Boston is large enough to learn your independence and small enough to make your own.

Henry Winkler

While Salem was a bit of a let down, Boston was a complete surprise in the best way possible. We didn’t have a long weekend in Massachusetts, but we did fill every second we had with adventures. Boston is a place I’ve always wanted to visit, but I lived SO far away. Pennsylvania might be a 7 hour drive away, but it’s much closer than VA, so we decided why not!? We’re already going to be in Salem, let’s plan a day in both places.

So plan we did! We didn’t have concrete plans all day except for part of the morning which gave us the freedom to explore and enjoy whatever the day threw at us. Here’s how it went!

A Morning Without the Dogs

We booked one excursion that wasn’t dog friendly, so we found a day care to put the boys in for the morning. I’ve never been more nervous since we’ve never, ever, ever put them in daycare. Yes, I know I’m lucky to have amazing neighbors and friends in my life to help out. This was very much a new experience for us, so I was nervous, but also excited about the possibilities it opened up. We dropped the boys off and drove into Boston.

First up, was breakfast at a bookstore! Could anything be more perfect? I’ve been following Trident Booksellers on Instagram for a while because a bookstore cafe is probably my favorite aesthetic. The dining area was tiny, a bit cramped, but it makes you be super happy about it. It’s cute, the food was great, and you’re eating right by an entire two floors filled with books. It made my morning. They also have a great selection of book accessories and fun items.

Fair warning, parking is SO hard to find on the street. Garages are a minimum of $20 a day and if you have to move your car… you’re paying again. That was hands down the biggest headache we faced and cost us a lot of extra spending than we had planned. Make sure if you go to plan a central parking location and just stay there. For us, that wasn’t possible with the dogs, but yeeeeeesh paying for parking was expensive.

Once we were fed and not in danger of being hangry, we went to the starting location of our excursion: the iconic duck boat tour. It’s probably the most tourist-y tour we could possibly do in Boston, but holy crap I was excited. There are several versions of this tour and we chose the one that starts at the Science Museum. I’m sure they would give you the details of which location sees what, but I couldn’t find it on their website.

Our boat was named Emma which I took as a fantastic sign. We boarded, our guide showed up in full costume AND in character, and we were off! We drove around the historical sites of the town like the site of the Boston Massacre, the old market, where George Washington and Queen Elizabeth II made speeches, where the Boston cream pie was invented, and even learned that most of Boston is built on a giant trash pit. Then, the part everyone was waiting for, we were water bound.

As we were learning about the places we could see from the water, the guide asked if any kids wanted to drive the boat. I immediately leaned over to Will barely containing my excitement and said “oh. my. GAWD. Do you think he would let an overly excited adult drive??? Oh please let him let me drive. WHAT IF” At that point he gave me a look to shut up, so my body basically hummed in excited anticipation until he finally said “okay, all the kids have gone. Any adults want to give it a shot?” One girl was quicker than me, but I was next in line. Turns out, not every adult wants to drive a duck boat. I’ll never understand why, but I was the last one to drive it. And they let me keep driving it. And keep on driving it. I drove that thing for 10 minutes and had a shit eating grin the entire time. Thank you duck boat tours for making my entire day.

Once we were back on dry land and out of the boat, we decided to explore for a bit and find lunch. We ended up at a place called Tip Tap Room and had an amazing time there. Hari was our bartender and she was incredible. We got a bunch of tips from her on where to go next and holy crap they had the best butternut squash soup I’ve ever tasted. Following her advice, we walked to the Beacon Hill area. I explored Beacon Hill Books which was CROWDED, but SUPER cute. They had lots of rooms to explore and nooks where you could sit with a good book if there weren’t 40 other people around you shuffling by. I think we hit it at peak time, so definitely make a stop there but be prepared for a crowd since the place is so popular.

We explored a few other shops like December Thieves, which was way out of my budget but had some amazingly unique pieces that were so interesting to look at. By that time, we wanted to pick up the dogs and start exploring with them. Vacation just isn’t the same without them. We drove to pick them up and they looked like they had a great time. Back we went to Boston with the whole family! Annnnd paid for parking again, thankfully for a final time.

An Afternoon With the Dogs

By now, I know that Will’s first choice in the afternoon any time we travel is to stop at a brewery. Luckily, there was a really cool one, Distraction & Democracy Beer garden, right by the main square that was dog friendly. It overlooked the square and had a great spot to rest for a bit. Then we walked them around some of the historical sites and down to the harbor. While it wasn’t the original harbor location where the infamous tea party happened, we still got to see the harbor.

We spent another 2 hours walking around and exploring with the dogs. They loved walking around, sniffing, and spending the day with us on an adventure. We had dinner at a local Mexican place and then called it a night!

We planned to get up super early the next day to beat traffic. Our maps app really wanted us to take the route through New York City again and we kept telling it absolutely not under no circumstances would we drive through NYC no matter how much time it delusionally thinks we will save. We successfully avoided NYC and made it home in record time.

The last two trips we’ve taken we did the experiment of let’s get up early and leave by 6 or 7AM to drive home. It’s a game changer. Getting home just after lunch and still having the rest of the day to prepare for the work week, relax, and just hang out with the pets is amazing. After spending 7 hours in the car, having that extra time feels so refreshing. Give it a try on your next road trip to see how you like it!