Insider’s Guide to Summer Fun in Boston with Kids

Summer happens to be my favorite time of year to visit Boston with kids. After a long winter, the city comes alive with summer activities. People are ready to be outdoors again and embrace the warm weather, creating an air of celebration that takes over the city.

Boston strikes the perfect balance between being educational and entertaining for kids.  You can sneak in bits of colonial and revolutionary history and children of all ages barely notice! When asked to share some of our experiences for Expedia’s Kids in the City program, I decided to focus on the unique summer activities that can help make a family vacation in Boston more memorable.

On the Expedia’s Kids in the City Boston page, I compiled an extensive list of what to do, where to stay and what to eat while visiting Boston.  Take note! Here are some additional summer family-friendly activities in Boston to consider …

Strolling through Faneuil Hall and Quincy Market.

Historic Charm on the Waterfront

We like to start our family time in Boston the Waterfront area.  Not only is this area packed with historic charm, but it’s also easy to navigate with kids. The new Rose Kennedy Greenway is a kid-friendly walkway that connects a few key spots like Faneuil Hall, New England Aquarium, and the North End.  This walkway also has sculptures, a carousal, a water fountain, and occasional food trucks, making it both beautiful and functional.

A fife and drum band marching through Faneuil Hall.

Festival Fun

We always try to time our summer visits with Boston’s unique local festivals.

Boston Harborfest. A week-long series of events starting June 28^th celebrates Boston’s colonial and maritime heritage.  With over 200 events, there are plenty of activities to entertain all the family members.  Don’t miss the re-enactments, Chowderfest and the tall ships, including the USS Constitution, that sail through the harbor.

The North End Cultural Festivals. The North End, Boston’s Italian neighborhood, is a year-round favorite of ours.  Even if we are just running into town for a doctor’s appointment, we make a point of stopping by to get some fresh pasta from DePasquale or Cannoli from Mike’s Pastries.  However, in the summer it’s even more enjoyable, as the weather is conducive to leisurely strolling around this authentic corner of boston.  We get a bite to eat here and there and just people watch.  I love to spy neighborhood ladies peering out of their apartment windows.

Multiple Italian festivals are popular in The North End when they close the streets to cars and only allow pedestrians. There is music, carnival rides, amazing food, and fun crowds. It’s our little slice of Italy while on US soil.  Check the North End Festival website for the most new dates.

The daily menu at DePasquale’s.

Jammin’ Out

Just walking down the streets, you’ll hear fife and drum bands, bagpipes, drum groups and the like.This lively time of year is perfect for relaxing and taking in some local music.

When staying at the Boston Harbor Hotel, we enjoyed the Summer Series, live music that they play weekdays on their terrace.  Some of the music appealed to my kids and some did not — it was hit and miss.  What is guaranteed, however, is the relaxed atmosphere overlooking Boston Harbor.

Another spot to hear some great music is walking around Faneuil Hall.  During the summer nights, the restaurant windows are all open and you can see the musicians at various pubs.  It’s an easy place to grab a bite to eat from one of the many food stations, then sit next to whatever entertainer you would like to watch.  My kids adore street entertainers.  Usually, there is a great break dancing group that flips, jokes and keeps the kids completely enthralled.

Having fun in the fountain on the Rose Kennedy Greenway.

Cooling Off

Okay, Boston summers can get hot … steamy hot. Add sightseeing and families definitely need some ways to cool off.  Our waterfront favorite is the splash fountain on the Rose Kennedy Greenway.  Kids have so much fun here.  Be sure it’s either at the end of the day or that you have access to a place to change because they get soaked.

Boston Common attracts tourists and locals alike to splash around in the Spray Pool. Starting June 27^th, the Spray Pool opens at 11:00 am each day. There’s even a lifeguard on duty and a snack shop.

Pools are ideal for summer travel.  Whenever we stay in a city during the summer, a pool is a must.  It gives the whole family a break, refreshing anyone who may have gotten grumpy during touring — including parents.  Boston has an extensive collection of family-friendly hotels with pools including: Boston Harbor Hotel, Intercontinental, Seaport Boston Hotel, Four Seasons Boston, and The Colonnade.

Inside Scoop: Boston takes its ice cream seriously. People are often found arguing about which of the local shops makes the ultimate ice cream.  One thing is for sure, you will have plenty of chilly options.  We love Gigi’s Gelateria in the North End, JP Licks in Back Bay. Toscanini’s makes a trip to Cambridge worthwhile.

Enjoying a gelato at GiGi’s Gelateria in the North End.

For great coverage from some of our favorite travel bloggers, go to Expedia’s Kids in the City page.  This group also offers additional insight on trips to Philadelphia, Denver, New York, Chicago, Washington, D.C., Los Angeles, San Diego and San Fransisco (by our own Dana Rebmann).

Editorial Note: Ciao Bambino was compensated to support the Kids in the City summer-travel campaign. Photos by Nancy Solomon