Boston With Kids: Fun Family Winter Break Activities

Guest Blogger: Ruth Mendes is a wife and mami of 4 active and globe-trotting kids (ages 12, 9, 6 and 4). She’s always loved a good adventure and truly believes that it’s possible to not only travel with, but actually enjoy exploring with children. Join her as she shares her family’s adventures and inspires you to get out of the house with your kiddos. Find Ruth’s blog at Have Kiddos Will Travel.

Thank you to the New England Aquarium, Boston Winter and Boston Tea Party Ships and Museum for providing four complementary passes for our family and to American Girl Boston for providing lunch for our family.  All opinions are my own.

Our Fun Family Boston Weekend

Winters in New England can result in a certain amount of cabin fever, which can only be exacerbated by a house full of young children. Our family’s solution is to bundle up and take advantage of the marvelous variety of fun family activities in the Boston area, which we did recently over our children’s winter break. Our trip ended up being the perfect opportunity to enjoy fewer crowds and unique outings in a quintessential New England city. With a mix of history, culture, restaurants, free and budget friendly activities, sports teams and museums, Boston is truly an amazing family travel destination.

Top Recommended Winter Activities in Boston

• Attend a Theater Performance: Boston is known for a variety of cultural theater experiences. During our trip, our family watched Urban Nutcracker which is just one of many family friendly theater experiences available. Check out this detailed list of family friendly theater options.
• Visit the Sea Life at the New England Aquarium: Boston’s New England Aquarium is located on the wharf, which is an ideal location for taking in many kid friendly Boston sites, including the Boston Children’s Museum, Legal Seafood and the Boston Tea Party Ships & Museum. In other words, the New England Aquarium is truly a great starting point for exploring Boston with kids! Plan on arriving early if you wish to avoid crowds and take advantage of several of the hands-on exhibits and staffed educational tables. The aquarium docents proactively went out of their way to interact with our children and, while this aquarium is not the largest in the New England area, I highly recommend it due to its location and the quality of the information provided by the staff.
• Step Back in Time at the Boston Tea Party Ships and Museum: From the moment that you walk up to the Boston Tea Party Ships and Museum, you will be transported back in time to the event that escalated the American Revolution.

• Experience Boston Winter: Boston Winter’s unique winter outdoor marketplace, located in the City Hall Plaza, offers an outdoor shopping market, ice skating loop and a wine tent. It’s conveniently located near many of the Boston attractions.  We enjoyed a Christmas Eve visit.

• Boston Children’s Museum:  Boston truly offers one of the best children’s museums and it’s a must see for families visiting the city.
  • Pro Tip: The museum offers discounted admission on Fridays between 5-9 PM when it’s $1 for everyone to enter.

Boston has many historic sites, including the Massachusetts State House, and as an added bonus, many of these historical stops are free! Be sure to:

• Explore Boston’s Public Garden:  Boston’s Public Garden is the first botanical garden in the United States. While you can ride the swan boats during the warmer months, ice skating is the main attraction in the winter.  This is a great place to enjoy the weeping willows and views of the Boston State House. No family trip to Boston would be complete without stopping by the statues honoring the Make Way for Ducklings book.
• Take a walk on the Freedom Trail: Some of our family’s favorite stops on the Freedom Trail include The Boston Common, The Massachusetts State House, Park Street Church, Old South Meeting House, Old State House, Faneuil Hall, Old North Church, the USS Constitution and the Bunker Hill Monument.

• Explore the Boston Omni Parker House Hotel:  The Omni Parker House Hotel is a historical landmark. The Hotel’s Parker Restaurant was where the Boston Cream Pie originated. Malcolm X was a busboy at the restaurant and President John F. Kennedy frequented the restaurant and hotel. This brochure provides information about the historical significance of this Boston Gem.
• Experience Quincy Market and Faneuil Hall Marketplace: The Quincy Market and Faneuil Hall Marketplace may be too touristy for some, but when visiting Boston during the holiday season with kids, you will want to stop by and enjoy the Blink light show and street dancers. Our kids braved the cold to watch the Blink light show, which runs from November 29th until January 1st every 1/2 hour from 4:30 – 10 PM.

• Explore the USS Constitution and Museum: The USS Constitution, which was nicknamed Old Ironsides, is the oldest commissioned warship afloat in the world and a real treat for families to explore. It is located at the Charleston Navy Yard.  Free admission is an added treat for those traveling with children.

• Eat and Shop at American Girl Boston:  While not located in Boston proper, those traveling into the city may consider adding a pit stop at American Girl Boston, a one of a kind store and restaurant, when traveling to Boston.

