Useful Tips For A First Time Visitor to Boston

If you’re visiting Boston for the first time, you may be wondering what to expect, how to get around, or what you should see. It’s an amazing city, full of history and charm, and you’re going to love it! I recently completed my very own first visit and I want to share some useful tips for first time visitors to Boston!

Where To Stay in Boston

Boston is one of the most expensive cities in America. If you’re looking to stay in the heart of downtown, prepare to fork over some big bucks. If you can afford it, it’s a no-brainer to stay close to the main attractions, restaurants, and nightlife within walking distance. But, not everyone has the deep pockets to do so.

The good news is there are more affordable options outside of the city if you’re willing to use booking sites like AirBNB. I found a place about five miles east of downtown for around $120 a night. It was a bedroom in someone’s home but it didn’t matter because I only needed it to sleep for the night. Look for spots that are close to mass transit lines and double check with the owners to confirm how long the walk or taxi/bus ride is to get to the train.

In Boston, the commuter train is referred to as “The T”. You can find a schedule, map, and ticket prices on their website.

How To Get Around Boston For The First Time

If you’re having some anxiety about getting around Boston using the subway, fear not! It’s actually really easy. The “T” (the name of Boston’s transit system) is simple to navigate. If you have a car and don’t want to hassle with driving in the city, you can even park your car at local transit stations for a couple of bucks and then hop on the train into Boston.

Don’t hesitate to ask locals once you get to the train station if you’re unsure which direction the train is going. I found that people in Boston were pretty friendly! Google Maps is pretty useful if you already use their app for driving directions. It will tell you which train to take and the closest stop to your desired destination.

Boston is also pretty walkable, so once you’re in the general area of the city you’re trying to get to, you can usually get to your desired destination by foot.

Things To See in Boston If You’re Visiting For The First Time

Boston is full of history and loaded with so many exciting attractions that it’s impossible to see it all in one visit! Having said that, you can do quite a bit with a little planning. Try and group together attractions that are in the same general area instead of bouncing around all over town. (A good rule of thumb for any city visit!)

Some of my personal suggestions of things to see in Boston for first time visitors include:

1. Boston Common

A beautiful park in the center of downtown with walking trails, sculptures, fountains, and plenty of green space. You can also find vendors and of course, there’s great people watching. It’s also a good central location to begin your exploration of Boston if you’re a first time visitor!

If you're a first time visitor to Boston don't miss Boston Common
Boston Common

2. View Boston

Located atop the Prudential Center is View Boston – a 59,000-square-foot destination that includes an open-air roof deck as well as two dining options. As a first time visitor to Boston, you’ll enjoy panoramic views and have a chance to see how the city is laid out to help you navigate during your visit. You’ll also enjoy a few really cool immersive exhibits that are included with your ticket. You can save money on admission to View Boston as well as other top local attractions with a Boston CityPass!

View Boston – At the top of the Prudential Center

3. Fenway Park

Even if you are not a fan of baseball, Fenway Park is an amazing piece of Boston history and the stadium tour is really informative. You’ll have a chance to sit in the oldest seats in Major League Baseball; discover some behind the scenes trivia about the oldest professional stadium in the country; and see the field from the popular “Green Monster”. (If you don’t follow baseball, that’s the name of the towering outfield wall at Fenway Park. I’m normally too cheap to do a baseball stadium tour but ponied up for this one and it was pretty good. (FYI – Do NOT bring any bags or backpacks with you to the tour, they’ll make you pay to check them!)

Fenway Park in Boston

4. Cheers Bar

I’m a sucker for 80s television nostalgia, so you may want to skip this one if you never watched the sit-com. The popular NBC comedy was set in Boston and inspired by a visit to a local bar in Boston. You can visit the Cheers bar and take a look around even if you aren’t interested in eating or drinking. They do have a small gift shop if you’re looking for a keepsake!

Cheers is a must if you're visiting Boston for the first time
Cheers Bar in Boston

5. Freedom Trail Sites

Depending on your love of history, the Boston Freedom Trail is full of some pretty amazing sites you’ll really enjoy. One of my personal favorite spots is the Canary Burial Grounds which is where iconic Americans like Samuel Adams, Paul Revere, and John Hancock are buried.

The trail is easy to follow – there are markings on the sidewalk that lead you from site to site. In total, it’s about two miles of walking.

Samuel Adams gravesite in Boston

6. Have A Great Italian Meal in Boston’s “Little Italy”

I’ve been to a lot of cities but Boston’s “Little Italy” is truly hard to beat. Everything from the architecture of the buildings to the fresh, incredible smells of pastas and sauces waffling through the streets – it’s amazing! I would totally visit Boston again just to have another meal here.

I can certainly vouch for one of the restaurants – Quattro Ristorante & Grill serves up one delicious lasagna! I’m drooling just looking at this photo again!

Little Italy in Boston

Some Cool Places To See Just Outside of Boston

1. See The Secret Crypt Where Two Presidents Are Buried

This one’s located in Quincy, about 40 minutes southeast of the city. It’s also not really much of a secret, but definitely unusual. Located in the basement of United First Parish Church, you’ll find the tomb where two former presidents are laid to rest: John Adams and his son John Quincy Adams. You can also tour the homes where these men lived in the Boston area through the National Park Service.

2. John F. Kennedy Presidential Library & Museum

I’m a huge fan of presidential museums and the one in Boston dedicated to JFK is terrific! The building is spectacular as well. It’s located outside of the city near the campus of UMass. There’s a huge, free parking lot if you have your own vehicle.

3. Tour Harvard University

It won’t cost you a dime to walk around the historic campus of Harvard University. There are guided tours available if you have the time and plan ahead. Beware that parking is an absolute nightmare in that area, so taking public transportation to get there is a good idea.

4. Visit The Very First Dunkin’ Donuts Shop!

You’ll notice Dunkin Donuts EVERYWHERE as you travel through the northeast but especially in Boston where the company was founded. The very first store is still there, though it’s been remodeled a bit. Still fun to stop in and grab a donut if you’re in the area to say you’ve been to the place that started it all!

Final Thoughts For First Time Visitors To Boston

Boston is a really fun town and you’re going to love all of the unique experiences you’ll find. Just be sure to take the time to plan out your days to maximize your time and energy. Don’t be afraid to ask locals for help or guidance and enjoy one of America’s most historic places!

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