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Boston Massachusetts Port Guide

Taking a cruise from Boston, Massachusetts gives travelers an exciting opportunity to explore America’s past and future. Boston is one of the most iconic cities in America, with reminders of its influence on the American revolution throughout the city.

During a Canada and New England cruise, you’ll have a myriad of ways to explore Boston whether you choose to focus on Boston’s history and its role in the American revolution, its gorgeous parks and tony neighborhoods, or its iconic sports and food culture.  

Cruises from Boston, Massachusetts

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Top Sights & Attractions for Cruises from Boston

Freedom Trail

For those who want to learn more about American history while in Boston, you can’t miss a walk along the Freedom Trail. The Freedom Trail is easy to spot, as it’s a 2.5-mile walk through the city of Boston that is marked by a red line. Top sites along the trail include Boston Common, Bunker Hill Monument, Old North Church, Massachusetts State Park, Old South Meeting House, the Paul Revere House, and many more. Along the way you’ll learn how these sites had significance to the American Revolution and which ones were frequented by former U.S. Presidents and political influencers. When cruising to Boston, a shore excursion that includes all or part of the Freedom Trail is a great way to experience it, as you’ll have an expert tour guide telling you about the sites.

Beacon Hill

Beacon Hill is a historic and affluent area of Boston that is home to beautiful Victorian brick homes covered in ivy and adorned with picturesque flower boxes. At night, the area comes alive with people descending onto the neighborhood to walk down its cobblestone streets and eat at one of the prestigious restaurants located in the neighborhood. The Massachusetts State House is also located in Beacon Hill.

North End

The North End is the oldest residential neighborhood in Boston and is also the city’s “Little Italy” neighborhood, as it’s home to a variety of Italian restaurants and delis. For dessert, Mike’s Pastry is famous for its Italian cannoli; you’ll often have to wait in a line out the door to try it, but most people will tell you it’s worth the wait. The North End is where many of the most popular sites along the Freedom Trail are located, including Paul Revere’s House, which is also the oldest building in downtown Boston.

Boston Common

The Boston Common is located at one end of the Freedom Trail and is where many visitors start the walk due to its scenic location. Boston Common covers 50 acres and is the oldest park in Boston. It’s a great place to walk around and see the ponds that are home to ducks and swans, and the many monuments located on its premises. From a historical standpoint, Boston Common is important because it played a part in the American Revolution as it was where British Troops gathered for a time and served as a campground and artillery base.

Prudential Center Skywalk Observatory Tours

The Prudential Center Skywalk Observatory is located on the 50th floor of the building and provides 360-degree views of Boston. It’s the highest observation deck in Boston that’s open to the public and you can also rent an audio tour headset to learn more about the main parts of the city you can see from the Skywalk Observatory.

Fenway Park

Fenway Park is probably Boston’s most cherished landmark for sports fans, and is a must-see for most visitors to Boston. It’s a stadium where the Boston Red Sox play and is the oldest ballpark for Major League Baseball. Even if you’re not a huge baseball fan, you can still appreciate the design, which has a uniquely shaped field and a massive wall alongside left field dubbed the Green Monster.

Stellwagen Bank National Marine Sanctuary

The underwater plateau that makes up Stellwagen Bank is rich in nutrients, making it a prime place for migrating whales to stop and feed. That also makes it the place to head for visitors to Boston who want to do some whale watching off the coast. During the summer months, you have the chance to see humpback whales making their way through the area. You also might see one of the 100+ other animals that call the 842-square-mile area of Stellwagen Bank National Marine Sanctuary home.

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Top Things to Do in Boston

Take a Guided Tour

Doing a shore excursion with a guided tour aspect through downtown Boston is a great way to learn about the history of Boston from a knowledgeable guide who can regale you with tales of Boston’s past. Another fun way to tour the city is to take a narrated excursion with some memorable transportation, like the duck boat or a hop-on, hop-off bus.

Go to an Ivy League School

Boston is in close proximity to some top universities. Just across the Charles River in Cambridge you’ll find Harvard University and the Massachusetts Institute of Technology (MIT). In addition to having pretty grounds and stately buildings, Harvard is home to a number of museum collections, including the Harvard Museum of Natural History, the Peabody Museum of Archaeology and Ethnology, and Harvard Art Museums.

Boston Tea Party Ships and Museum

One of Boston’s defining moments in history is the Boston Tea Party, and you can learn about that event in an interactive and fun way at the Boston Tea Party Ships and Museum. You’ll be escorted on a 1-hour tour through the facility by a guide dressed in 18th century garb. During the tour you’ll get to participate in reenactments like a city hall meeting as well as tour a ship fully rebuilt to reflect the ship that was ransacked during the Boston Tea Party. You’ll also get to help reenact the tea being thrown overboard while seeing the ship.  

New England Aquarium

The New England Aquarium is a family-friendly attraction in Boston that has thousands of sea creatures you can see. It’s located on the Central Wharf of Boston and overlooks Boston’s harbor. Popular animals to see at the aquarium include penguins, sea turtles, northern fur seals, and the giant Pacific octopus.

