Insider Tips on What To Do in Boston

What to do in Boston
Image: Dreamstime.com

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

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!

what to do in boston
Fenway Park

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.

what to do in boston
Kate in the Public Garden

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.

Check out the North End Pizza Tour and the city’s oldest neighborhoods

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.

Tours, Sightseeing & Passes

Viator is the industry leader when it comes to tours, activities, tickets and passes with a list of hand-picked tours and things to do in Boston from local insiders.

Check out the Boston City Pass and the Boston in One Day Sightseeing Tour.

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.

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:

Planning a Trip to Boston

Accommodation in Boston

  • Booking.com has 150+ properties in Boston including hotels, apartment, and hostels. You get free cancelation on most rooms and a best price guarantee.

Flights to Boston

  • Skyscanner is a comparison website that searches millions of flights. Once you find your best deal, book directly through the airline (no extra fees).

Car Rental in Boston

  • RentalCars.com is the world’s biggest car rental booking service that compares all the major brands like Hertz, Avis, Alamo, and Europcar.

Tours & Sightseeing

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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.

37 thoughts on “Insider Tips on What To Do in Boston”

  1. We drove through Boston a few years back on a car trip and intended to stop, but we were completely overwhelmed by the incredibly high cost of parking and the crazy congestion of downtown Boston at lunch time, so unfortunately, we got frustrated and never stopped 🙁 Public transit is DEFINTELY the way to go when we return!

    Boston has been high on my list of places that I want to visit for a while, now! Thanks for the great information!

    1. Yes, Shanna, parking is a nightmare during working hours. If you’re coming from the north, I recommend parking on the outer stops of the T. Alewife and Wellington always have tons of parking; other stops are more of a gamble between 8 AM and noon.

  2. Don’t care about the Red Sox, but want to see a game? Check the schedule. If they’re playing a non-rival that isn’t great, wait until the 2nd or 3rd inning and you can get really cheap tickets from scalpers.

    Just watch the first inning or two over at the Cask’n flagon and then buy your tix. Get the centerfield bleacher seats if you want that real authentic experience… but make sure you lather on the sunscreen.

    Oh… and go to anna’s taqueria before the game and sneak a burrito in… kill two birds with one stone!

    1. Awesome tip, Tony! Fenway also has a section for legal scalpers (who sell tickets at face value). If not, there’s a guy on the corner of Boylston and Ipswich who always seems to be selling tickets.

  3. Wow! I’ll definitely make a note of these tips for my next stay in Boston. I’ve been there often, but there are quite a few I didn’t know about. And I absolutely agree with your tip for a side trip to Rockport. This is a gorgeous place to visit.

  4. Pretty good collection of tips – I’m a huge fan of Anna’s Taqueria as well. Always made sure I lived within walking distance of one of ’em.

    Central Square is probably my favorite places to hang out, too.

  5. Oh I LOVE Boston. I lived there for a year when I was 21. A couple of other things I loved there was the Children’s Museum if you’re traveling with kids, and if you get time, head down/over to Nantucket Island. Not far, but also a world away. Such a pretty village-like atmosphere.

    I hope to bring my own kids back to Boston one day. Seriously one of my favourite travel spots so far

  6. Traveling to Boston in October haven’t visited in nearly ten years, We got a great deal with Tour America. Thanks for the tips they will come in useful.

  7. Boston also now has a fantastic bike share program – Hubway! My wife and I gave up the car a few months ago and now get around by foot, public transit, and bike. Winter makes it harder, but it’s totally doable – avoid a car in town at all cost!

    We’ve been so inspired by your blog and others – we are leaving for our own RTW trip in 2 short months! We’ll be keeping a blog and hopefully helping inspire others to do the same. Thanks for all the great info – keep it coming.

  8. Another fun, and educational, sidetrip is to Lexington and Concord. I went there last year and it was great. Both towns are really nice and beautiful. I especially liked walking around the Lexington Green where the Revolutionary War started. And there are old historical homes there.

  9. Another great side trip is to Lexington and Concord. Very pretty there and plenty to see. There are lots of historical buildings and parks. I especially like the Lexington Green.

  10. Great information about Boston. I went to school there and grew up in Maine – you should consider stopping by in the summer – amazing place.

  11. I’m going to Boston for the first time in August. I love history and so I’m going for all the historical things and the other fun ideas you mentioned above. This blog has made me even more excited about my trip! I want to tour the witch trials Museum in Salem. I wasn’t planning to rent a car when there for the week. What’s the best way to travel to the museum? Should I rent a car for a day? is it close enough for a cab? What are your thoughts? Maybe I should rent a car from the airport, go straight to the museum and then return the car before checking into my hotel.

    1. Corey– You can take the Ferry to Salem, depending on the time of the year. Driving in Boston is a nightmare with one-way roads and traffic and parking is expensive too. You are better off taking a ferry or seeing if you can get on a tour bus or something. I would think a cab both ways would be more expensive than renting a car though.

  12. Great tips! Another day trip idea is head south of the city to Plymouth which has a lot of great history, restaurants and more (although “the rock” itself is a little underwhelming)!

    I agree that there’s so many great festivals and events in Boston, it seems like there’s always something happening– especially in the summer with free and cheap events! I love all the North End Festivals in the summer too and free concerts 🙂

    1. Great Recommendations. I’ve not been to Boston yet, but it’s been on my list for a while. I’ll have to make a quick trip of it. thank you

  13. You didn’t cover anything about Boston Harbor. There are ferries, cruises, water taxis, the harbor islands and more. Especially if you want to avoid the Boston traffic and congestion.

  14. My daughter and I will be flying from MN to Boston , Aug. 9 -17,we are wondering where would be the best location to be centrally located to use public transportation? We would like to take one of the Boston Tours, a Red Sox Game, and go to
    Castle Island. What are your recommendations? Thanks for your help!

  15. HI Craig, thanks for your post. It is very informative and I like your picture a lot! I went to Boston several times but still found your post contains many places(especially restaurants) that I have never been to. Definitely will check them out when I am there next time. Also I think it is better if you contains the Waterfront in your blog, I think it is close by the Quincy Market, I actually found it from another itinerary couple of months ago and I didn’t notice this place till then. It is a good spot to digest the food after a big lunch at the market. 🙂 Thanks again.

  16. My wife and I are going this winter , regardless all the comments about avoid this season. Is it that hard ? We would love to see an NHL match and any other sport.

    We hope to manage with the public transport although we can easily rent a car. Then we might head to Vermont to the mountains for a lesson of skiing.

    Any advice is very welcome,
    Nice blog !!

    Agustin.

  17. If you’re going to the North shore and Salem specially you absolutely must go to Champions Pub in Peabody for their world famous melt in your mouth marinated steak Tips. Monty’s pizza in Lynn has unreal razor thin pizza that is too good to be true and if you have kids like I do know you have to take them to the Salem Willows for the popcorn and fun. Those were the best memories of my childhood.

  18. This insider’s guide of Boston is a gem because it covers all the bases. Whether you live here or are only spending a short period of time, there is something on here for everyone.

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