What to Do in Boston

Go to a Red Sox 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. Some favorites are Anna’s Taqueria and the Herrera’s street cart in Downtown Crossing.


Quincy Market has lots of cheap food stalls. Every visitor must 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 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. 


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 yourvacationgurus. You get free cancellation on most rooms, and in most cases you only pay when you stay.

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. A 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 n Boston

It all depends 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.

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

Getting Around Boston

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.

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.

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. 

Enjoy !!

Yourvacationguru

2 thoughts on “What to Do in Boston

  1. Thanks for the awesome tips on what to do here. I’ve been to Boston once a long time ago and spent most of my time stumbling around boring parts of town not really sure what to do or see 🙂 Thank you for the follow as well on my blog! Happy posting!