As one of the birthplaces of the American Revolution and a vibrant melting pot of different communities, Boston is one of the quintessential American cities. There are museums, sports, the bay, history, a mix of great restaurants, to name a few. You may find a combination of these and other attractions in other cities, but Boston combines them in a way that is truly, uniquely Boston. Considering it’s so simple to get to, especially for people on the East Coast of the United States, it’s a place you should experience at least once. You’ll find an incredibly interesting and lively city with residents who are friendly and proud of the place they call home.

Why Boston is Perfect for Seniors

Boston has a distinct mystique from its evolvolution from major colonial cities to signature cultural hub. Whether you’re looking to tour the historical district with a costumed guide or explore one of the many movies sets, Boston has something for everyone. There is plenty to discover just beneath the surface, proving that Boston isn’t just a place in the history books.

Old State House - Senior Trip to Boston

Speaking of beneath the surface, Boston has a subway, called the T, that is both comparatively inexpensive and convenient for getting to the major tourist attractions. Boston also has a robust bus system, taxis, and ridesharing to help you get around. To further help you save money, you can get a CharlieCard, which is a reloadable card that you can use to pay fares on the T and buses. Similarly, there is the CharlieTicket, which is also valid for Commuter Rail and ferries, and the mTicket, a smartphone app. Finally, if you’re looking to see the sites but are a little concerned about the walking, there are many hop-on hop-off bus tours that run at a regular schedule so you can stay at an attraction that interests you and catch the next bus when you’re ready to go.

Where to Stay

When it comes to places to stay in Boston, you’re spoilt for choice. Even outside of central Boston, Cambridge is right across the Charles River, is a beautiful area, and is close to Boston’s city center. But, if you’re looking to stay in the center of Boston, it’s tough to beat these neighborhoods.

Beacon Hill

Acorn Street - Senior Trip to Boston

Looking for brick-lined homes and cobblestone streets? How about an area synonymous with old money Boston and the Boston Commons? Then you’re looking for Beacon Hill neighborhood. Just to the west of the historic center of Boston, there aren’t as many hotels in this area, but you’ll be staying in one of the nicest, most walkable areas of the city.

Back Bay

Moving slightly more to the west, you’ll enter the Back Bay neighborhood. While it’s a bit more of a walk to the downtown area, it’s still easy to get to. It also edges right up to Fenway Park while boasting its own worthwhile attractions like Trinity Church and the Charles River Esplanade. There are also more hotels than Beacon Hill while being a bit more residential, too.

North End

To the extreme north end of Boston, you’ll find the North End neighborhood. Known as Boston’s Little Italy, the North End is also part of Boston’s Freedom Trail, including attractions like the Paul Revere House, the Old North Church, and Copps Hill Burying Ground. A smaller neighborhood, it’s packed with (primarily Italian and seafood) restaurants, parks, and stuff to see and do.


Directly to the south of North End is Downtown Boston. In terms of location, accommodation choice, history, and attractions, it’s difficult to beat Downtown. It’s the home to the majority of the Freedom Trail, Long Ward, the Aquarium, and public markets like Fanueil Hall or Boston Public Market. If you’re looking to get a feel for Boston in a single neighborhood, it’s Downtown, making it maybe the best option for first-time visitors.

What to Do

This is not an exhaustive list of things to do in Boston. In fact, we’ll barely scratch the surface. If we were trying to cover everything, this article would be thousands of words long, and we wouldn’t be able to cover anything else. Instead, this section will hopefully give you a flavor of what you can do in Boston. You can even have a wonderful time just wandering the streets. In fact, we encourage it! It’s a beautiful city, and you’ll find farmers’ markets, food halls, and plenty of shopping without even having a plan. But if you want to have something planned, you should definitely include the following ideas.

Walk Through American History

Paul Revere Statue, Old North Church - Senior Trip to Boston

We stand by our earlier statement that “Boston isn’t just a place in the history books.” It’s a living, growing city with much to offer. But, it’s also been the site of some of the most pivotal and fascinating history in the story of the United States. While you’re staying in Boston, make sure to do the Freedom Trail, which is a free self-guided tour of the spots that played key roles in the Revolutionary War, as well as American history before and after the war. Similarly, you can visit the Boston Tea Party Museum, where you can learn more about one of the foundational events of the pre-war revolution. If you want more guidance, there are many, many tours with professional guides who can give you insight and deeper explanations of the sites and the events that occurred at them.

