top of page
  • Writer's pictureBrett Hayden

First Timer's Guide to Boston

Updated: Feb 11, 2022

If you love history, culture, and great food, you will love Boston. With history dating back to before the signing of the Declaration of Independence, there's so much to see, do, and learn in this city that it can be overwhelming to navigate. That's why I've created the First Timer's Guide to Boston, a central location for knowing where to stay, where to eat, what to do, and things to note about this great city. Let's jump right in!

Where to Stay

If there's one thing to note about Boston that's not so glamorous, it's that it can be expensive! I assume this is especially true during the month of October with travelers coming to see Salem, run the Boston Marathon, and enjoy the crisp autumn weather in New England.

For these reasons, consider staying outside of the downtown area. I highly recommend the Seaport District. It's a trendy neighborhood close to the water, felt very safe, and just a short transit away from everything you'll want to see. We opted for the Hampton Inn at Boston Seaport and were highly satisfied with our stay - one of our rooms even had an ocean view!

To be close to the airport, consider staying in the Revere area. Again, just a short Uber, bus, or subway ride from everything you'll want, and being close to the airport will save you some money heading out of town!

Where to Eat

If you remember nothing else from this post, remember this: eat dinner at Mother Anna's in the North End, you won't regret it! The Gnocchi Juliana was to die for, and I've heard from multiple trusted sources that the Linguine with Shrimp and Clams is incredible as well. Pair any of these with a bottle of their Pinot Noir, Votre Sante and end your meal with Mama's handmade cannolis. I promise you will be dreaming of this meal long after you leave the Bay State (I know I was). Not to mention, the ambiance of this little restaurant will make you feel like you got on the wrong plane and landed in Italy, it was so charming!

When visiting the East Coast it's only right to eat some seafood (or a lot of it). We had some amazing seafood at Boston's oldest restaurant, Ye Olde Union Oyster House. There's a reason they've stuck around since 1826! Treat yourself to a whole lobster and the house clam chowder, it's amazing. And of course, you can't go to an oyster house without getting some freshly shucked oysters! The Oyster House was one of John F. Kennedy's favorites when he lived in Boston, and you can even sit in his favorite booth. Pretty neat to know you're sitting right where our former president did all those years ago!

What to See

There are so many things to do in Boston that it's hard to narrow it down. Lucky for you I've created a free guide to seeing some of the best spots in Boston. You can sign up for my emails here and receive a free guide book and itinerary for the perfect week in Massachusetts! Here are the spots you'll hit in Beantown:

Freedom Trail

You can't go to one of the most historic cities in the country without taking a walk through the past. The Freedom Trail highlights significant monuments, buildings, sites, and museums that tell the story of the American Revolution. Much of the history dates back to before the United States as we know it existed (how exciting!). We thought the best way to experience the Freedom Trail would be on foot, so we opted for a walking tour. It was a 90 minute tour that took us to all the stops on the trail, explained their significance to the Revolution, and conveniently ended at the Samuel Adams taproom near Faneuil Hall (cheers!).


Being a history nerd myself, I knew I needed to see the oldest and one of the most prestigious universities in the country. On top of that, Harvard's campus is also beautiful and in such a charming part of the city. You can do a formal tour of the school, but we opted to just walk around the grounds, and may have snuck into a building or two, before buying an honorary Harvard sweatshirt at their bookstore, the Coop.

Cheers Bar

"Where everybody knows your name..." Well, not really. There were plenty of people in the "Cheers" bar and not one of them knew my name! It was still very neat to see both the historic bar that inspired the 1980s TV series "Cheers" called the Bull & Finch Pub, as well as a re-creation of the bar as it's seen in the show. I certainly was glad I went.

Fenway Park

If you're a sports fan, you're going to want to see America's "Most Beloved Ballpark." You can take an hour long guided tour of Fenway for just $21 and see the "Green Monster" up close. Just make sure the Sox aren't playing when you do!

