A family vacation in Boston will give you time in a big city, as well as time near the ocean. Basically, this is a destination that will check off all the boxes for your family when it comes to time away from home. There are so many things to do in Boston to keep everyone busy. It is easy to make sure everyone gets to do a few items on their list during a family trip to Boston. Today, I am going to share the best things to do in Boston with you. This way you can get an idea of what you may want to add to your itinerary for your next vacation.  

Best Things to Do in Boston 

Take a Walk on the Freedom Trail 

One of the most popular historic sites in Boston is the Freedom Trail. This trail is two and a half miles long. During your walk, you can stop at numerous museums, historical sites, churches, and cemeteries.  

You can take a guided walking tour, or head out on your own for this walk. Depending on how much time you have, you may not be able to stop at all the sites. However, you should try to stop at the following sites on the Freedom Trail: 

• Boston Common – Walk through the oldest park in the US. 
• Granary Burying Ground 
• Old Corner Bookstore 
• Old State House 
• Faneuil Hall 
• Paul Revere House – You can tour this house to see how the Revere family lived. 
• Old North Church 
• USS Constitution 

Check Out the Marine Life at the New England Aquarium 

This aquarium isn’t huge. However, it is an excellent place to spend a few hours getting close to marine life. Sea lions, seals, penguins, stingrays, sharks, and more can all be found within the exhibits.  

Quite a bit of the marine life can be seen inside the two hundred-thousand-gallon saltwater Ocean Tank. Others are in the touch tanks or outdoor pools.  

I recommend visiting here before heading out on a whale watching adventure. Although, we will want to plan your time at the aquarium carefully. This is a popular field trip destination. It is usually crowded throughout the week.  

Go Out on a Whale Watching Tour 

One of the best things to do in Boston is head out onto the water to see dolphins and whales. The tour guides seem to know where the whales and dolphins are spending their time each day. So, there is a high chance you will see the creatures you want to while on this family adventure on the water.  

Take a Stroll on the Esplanade 

The Esplanade is a three-mile path that goes along the Charles River. You can easily walk along this path. However, there are lots of people who will be riding their bikes along it too. Take the time to stop and watch the boats out on the water.  

Visit the Isabella Stewart Gardener Museum 

If you need to choose one of the museums in Boston to visit, I recommend heading to the Isabella Stewart Gardener Museum. Inside, you will discover a massive art collection, as well as books, manuscripts, and historic objects.  

Keep an eye out for the detailed architectural elements scattered throughout the museum. And take a break in the courtyard if you have the time.  

Grab a Bite to Eat at High Street Place 

You will need to eat to stay fueled for your family vacation in Boston. There are plenty of restaurants to choose from in this fabulous city. But if your family wants different things, you will want to visit High Street Place.  

This is not your usual food court. This is a high-end eatery with some of the best food in Boston. Someone can have a bagel piled high with pastrami from Mamaleh’s while everyone else grabs a sandwich elsewhere. Artisanal donuts from Blackbird are a must for breakfast for the whole family.  

Oh, and champagne can be purchased from Moët & Chandon.  

See, you really can’t go wrong with a visit to High Street Place!  

Wander Through the Public Garden 

So many people cross through the Public Garden in Boston without giving it a second thought. Don’t do this during your family vacation in Boston!  

Take the time to walk alongside the lagoon to check out the flowers. Or indulge in a ride in the lagoon on one of the Swan Boats. Maybe enjoy a picnic nearby, as you talk with the kids and make a few memories.  

Read at the Boston Public Library 

Reading is always a good thing to do at the Boston Public Library. However, there is so much more you can do within this building.  

Head over to the Norman B. Leventhal Map Center to see more than two hundred fifty thousand geographic objects. Take an Art & Architecture Tour to see some of the architectural gems in the building. Or attend one of the free events that are held throughout the year.  

Go Shopping on Charles Street 

Charles Street is within the famed Beacon Hill area in Boston. It is one of the best places to take family pictures in front of Federal-style brick row houses and on gaslit corners. But you will also love shopping while walking along this street.  

Beacon Hill Books & Café is a bookstore and cafe located inside a townhome. It is a wonderful place to purchase books or simply hang out. You may also want to purchase some truffles from Beacon Hill Chocolates for a little treat.  

If your family can’t get enough of bookstores while on vacation, head over to the Brattle Book Shop. This bookstore is located near West Street. They have three floors of used books. Plus, they fill carts and shelves in the alley. Let’s just say, if you can’t find what you’re looking for at this bookstore, you probably won’t find it anywhere!  

Make Reservations at the Lookout Rooftop 

The Lookout Rooftop is one of the best rooftop bars in Boston. You must have a reservation to spend time sipping cocktails on this rooftop.  

If you are searching for a family friendly bar in Boston, I recommend Cheers Beacon Hill. All ages are welcome there and the food is good too.  