Museums, Zoos, and More

Boston is home to many different museums. Whether you’re a fan of art or just looking for something for a rainy day, you have plenty of options. The Museum of Fine Arts has a world class collection that spans centuries of work from all over the world. Alternatively, the Institute of Contemporary Art of Boston is more focused on modern art. There’s also the Museum of Bad Art, the Museum of Science, the Peabody Museum of Archaeology & Ethnology, and the Boston Children’s Museum. Across the river, you’ll find the Harvard and MIT campuses with museums like the Harvard Art Museums, the Harvard Museum of Natural History, the Harvard Museum of the Ancient Near East, and the MIT Museum. If museums aren’t interesting to you, try one of the zoos, like the Franklin Park Zoo or the Stone Zoo, or the New England Aquarium. The Boston Public Library is a gorgeous building worth a stop, while the notable colleges nearby like Harvard and MIT are right there to explore. With all this so close together, it’ll be tough to run out of things to do.

Get Your Fill of Sports

Fenway Park - Senior Trip to Boston

Boston is not only blessed with an abundance of history but also sports teams. No matter what team sport you’re a fan of, Boston is likely to have a team that plays it. In fact, depending on the sport, Boston (or the nearby area) hosts some of the most storied and successful teams in most sports. Fenway Park, located a short ride from Downtown, is the home of the Boston Red Sox, one of baseball’s biggest teams. Even more central is TD Garden, home to the Boston Celtics and Bruins, who play basketball and hockey respectively. A short drive south of Boston will get you to Foxborough, MA, where you’ll find Gillette Stadium. This stadium hosts one of football’s most successful teams, the New England Patriots, and one of Major League Soccer’s original teams, the New England Revolution.

What to Eat

In Boston, you won’t be going hungry. That’s for certain. You’ll find an incredible spread of restaurants with different cuisines and styles. Boston has a vibrant food scene that doesn’t get nearly enough attention. We highly recommend exploring what the city has to offer during your stay. One of the best ways to do this is with an organized food tour. A tour can showcase sometimes missed gems or help you avoid tourist trap restaurants while giving you fascinating background information on the stops and foods you’ll see.

Boston Seafood - Senior Trip to Boston

As mentioned earlier, Boston has a thriving Little Italy where you can find some of the best Italian food this side of the Atlantic, but that’s not all. Just south of the Beacon Hill and Downtown neighborhoods is Boston’s lively Chinatown, the heart of Boston’s Asian community where you can find dim sum, sushi, dumplings, pho, and more. Boston’s famous Irish heritage is more spread throughout the city, with historic and notable Irish pubs an essential stop during your trip. New England in general is also famous for its seafood, and Boston is no exception. Since the Atlantic is right there, you’ll have access to some incredibly fresh seafood, too. Together, this makes Boston one of the best places to get fresh, delicious seafood, whether it’s fish, crab, or oysters. If you’re not sure what to try, don’t miss out on one of Boston’s many food markets, which are a fun way to try many different vendors’ foods.

Day Trips from Boston

You could easily spend your entire time in Boston exploring the streets, relaxing, or eating your way through the neighborhoods, but you can also use it as a jumping off point to explore New England or America’s colonial history. In fact, you can see some significant or interesting destinations only a short trip away.


Plimuth Plantation - Senior Trip to Boston

The first day trip is a place that every child in the United States grows up familiar with. Plymouth, MA, is only an hour away from Boston, making it a great stop for anyone interested in the early days of the colonies. The town keeps much of its colonial charm, making it a nice break from the modern city of Boston. You can even see Plymouth Rock, where the pilgrims reportedly stood when they first entered the New World, or the nearby Plimuth Patuxet Museums that painstakingly recreate the historic English settlements, Native American community, and the Mayflower ship. There’s still plenty to do in modern Plymouth or you can just kick back and enjoy the beautiful seaside town.


The town of Salem is only a short 40-minute drive or a 30-minute train ride from Boston. Most people are familiar with the Salem Witch Trials in some way, but visiting the place where it happened is a different experience altogether, especially around Halloween. Salem has fully embraced its dark history, making it a spooky place to stop in at any time. Of course, the famous witch trial landmarks aren’t the only things of interest to see in Salem, with a heritage trail, colonial village, and more to explore!

Lexington and Concord

Minuteman Statue & Battle Green - Senior Trip to Boston

Want to see where the “shot heard round the world” was fired or where the Continental Army showed the British Army that this revolution wasn’t going to be put down easily? Head west of Boston for just around 30 minutes to the towns of Lexington and Concord where the Revolutionary War became an armed conflict. It’s entirely possible to do both in one day, having lunch in one and dinner in the other before heading back to Boston. Make sure to visit the Minute Man National Historical Park between the two cities that commemorates where the first battle of the Revolutionary War occurred.

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Since the founding of the original 13 colonies, Boston has been one of the most significant cities in what would become the United States. Today, whether you’re interested in theater, food, sports, film, and more, you can find it in Boston. All the more reason to give this jewel in New England a try, even if it’s only for a long weekend. You won’t be disappointed.

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