Travel Guide: Summer in Boston (with a toddler)


My heart is in Boston. I absolutely love this city, and always have. My father grew up in Scituate, MA and we travel to the Cape annually for our summer vacation. In 2009, my parents bought a house on the Cape and in 2010 my sister officially started paying state income taxes to the Commonwealth, so we are there a lot.

While you can totally have a glam, adult-only experience, Boston is actually very kid-friendly. It’s a walking town, so as long as you’re prepared to walk, you can enjoy a fun day or week in Bean Town. And for the record, this is a summer travel guide, because you may be disappointed if you try to see a Red Sox game in January.

The Locals:

People from the Commonwealth of Massachusetts are… well, have you heard the term “Masshole?” All jokes aside, Bostonians are friendly, helpful, hard-working, but take no bullshit.  Also –  they talk funny.

The Lay of the Land:

Boston appears much larger than it is. You can easily get around to the many neighborhoods on the transit system (the “T”) or walk! Uber, taxi, and the hop-on/hop-off trolly are all good options to get you around town.

Back Bay: You know you’re in Back Bay by the neatly laid-out streets (in alphabetical order) on a grid. It starts from the Public Garden and heads west along the Charles River toward Fenway.

The South End: A hip neighborhood with amazing architecture that used to be a little rough, the LGBTQ community has regentrifyed the area and now it’s fully of  great restraurants, bars with an emphasis on the arts.

The North End: Little Italy and very authentic. If you walk the Freedom Trail, you’ll end up here for some amazing historical sites, but make sure to enjoy the Italian culture, specifically the food!

Beacon Hill: A quaint area east of the Charles and west of the Common. Known for the winding cobblestone streets, and very, very expensive homes.

The West End: The neighborhood along the Charles northeast of Charles Street. It has little pockets of residential, government, and retail.

South Boston (“Southie”), East Boston, Roxbury, Brookline, Fenway and Charleston: Neighborhoods surrounding the area saturated with the most attractions. All have something to offer, but if your time in the city is limited, focus on the neighborhoods listed above.

The Seaport: the newest neighborhood. In the last 10 years, we lost Jimmy’s Harborside and gained a lively, trendy neighborhood with great night life.

Where to stay:

Boston Marriott Copley: (Back Bay) Connected to an indoor mall, which is perfect for rainy day activities or just getting to the pedestrian areas without having to cross busy traffic.

Boston Harbour Hotel: (Downtown) Beautiful and luxurious. A fixtures the Boston Harbour skyline.

The Liberty:  (West End) A short walk to Beacon Hill, the Public Garden, the Common and Back Bay. It’s an old jail, and one of the coolest hotels in Boston.

The Seaport Hotel: Right on the Seaport and a short walk to Back Bay and Downtown.

Where to eat:


Tatte. (Beacon Hill and Back Bay): Let’s just say that I may have planned a “surprise trip” to Boston to see family just so I could go to Tatte.

The Paramount (Beacon Hill and Southie): You may see some locals at this legit diner. Don’t be overwhelmed by the line – Bostonians know how to get in and get out, so you’ll find a seat.


South End Buttery (South End): I famously notoriously got picked a very big fight with my now-husband here and we still had a great meal. See, for brings people together.

Stephanie’s on Newbury (Back Bay) or Stephie’s on Tremont (South End) or Stephie’s in Southie: Their tagline is “Sophisticated Comfort Food”… sign me up.

Salty Pig: (Back Bay) Meats and cheeses. Where can that go wrong?


Note: Make reservations!

This is where you may run into some issues with kids as most of the good restaurants will be small and intimate, meaning – hard to accommodate kids. I did my best, but here are the best restaurants if you can get a sitter, and check out my post about out-of-town child care when you travel

Figs: (Beacon Hill) Pizza, but better. It’s a small restaurant, so it’s tough with kids BUT they do carry-out. Worth having a picnic in the Common or your hotel room.

Papa Razzi:  (Back Bay) Family-friendly Italian that’s actually really good.

Union Oyster House: (Downtown) The oldest restaurant in town and arguably the best oysters.

Legal Seafoods: (All over) Really good, fresh seafood.

Abe & Louie’s (Back Bay): A good steak house with all the accoutrements.

Joe’s American Bar & Grill (Back Bay and Downtown)  Just like it sounds.

Sweet Endings:

Modern Pastry: (North End): Everything you would expect from world-famous Mike’s Pastry, but better.

Emack & Bolio: (Backbay) Delicious ice cram.

Taiyaki NYC (Seaport): A new spot with ice cream in fish-shaped cones.

J.P. Licks: (Beacon Hill) Considering how prime the real estate is on Charles Street, this ice cream parlor must be killing it.

What to do:

Catch a Game at Fenway: Even from the nose-bleeds, being in the presence of the Green Monster is totally worth this once-in-a-lifetime experience.

Walk the Freedom Trail: It’s not as long as it appears and it’s totally free! (Don’t get tricked into paying for a tour) Start in the Common, and you’ll pass some incredible land marks. Make a detour at Fanueil Hall and Quincy Market for lunch. Don’t miss the street performers too. Finish at Paul Revere’s house in the North End so you can have a great reason to have dinner there.

A museum: The Museum of Fine Arts, the Boston Tea Party Museum, Boston Children’s Museum, Museum of African History, Harvard Museum of Natural History…  JFK Library, Old North Church…so many. History is so well-preserved in Boston. Learn something new!

What you cannot miss:

Quacking on a Duck Tour: It’s cheesy, it’s awkward, it’s the perfect thing for a toddler or any kids and you see so much, including the view from the Charles River!

A walk down Comm Avenue in Back Bay. Some of the most incredible homes line the avenue, which has a beautifully tree-lined walking trail in the middle. Grab a snack then burn off some energy with a nice long stroll.

The Make Way for Ducklings Statue in Public Garden: The Public Garden, not to be confused with the Common (just across the street) is glorious in summer. The swan boats can take you for a ride around the lake and there are some picture-perfect spots all over the garden. In the northwest corner, you’ll find Mrs. Mallard and her seen ducklings (Jack, Kack, Lack, Mack, Nack, Ouack, Pack, & Quack, of course). If you’ve never read the book, grab a copy on Charles Street, on the other side of Beacon Street or right here.

Pastries in the North End: (See above)  Enjoy the rich Italian culture of the North End with some home-made pastries. The entire family will enjoy!

Seafood: There are so many great restaurants. Everything is fresh and delicious.

What to do is weather ruins your plans:

See the Penguins at the New England Aquarium: This amazing facility has a wide variety of sea life with a focus on education.

Sam Adams Brewery Tour: (Outside the city): You may need to grab an Uber or hop on the Orange line, but its the perfect rainy-day activity if you like beer. Don’t worry, kids get root beer.

Going to Boston? Tag me @mrsmakeitrainka and let me know how you liked it! Safe travels.

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I'm an award-winning, expert attorney in Jacksonville, Florida. I represent professional women and their families who are injured or arrested in Florida. I love my job and am proud to have a career, but when I became a mother, I learned that working moms are uniquely tasked with having to achieve "balance." (whatever that is.) What I really wanted was freedom - freedom to practice law in a way that works for me and my family. Through the support and advice of other working moms, I have found success by developing a personal brand that allows me to create my own clients and practice law in a way that gives me freedom. Now it's my turn to help other lawyer moms learn how to do the same and make it Rain(ka).