Updated: Aug 12
Family Trip like you own the city
Special shout out to one of my best friends and college roommate for hosting us in her native city time after time! As my family grew she continued to welcome us. I don’t think I’d appreciate the unique story of Boston with out Loren. On college breaks she’d take me home with her. Her family would host dinners and make sure to show us around, giving us all of the history of each stop. And even now, from across the Country we visit. Not as often as I’d like but every time we do there is some adventure, exploring and great memories made. She was originally from Massachusetts but has since moved to New Hampshire and the excursions still get better every time! Some friends are great friends, some friends are family. Loren is a part of our family ❤
From our family to yours – these are the things you must see when you are in Boston - Links added for your planning convenience, underlined titles will take you to the site for that place.
What I love most about Boston, is you can do so much in one day. This city is compact and easy to navigate. While each time we go we see and do more, a well-planned day could cross most of these items off your bucket list. Of course, if you are not in a hurry, stay, linger, and go deeper. The pace my children move keeps me on the go, and I never stay longer than my kid's interest lasts. Younger children with shorter attention spans helped make this itinerary. 📜
After the first time we went there (my children were 3 and 5 at the time), we talked about this place for years. We went to several children’s museums after, and would compare each to this – and this always remained this was their favorite!
Boston Children’s Museum is the second oldest, and one of the most influential children’s museums in the world. It was founded in 1913 by the Science Teachers' Bureau, a group of visionary educators dedicated to providing new resources for both teachers and students, as a center for the exchange of materials and ideas to advance the teaching of science. For over 100 years it has been engaging children in joyful discovery experiences that instill an appreciation of our world, develop foundational skills, and spark a lifelong love of learning. Seems appropriate to me that this was our first ever Children’s Museum experience. Plan to spend a few hours, and loop through all of the rooms and floors trying experiments, and figuring out how things work. Children (and parents) of all ages will enjoy!
As a teacher, this is a big one for us.
My youngest who needed speech and language support taught me that experiences outweigh words. Showing the child, and taking them to a real-life place will help connect with whatever you are trying to teach. This was like a school field trip for me. We read the signs, we paused to discuss, we imagined the world at the time of the revolution.
The Freedom Trail Foundation's most popular tour highlights the revolutionary history that covers 16 historical sites and stretches 2.5 miles. (Sites listed below). This is one of the biggest draws for Boston - it's history.
Established in 1951, this red-bricked trail will teach you almost all you need to know about Boston’s history. You can download an audio podcast to accompany your walk or you can go on an organized tour led by one of Boston’s many historic characters. Expect to spend a few couple hours walking the trail and much, much longer if you enter every site along the trail.
Along the trail, a true history lovers gem, Paul Revere House is one stunning piece of history and one of the best things to do in Boston, for sure. It’s an easy little stop to make on your trail across Boston (and still looks like it did way back in the late 1700s). With period pieces, fine silver, original furnishings, architecture to admire, and historic fireplaces - this is a great place to get a glimpse of American history that’s alive right in front of you.
On this trail you will also encounter Faneuil Hall — Boston’s 275-year-old meeting hall. Take a step back into history within the Great Hall as you sit and imagine the lively debates that took place here. This free site features National Park Service rangers who give 15- to 20-minute daily talks on the building’s history. Hidden upstairs is The Ancient & Honorable Artillery Museum another free, and historical venue work checking out.
Just a short walk from Faneuil Hall brings you to the Holocaust Memorial, a series of glass towers with a central path, inscribed with seven-digit numbers, evoking the numbers tattooed on the arms of the concentration camp prisoners.
The following are the stops along the Freedom Trail:
Open Historic Sites Boston Common Boston Common Visitor Information Center, Daily, 8:30 am – 5 pm) Granary Burying Ground* King’s Chapel Burying Ground* Boston Latin School Site/Benjamin Franklin Statue Old Corner Bookstore Old South Meeting House (starting June 16, Wednesdays – Sundays, 10 am – 5 pm) Old State House (starting June 16, Wednesdays – Sundays, 10 am – 5 pm) Boston Massacre Site Faneuil Hall (starting June 24, Wednesdays – Sundays, 11 am – 7 pm) Paul Revere House (Wednesdays – Sundays, 10:00 am – 4:30 pm) Old North Church (Thursdays – Saturdays, 10 am – 4 pm, starting June 14, Tuesdays – Saturdays, 10 am – 4 pm) Copp’s Hill Burying Ground* USS Constitution (Fridays – Sundays, 10 am – 6 pm) USS Constitution Museum (Daily, 10 am – 5 pm) Bunker Hill Monument (Grounds only, open daily; Museum, Wednesdays – Sundays, 10 am – 12 noon & 2 pm – 4 pm)
* Please Note: Historic burying grounds are open daily from approximately 10 am – 4 pm.
For kids with lots of energy – make the trek over the bridge to Bunker Hill Monument and take the challenge of climbing the 294 steps to the top. It’s not that far – just over the bridge in fact (1 easy mile from TD garden) and quite an accomplishment and the views are your reward.
