Boston Weekend 2019: Travel Diary

August 2019                                    NJ —> Boston

With our Portugal trip well behind us and no major vacations on the horizon, we decided to close out Summer with a quick roadtrip to meet up with my parents who were visiting Boston.  Since this was Asher’s first real road trip and definitely his longest (4 hours in a car are we crazy???), the best parenting hack we came up with was…have grandpa join us for the ride up!  This ended up being an absolutely necessary hack because we poorly timed out departure and ended up picking Asher up from daycare during nap time.  After loading up the backseat with every toy and snack my father might need to keep Asher happy, we hit the road.  We hit a little rush hour traffic as we passed through the bigger towns (see earlier note regarding our poor timing), but we mad it to our rental* just in time for dinner.

*The apartment/VRBO we rented was NOT close to downtown at all or realistically close to any public transit.  The apartment itself was honestly “blah” so I’m not going to bother linking the listing.  If we do this trip again (we probably will) I would much rather spend the extra $ to be in Boston proper in a hotel or Airbnb because we ended up paying a lot to drive into Boston everyday and pay parking (in addition to having to crocodile wrestle a toddler into a carseat several times a day).

Day 1 – One if by Land, Two if by Sea

With a toddler (and grandparents) to manage, I wanted to be sure we kept the weekend itinerary loose and flexible to account for varying energy levels, appetites, and interests.

A hit for all ages and a great way to start the weekend, Boston Common and The Public Garden were out first stops of the day.  We parked in the centrally located parking garage under Boston Common and came out next to the Frog Pond and Carousel.  Asher was unsure at first but with Grampa by his side he braved his first carousel ride!

From there we strolled through the Common into the Public Garden to make our way to the famous Swan Boats. One of my fondest memories from visiting Boston as a child was riding these very same boats, so it was a true joy to share this memory with Asher and Mike.

A toddler’s visit to the Public Gardens would not be complete of course without a quick stop visit to the famous Mrs. Mallard and her ducklings! Though I think the real life ducks proved more entertaining than the statues, Ash was a real trooper to indulge in my “Make Way for Ducklings” Photo sesh.  

Well fortified with snacks (some of which were shared with the real life duckies) we headed out of the park to Beacon Street to take in some New England architecture and history as we made out way to the Freedom Trail.  NOTE: While I would have loved to do the entire Freedom Trail tour, we didn’t stick too strictly to the trail’s path (see prior comment re: toddler/grandparent energies and appetites).  We did make our way past the Massachusetts State House, King’s Chapel & Burying Ground, Old State House, Boston Massacre Site and Faneuil Hall.  Behind Faneuil Hall was the Faneuil Hall Marketplace where we stopped for lunch at Anthem Kitchen & Bar and some light souvenir shopping.

Next we made our way down to the water and the New England Aquarium.  Thankfully this aquarium is small enough that we only needed a couple of hours there.  I think aside from the huge penguin exhibit at the entrance, Asher’s favorite part was the central spiral ramp that connects all the floors of the aquarium and wraps around a giant cylinder tank.  He could have probably run circles up and down that spiral for the entire trip if we let him.  

After picking up our requisite souvenirs and carefully strapping a wiped out toddler in his stroller, we decided to do a Boston Harbor Cruise before dinner.  Having grown up surrounded by desert, your girl will never say no to a Harbor Cruise!  Unfortunately, growing up surrounded by desert did not protect your girl from seasickness 🤢, so I spent most of the cruise inside nursing a ginger ale while Asher slept.  Nevertheless, the cruise was very informative and we got to see a large amount of Boston Harbor and the surrounding islands.  Afterwards we made our way back to Faneuil Hall Marketplace for dinner at one of my all time favorites: Wagamama.



Day 2 – From Tea Party to “Hahvahd Yahd”

For our second full day in Bostonm we started off at the Boston Children’s Museum. I had really wanted to take Ash to the science museum (another fond childhood memory for me) but in the end I realized this was definitely way more his speed.  

