Give us a little more information and we'll give you a lot more relevant content
Your child's birthday or due date
Girl Boy Other Not Sure
Add A Child
Remove A Child
I don't have kids
Thanks For Subscribing!
Oops! Something went wrong. Please contact

How To Take A Family Vacation In Boston Like You Know A Guy Named Sully

Flickr / hjl

Boston is about more than just the three Rs: Red Sox, Revolutionary War, and dropping your “Rs.” It’s also a beautiful, walkable city that is at its best when those 152,000 college students skip town every June.  If you’re going with kids, you probably want to avoid splashing around on a Duck Tour, buying Cheers merchandise, or fighting with fanny pack gawkers at Faneuil Hall. Here are a few ways that one wicked local dad spends his time — and there are zero instances of parking, Harvard, or yards.

All hotel and restaurant recommendations come care of the family travel experts at Passported; check out their full Boston guide here.

Tips From A Local Dad
Casey Soward is the father of 2 and Executive Director of the Cabot Theater in Beverly, MA — a newly renovated historic theater that is becoming one of the best (and most intimate) live music venues in the state. When his kids aren’t watching from the wings, you can probably find them at one of these kid-friendly activities.

Hit Christopher Columbus Park: You’re probably already down by the wharfs to go to the aquarium, so why not get some fresh air at a park with a stellar harbor view? “This place has it all,” says Soward, “It’s a great park with a playground overlooking the ocean, essential public restrooms, and the North End, Faneuil Hall, and the carousel are just a short walk away. Also, if you’re a single Dad like me, it’s a great place to chat with interesting women from all over the world.” If you’re not a single dad like him, forget that last part.

Science The Hell Out Of It At The Museum Of Science: You could either go over to Harvard and beat up some smart kids — or you could encourage the smartness in your own. “You can easily spend an entire day here learning about the human body, electricity, taking in animal shows, or seeing some of their cool IMAX movies,” says Soward. They also validate parking, which, in Boston, is worth the price of admission.

Take A Cruise On The Boston Harbor Islands Ferry: “For the price of one ticket, you can spend an entire day island hopping around these cool and unique islands,” he says. “If the kids get bored at one, you can just keep jumping around.” Plus, you can turn it into the family-friendly booze cruise it wasn’t intended to be: “The boats have an unexpectedly great selection of craft beer.”

Spend The Day At Peabody Essex Museum: A lot of museums are great for inducing naps in both kids and adults. Not this one. “It’s one of the great art museums in the region with one of the largest collections of Asian Art in the world. It also has a Maker Lounge, where you can design or tinker with innovative projects as a family, a huge LEGO collection, and the only complete Qing Dynasty house outside of China.” Is it made of LEGOs? Sadly, no.


Charles Hotel
How To Take A Family Vacation In Boston

  • The 294-room Charles Hotel sits in the center of Harvard Square, a few blocks from campus and surrounded by the area’s shops and restaurants.
  • Decor tends towards New England traditional, with black-and-white checked quilts and Shaker-style furnishings.
  • Despite the city setting, the Charles has resort-style amenities, including four restaurants, a huge health club, indoor lap pool, a spa, and hair salon.


  • Families of 4 who want separate sleeping areas should book connecting deluxe rooms.
  • Cambridge suites have a sofa bed and separate king bedroom, but the parents’ area is separated by folding doors and lacks windows.
  • Boston suites are the first category of suite with a truly separate bedroom for parents and sofa-bedded living area for children.


  • The Charles is the place to stay in Harvard Square, so expect to see visiting professors, parents with entering freshmen, and corporate recruiters looking for the next round of hires; it feels truly connected to the university.
  • The indoor pool has set hours for family swim and is good for serious lap swimming at other times.
  • The hotel’s restaurants range from gourmet to casual and all are delicious, so on a cold day, there’s no need to venture out for dinner.


  • Bathrooms don’t have the spa style of a Mandarin Oriental, but they’re perfectly modern, down to the television screens in the mirrors (cartoons make bath time manageable).
  • Downtown Boston and the historic city sights are require taking the T or a 15-minute taxi ride.
  • Design isn’t particularly memorable, but don’t miss the fantastic art, particularly the Doug Hilson chalkboard-style portraits of Harvard luminaries.

Four Seasons Boston
How To Take A Family Vacation In Boston

  • Overlooking the Public Garden, the Four Seasons has one of Boston’s most coveted settings with beautiful city and park views.
  • The hotel’s 273 rooms feel like a stylish Beacon Hill apartment, with crown moldings, French doors in the suites and New England plaid accents in bed skirts and curtains.
  • Amenities include a sizeable gym, an indoor pool, a restaurant and lounge, and complimentary coffee and pastries daily plus car service for drop-offs in a 2-mile range.


  • One complimentary rollaway or crib can be added to any room category.
  • Families of 4 should book either connecting deluxe rooms or an executive suite with a sofa bed.
  • For more space, the executive suites can connect to a deluxe double room to create a large 2-bedroom suite.


  • The location by the Public Garden and Boston Common puts families easy walking distance to the city’s main sights, restaurants and shopping.
  • The indoor rooftop pool has great views and is full of splashing tots year-round.
  • The focus on children extends to the grab-basket of toys offered upon check-in, complimentary weekend cookie-making classes and a “Raid the Kitchen” invitation to literally “raid the kitchen” on Friday and Saturday nights.


  • The hotel’s restaurant feels formal, but there are plenty of more casual options in the neighborhood.
  • The Four Seasons lacks a full-service spa, but there are great day spas in the neighborhood or the concierge can arrange for in-room treatments.
  • Parking is expensive, but there’s no need to rent a car when staying in central Boston.

Langham Boston
How To Take A Family Vacation In Boston

  • Langham’s Boston location sits in the city’s financial district, a few blocks from the train station and the seaport.
  • The 318 rooms have a classic look and traditional furnishings, with the best views overlooking Post Office Square.
  • Weekends at the Langham are for serious eating, starting with the famous chocolate bar (over 100 kinds of chocolate treats) at Saturday lunches. Sunday brunch includes live jazz. Work it off in the lap pool and fitness center.


  • Loft rooms have a king bed on the upper level that overlooks a living room with a queen sleeper sofa.
  • Superior or deluxe rooms with 2 double beds can sleep a family of 4.
  • Larger families can spread out in a one-bedroom suite, which can have two double beds in the bedroom and a queen-sized sofa bed (sleeps up to 6).


  • Kids will love the hotel’s retro pink taxi, which offers free rides within 2 miles.
  • The heated indoor pool is nice for a splash year-round.
  • The Chuan Spa has therapists specially trained in Chinese medicine (the Langham brand is headquartered in Hong Kong), and their holistic treatments are top notch.


  • The financial district location lacks the charm of Back Bay, and the maze of narrow streets can be difficult to navigate; take a taxi rather than driving yourself.
  • The city’s main historic sites and the prime dining and shopping neighborhoods are longer walk or taxi ride away.
  • During the week, the hotel feels more business focused and is popular with executives, but weekends have the leisure-oriented crowd.


Henrietta’s Table
Casual and kid-friendly in the Charles Hotel, excellent breakfast and brunch.

The Barking Crab
Open-air seafood shack for fried clam sandwiches near the ICA.

Thinking Cup
Coffee shop with pastries and sandwiches, good for a pick-me-up while shopping Newbury St.

Regina Pizzeria
A classic pizzeria in the North End, open since 1926.

Date Night
Craigie On Main
An upscale take on comfort food near Kendall Square, reservations are a must.