Family Travel Guide to Boston, America’s Most Historic City

As our kids are getting older, our summer vacations are a chance for us to spend quality family time together before the school year and crazy fall activity schedule descends AND share new experiences together.  We chose to head to Boston in the summer of 2017 to soak in a vibrant city that is rich in American history. With so much to do and not sure where to start, I called on a friend from college who lives in Boston with her family for her tips. If Boston is on your family bucket list, read our family travel guide to Boston for our Top 5 Tips and Tricks for your next family vacation! Most of these tips are based on her excellent and thorough recommendations.

Boston Family Vacation Top 5 Tips and Tricks

A family travel guide to Boston

STAY

We stayed at The Westin Copley Place in Back Bay that centrally located and walking distance to Newbury Street, Boston Public Libray and even Fenway Park (~30-minute walk).  We redeemed SPG points (now Marriott Bonvoy points ) plus a small cash upgrade for a spacious corner room with enough space for our five. The Westin Copley Place in Back Bay is now a category 6 (50,000 point/night). TIP: One great perk of the Marriott Bonvoy program is that all award stays of four nights or more get a fifth night free.

Another alternative is the Hyatt Regency Boston which is in downtown Boston, and close to the museums, theater, and universities  

PLAY

There is so much to do in Boston! Listed below are our favorite spots

Fenway Park, an iconic American ballpark that is home to the Boston Red Sox, is a must if the Red Sox are at home (and we are die-hard Chicago Cub fans)

Embark on a 90 minute Duck Boat Tour of Boston’s historic landmarks before splashing into the Charles River.  They leave out of three different locations, making it quite easy to find a convenient time to go.   

Boston is abundant in excellent universities (e.g., Harvard, MIT, Boston College, Boston University).   We navigated the Boston’s subway system (“the T”) and rode the subway to Harvard, toured the campus (since its never too early to start touring colleges (:)) and walked around Harvard Square.  

SHOP

Faneuil Hall/Quincy Market often referred to as the home of “free speech” and the “Cradle of Liberty” and was one of America’s first public meeting venues.  Today it is a good place to stop and have lunch, pick up a few souvenirs from Boston and catch a street performer. 

For the best shopping and people-watching in Boston ꟷ definitely, don’t miss Newberry Street and Back Bay. It’s full of great stores ad restaurants. You can also cross the finish line of the Boston Marathon one street over!

TIP: In Massachusetts, all clothing and footwear items at $175 or less are exempt from sales tax. This is a 10% savings for our fellow Illinois people.

EAT

Wander the streets of North End for some delicious Italian food.  We ate at La Famiglia and enjoyed dessert from Mike’s Pastry ꟷ the line may be long but the pastries (especially the cannolis) are worth it! North End has the distinction of being the city’s oldest residential community, where people have continuously inhabited since it was settled in the 1630s. The North End is home to the  Old North Church where Paul Revere began his infamous midnight ride that preceded the American Revolution.  Although small, only 0.36 square miles, the neighborhood has nearly one hundred establishments a variety of tourist attractions and is best known for its fine Italian restaurants. 

We enjoyed our morning brew and breakfast at Thinking Cup on Newbury St (a 7-minute walk from The Westin Copley Place in Back Bay )

FUN

The Freedom Trail is a 2.5-mile, red-lined route that leads you to 16 historically significant sites.   We opted for a walking tour and recommend purchasing discounted online tickets here.  Led by 18th-century costumed Freedom Trail Players®, tours feature tales of high treason, mob agitations, revolutionary actions, and partisan fights of the American Revolution.

Highly recommend strolling through Boston Common/Public Garden, the epicenter of the city and close to everything.   The swan boat rides are a cute option for younger kids.  You visit the Ducklings (Jack, Kack, Lack, Mack, Nack, Ouack, Pack and Quack), and see some cool outdoor sculptures. It was HOT when we were in Boston so we cooled off in the frog pond in the middle of the park. 

We also took the Island Queen Ferry to Martha’s Vineyard for a day trip, shopped in one of the first Vineyard Vines stores, biked around the island, splashed in the ocean and grabbed a quick bite before catching the last ferry back to the mainland. 

Other day trip options: If you want to get out of the City, the Cape is a short drive away. You can visit Hyannis and take a ferry ride to the Islands (Martha’s Vineyard is closer). There is a ferry from Boston to Provincetown as well. Plymouth is also a good day excursion from the city and not as far.

Other Recommended Activities that We Did Not Have Time to Try

• Charlestown: You might enjoy the USS Constitution (Old Ironsides). You can take tours, etc.  
• The Esplanade: Great area along the Charles River. It is a state-owned park with many boating opportunities. Sometimes you get to see some great sailboat or crew races.
• JFK Library: If you want to do an indoor excursion, the Library is pretty interesting. I don’t think it’s worth going out of your way for unless you really like presidential history.
• Museum of Fine Arts: Great collection of Art, if you’re looking for museum-type activities. There is a new Art of the Americas wing that is fabulous.
• ICA: The Institute of Contemporary Art is our newest museum. It’s right on the water, and it’s really fabulous. They have a whole section with old Apple computers. Quite amusing.
• Seaport: This is the “newest” section of Boston, and it’s where many of the new restaurants are. It’s not necessarily a mecca for kids/hanging out, but it’s easy enough to walk around and eat (also where the ICA is). There are good water views from here (you can watch the planes take off and land!).

Get ready for a lesson in American history that is both fun and educational! Have you been to Boston? What are your must dos?

Hope our family travel guide to Boston helps your family!

Happy Travels!

Bridget, Family Galavant