Don't miss this legendary ship. It's still a commissioned ship of our Navy and the oldest commissioned ship in the world.
Commissioned in 1797 and named by George Washington, “Old Ironsides” is a heavy frigate that was used in the War of 1812 and later in the Civil War. It’s the oldest ship in the world that is still afloat, and its popularity has stopped it from being scrapped on multiple occasions. The ship is permanently docked in the harbor and free tours are offered every 30 minutes. It’s a wonderful way to get a sense of what life at sea was life over 200 years ago! Navy personnel attend to the ship. You can climb down the ladders and go below deck for more cool info on how it all works.
Charlestown Navy Yard, ussconstitutionmuseum.org. The ship is open daily from 10am-4pm (with extended hours in the summer) and the museum is open 10am-5pm (with extended hours in the summer as well). Admission is free, though the museum has a suggested donation of $10-15.
After you’re done, hop on an MBTA ferry at the dock on Baxter Street and zip on over to Long Wharf and the New England Aquarium.
~~Some of our favorite memories happened here~~
Hop into a duck boat—renovated World War II amphibious vehicle—for a thorough tour of Boston. Building and growth recognition and relevance will help you to connect the story through time.
Ok this was another favorite. As tours can be a little lost on young children, this one comes with a fun driver who makes a big impression. Once the boat goes amphibious, the driver allows the kids to come up and take a turn driving. My kids snapped to life and thought they were soooo cool!
You will see Boston Common, Quincy Market, and the Celtics' home turf at TD Garden. The splash into the Charles River for a view of the city by boat gets a lot of excitement. Learn all about Boston's history and landmarks as you go by, with your guide narrating all of the story for you.
Read more about Boston Duck Boat Sightseeing City Tour with Cruise Along Charles River 2021 - https://www.viator.com/tours/Boston/Boston-Duck-Tour/d678-3037DUCK?mcid=56757
Located in the Back Bay Boston The church is situated in Copley Square. We loved the architecture and history here!
Trinity Church is the only church in the United States and the only building in Boston that has been honored as one of the "Ten Most Significant Buildings in the United States" by the American Institute of Architects (AIA). In 1885, architects voted Trinity Church as the most important building in the U.S.; Trinity Church is the only building from the original 1885 list still included in the AIA's current top ten list. The building was designated a National Historic Landmark on December 30, 1970.
The church also houses sculptures by Daniel Chester French and Augustus Saint-Gaudens. Aside from it's historical relevance, and architectural significance, It is a bit of an art museum. Stained glass and huge innate murals stretch the imagination and push the styles into realms never seen prior.
* This does have a $10.00 entry fee, per person.
Before leaving Copley Square (especially if you have children) check out the Boston Public Library!
The children's section is a great stop to cool off or take a break, even look up some of the places you are visiting. The library does give passes for the audio or walking tour if they have any in stock. It's a great resource if you are wanting to get more information.
The Seaport area has enjoyed significant development in recent years. Stop by the Lawn on D to play in Boston's community 'backyard'. This park and playground oasis for children and adults is just a short walk from the seaport area, over near the Boston convention center.
There’s always something wonderful to enjoy, this area is stocked with art, shopping, places to eat, and so much to do! Whaling tours, museums, hotels, this area is poppin'!! From the open green spaces, artisans’ markets, well-manicured gardens, revolving art installations, splash fountains, colorful murals, food trucks — and of course the Greenway Carousel This one-of-a-kind carousel features uniquely designed animals native to Boston, and it’s a terrific photo op.
** While you are in the Seaport Area, the New England Aquarium located at 1 Central Wharf, is a cool place to walk by. You may be able to spot their seals! Their seal exhibit is located to the left of their front doors and is free to the public. Worth a stop by as seals can be friendly curious creatures who love to say hello!
Central to the city of Boston and a most beautiful botanical park, is Boston's Public Garden. The Public Garden is a lush, meticulously maintained botanical garden space of nearly 4 acres, with enormous trees that are hundreds of years old shading wonderful walking paths, beautiful sculpture fountains and lots of benches to sit and take it all in.
~~~ Family fun as the family grows ~~~
Famous for being America’s first public botanical garden, you can see plenty of exotic trees, colorful flowers, and even take a ride on the swan boats that accentuate your adventure.
Swan boats are only open in the summer months.
This is one of those great ideas you could take advantage of, to make a unique memory in a fun city.
Tickets purchased at the swan boat dock prior to boarding.
Children $3.00 (age 2 to 15 years) Under 2 yrs. Free
Spend some time people watching or duck watching by the pond, and make sure to see the Make Way for Ducklings statues! Depending on the season, the city of Boston dresses them up: sometimes in bonnets, other times in Tom Brady jerseys. And they’re every bit as cute as they sound.
Boston is known for displays of public art
The North End is home to six of Boston's publicly accessible artworks.