If you find yourself with extra time, there’s always more to explore in Boston! Check out Downtown Crossing, Boston’s Chinatown, Boston’s Harbor and Wharf, Harborwalk, Copley Square, Museum of African American History, Museum of Science, Charles River Esplanade, President JFK’s Library and Museum, Cambridge and Harvard Square.

Restaurants

I don’t believe in breaking the bank when traveling with four children. My dining recommendations include a variety of budget friendly eateries as well as restaurants.  This would not be my restaurant list for an adults only trip to Boston.

• Chau Chow City offers dim sum in Chinatown.
• Merengue Restaurant is a one of a kind cultural dining experience with its Dominican cuisine and is a must do if you have a car or are headed to the zoo.
• Barking Crab, with it’s convenient location near the Boston’s Children’s Museum, is a favorite for those times when your children need to eat now. While this Boston dive doesn’t offer a children’s menu, the selections are New England specialties that are favorites for kids of all ages. Our kids love the clam chowder and fish and chips while we adults indulge in lobster rolls.
• Maggiano’s Little Italy. On this particular trip to Boston, we experienced one of those family crisis moments when our kids were just “starving,” at 2 pm on Christmas Eve and we had originally planned on heading home to Connecticut for dinner. We decided to risk walking in to Maggiano’s without a reservation. The hostess laughed to my face, but I noticed an open 6 top at the bar area. Lesson learned, Bostonians don’t play with their Christmas Eve Italian dinner, and the restaurant is fully booked weeks prior to Christmas. We ended up enjoying an amazing family style Italian dinner prior to heading home to open our Christmas pajamas and tuck our kiddos to bed on Christmas Eve. Pro tip: they did have a kid’s menu, but we also recommend ordering family style as the portions are humongous which ensures that you will have leftovers for lunch the next day.
• Union Oyster House, a historical icon located just steps from City House Plaza and Faneuil Hall, with the Freedom Trail literally on it’s front steps. Where else can you combine history and delicious food while breaking bread with your kids at a restaurant where President Kennedy dined? Pro tip: go in between meal times to avoid huge crowds and stick to appetizers, like the clam chowder and calamari, to avoid sticker shock. You are truly there for the history and memorabilia, so no need to feed children 3-course meals while visiting.
• South Street Diner, an old school diner, is one of those experiences your children will talk about for years to come. It’s a typical American diner and local favorite, so take advantage of the fact that kids don’t know how to sleep in while on vacation and head early to ensure a table. You will love watching your kids experience folks sitting at stools and telling stories like family. The food is great and the value can’t be beat.
• Boston Chowda Co. We are complete foodies and thus our children have sophisticated palates and by the time they can sit up, absolutely love a good cup on New England Clam Chowder on a cold day. The Boston Chowda’s location in Faneuil Hall provides convenient access for a quick snack or pick me up in order to ensure that are kids have the energy to explore the city.
• Cask ‘N Flagon is a real treat for baseball fans.
• P.F. Chang’s is located in the theater district near Chinatown and the Boston Common. This chain restaurant provides consistent family friendly options when you need to feed a large family ten minutes ago.
• Abigail’s Tea Room is a budget friendly option for tea and light lunch.
• Yard House. With its proximity to Fenway Park, Yard House provides  great food, ambiance and a typical Boston experience for families. Take advantage of their weekday (3-6 PM) half price appetizer offerings.

Accommodations

Our favorite Boston area hotel for large families is Marriott’s Custom House. This Marriott timeshare hotel offers larger rooms and a prime walking location for families looking to explore Boston on foot.  Our room offered our family space to spread out with a king-sized bed in the main bedroom and a separate living room with a pull-out couch, table and kitchenette.

From the living room portion or our room, our view included Boston Wharf, Logan International Airport, the New England Aquarium and many more Boston sites.

We also enjoyed the amazing view of Boston from the Hotel’s 26th floor observation deck.

The Hotel’s dome was a sight to see.

The one-of-a-kind clock tower makes the Marriott Custom House identifiable from a distance.

Final Thoughts

Our winter break in Boston was fabulous.  We are glad we were not dissuaded from traveling by the cold temperatures.  If you have additional time and access to a car, we also enjoy visiting the nearby New Bedford Whaling Museum, Plymouth Plantation, Gloucester, Cape Cod and the Islands,  Old Sturbridge Village and the Decordova Museum and Sculpture Park. The towns near Boston offer a playground environment for families and thus if you have more than a weekend to explore, I highly recommend spending time in these nearby areas.

Boston is one of those great American cities we haven’t visited yet with our kids, but Ruth’s post was inspiring and now we can’t wait to plan our trip to visit this historic city!

Visit Ruth’s blog for additional details on their experience, including their visit to the New England Aquarium, the Boston Tea Party Ships & Museum, the American Girl Natick Bistro, and their stay at the Marriot Custom House.

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