Insider's Guide - What to do and Where to go in Boston

If you're looking for a taste of New England's distinct four seasons, fresh seafood, history, and professional sports of all kinds, there's nowhere better than the city of Boston.

It's here that over 28 million people come to visit each year to explore each of the neighborhoods, check out museums and other landmarks, and enjoy Boston staples like lobster rolls, Fenway Park and the Freedom Trail.

This place is full of food, culture, and entertainment, making it the ideal spot for your next vacation! Here’s our ultimate guide to Boston for everything you need to know before you go. 

Sightseeing & Attractions

Freedom Trail

freedom trail boston Learn the history of America as you walk along the Freedom Trail. The trail is 2.5 miles long and runs from Beacon Hill to Charlestown. You can take a free tour or simply follow the directions and make the walk on your own.

Step inside the places where the American Revolution was launched, from pews and pulpits, private homes and public offices. Learn all about the people who shaped the US nation and experience over 250 years of history, as it began in Boston. 

The trail includes 16 important sites including Boston Common, Massachusetts State House, Park Street Church and more. 

Beacon Hill

beacon hill boston Beacon Hill, a neighborhood of Federal style row houses, is not only a historic part of Boston but also one of the most desirable areas to live these days!

It’s worth having a walk around the area to view its brick sidewalks and narrow streets with their prettily decorated lamp posts and fences.

As you explore the district, passing through Charles Street and Louisbourg Square, home to some of Boston’s most lavish properties, you’ll understand why it’s such a popular spot. There are also lovely cafes and shops to explore.

You’ll find the picturesque Acorn Street on Charles Street - Boston’s most picturesque street. Acorn Street is one of the most photographed streets in America. While it has recently become illegal to have a full-on photoshoot on Acorn Street, you’re welcome to bring your iPhone and snap a few pictures as you please. 

Fenway Park

fenway park boston While in Boston, you just have to go on a tour of Fenway Park, home to the famous Boston Red Sox. It will make attending future games even more fun!

Fenway Park is the oldest ball park in Major League Baseball history and, though relatively small and only able to seat 40,000 spectators, has certainly seen plenty of exciting baseball, soccer and hockey action, not to mention political and religious campaigns!

Fenway has hosted the World Series ten times, its inaugural season starting from the 1912 World Series. You will tour the stadium, visit the club house, press room, and the seats above the ‘Green Monster’ - nickname for the 37ft high left field wall - popular because it’s only 310 feet away from home plate.

Catch any number of sports games here from football to hockey to baseball (of course).

Skywalk Observatory

skywalk observatory boston For a magnificent view of Boston, head to the Skywalk Observatory which is the city’s only sky high vantage point offering a sweeping 360 degree view.

The Observatory is situated in the Prudential Tower (spoken of locally as ‘The Pru’). You can learn a lot about Boston’s history by listening to one of the available Acoustiguide tours (available in a variety of languages) which details the history of this great city.

Or you can simply enjoy the view! Visit during the day or in the evening, when you’ll be able to appreciate the glittering view of Boston lit up at night.


Boston Public Garden 

boston public garden

These charming public gardens were created in 1634 and modified in the Victorian Age, when over 80 species of plants from both local and varied locations around the city were introduced. Part of the Beacon Hill neighborhood, the Public Garden is the oldest public garden in America.

Vibrant floral patterns were created using new techniques of hybridizing and propagating, eventually leading to the importing of exotic trees and plants.

Stroll past the famous Swan Boats operated and created over 100 years ago, and take in the lake, fountains and variety of trees.

Bring your own picnic set up, or choose to eat at the rotating food trucks that come and go throughout the year.

The Arnold Arboretum

arnold arboretum boston This is a lovely spot to relax and enjoy a spot of lunch, or maybe you want to spend the whole day here. Harvard University’s Arnold Arboretum was designed by American landscape architect Frederick Law Olmsted and is the second largest ‘link’ in the Emerald Necklace, which consists of a 1,100 acre chain of parks that are linked by waterways and parkways throughout Boston.

The Arboretum consists of trees and shrubs from all over the globe which are all well marked and described. Follow the regular pathways or venture out to find your own route.

You can take the red line from Boston to Harvard, getting off smack in the middle of this elite university. Take a free walking tour of the school, then relax in the beautiful park. There are also tons of bars and restaurants to keep you occupied.



beehive boston

Located in the South End, Beehive is a lively restaurant with music every night.  Not only is the food great but the atmosphere is top-notch. If you can’t make it in for a full dinner, hang out at the bar and listen to whoever is playing for the night.  Or if you’re in town for brunch, stop by for their live jazz weekend brunch.

Neptune Oyster 

neptune oyster boston

Located in the North End, Neptune Oyster is the place to get the best, and most fresh seafood in Boston. Some say they serve the best lobster roll in all of Boston. While you’re unable to make reservations, the wait is totally worth it.


pomodoro boston

Also located in the North End, in Boston’s Little Italy, Pomodoro is a small, quaint hole in the wall.  With no sign above the door, Pomodoro is the perfect intimate setting for a romantic dinner outing serving fantastic Italian food.

Being such a small restaurant, the service is always extra incredible. Your wine glasses will never be empty and dessert on the house is often served to everyone!  Pomodoro is cash only but there is an ATM across the street.

The Friendly Toast 

the friendly toast boston

With multiple locations throughout Boston, The Friendly Toast is your go-to place for brunch!  Serving mimosa flights, bloody mary flights, and breakfast, lunch, and dinner all day every day, The Friendly Toast can conquer any craving.


Citrus & Salt

citrus and salt boston Located in Back Bay, Citrus and Salt is a Mexican tapas restaurant. With a quirky, edgy atmosphere, it’s a fun place to sip on cocktails at the bar as you watch the bartenders whip up endless margaritas.


drink boston

Located in Seaport, Drink is a menu-less cocktail bar. Describe to the bartender what you typically like to drink and they make it up for you!  While Drink doesn’t have a cocktail menu, they do have a wine and food menu.

Night Shift Brewing

 This place serves local craft beers in a lively atmosphere. Located in Everett, hang out at Night Shift more for the atmosphere than the beer.

But if beer really is your thing, be sure to visit one of the many Boston breweries. Most run tours that focus on the city’s popular brew/pub scene with the chance to learn all about the mechanics and history of brewing beer, as well as tasting some (lots)!

Enjoy learning all about the making of beer, talk with some brewery owners, participate in either a lunch or dinner and sample award-winning pilsners, stouts and other beers.

Samuel Adams runs a fun, interactive and free brewery tour that’s not to be missed! Led by people incredibly passionate about Sam Adams and the art of beer making, this is a fun way to spend the day rain or shine!


Newbury Street

newbury street boston

Newbury Street is referred to as the ‘Rodeo Drive’ of Boston. Located in Back Bay, you’ll find a number of stores ranging from designer to boutiques, and cheaper stores such as Nordstrom Rack. 

Quincy Market

quincy market boston One of Boston’s favorites, Quincy Market is located in a historic area constructed in 1824 and named in remembrance of Mayor Josiah Quincy, who had arranged its construction without any debt or tax. The colorful, always lively market is made up of interesting knick knacks, souvenirs and a fabulous food hall that has so many delicious options you really will be spoilt for choice.

There are even tables set up for chess and other board games you can play. And for all of you “Cheers” fans out there, there is a replica of the famous bar there too!