Boston Public Library

The Boston Public Library is one of the most beautiful places I've ever seen. Amazing architecture, iconic study halls, more books than you can count, and a courtyard from a fairytale all reside at the Library. This is another one you can take a formal tour of, but we enjoyed exploring it on our own. Lots of students use the library to study and read, so be sure to keep quiet!

Brattle Book Shop

Book lovers, this one's for you! Brattle Book Shop is a partially outdoor book store that is home to many rare first editions. You'll find all of the greats and those long forgotten on this multi-level book store. I could've spent hours searching through the stacks and shelves at Brattle.

Beacon Hill/Acorn St.

To see one of the most beautiful and iconic neighborhoods in Boston, head to Beacon Hill. The neighborhood is home to the "Most Instagrammable Street in Boston," Acorn Street. Living up to its title, Acorn is a slim cobblestone street on a slight hill that is so picturesque that several people (ourselves included) were in line on both ends to take photos. One couple was even taking engagement photos in this spot while we were there. But don't worry, it wasn't overwhelmingly busy. Once you've snapped the perfect insta-worthy pic, stroll around the rest of the neighborhood and take in the beautiful architecture of the area.

Boston Common, Central Burying Ground, Public Gardens

You can't do anything in downtown Boston without seeing Boston Common. This spacious park in the heart of the city is where our Freedom Trail walking tour began, and happens to be America's oldest park. Central Burying Ground was established in 1756 in the Boston Common and is the rest placing of many notable historic figures. The beautiful area adjacent to the Common is the Public Gardens, home of the iconic Paul Revere statue.

Samuel Adams Boston Brewery

We had to make a stop a little south of the city to see where one of the most iconic Boston brews is made. Take a tour of the Samuel Adams Boston Brewery with a complimentary beer in hand and see the brewing process first hand. Then when you're all boozed up, make a stop at their gift shop and get some gear and souvenirs.

Tall Ship Boston Bar

After a long day of exploring, take a load off at one of the coolest bars I've ever been to. The Tall Ship literally includes a bar onboard a ship, and has panoramic views of the Boston Skyline. It's a must stop for sure!

Things to Note

You learn a thing or two via trial and error when you travel somewhere for the first time! Here's what I learned during my first visit to B-town.

Get a T pass

The T is Boston's subway, bus and train transit service. Trust me, you do NOT want to spend hundreds of dollars trying to Uber from place to place all week. Instead, opt for the $22 weekly pass and experience what it would be like to live in big city life for real. Everything you need to know about getting from one place to another using the subway or bus system you already hold right in your hand. You can use Google or Apple Maps to guide you through the transit system. Even if you've never used public transportation before, now's the time to give it a try, you may be surprised at how easy it is once you get the hang of it.

Wear comfortable (but cute) shoes

Even with the wonderful T, you will still need to do some (okay, quite a bit) of walking to and from the places you want to see. The fashion in Boston, and especially in the fall, is amazing, but don't forgo comfort just so you can wear those cute new booties. Go for comfortable shoes for the entire trip. You'll likely exceed your 10,000 steps for the day most days, so go easy on your feet!

Do you ever get that feeling that you wish you could reread your favorite book for the first time, or rewatch your favorite show as if you've never seen it before? I think that's how I'll always feel about visiting Boston for the first time. I had been dreaming about visiting this historic city all my life, and I wouldn't have changed a thing about my first trip.

I hope this guide has inspired some inspiration or ideas of what to do during your first (or tenth) trip to B-town. If you liked what you saw here, check out my First Timer's Guide to Salem, MA - the *perfect* side trip to take the next time you find yourself in the Bay State.

If you're thinking about planning a trip out to Massachusetts but don't know where to start, allow me to save you some research and planning by downloading my guide book and itinerary to a week in Massachusetts. All you have to do is head to my homepage and sign up for emails. A link to download the goodies will be in your inbox!

Happy travels!

178 views0 comments

Recent Posts

See All
  • Black Facebook Icon
  • Black Pinterest Icon
  • Black Instagram Icon
bottom of page