TRAVEL GUIDE TO BOSTON

You’ll find a plethora of things to do in Boston especially on your first visit to the city. I loved our time spent there because it’s not only full of American history, but it reminds me so much of New York City. You all know by know about my love for NYC and my husband’s distaste for it, but even he loved Boston. The city has all the makings of NYC but on a much smaller scale. It’s super easy to get around so having a car isn’t a must and it also has a sort of charm to it that you don’t get with NYC.

On your first visit, you’ll want to do some touristy activities that the city has to offer. Use this guide to discover the top things to do while in Boston for first timers. And, further down you’ll find a few recommendations on where to stay and eat that will get you out of your tourist comfort zone!

Disclosure: Some of these links are affiliate links, which means when you purchase something using these links, I may earn a small commission at no additional cost to you. However, I link these companies because I have used them or truly recommend them based on their quality and the experience I had.

BOSTON HOTELS

There are three neighborhoods of Boston that are great for first time visitors — Beacon Hill, Back Bay and North End. Most visitors choose to stay in Back Bay because of it’s proximity to attractions, shopping and restaurants. Similarly, Beacon Hill has everything that Back Bay does, but with it comes a higher price tag. Then there’s the North End for the history-buff’s. This area is also home to so many great Italian restaurants and some of the best bakeries. Take a look below at my hotel recommendations by each area:

You can also use the booking finder below to find the perfect hotel stay for you!

10 THINGS TO DO IN BOSTON ON YOUR FIRST VISIT

Whether you are looking for a weekend escape to a new city, a couples getaway or even a solo trip, Boston is great for all types of travelers. You’ll find something for everyone with a charming take on American history.

1. WALK THE FREEDOM TRAIL

The Freedom Trail is one of the most touristy things to do in Boston, which doesn’t make it a bad thing. Bryan and I really enjoyed this historic walk. The best part of this walk is it’s totally free and the city has made it super easy for you to do it on your own. All you need to do is follow the brick-lined path around the city starting in Boston Common. Each stop on the walk has a description of the historical significance making it easy to learn without a tour guide and go at your own pace.

If you want the full experience with a tour guide, check out these tours offered. You don’t have to do all the sights in one day, but most can be seen all in one. Below are a few of the stops you’ll see along the Freedom Trail.

BOSTON COMMON

faneuill hall

paul revere’s house & statue

2. CATCH A GAME AT fenway park

Aside from Wrigley Field which holds a special place in my heart, Fenway Park — the oldest in the MLB — is one of the coolest stadiums I’ve visited. If you are in the city during the MLB season, don’t pass up the chance to see the Green Monster. Even if you visit during the off-season, you can still get a tour of the park. Check those out here.

3. BOSTON MARATHON

My first visit to Boston coincided with the Boston Marathon because well, I ran it! While the end of that story isn’t my favorite (that’s a story for another time) it’s still so exciting to see how much the city celebrates this marathon. There is truly not another marathon like it and even if you are visiting when the Marathon isn’t happening, you can still check out the finish line. It gets repainted every year.

4. GRAB A DRINK AT CHEERS BAR

Sometimes you want to go where everybody knows your name, right? If you are in the mood for a pint, head to the Cheers bar where the show Cheers originally got their inspiration from. While definitely touristy, this is a no brainer on your first visit!

5. VISIT THE BOSTON TEA PARTY

As I mentioned, Boston is the city to go to if you want to indulge on all things history. For a brush up on your American history, you can check out the infamous Boston Tea Party that took place in the Boston Harbor. You’ll find the Boston Tea Party Museum here where you can learn all the juicy details of the tea party.

6. WALK AROUND BEACON HILL

Boston’s Beacon Hill is one of the prettiest areas in the city. Here you’ll find cobblestone streets, gas street lamps, historic brick buildings, boutiques and plenty of antique shopping. This area is very charming and makes for a great area to walk around and explore.

7. eat a world famous cannoli

While in Boston, do as the Bostonian’s do…or rather eat like they do? They don’t just have one world-famous cannoli bakery but they have two that are on the same street and are considered rivals. The debate on whether Mike’s Pastry or Modern Pastry has a better cannoli can stir up quite the argument depending on who you ask so naturally I had to try both. They each were great in their own way, but I have to go with Modern Pastry on this one. Sorry, Mike fans.

8. SHOP ON NEWBURY STREET

Hi, my name is Liz and I have a shopping problem. After a disappointing Boston Marathon experience, I had to indulge in some shopping. And, the best retail therapy was found on Newbury Street. If you love browsing boutique shops intermixed with great restaurants, coffee shops and larger retail stores like Zara then head to Newbury street. This area is very quaint so even if you aren’t in the mood for shopping, you can still head here for a leisurely walk while partaking in some window shopping. Some of my favorite stores were LIT, Pink Yotto, Bobbles & Lace, Tracksmith and No Rest for Bridget.

9. EAT AT THE OLDEST AMERICAN RESTAURANT

One of the coolest things about visiting historic cities like Boston is that you can experience things like eating at America’s oldest restaurant. Union Oyster House is your go-to spot for this experience. Enjoy some oysters and their classic clam chowder at this Boston staple. Although it’s the oldest American restaurant this doesn’t necessarily mean it’s the best — but it’s still worth a visit.

9. try the original boston cream pie

Rounding out my list of things to do in Boston for your first time is trying the original Boston Cream Pie. It’s been said that this dessert originated at the Omni Parker House so those with a sweet tooth should head here before leaving. The Omni Parker is also known for being a great hotel in the Downtown area although it’s on the pricier side.

where to eat & drink in boston

If your first time in Boston is full of touristy activities, it’s always nice to break those up with a few restaurants where you can eat good food and experience the city like a local. Take a look below at a few restaurants, coffee shops and bars that are worth a visit.

+ if you have more time in boston

For those who have more time to spend in Boston, check out some other activities you can do while in the city.

+ ISABELLA STEWART MUSEUM
+ BOSTON DUCK TOURS
+ HARVARD VISIT
+ MUSEUM OF FINE ARTS
+ GHOST AND GRAVESTONES TOUR

I hope you enjoy your time in Boston whether it’s your first time or 21st time. If you are looking for another historical city that has just as much if not more charm then check out my Charleston travel guide.

Questions? I’ve got answers. Reach out on Instagram!

happy travels, liz stanford

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