I’ve visited Boston, Massachusetts a number of times over the years, and I’ve always enjoyed every visit. This list of things I did isn’t all-encompassing, but it hopefully will give you a flavor of the things I’ve enjoyed here.

Boston Common

Right around Downtown Boston, you’ll find Boston Common to be a quite large, expansive park that’s a beautiful walk in the summer. You’re sure to find plenty of nature frolicking between the clearings of trees. Even when I don’t stay in a hotel immediately nearby, I try to make an effort to visit Boston Common a couple of times each trip. If you come in the morning, you’ll find plenty of joggers.

As you would expect, within the boundaries of the park, you’ll find plenty of things to do with kids. There is a carousel (not free), a public wading pool during the summer months (frog pond), and a well-maintained playground (tadpole playground). My kids didn’t accompany me on this latest visit to the grounds, but I know this is where they would have spent their time if they were with me.

On the western side of the park, you’ll find the large swan boats during the summer. Back in September 2018, we took Alex on the boats and he loved watching the ducks swimming by as we passed. Prices aren’t too expensive ($4.50/adult, $3.00/child in 2024) but expect to find a line. Generally lines aren’t too bad though since there are a lot of seats on each boat.

Freedom Trail

Walking the Freedom Trail is the thing that pretty much every visitor is expected to do. It’s a lengthy walk start to finish (and it’s real torture that a very tall climb awaits you at the end). My recommendation if you’re wanting to do this is to go early. I started at Boston Common at 8:30 AM and thought it was perfect—not hot, no other tourists, and I ended up by Old Ironsides just before it opened at 10 AM.

On the walk back (yeah my feet didn’t like that I walked it both directions), there were way too many tourists and tour guides, as it seemed they finally woke up to walk the trails. Personally, I don’t think the guides are necessary; there are plenty of welcome centers and posted signs along the path that offer up history lessons for those interested.

About halfway through the walk, you’ll come across Mike’s Pastry in the North End. There’s a little bit of a rivalry between Modern Pastry across the street and Mike’s Pastry, but if you start your walk too late, the lines here are unbearably long. If you just want to try the cannoli, come here in the morning and there is absolutely no line.

Old Ironsides

The part of history I always liked when I was in grade school was anything involving wars as the battles kept me more interested than periods of peace. Being able to walk through Old Ironsides brings back some of that intrigue as I get to discover what life was like for those soldiers ages ago. This is another attraction that can get packed later in the day, so I definitely recommend coming here right when it opens. Visiting Old Ironsides is free, but adults need to show ID. I made the trek with my backpack and I was fine bringing it in to the exhibit (I had water and a laptop on me), but there is a TSA-like security process.

I love being able to descend the decks to see how the crew lived while at sea. It really makes me wonder exactly how many times the sailors bumped their heads on the ceiling as they scrambled to their positions during emergencies.

Bunker Hill Monument

At the end of the Freedom Trail is the massive Bunker Hill Monument. Again, this is another free attraction where, if you scale it, you’ll get nice views of the city. Remember, the operative word is “if”. You’ve walked the whole Freedom Trail and then your reward is to climb this nearly 300-step staircase that circles the interior of the tower. If you weren’t tired on your journey to the monument, this will wear you out.

Once inside the small welcome center, you’ll find a statue of Joseph Warren, an important figure during the American Revolutionary War who died at the Battle of Breed’s Hill. Fun fact is the Bunker Hill Monument is actually found at Breed’s Hill, not nearby Bunker Hill.

The walk up the monument is a bit dark in spots, but you’ll see numbered stairs to give you a sense of how much longer you have to go. When you see step 294, you’ll know you finally made your way up.

At the top, you’ll get great views of the surroundings from all directions. But a word of warning–don’t drop anything while you’re up here. There is an open grate and it would be miserable to drop your anything only to lose it forever if it falls through the grate. When you’re done up here, good luck on the way down as I find it was much harder on the knees coming down than it was going up.

Boston Duck Tours

Another activity that we did back in September 2018, though I can’t imagine much has changed since then as the formula remains the same. You’ll get to ride on an amphibious vehicle as the tour around town starts out on land, but then moves out to sea. The one downside to this setup is the land tour will take you by interesting sights and important locations, but the aquatic tour usually is out of the way and doesn’t show you much other than just to give the novelty of now being a boat.

Two-year-old Alex enjoyed the trip and was even called out by the captain for being too shy to come sit by the controls to see what life was like up in the front. Of all the locations we’ve been to with a similar Duck Tour, I feel like Boston has the drivers with the best energy and with the most interesting pathing through town.

The tour also took us by the excellent Museum of Science, another must-do if you’re bringing kids to Boston. I unfortunately don’t have any photos of the interior here, so I am not going to have a dedicated section in here, but it’s worth a couple of hours of your time.

Carmelina’s

If you’re looking for a nice place to eat, check out Carmelina’s in the North End. There are lots of Italian restaurants in the area, and while I did check out a few places, I feel like none of them compared to Carmelina’s. The pastas were fresh, with a tantalizing mix of flavors in each bite. We ordered a bunch of entrees to share family-style and it was simply scrumptiously divine. Just note that the restaurant is small and it can take a long time to get a table (waited well over an hour), so hit up a nearby bar or go wait for a cannoli at Mike’s Pastry if you have some time to burn.

And while you’re in Boston, see this post for my thoughts on the Hilton Boston Park Plaza.

What do you like to do in Boston?