When you think of things to do in Boston, what comes to mind first? Is it seeing Boston Red Sox play, learning about Boston Tea Party, Boston Italian Mobs, and Boston Molasses Disaster?

Is it walking Boston Freedom Trail, or perhaps if you are an athlete running a Boston Marathon? Or do you simply think it would be lovely to visit this biggest city in New England, go sailing, and see a show?

Those are all great answers, and if you are wondering what to do in Boston, keep reading, and I will walk you through some fun ideas! East Coast is so rich in history, and being on the water, it has and will always be truly appealing.

Americans will never cease to appreciate the fact that every immigrant brought their own food with them when they moved to this country! Boston is a shining example of that.

Table of Contents

1. Savor Italian Restaurants of North End

Family-owned restaurants in Boston that are passed from generation to generation have maintained their quality of cuisine, beautiful architecture, and luxury of character.

May is my favorite month, and there are a number of reasons for that. My birthday is a key factor here.

I call it birthday month because I take time and reflect on how much God has done for me, the wonderful people I get to call friends, my Ukrainian family, my three sets of Minnesota parents, my favorite husband and our girls, and all the blessings. Just one day, May 18th, is not enough for that.

This year I asked my husband to bring me to a fun city. His busy roofing season is March through November, and he cannot be vacationing through these months, but he made an exception and took me to Boston for a long weekend.

It was glorious. I haven’t been to Boston since 2011 and it was his very first time.

It is very easy to get places around the city using public transportation. There is a free shuttle that takes you from Boston Airport to blue line and all you need is this magic Charlie card and you can get around the city effortlessly.

You can pay for one ride, one day, three days or more.

We landed on the 18th at 10 am and thought we were ready for the day. Except we didn’t realize until we got to our hotel that we haven’t really slept since the end of October.

It was amazing to get 7 or 8 hours of uninterrupted sleep. It’s funny how at different life stages we feel gratitude for very different things.

I think I used to be a way better tourist, or so I thought. I would be up by 7 am, with a plan and a map ready to take on the world. Not all my trips in the past were lengthy, but I would get to see so much.

All that changed. This trip felt slower, we decided on “what to do in Boston” and our itinerary the day of and sometimes we would opt out of some sights and choose rest instead. I think it has to do with having kids. Am I right?

2. Enjoy Architecture and Take Pictures

We enjoyed random things, stopped and took multiple pictures of doors, North End buildings, balconies, especially I couldn’t get over how darling copper oriels of Solari Building were.

Boston’s fast pace, public transportation, hearing different languages, architecture, waterfront, cobblestone roads, ships and boats, live music in parks, fashion, walking to a restaurant or to get groceries all those little things brought me back to Kyiv and my twenties after college.

We appreciate fun restaurants and if you are getting suspicious, because it sounds like we went to too many in those short three days, you are right! We absolutely love to eat!

Joe’s Waterfront was so delicious, that we ended up going there twice. They serve brunch on Saturdays and Sundays otherwise lunch and dinner during the week.

They started us out with a bread basket. Bread smelled and tasted as good as in Europe. New England Clam Chowder served in a bread bowl was spectacular and we loved their cod.

Great service, friendly staff and wonderful menu are those main three things we all look for when dining out. Joe’s Waterfront exceeded out expectations.

We got lunch at Ristorante Lucia Boston and loved it. There were a lot of staff members from Italy which solidified all the reviews we read about it. Wonderful Italian food, that is worth trying.

There were multiple restaurants that had no more than 6 tables inside and they produced lines of 20-30 people on a daily basis. Giacomo’s Ristorante in Boston’s North End was one of those places.

One of the days during our trip it was pouring and people were willing to keep standing to eventually dine in. I wonder if they don’t offer reservations or they just could boast of that high quality food that is worth getting wet for.

We had to find out for ourselves and Noah ordered us a take-out there. It was glorious, we walked up to the front door and the host handed us our order.

3. Stay in North End

One thing that really surprised me is that North End (unofficial Little Italy) has more than 110 Italian restaurants and it’s only a one square mile area that is adjoining the Boston Harbor. North End is this maze of narrow streets and stunning buildings where Europeans started settling in 17th century.

Even Boston Freedom Trail winds through some parts of North End.

Noah and I love harbor cruises, we do them every time there is a possibility.

4. Go on a Cruise

You get to experience a city from a different perspective and hear about historic milestones, both good and bad. Boston Historic Cruise didn’t disappoint, it was fully narrated and I learnt a lot of American history nuances that I didn’t know.

5. Go Whale Watching

The second option was a whale watching tour that takes four hours. It sounded intriguing but since we only had three full days we decided to walk the famous Boston Freedom Trail instead.

6. Walk Boston Freedom Trail

Boston Freedom Trail is a two and a half mile red-brick route that takes you to 16 significant sites that tell you a story of the American revolution. You will see and experience battlegrounds, cemeteries and churches.

They remain wonderful reminders of the events that have played a key part in the formation of American history.

We stayed at Battery Wharf Hotel. It looked very elegant and came with a view. I took a picture of it from the boat. Doesn’t it look lovely?

It was very convenient because the nearest metro station (Aquarium) was a quick 5-minute walk.

7. Take a Boston Mob Tour

There was one unusual thing we decided to do! We took a Boston Mob tour. I bet you saw Black Mass and The Departed many times and might have wondered about the characters involved and whether or not those movies were based on true stories. This tour showed me, that they really were.

It is a rather personal tour, where you get picked up in a limousine and there is a driver and a guide in the car.

You get to ask questions and receive a private lesson on this darker part of Boston history.

Our chauffeur took us through Southie, Boston Proper and North End and we learnt some shocking details about notorious crime families and even drove by James “Whitey” Bulger’s house, his liquor store and his hangout, where many people lost their lives.

Despite the tour’s focus on Boston’s crimes and darker history, we found the city itself to be refreshing and welcoming. From its rich culture to its beautiful sights, Boston has something to offer everyone.