfoundland; Red Bay, Canada; Nanortalki, Greenland, Paamiut, Greenland; Qaqortoq, Greenland; St Anthony, Newfoundland; St Johns, Newfoundland; Sydney, Nova Scotia; Halifax, Nova Scotia and disembark in Boston.

The MS Rotterdam cruise ship is also docked at the wharf as Sydney is a regular stop for cruises.
The MS Rotterdam cruise ship is also docked at the wharf as Sydney is a regular stop for cruises.

Holland America Amsterdam

7-day Canada and New England Discovery

Ports of call include Bar Harbor, Maine; Halifax, Nova Scotia; lovely Sydney on Cape Breton Island; Charlottetown, PEI, Quebec City and Montreal, Quebec.

You can also book the cruise with ports in reverse order ending back in Boston. 

14-day Canada and New England Discovery

Sail aboard the Amsterdam to Bar Harbor, Maine; Halifax, Nova Scotia; Sydney, Nova Scotia; Charlottetown, PEI; Quebec City; Montreal and then all the ports again in reverse.

Holland America Zuiderdam

10-day Newfoundland & New England Discovery

There are two dates for this itinerary sailing from Boston to Rockland, Maine; Halifax, Nova Scotia; St Anthony, Newfoundland; St Johns, Newfoundland; Havre St Pierre, Baie-Commeau and Quebec City, Quebec.

RCI Brilliance of the Seas

7-night Canada Cruise

Leaving Boston, this cruise calls at Portland, Maine; Bar Harbor, Maine; Saint John, New Brunswick; Halifax, Nova Scotia and two Sea Days.

11-night Beantown and Beaches

Head south to the Caribbean on this one-time Repositioning Cruise with ports of call at San Juan, Puerto Rico; Willemstad, Curacao; Oranjestad, Aruba; George Town, Grand Cayman and disembark in Tampa, Florida.

Celebrity Summit

Celebrity Summit in Sydney Nova Scotia.
Celebrity Summit in Sydney Nova Scotia.

7-night Boston to San Juan Repositioning cruise

In Mid-October the Celebrity Summit relocates to its winter home port of San Juan calling at Philipsburg, St Maarten; St John’s, Antigua and Charlotte Amelie, St Thomas USVI.

11-night Boston, Maine and Canada

Ports of call on this popular itinerary include Portland, Maine; Bar Harbor, Maine; Quebec City; Charlottetown, PEI; Sydney and Halifax, Nova Scotia and back to Boston.

11-night Boston to Fort Lauderdale

This repositioning cruise in mid October visits San Juan, Puerto Rico; Kralendijk, Bonaire; Willemstad, Curacao; Aruba; Key West, Florida and Fort Lauderdale.

There are also cruises from Boston aboard several small luxury vessels including:
RitzCarlton Azora
Ponant Le Champlain
Seabourn Quest

Popular Ports of Call on Boston Cruises

Bermuda (Royal Naval Dockyard)

Experience Bermuda’s famous pink sandy beaches, crystal caves, historic homes, maritime history and some of the world’s top golf courses.

Spend the day relaxing on beautiful Horseshoe Bay Beach.

You can also enjoy shopping and dining in this charming port of call with its colonial architecture.

Clear water and beautiful shores of Horseshoe Bay in Bermuda are no exception.
Clear water and beautiful shores of Horseshoe Bay in Bermuda are no exception.

Halifax, Nova Scotia

Take a guided tour of the Halifax Citadel National Historic Monument or spend time in the huge Maritime Museum of the Atlantic.

The Victoria Gardens and Peggy’s Point Lighthouse are worth a photo.

Halifax Nova Scotia skyline with halifax Harbour, the second deepest harbour in the world.
Halifax Nova Scotia skyline with halifax Harbour, the second deepest harbour in the world.

Bar Harbor, Maine

Take a cruise excursion to Acadia National Park for stunning coastal scenery, boardwalks and wildlife.

Portland, Maine

Portland has many fascinating things to see and do with its Old Port restaurants and shops, beautiful beaches and the historic Portland Head Lighthouse (circa 1791).

The Portland Head Lighthouse sits along the rocky coast of Maine
The Portland Head Lighthouse sits along the rocky coast of Maine.

Martha’s Vineyard

Rent bicycles and explore this relatively flat island.

The sandy beaches have shallow waters for swimming and watersports.

Ride the historic Flying Horse Carousel or take a tour of Gay Head Lighthouse.

Lighthouse in Gay head in Martha`s Vineyard.
Lighthouse in Gay head in Martha`s Vineyard.

