Insider Tips on What To Do in Boston From a local

Looking for travel tips on what to do in Boston, Massachusetts? You are in the right place!

As part of our city guides series, we interviewed Kate McCulley who grew up about 20 minutes north of downtown Boston.

Kate shares with us her insider tips on what to do in Boston for those looking for the Boston highlights and the best places to eat, sleep, explore, shop, and party.

What to Do in Boston for first time visitors

Go to a Boston Red Sox basbeall game!

Sing Sweet Caroline, do the wave, and start a “Yankees Suck” chant. Believe me, you’ll love it even if you’re not into sports — it’s a cultural experience!

Be sure to follow the Freedom Trail from Boston Common to the North End, or even the Charlestown Navy Yard if you’re up for a longer walk. It shows you most of Boston’s most famous historical sites.

Take a ride on the swan boats in the Public Garden if you’re visiting during the summer.

Best Neighborhoods to Explore in Boston

Boston is a city of neighborhoods. Be sure to check out the North End, Boston’s historically Italian neighborhood. Cross the river and get intellectual in Harvard Square.

The South End is a beautiful neighborhood and one that not a lot of tourists explore.

Where to Eat in Boston

If there’s anything I can talk about all day, it’s food in Boston!

It seems like Boston has a million burrito joints.

• My favorites are Anna’s Taqueria and the Herrera’s street cart in Downtown Crossing.
• Quincy Market has lots of cheap food stalls. I always make every visitor go to Modern Pastry in the North End — NOT Mike’s Pastry across the street — and have a cannoli. They make great chocolate cheesecake, too.
• Bottega Fiorentina is a shockingly cheap Italian restaurant and deli in the middle of pricey Newbury Street.
• Flour is an amazing bakery and they make killer homemade Oreos and cornmeal lime cookies.
• For a special night out, I LOVE Cuchi Cuchi in Cambridge. It’s the girliest restaurant ever — the staff wears costumes from the 20s-50s, they serve vintage cocktails and small plates from around the world, and the decor is eclectic and features a giant sparkly mermaid. Try the Guatemalan seafood avocado.
• A  few other great upmarket restaurants: Union, the little black dress of Boston dining (you’ll get it when you go there).
• Coppa, the best place for Italian cured meats and where I’ve celebrated my last two birthdays; and Toro, the city’s best tapas place and home to some incredible corn.

Where to Drink in Boston

• 28 Degrees is an incredibly stylish martini bar in the South End and home to the world’s best frozen Bellini. Be sure you check out the cool bathrooms, too.
• Eastern Standard is an upscale restaurant, but the bar is THE place to be for 25-40-year-old professionals on Sunday nights.
• Boston is covered with Irish pubs, both authentic and not-so-authentic — you’ll find actual Irish servers, bartenders, and musicians at The Burren in Davis Square.
• Where to Drink with the Locals in Boston:
• Hit up legendary sports bar Cask’n Flagon during a Red Sox game and you’ll REALLY get a taste for Boston!
• If the Red Sox are in town, check out the Bleacher Bar across the street — which is actually inside Fenway Park and lets you watch the game without paying for a ticket!

Where to Stay in Boston

The HI-Boston hostel is in a perfect location, right by Back Bay and Fenway Park. I should know, I used to live a block away.

For high-end, you need to go to the Liberty Hotel, formerly the Charles Street Jail. They have preserved the jail theme so well – the bars are called Alibi and Clink and feature jail bars and celebrity mug shots — and its style is off the hook.

It’s THE place to be most nights, particularly if you’re looking to pick up a surgeon or hedge fund manager.

For more places to stay in Boston choose from the largest range of hotels, apartments, and guesthouses with our partner Booking.com. 

Best Markets & Shopping in Boston

The Faneuil Hall Marketplace is loads of fun, though most locals wouldn’t be caught dead there. I kid, I kid. It’s fun.

If you’re into cool little boutiques and vintage shops, I recommend Newbury Street in Back Bay (closer to the Mass. Ave. end), Charles Street in Beacon Hill, and Tremont Street in the South End.

Events & Festivals in Boston

No city in America does the Fourth of July better than Boston, with the Boston Pops and Pops Goes the Fourth concert!  If you want to watch the concert on the Esplanade, get there early — think 9 AM — and stake out a good spot. Same for seeing the fireworks.

Marathon Monday, the day of the Boston Marathon, might as well be a holiday. Everyone goes to cheer the runners on. My favorite spot is at the final corner, on Boylston St. at Hereford St. in Back Bay — the runners get SO excited as they make that final turn.

Best Area for a Night on the Town in Boston

It all depends on what you’re looking for.

If you’re into live music, check out the further-out neighborhoods of Allston or Somerville. If you want to hit the big clubs, head straight for the Theatre District.

Personally, I love the hip atmosphere, cool restaurants, and smaller dance clubs of Central Square in Cambridge.

Boston is America’s Walking City. It’s very easy to get around on foot and the T (the subway), and I think that’s the best way to see Boston.

There’s nothing better than a stroll across the Mass. Ave. bridge and down Marlborough Street in Back Bay on a warm summer afternoon, admiring Boston’s beautiful architecture.

Finding WiFi in Boston

It’s not as good as I’d like, but it’s getting better. You’ll find WiFi in most cafes; restaurants are slowly catching up.

Websites & Resources for travel to Boston

Sign up for Gold Star Events before your trip — they have half-price tickets to sports games, museums, and performances throughout the city.

Favorite Side Trip from Boston

Drive up to the North Shore and see some nice seaside towns — Rockport, Newburyport, and Salem. My favorite town is actually over the state border: funky Portsmouth, New Hampshire.

Best Time to Visit Boston

Fall is absolutely beautiful with the leaves changing. Summer is very hot and humid — I personally can’t get enough of it, but it’s not for everyone.

Avoid winter if you can. The snow lasts all winter and makes it hard to get around on foot, which is a shame, as long walks are one of the pleasures of visiting Boston.

Getting There & Away

Flights to Boston: Budget airline Southwest now flies to Boston from all over the country.

You can also get super-cheap bus tickets from New York on the Megabus or Bolt Bus — the ride is about 4.5 hours.

The train is very expensive, but you can occasionally find deals from New York, Philadelphia, or Washington, DC.

Best insiders tip for Boston

Southwest Corridor Park. It was originally supposed to be a highway, but the highway never happened, so it became a park that winds all the way from Back Bay to Jamaica Plain.

In the Back Bay/South End portion, you’ll find beautiful greenery and dog parks sandwiched between rows of immaculate brownstones. It’s one of my favorite places in Boston to get away.

I Love Boston because …

It’s the best place in the world to take a long walk!

Boston Travel Videos

Need More Boston & Massachusetts Tips?

Start here:

• 17 things to do in Boston with kids
• How to see a Boston Red Sox game at Fenway Park
• Walking the historic Freedom Trail in Boston
• How to spend 3 days in Martha’s Vineyard

Planning a Trip to Boston

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BIO: Kate McCulley grew up 20 minutes north of downtown Boston. After college, she lived downtown for four years, and then quit her job to go traveling. Kate runs the popular solo female travel blog Adventurous Kate, the story of how a twenty-something girl from Boston decided to upend her life to travel the world.

Do you have any tips on what to do in Boston? Please share in the comments.