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
- Boston’s Prime Cruise Location
- Where to Park
- Must-See Attractions Around Boston’s Cruiseport
- Cruise Lines Using Boston as Home Port
- Cruise Itineraries Sailing from Boston
- Popular Ports of Call on Boston Cruises
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.
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.
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.
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.
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.
There are four major cruise lines using Boston Flynn Cruiseport:
- Holland America Line
- Norwegian Cruise Line (NCL)
- Royal Caribbean International (RCI)
- Celebrity Cruise Line
There are also some smaller vessels that use Boston as their home port for their 2020 cruise itineraries. These include:
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!
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!
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.
Holland America Zaandam
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.
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.
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:
Ponant Le Champlain
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.
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.
Bar Harbor, Maine
Take a cruise excursion to Acadia National Park for stunning coastal scenery, boardwalks and wildlife.
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).
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.
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.
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.
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.
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.
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