Visiting Boston? Here are 11 Things You Absolutely Shouldn’t Miss

Boston is undoubtedly one of the coolest places I’ve ever visited in the USA. If you’ve been following along with my blog or Instagram you’ll know that I am by no means a big city person, but the rich history, architecture, unique neighborhoods, and public green spaces in Boston won me over.

Last summer, in the middle of a humid heat wave, I spent a few days exploring Boston. Although my short amount of time was too brief to really get a complete feel for the city, I did manage to experience many of the sites that make Boston so appealing to visitors and locals alike.

If you’re planning a trip to Boston this year, here are eleven things you absolutely shouldn't miss!

1. Skywalk Observatory

The Skywalk Observatory at the top of the Prudential Tower is a must on a sunny day in Boston.

At 50 floors up you’ll have an unbeatable 360-degree view of the entire city and surrounding landscape. Audio guides with interesting facts and history about the city are available to listen to while you admire the views. If you'd rather grab a bite to eat you can ride up to the 52nd floor and dine in the Top of the Hub Restaurant.

For ticket prices and hours of operation check out the Skywalk Boston website.

2. BEACON HILL

Beacon Hill is one of the most charming (and expensive!) neighborhoods in Boston. Wander along the cozy cobble-stoned streets and admire the historic brick buildings, intricate doorways, unique door knockers, and hanging planters full of blooming flowers.

3. WALK THE FREEDOM TRAIL

A trip to Boston simply isn’t complete without checking out the Freedom Trail. The 2.5 mile (4km) long Freedom Trail is a self-guided walk that begins in the Boston Common and winds it’s way past 16 historic landmarks all the way to Charlestown.

You can easily walk portions or the whole trail by following the brick line and markers implanted into the sidewalk.

4. BOSTON COMMON

The Boston Common is the oldest city park in the USA and consists of 50 acres of land! It’s truly the perfect place to hang out and relax on a warm summer day.

The Common also marks the beginning of the Freedom Trail, and is a good starting point if you’re heading towards Beacon Hill.

Next to the Boston Common you’ll find the Boston Gardens, where you can take a ride in one of the iconic swan boats. For more information check out the Swan Boats website.

5. SAVOR A LOCAL NEW ENGLAND BEER

Craft beers are all the rage these days so don’t miss out on trying a few while you’re in Boston. There are plenty of New England breweries to choose from.

My suggestion? Whale's Tale Pale Ale brewed on Nantucket Island.

6. BLACK HERITAGE TRAIL

Shorter than the Freedom Trail, the Black Heritage Trail is one of those touristy must-do things in Boston that comes with a compelling history.

You can easily combine the Black Heritage Trail with a visit to the Boston Common and Beacon Hill neighborhood. You can find a complete map of the Black Heritage Trial here.

7. Fenway Park

Baseball culture runs deep in Boston. Fenway Park is the USA’s oldest Major League baseball stadium and home to the city’s beloved Red Sox team. All over Boston you'll find Red Sox logos and memorabilia, on cars, stores, bars, shirts, and hats.

If you’re interested in learning more about the history of Fenway Park you can book a tour here. If you’re in town when the Red Sox are playing you can book tickets to a game here.

8. Boston Cream Pie

Did you know a Boston Cream Pie isn't actually a pie, but a cake?

It's said that the first Boston Cream Pie was invented at the Omni Parker House Hotel in Boston in 1856. Today, this cream filled cake is the national dessert of Massachusetts and can be found all over the city.

9. view a different side of Boston with a Harbor Tour

Most Boston harbor cruises depart from Long Wharf and last approximately an hour, although you can book longer sightseeing and whale watching trips too.

The harbor cruises include live commentary about the history of Boston and the harbor. Be sure to get there early in the summer months, as this tends to be the busiest time. I enjoyed photographing Boston from a different perspective with a Boston Harbor Cruises tour.

10. Spend some time people watching on Newbury Street

Newbury Street is one of those places where I could have spent a whole day sitting in a cafe watching people pass by. One of the coolest places I found was Trident Booksellers and Cafe, like the name suggests it's a cafe and book store in one!

If sitting around all day isn’t your thing, you can also power shop through eight blocks of stores and boutiques.

11. Visit one of Boston's historic (and creepy!) cemeteries

Throughout downtown Boston you’ll find numerous burial grounds that are the final resting place of Revolutionary War-era patriots like Samuel Adams and Paul Revere. Boston’s historic cemeteries, and especially the eerily carved, decaying gravestones, completely fascinated me.

Notable cemeteries you should visit are King’s Chapel Burying Ground (the oldest cemetery in Boston and a site along the Freedom Trail) and Granary Burying Ground.

Where to stay

There are plenty of hotel options in Boston, but pay attention to location when you're making a booking. Although the prices may be a bit higher, it's worth being located in the city center within walking distance to most of Boston's attractions. My pick is the Sheraton Boston Hotel.