2 hours north of New Haven, we reached Boston! I’ve only been to Boston once, for a girls trip to visit my college besties 10 years ago (recaps part 1 and part 2). I remember enjoying it and though I don’t consider myself much of a city girl, I was really excited to explore this historic city with my family.

We checked into our hotel, Westin Copley Square in the Back Bay area. My friend, Alexis, recommended this hotel and she nailed it. From the location to the amenities and the view, it was a perfect spot to stay for our quick two night stay.

Westin Copley Square Boston

We wasted no time dropping our things and heading out to explore the city. First on our agenda was lunch, since all we had ingested thus far had been coffee. Recommendations took us to Tatte Bakery. The bright and airy bakery was a bit froufrou for my kids, though I wanted to try everything on the menu! The tomato soup and grilled cheese option totally worked for the kids and David and I shared the lamb plate (deliciously seasoned) and the turkey avocado sandwich on the softest bread ever. Very good!

We had a short amount of time before our scheduled Duck Tour so we treated ourselves to an ice cream pick me up at JP Licks, which was delicious. I had an espresso Frappuccino and ohhhh my goodness was it tasty!

We arrived to our Duck Tour launch location in Copley Square right on time, excited for our tour of the city in an open-air vehicle that goes from land and splashes right into the Charles River. I had done the duck tour before, again a decade ago, but was just as excited. There’s not much I love more than seeing the sites and hearing the history of a city on a beautiful day. We all thoroughly enjoyed the 80 minutes drive around Boston and the kids both got to drive the duck on the Charles River! What a fun memory.

After the tour we spent some time wandering the Prudential Center, as I had to swing by a pharmacy to get some cream for a cut Kaitlyn had on her eye. This took us right up to dinner time. We hadn’t made reservations anywhere but we lucked out bigtime getting a rooftop table at Eataly.

I had heard of Eataly but wasn’t familiar with what a unique place it is- a combination of a market with fresh pastas, fish, and meats, casual eateries, and an upscale restaurant. The upbeat vibe of the rooftop and the absolute gorgeous weather made for a fabulous first dinner. I ordered their specialty gin and tonic summer refresher and we split a bunch of small plates, including squid, burrata and bread, and spaghetti. We walked back to the hotel as the sun was setting to shower up, get some sleep, and prepare for a full day of siteseeing!

Traveling with the kids is at such a sweet spot right now. The are old enough that they are super self sufficient, carrying their own bags and sleeping soundly. They are still young enough that they want to hold our hands and are excited to be together. I hope it lasts for a while!

We woke up around 7:30 the next morning and had to wake the kids. We got dressed and headed out in search of breakfast. We walked over into the Beacon Hill neighborhood to The Paramount, an adorable little spot. It might have been one of my favorite breakfasts while traveling. The picture doesn’t do it justice, but the avocado toast topped with heirloom tomatoes, bacon, and sunnyside up eggs with basil was ridiculous.

Feeling fueled up, we started on our mission of the day- walking The Freedom Trail, a 2.5 mile long trail through the city that visits some of the most historic sites of the city. We began in the Boston Commons. David used his ChatGPT to give us quick, 2 minute synopses of each of our stops, which made it fun that we could go at our own pace.

As we made our way through Faneuil Hall, our radars told us rain was headed our way. We decided to change course and walk to the Museum of Science. I had heard it was a great spot for kids, and everyone must have gotten them memo because it was slammed with camps and families. The museum itself though was impressive. It’s massive and has a plethora of engaging, hands on exhibits. We saw the 4d Sea Lion show and wandered through many of the exhibits before checking the radar and seeing it had cleared. Since The Freedom Trail was our priority, we only spent about 2 hours at the museum, though we could have spent many more.

We took off across the river into Charlestown to see the Bunker Hill monument. The neighborhoods over there are beautiful and peaceful; so fun to walk through. However, at this point we were starting to fade. When David started giving Kaitlyn a piggyback ride, we decided we were in need of a pick me up so we took a load off at Pier6 in Charlestown, which had an incredible view of Boston!

A little rain passed through as we refueled ourselves with shrimp, dips, margaritas for the adults, and Shirley Temples for the kids. Boy, did that do the trick! Our sweet server even brought the kids out a surprise cup of cherries to share. Spirits, lifted!

Refreshed, we walked over to explore the USS Constitution, also known as Old Ironsides (or Old Metal Bones as Kaitlyn thought). It’s an old Navy vessel and it was really neat to be able to fully explore it.

From there, we headed back over the bridge into North End. Since Paul Revere is one of my favorite Bostonian stories, I was tickled to see The Old North Church, where they gave the signal of two lanterns to signal that the British were preparing to attack from the water (one if by land; two if by sea).

We officially accomplished seeing ALL the sites on The Freedom Trail at The Paul Revere House. Unfortunately it was closed, as we arrived around 5:00, so we couldn’t go inside, but it just gives us a reason to return!

We had used a pastry treat as a carrot to keep Kaitlyn moving, so we headed straight to Modern Pastry. Kaitlyn picked out some crazy green cake thing and Hailey picked out a Boston Cream Cupcake. Hailey loved hers and Kaitlyn hated hers. It was hilarious but also sad, so we let her go back and get a new pick- chocolate mousse cake more than made up for it!

We were ready for dinner at this point. I walked us over to Neptune Oyster Bar, hoping we might luck out, but the line was out the door and not moving quickly. David took the lead and picked a random nearby restaurant, Rabias Dolce Fumo.

It was a friendly establishment where we were able to sit right down. It ended up being a great spot for the evening. Mom had some excellent clam chowder and we all shared the evening’s special, a massive seafood pasta!

With satisfied appetites, we began our walk back to Back Bay, stopping to watch street performers along the way and wandering through a farmers market. We finally made it back to the hotel around 8:15 with aching feet, but thrilled with our day of exploration, all 11 miles of it!

We all slept solidly that night, despite Kaitlyn talking in her sleep, per usual. At 2:00 AM I heard her say, clear as day, “If you love your outfit, then I love your outfit, because no one can make you wear something you don’t like.” – and if that doesn’t give you perfect insight into Kaitlyn, I don’t know what does! Ha.

We got up and walked to breakfast at an energetic little spot called Friendly Toast. The coffee and omelet were excellent., and the service was wonderful. Fueled up, we headed back to the hotel to pack up our things, get in the car, and head north. Next stop, Maine!


Leave a Reply

Your email address will not be published. Required fields are marked *