Boston is a city of World Series champions, and I’ve long been a champion of Boston as a winning city to visit! Have you been to Boston? It may seem like a strange question, but I find that a lot of people haven’t been to one of my favorite cities. I’m not exactly a tourist there, and not exactly a local, either. I’m sort of an in-betweener because I went to college there and lived in Boston after that, so I know the area really well. 

I’ve been on a kick lately of spending more time in East Coast cities that I love. Boston is for sure one of my top five favorite American cities. Here are some of my choices for places to see. There’s a ton of history to explore in the Boston area, but I’m skipping those more obvious sites, and suggesting some that are a bit more off the beaten path. And we’ll get to food and coffee in a minute!

The Boston Public Library system was founded in 1848, so the original building is a classic architecturally wonderful structure. It’s on Boylston Street. Between 2013 and 2016, it was renovated and a modern extension was added. It’s awesome! Often times I find library renovations, or even new library buildings, like the one in San Diego, lacking in design, lighting, spaces for working and reading, and a generally welcome feeling. The addition to the Boston Public Library gets two thumbs up from me. Do stop in and see for yourself.

While we’re on the topic of libraries, the Mapparium at the Mary Baker Eddy Museum is a phenomenal site. It’s hard to describe because it’s a three-story-tall map! The whole Christian Science complex is going through a major renovation right now, but the Mapparium and museum are indeed open. Check the hours before you go, as they are closed on certain days and close early on others. It’s an easy walk from either the Copley Station T line or the Symphony stop on the Green T line.

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While you’re in the area of the Boston Public Library and the Mapparium, I have a store for you to visit. And it’s in a mall. Yes, me, the stay-out-of-the-malls-and-walk-the-streets traveler loved EATALY. It’s everything Italian under one roof and I mean EVERYTHING. The Prudential Center Mall used to be a place filled with offices, but over the years, the ground floors have been filled with retail shops. That doesn’t interest me, except for Eataly. If like me, you’ve been to Italy lately, it will make you start reminiscing about your trip. If you haven’t been to Italy, Eataly will make you go home and book your trip right away.

You’ll for sure visit the Boston Commons while you’re there. It’s not the biggest city park, but it’s charming with lovely gardens. Don’t miss the statues from the book Make Way For Ducklings!

Sometimes when a hotel’s architecture strikes my fancy, I like to wander into the lobby and see what it looks like from the inside. I did this at the Boston Harbor Hotel and I found an exhibit that I want to tell you about. I like history and geography, and in the lobby, I found an amazing exhibit. Four huge walls were filled with lots of old maps of Boston! If you’re interested in this kind of thing, stop into the hotel. It’s an exhibit that lives at the hotel so it will be there whenever you go.

• If I’m paying cash for a hotel stay, I always use Pruvo to monitor for price drops!

The New England Holocaust Memorial is outside and down by the Boston Harbor. It easy to miss because it’s in the midst of all the harborside shops, so you may have walked right by it and not noticed. It’s a series of towers, each representing one of the extermination camps, and rather than listing names of those who were killed, it lists identification numbers. It’s a powerful site to see.

I’ve got three walks to recommend because Boston is a walker’s paradise. I averaged about 11 miles a day and one day I walked 16 miles!

Along the Charles River is an esplanade. There are many entrance points, but I like to enter off Massachusetts Avenue and walk towards downtown. It’s beautiful. There are plenty of benches to stop and relax for a bit, lots of grassy areas for a picnic, the public restrooms are clean, there are huge playgrounds for kids, and it’s always fun to people watch, too.

My next walking suggestion is to exit from the Boston Commons and start your walk along Commonwealth Ave. Most people head to Newbury Street because that’s where all the shops are. However, Commonwealth Ave has a tree-lined walking path right down the middle of the avenue that is filled with statues and benches that make for a great stroll or run. Don’t miss this. It’s usually only the locals who walk here, so even on a Sunday, it’s not very crowded.

You’ll likely be in Cambridge at some point during your Boston holiday, so if campus is not too crowded, walking through Harvard’s campus is nice to do. Even walking the perimeter of the campus and staying on the streets gives you a good sense of the area. It’s beautiful and historic!

Now can we talk about food in Boston??

For me, it’s all about fish and Italian food. The fish in Boston, anywhere you order it, is great! I’ll keep it simple. Head to Boston’s North End. You’ll be there anyway if you see any of the Freedom Trail and other historical sites. Though I do have my favorite places to eat, trust me, it’s all good. Polcari’s Coffee is a market that has been there since 1932. It’s a fun place to stop into. Even if you get food to go from any of the North End restaurants, there are plenty of parks and benches in the North End where you can sit and eat.

Do not leave the North End without going to Mike’s Pastry for a cannoli. DO NOT! Do not let the crowds deter you. The lines move FAST. It’s cash only, but forgoing the points on your credit card is OK, trust me! You’ll be elbow to elbow with a hundred of your new best cannoli-eating friends, so laugh it off and enjoy it. Yes, I know they just opened a new store in Harvard Square. I’m a North End snob, so get your cannoli there, not in Harvard Square :)

Like lobster? Good! Here’s my spot for your lobster roll. James Hook is not in the North End, but rather more towards the seaport area. It’s actually just past the Boston Harbor Hotel. It’s been there since 1925 and looks like a temporary trailer, but it’s not. You eat outside at their picnic tables. There are plenty of other places for lobster rolls and the prices are all pretty much the same, but I prefer this one for both the lobster roll and the fun ambiance. And don’t forget to request they grill your roll – it tastes better.

I’m going to stray from fish for a minute and admit to finally having tried Shake Shack. There’s one on Newbury Street and I’ve never been hungry when I’ve passed it. But this time, I didn’t eat breakfast and planned to have Shake Shack for an early lunch. I was hoping it wasn’t crazy crowded as it usually is, and I lucked out. We were even able to get a table with no waiting! I very rarely eat burgers out. I had a burger, fries, and a chocolate milk shake. ALL very good. The small milk shake was enough for two! I’ve heard people say it’s like the East Coast version of In-N-Out Burger. I think Shake Shack is much better!

Here’s my hotel choice when I’m in Boston, and here’s where to get the best coffee in Boston  and in Cambridge.

Hope these suggestions make for a fun time in Boston. Let me know what you have to add to this list!