Watch a Red Sox Game 

You can’t go to Boston during late spring, summer, or fall and not catch a Red Sox baseball game at Fenway Park. Grab pictures of the Green Monster. Eat a hot dog or two. And hopefully watch a winning game.  

Oh, and if you miss baseball season, you can take a behind the scenes tour of Fenway during the off-season.  

Shop at the SoWa Farmer’s Market 

On Sundays, head to the South End of Boston to go shopping at the SoWa Farmer’s Market. Vintage items, entertainment, and food trucks can be found at the SoWa Open Market nearby. You can easily spend a good part of your day exploring this section of the city. 

Visit the Museum of Fine Arts 

The Museum of Fine Arts is where you will find the world’s largest collection of ancient Egyptian treasures. Head to the European Wing to see the Claude Monet gallery. Another gallery holds ancient coins, while another is full of works by John Singer Sargent.  

Go Shopping at Faneuil Hall  

Okay, so I mentioned Faneuil Hall when I was saying walking the Freedom Trail was one of the best things to do in Boston. You don’t need to walk the trail though to go shopping at this marketplace. You can simply head over there to shop at the four main buildings. Those buildings are Faneuil Hall, Quincy Market, North Market, and South Market.  

The oldest building is Faneuil Hall. It was constructed back in 1742. The other buildings were added later to create space for the more than one hundred shops and restaurants found there today.  

This is quite a touristy area. Keep that in mind if you do decide to visit during your family vacation in Boston.  

Explore the Massachusetts State House 

The Massachusetts State House is located on land that used to be John Hancock’s cow pasture. This building was completed in 1798, so it has been in place for quite some time. The dome was installed at the top in 1802 by Paul Revere. At that time, it was copper, but has since been covered with gold.  

Tours of this state house are offered throughout the week. It is best to take a guided tour, so you don’t miss any of the history shared inside.  

Learn How Beer is Brewed at the Samuel Adams Brewery 

A guided tour of this brewery will have your entire family learning how the beer is made. These tours are perfect if you love tasting new brews. Or you just want to enjoy a drink when the tour is finished.  

It is important to note that the Samuel Adams Brewery is outside the city center. But it is still worth a visit if you have the time.  

Take a Ferry to the Boston Harbor Islands 

Not everyone wants to spend days in a busy city like Boston. If your family needs to escape the hustle and bustle for a little bit, take a ferry to the Boston Harbor Islands.  

There are thirty-four islands in all. However, the most popular islands to visit include:  

• Spectacle – Perfect for hiking adventures 
• Georges – Perfect for those who love history 
• Peddocks – This island offers a little bit of everything 
• Lovells – Best for beach lovers 
• Grape 
• Bumpkin 
• Thompson 

Visit the John F. Kennedy Presidential Library and Museum 

Most people seem to want to learn more about President Kennedy and his short term in office. One of the best places to do this is the John F. Kennedy Presidential Library and Museum. Inside, you will find exhibits filled with his presidential papers, memorabilia, and even a replica of his desk in the Oval Office.  

Another space is filled with items that were Jacqueline Kennedy Onassis’.  

Experience the Boston Children’s Museum 

Younger kids will love the exhibits at the Boston Children’s Museum. The interactive exhibits will have your kids learning about science, culture, health, art, and so much more.  

Construction lovers will enjoy spending time in the Construction Zone. Others will love creating music inside The Common.  

Plan on spending a little more time than you planned at this museum. Kids usually can’t get enough and don’t want to leave.  

Walk Along the Rose Fitzgerald Kennedy Greenway 

The Rose Fitzgerald Kennedy Greenway is one and a half miles long. It is an outdoor space that links multiple gardens and parks together in an old highway tunnel.  

This walkway is busy throughout the year. However, during the summer months it is even busier thanks to the summer concert performances, food festivals, and other weekly events.  

Learn About the Boston Tea Party 

Anyone who is interested in learning more about the Boston Tea Party needs to visit the Boston Tea Party Ships and Museum. Two of the three ships have been recreated. Those ships are the Eleanor and the Beaver. You can explore them both during your visit.  

Your family can also check out the exhibits at the museum, which includes an authentic tea chest from the Boston Tea Party.  

Take a Boston Duck Tour 

Short on time while on a family vacation in Boston? Or want to see the sights quickly?  

Well, taking a Boston Duck Tour will have you seeing all the important attractions in a short amount of time. This amphibious vehicle will have you exploring the streets and the river, as your tour guide shares information about everything you are passing by.  

These are some of the best things to do in Boston. I can add many of them to your itinerary, as I am personalizing it for your family vacation. And don’t worry, I can add other attractions and things to do for your family trip. You won’t need to feel stuck doing these things. I can make it so you can experience Boston your way.  

So, are you ready to have me create a personalized family vacation itinerary for your trip to Boston or another destination?  

If you said yes, I would like to invite you to click here to schedule a personalized family vacation planning session with me. When you click on the link, you will be taken to my digital calendar to schedule a time that is convenient for you.  

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