The parking for the museum was a few blocks away so we actually passed the Boston Fire Museum on the walk over.  There was no way Asher was going to pass a perfectly good fire truck untouched so we of course made a quick detour to explore the museum.  The museum had a few engines from different eras and even had one you could climb onto for pictures.  The volunteers working there were delightful.  Free plastic fireman’s hats were everywhere to take, they had a modest souvenir counter and an even more modest request for donations.  There is no entrance fee so we happily gave a donation. It was such a quaint kid-friendly museum, if you are traveling to Boston with a toddler or kid, it is a must see!  If you’re lucky you’ll even get to spend some quality time with Sparky their adorable firehouse dog 🐶.

Another must see if you are visiting with kids is of course the Children’s Museum.  It was deceptively huge and even though we spent several hours there, we definitely didn’t see everything.  There was so much there to explore and do for kids of all ages (including 67 year old kids who got a little too enthusiastic in the kinetic energy room 😏).  Asher loved the Bubble Room because …bubbles.  I loved the Arthur and Friends room because…nostalgia.  We could have easily spent a whole day there but since  this was our last full day we had to keep it moving.

Just a short stroll across the bridge got us to the Boston Tea Party Museum.  Another deep pull from Tara’s nostalgia library, this museum is literally the FIRST thing I think of when I think of Boston.  I can still remember how excited I felt pretending to travel back in history and the thrill of tossing that “tea” into the harbor!  Even before we left home I told Mike this was at the top of my must see list.  It was as fun/funny/educational as I remembered and they have definitely added some great new features to make it more engaging.  BUT the best part is and will always be, doing our patriotic duty of hurling that tea into the water!

While I would have been perfectly content to take high tea in Abigail’s Tea Room & Terrace in the museum, I’m sure everyone else was hoping for hardier fare, so we walked to the nearby Trillium Brewery.  The food and drinks were amazing and the place was huge. It was pretty packed which is not surprising for a Saturday afternoon but we were still able to get a table pretty quickly.  I would not have minded handing out a bit in their downstairs patio but we had dinner plans with family in Cambridge so we wanted to squeeze in some collegial exploration (gotta get Asher ready! jkjk).  It was a short be beautiful drive along the Charles River to Harvard Square.  We strolled through campus and channeled Rory Gilmore circa season 1.  Of course we had to stop by the COOP (Harvard’s School Store) to stock up on the necessary aspirational Harvard gear for Ash. Tiger mom? Me?

Since it was the week before classes start, it was already bustling with students getting settled.  I definitely got heavy nostalgia vibes for our own college days.  we would have given the toe of the John Harvard statue a rub for good luck but it was literally packed with parents making their kids do the same 🤣. In any event we had to head to dinner.  We ate at Gran Gusto in Cambridge.  Even though it was very unassuming and we almost missed it, the food and wine was amazing.  Definitely worth a stop by if you are in the Cambridge area.  



Day 3 – Road Home with a Quick Time Travel Detour

On Sunday we packed up the car for the long drive back home. We decided to break up the journey by making a stop at Old Sturbridge Village.  OSV is a living history village where you can literally step back in time and see what life was like in a New England colony.  Fun fact: I have never met a living history experience I did not LOVE.  So it is no surprise that I would 100% recommend checking this out if you find yourself on the road between Boston and the NY area.  Ash was of course a little too young to get all the historical knowledge but he loved all the animals.  This was actually a really great stop to wind down a bit from our trip.  There is something so tranquil about being in the countryside on a farm.  Maybe it’s all that “simple life” feeling about a farm where the last thing on your mind is email, commuting, or staff meetings. If you are a history buff like us or if you just want a more slower paced kid-friendly activity, this is a great stop.



We hope you enjoyed our travel diary for Boston and stay tuned for our next adventure!

If you have any questions about this trip in particular or have suggestions on where we should go next, please leave them in the comments below! And be sure to follow us on instagram (we have even more photos from the trip saved in our story highlights).


M&T (and Asher too!)


We are the Khaimovs and welcome to our family! Come on in and join us as we juggle work, family and life all while trying to just keep on #khaimovinandshakin

Khaimovin & Shakin in your Inbox

Leave Some Love