North End Library Mosaics (2009) - located at 25 Parmenter Street.
Paul Revere sculpture (1940) - located at the Paul Revere Mall, between Hanover Street and Salem Street.
Merchant Marine Memorial - located near the Andrew P. Puopolo Junior Athletic Field, on Commercial Street.
Benjamin Franklin Tablet (1946) - located on the corner of Union Street and Hanover Street.
Christopher Columbus sculpture (1979) - located in the Christopher Columbus Waterfront Park, near Atlantic Avenue.
Massachusetts Beirut Memorial (1992) - located in the Christopher Columbus Waterfront Park.
** One cool thing about the North End is the old neighborhood feel. Bakers rolling parties and the smells of delicious things to eat, this very inviting part of town is worth a stroll through to get the whole experience of Boston life.
Explore the Black Heritage Trail
There are 14 sites located around Beacon Hill that make up this walking tour, covering important parts of African American history. Massachusetts was the first state to declare slavery illegal - in 1783. You will learn a lot about the history of slavery and the African American experience by taking this tour. Free maps are available at the Abiel Smith School if you want to do a self-guided tour, though there are several companies that also arrange guided tours.
Walk the Irish Heritage Trail
Americans of Irish descent form the largest single ethnic group in Boston - over 20% of the people in Massachusetts claim they have Irish ancestry. This historic free walking trail will take you around the city focusing on contributions made by the city’s thriving Irish community. There are 16 sites along this 3-mile walk which you can visit consecutively or in tandem with one of the city’s other historic walks.
The Coit Observatory at Boston University offers free stargazing with telescopes and binoculars every Wednesday evening (weather permitting). It takes place outside (obviously) so just make sure to dress for the weather. There is limited space, so you need to reserve your spot in advance.
725 Commonwealth Avenue, bu.edu/astronomy/events/public-open-night-at-the-observatory.
**I know Boston is also known for it's art museums, however we have not yet explored so I did not include these. We are not baseball fans, but Fenway Park is still quite a landmark, worth seeing. We did stop by on our wat through. There are libraries that have impressive collections as well as architectural significance. In the future, and now that the children are older we hope to check these out! This Best of is meant for families that need to keep the children entertained, and I am sure each family can add or subtract as needed.
Both follow the following ticket cost:
Child (Under 3)Free
Members, all ages Free
If you are looking for more museums (I usually am when I can get the family excited or sneak away)
This site tells you which are free all the time, or which have free days. I always try to minimize entry costs as they add up when you have a bigger family.
Booking Your Trip to Boston: Logistical Tips and Tricks
We are typically road tripping from NY when we visit. We’ve also taken the train (Amtrak) before to visit.
Book Your Flight ✈
Use Skyscanner or Momondo to find a cheap flight. They are my two favorite search engines will search websites and airlines around the globe so you always know no stone is left unturned. Use Skyscanner first because they have a bigger reach!
If you are lucky enough to have a best friend/ family in the area that is always a bonus!
You can book your hostel with Hostelworld as they have the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as they consistently return the cheapest rates for guesthouses and cheap hotels. HI Boston has raving reviews and I have heard great things.
Homewood Suites by Hilton Boston Seaport seemed the most reasonable family option to us. The ability to be well located, have a kitchen (saves money on eating out), offers free breakfast, and studio suites with fantastic views seemed like a slam dunk.
Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. The companies that offer the best service and value are:
World Nomads (for everyone below 70)
Insure My Trip (for those over 70)
I'd like to point out there is much to do in the surrounding vicinity if you have enough time to venture out.
Some of our favorites include:
The White Mountains (WOWOWOW! New Hampsire get a way with trails, hiking, State Park and much more to see and do)
The Kancamagus Highway (breath taking view on switch back roads of mountains)
Jackson Falls - New Hampshire (Scenic nature experience, we LOVED this excursion)
Old Sturbridge Village (we used to take field trips here to learn about how the settlers lived)
Salem Massachusetts (known for witch museum and extensive history burning witches)
George's Island (Civil war era Fort and fun to explore/ look into another era of time)
Affordability meter: 8/10
On a scale of 1-10 how affordable is this day?
We had this trip planned and other than gas to get there mostly all of the things we did were free. The Duck Tour was the most expensive splurge, and well worth it, especially as we found the tickets on groupon and got a great price! This city can be done very affordably for your family.
Thank you for coming by, please leave feedback about your trips and Boston favorites!
Where ever you go and what ever you do - enjoy every moment of your journey!
Travel safely and God Bless,
Please see our complete adventure that took us to Jackson Falls, the Kancamagus, and White Mountains HERE
Or if you find yourself in Washington DC looking for some fun family ideas click here...
Want to hit NYC? We got you covered! Click here for the Best of NYC
A note from the editor:
The information in this article was accurate when published but may change without notice. Confirm details when planning your trip.
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My goal is to make traveling easier for families and cut down on the planning process. 💜