Museum of Fine Arts

Boston’s Museum of Fine Arts is worth a visit during a Boston cruise port of call if you love art since it houses one of the most comprehensive art collections in the world. Over 400,000 pieces line the walls and floors of the Museum of Fine Arts, ranging from ancient sculptures to contemporary paintings.

Top Food and Drink Spots Near the Boston Cruise Port

Fresh Lobster at Legal Sea Foods

Legal Sea Foods is a Boston institution and one of the top things to try while there is the lobster. Legal Sea Foods is located on the waterfront of Long Wharf and offers views with your meal. Besides lobster, there is a variety of other seafood including clam chowder, wood-grilled fish, and raw oysters.


Beers at Cheers

Another institution in Boston is the Cheers Bar. For fans of the Cheers TV show, this is a can’t-miss dining experience in Boston since you can eat in the bar and restaurant where the exterior shots of Cheers were filmed. The Cheers Bar is located in Beacon Hill and has a menu featuring items that play on the names of characters in the show like the Giant Norm Burger or Frasier's Chicken Panini.


Italian Dining in Little Italy

The Italian cuisine in Boston’s North End is delicious and prevalent. It ranges from casual brick-oven pizza to upscale lobster ravioli to traditionally prepared tiramisu and more Italian delicacies.


An Irish Pint

Boston has a strong Irish heritage that extends to a plethora of Irish pubs. Head to one for a pint of Guinness and live Irish music. You can often find traditional Irish fare served alongside fresh seafood at many of the Irish pubs in Boston.


Quincy Hall snacking

Faneuil Hall Marketplace has a variety of dining ambiances and cuisine. The large shopping center is home to over 17 restaurants plus has the popular Quincy Market Hall Colonnade, a long hall where you can sample over 30 food merchants serving up east coast and international cuisine.

Culture & History of the Boston Cruise Port

Boston has an important part in the history of the United States of America. The city was originally founded in the first half of the 17th century by Puritans who immigrated to the new world from England.

Over the next century and a half it would grow in size as more people moved there from overseas and the other British colonies. During that time it would also become a hotbed for strife between the colonies and England, with the Boston Tea Party and the Boston Massacre becoming defining moments in the conflict between patriots and loyalists that led to the American Revolutionary War.

Today, Boston is defined by its museums and sites showcasing this history as well as the high caliber universities that result in many new grads putting down roots in Boston. The city and its residents are also known for a strong Irish and Italian heritage, devotion to the city’s sports team, and a thick Boston accent.

Boston Port Facilities & Location

Your cruise from Boston will set sail from Boston’s Black Falcon Cruise Terminal. If you have time before or after taking off on your cruise vacation, you can walk to downtown Boston from the cruise terminal. It's roughly a mile and a half between the cruise terminal and downtown. If you would prefer to avoid the long walk into downtown Boston, shuttles to Quincy Market are available and there is a bus stop near the cruise terminal that will take you further into Boston.

Transportation in Boston

Metro and Bus System

Boston’s subway system is referred to as the “T” and has an extensive route system that consists of an underground metro and buses that operate along cables. The routes operated by the T (under its official name of Massachusetts Bay Transportation Authority, or MBTA) go all over the city center and beyond into Cambridge and other suburbs of Boston.


Water Shuttle

A water shuttle or water taxi can take you from the cruise terminal to Boston points of interest along the harbor, such as Faneuil Marketplace, Bunker Hill, the USS Constitution, or the North End.



Taxi ranks, also called cab stands, are located throughout the city and are an easy way to get a cab, though you may have to wait for a bit depending on the time of day and location. In addition, you can call for taxi service or hail one from the street. Also, legally certified taxis in Boston have to accept credit cards.

Shopping Near the Boston Cruise Port

Boston has no shortage of places to shop, whether you’re looking for marketplace crafts, kitschy souvenirs, or national chains. For all three, hit up Faneuil Hall Marketplace, home to the aforementioned Quincy Market and a lot of shops.

For department stores and traditional malls, Boston’s Back Bay is the place to go, with indoor malls found at Prudential Center and the Copley Place Mall.  

Local Currency & Tipping Customs

Boston is located in the United States so the city accepts the U.S. dollar, and you’ll be able to find ATMs dispensing U.S. dollars all over Boston. Tipping is very common, especially in restaurants, bars, and taxis. A common tip amount for restaurants, taxis, and most other services is 15% to 20% of the total amount.

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24-hour In-Room Dining

Boston, the capital of Massachusetts, is one of the most historic cities in North America and home to many leading universities, including world-renowned Harvard in neighboring Cambridge. As one of the oldest established cities in the United States, this cultural capital offers an abundance of historic sites and national treasure to discover. Stroll the 2.5-mile Freedom Trail that connects about 16 of Boston’s landmarks such as Boston Common, the Old Corner Bookstore, and Paul Revere’s House or visit the first-class Museum of Fine Art and Boston Symphony Orchestra and so much more. Head to the Seaport District for fresh seafood, local specialties include cod, steamed lobster, oysters on the half-shell and creamy chowders. Then venture to the birthplace of America’s original craft beer, the Samuel Adams Brewery, to find out how the ales and lagers are made, perhaps sample a few, and learn about this great patriot. There’s such an amazing cross-section of rich history, music, art, literature and theater to explore on a cruise to Boston.