Boston: 48 Hours with Kids

Historical tour

Check into your hotel, put on your walking shoes and set out to explore the city. To orient yourself, I suggest starting with a family-friendly historical tour. A local historian will guide you through the cobblestone streets of the North End and share insights into the history of Boston, and the United States in general, as you trace the steps of the American Revolution.

Lunch in the North End

After the tour, enjoy lunch in the North End, Boston’s oldest residential area and the cultural center of Italian immigrants to the city. As you walk down Hanover Street, you will see dozens of bakeries, cafes and restaurants. They all feature traditional Italian delicacies, such as homemade pasta, cannoli, tiramisu, gelato and pizza. I recommend stopping for a hearty Italian lunch at Mamma Maria or Antico Forno. For something more casual, head to the famous Regina Pizzeria.

Cannoli Tasting

After lunch, stop for a fresh cannoli at one (or both!) of the iconic bakeries in the North End: Mike’s Pastry and Modern Pastry Shop. There’s a fierce rivalry between these two neighboring cannoli spots, with Bostonians split on who makes the best pastry. To dive even deeper into the foods of the North End, sign up for a Cocktails and Cannoli Tour. You can take part in a blind tasting of these two historic cannolis. One thing is for sure, Boston takes its pastries seriously!

Boston Tea Party experience

With bellies full of pasta and cannolis, it’s time to get back to learning about the history of Boston by checking out the interactive Boston Tea Party Ships. At this unique museum, join live actors in a historical reenactment of a pivotal event in American history. Enter the meeting house, meet “Sam Adams,” step aboard a replica ship and throw crates of tea into Boston Harbor. This hands-on experience is great fun and brings history to life for the entire family.

Dinner in the Seaport

Boston’s Seaport area is a bustling area filled with great shops, restaurants and attractions, along the edge of Boston Harbor. There are lots of family-friendly places to enjoy fresh seafood and water views. Check out Legal’s Harborside or for something more casual, The Barking Crab. Enjoy a lobster roll, oysters and clam chowder for a real taste of Boston.

Cruise around the harbor

There’s nothing like seeing Boston from the harbor. Take a sunset sail aboard the Schooner Adirondack III and listen for the cannon being shot from the U.S.S. Constitution, shot nightly at sunset. For a unique experience, take a ride on a pedal boat (a partially bike-powered boat) with Cycle Boat Boston.

Boston Common

Grab some coffee and head to Boston Common, America’s oldest public park. Be sure to find the famous bronze duck statues inspired by the children’s book Make Way for Ducklings, ride the carousel and hop on the iconic swan boats for a relaxing ride under the weeping willows.

Walk the Freedom Trail

Boston’s Freedom Trail is one of the best ways to explore the city and immerse yourself in its history. The tour is two-and-a-half miles long and is marked by a red line through the sidewalk and streets. Pick up the trail in Boston Common and walk to a few of the historical sites. I am particularly fascinated by the historic gravestones at the Granary Burying Ground, where Paul Revere, Sam Adams, John Hancock and other revolutionary war figures rest.

Lunch at Quincy Market

Stop in this historic food hall, where everyone is sure to find something they like, though I suggest a bread bowl of clam chowder.

Shopping on Newbury Street

If you have shoppers in your family, head to Newbury Street. Here you will find historic brownstones that have been converted into a shopper’s paradise. There are also plenty of cafes and restaurants nearby if you need an afternoon snack.

Sports city

If your family likes sports more, think about visiting Fenway Park, where the Red Sox play, to see the Green Monster for yourself. Basketball and hockey fans will also enjoy a tour of TD Garden, where the Celtics and Bruins play, and a visit to its Sports Museum. You can learn about Boston's sports history there.

Dinner at America’s oldest restaurant

Located right on the Freedom Trail, the Union Oyster House is a perfect stop for lunch or dinner. Not only is the food delicious, but the restaurant also has a true sense of history. You can imagine Daniel Webster himself stopping in for some fresh oysters and a pint. Be sure to make a reservation in advance!

Boston ghosts and graveyards trolley tour

Wrap up your last night in Boston with a fun tour on a “haunted” trolley. Your kids will love the spooky stories and soak in one last dose of history.