Newport, Rhode Island

You’ll want to check out some of the opulent mansions that this port city is known for.

isit the Breakers Vanderbilt Mansion and the breathtaking Beaux-Arts Marble House. Guides recreate the era when wealthy families competed to host the most lavish parties at these summer homes. 

Newport is a seaside city in Rhode Island, It is known as a New England summer resort and is famous for its historic mansions and its rich sailing history.
Newport is a seaside city in Rhode Island, It is known as a New England summer resort and is famous for its historic mansions and its rich sailing history.

Charlottetown, Prince Edward Island

Said to be the “Birthplace of Canada”, Province House hosted the Charlottetown Conference in 1864 leading to the founding of Canada.

St Dunstan’s Basilica has outstanding architecture and nearby Cavendish was the setting for the classic novel Anne of Green Gables. 

Charlottetown is the capital and largest city of the Canadian province of Prince Edward Island, and the county seat of Queens County.
Charlottetown is the capital and largest city of the Canadian province of Prince Edward Island, and the county seat of Queens County.

Cape Breton Island

Step ashore in Sydney and take a guided tour of the island’s highlights.

It is home to the Highland Village which captures the history of the Gaelic settlement in this remote corner of Canada’s northeast coast. It is also home to the world’s largest fiddle statue (60 feet high) on Sydney waterfront.

Sydney is a former city and current community located in the Cape Breton Regional Municipality of Cape Breton Island, Nova Scotia, Canada.
Sydney is a former city and current community located in the Cape Breton Regional Municipality of Cape Breton Island, Nova Scotia, Canada.

If you need an added incentive to book a cruise from Boston, bear in mind that Flynn Cruiseport Boston supports 1,000 local jobs, generates $56 million of revenue for related businesses and contributes $23 million in federal, state and local taxes.

Happy cruising!

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15 thoughts on “The Ultimate Guide to Cruises from Boston

  1. I actually had no idea that cruises could leave from Boston. I’ve been wanting to see more of Canada lately – particularly Nova Scotia, New Foundland, and PEI. I never considered taking a cruise to see them rather than the long drive, but now I would!

  2. We visited Boston for the first time and found so much to see and do. But we did not get out on the water when we visited. Nor have we thought about starting a cruise in Boston. Good to know that is an option when cruising starts again. We would definitely come in early to enjoy all that there is to do around the cruise port.

  3. Great post, very useful information. I have visited Boston many times and taken some Boston Harbor cruises, but never an actual cruise. The Freedom Trail is definitely a must do and great way to see the city. The New England and Canada fall cruise sounds lovely, would love to visit those areas for the fall colors. Martha’s Vineyard has been on my list for the longest time. I will keep these tips in mind if I ever take a cruise from Boston.

    1. Oh yes the freedom trail was amazing! But being the foodie that I am I enjoyed tasting lobster and clam chowder as well as touring the old pubs more.

  4. Wow! I really miss travel and a cruise from Boston to New England sounds exciting.

    Happy to know they have a parking service with a free shuttle and we have a place where we can safely leave our car. Thank you for the heads up about the rates. Will sure to book ahead.

  5. Boston certainly matches my imagination as I am a great lover of cruises.I would in fact love to reach Boston two days before, relax a day and then see the historic sights and attractions close to Flynn Cruise port.I wouldn’t miss out on Fish Pier & New England Clam Chowder and feast on the seafood dishes.Would love to do the 5 day Bermuda cruise from Boston. Thanks for the very informative post on the different options.

  6. I quite liked the suggestion that one must arrive a couple of days or maybe a day before in Boston to explore. Boston has so much to offer. The port area looks great and the parking details are absolutely necessary. Thanks for guidance. Also, it was good to learn about cruises starting from there.

    1. It is super important to get there early to avoid stress. I’m glad you enjoyed learning more about the topic.

  7. I always knew Boston as an University city and never knew that this has wonderful port and so many cruising options are there. Once this pandemic gets over, I would now visit Boston again and select some 5 to 6 days cruise options. Once I visited Boston and had some Universities tour only. And it would be great to see some historic sights and attractions close to Flynn Cruiseport too here.

  8. What a wonderful posting on what to do in Boston! I never considered cruising out of Boston before. There are so many great options! This city just has so much to see and do. I would love to check out and explore the water front here! Hopefully this pandemic will be over soon!

  9. Wow Great post on Boston! There are so many amazing cruises out of Boston, I would never have assumed that at all! I have had friends who have been to Boston and said its beautiful in fall so I would love to visit! Horseshoe bay looks stunning! wow what a beautiful beach. Marthas Vineyard also looks like a great stop! I hope I am able to visit Boston one day and hey I might even take a cruise too!

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