Exploring Boston and the coastline!
We visited Massachusetts during a 2 week roundtrip around the North East USA. We really enjoyed seeing both the city side and the coastal towns of Massachusetts.
This trip took place July 2021.
We visited the following locations – check it out!
Check out the whole vlog here:
Boston
Our time in Boston was short, but packed with a lot more than we expected.
We drove into the city in the afternoon and headed straight to Boston Common, parking nearby so we could explore on foot. The park is beautiful and felt like the perfect way to ease into the city.
One of the highlights for the kids was the Frog Pond area — a big shallow fountain where they could run through the water. It was surprisingly fun and an easy way to burn off energy after a travel day.
We also wandered around the pond, spotted the bench from Good Will Hunting, and walked past the exterior of the iconic Cheers Beacon Hill.
That evening, we headed to one of the main reasons for our visit — a game at Boston Red Sox home stadium, Fenway Park.
We grabbed a quick dinner nearby at Tasty Burger before walking over to the stadium. Getting there early gave us time to explore the area, check out the team store, and just take in how historic the ballpark feels.
Fenway itself really is something special. Even if you’re not a huge baseball fan (we’re not), it’s hard not to appreciate being in such an iconic place. One thing we immediately noticed was how small the seats are — definitely built for a different era!
The atmosphere inside the stadium was incredible. It was packed, loud, and full of energy, and we even got to see a home run inside the park, which felt a little unreal in the moment.
Even though our time in Boston was short, it ended up being one of those cities that leaves a strong impression. There’s still so much more we didn’t get to see, which just gives us a great reason to come back someday and explore it a bit more slowly.
Rockport (lodging: Rockport Inn & Suites)
Wow — Rockport is one of those coastal towns that just feels instantly charming.
We spent three nights here and used it as a home base to explore the surrounding coastline. It ended up being a really nice pace for this part of the trip — slow mornings, easy evenings, and plenty of time just wandering.
We stayed at the Rockport Inn & Suites, which worked really well for us. The location made it easy to get in and out of town quickly, and the property itself was comfortable with a nice pool, a good breakfast, and plenty of outdoor seating areas where we could just sit and relax between outings.
One of the absolute highlights of Rockport is Bearskin Neck.
It’s a small, walkable stretch of town filled with little shops, restaurants, and constant ocean views. Everything feels close together in the best way — you can just wander without really needing a plan.
We also walked out onto the jetty for views back toward the harbor, which was one of our favorite simple moments of the stay. Watching the boats, the water, and the coastline all from that one spot really captures what Rockport is about.
We also enjoyed a few meals in town, including a stop at The Fish Shack, which had great seafood and a relaxed waterfront feel.
Rockport was one of those places where the highlight wasn’t a single big attraction — it was just the town itself. Easy to explore, beautiful views everywhere you turn, and a great base for a few slower days along the Massachusetts coast.
Gloucester (Whale Watching)
One of the main things we really wanted to do while we were in this part of the coast was go whale watching — something none of us had ever done before.
We booked a trip with 7 Seas Whale Watch, and we’d absolutely recommend them. The tour we did left around 8:30am and lasted about three hours. If you want the tour we took, check it out: Whale Watching Tour.
We headed out from shore and didn’t have to go far before we started seeing whales. It was one of those experiences where you’re constantly scanning the water, camera in hand, trying not to miss anything — I definitely went into full “tourist paparazzi” mode taking way too many photos. Honestly, I’d love to go back again just to experience it without feeling like I needed to capture every second.
What made the trip even better was how knowledgeable the crew was. There were researchers on board who shared so much information about the whales in the area, and it made everything we were seeing feel more meaningful.
We even got to see a whale they called “Spoon,” who was swimming all around us and popping up in different directions. We saw several whales throughout the trip, including a couple that were resting near the surface — you could actually see parts of their huge bodies just below the waterline.
One of the coolest moments was seeing what they called a “rainbow blow,” when a whale exhales and the sunlight catches the mist just right, creating a rainbow in the spray.
A quick practical note: a lot of people on our boat got seasick. If you’re prone to motion sickness at all, I’d definitely recommend taking something like Dramamine beforehand — it can make a big difference in how much you enjoy the experience.
Overall, whale watching in this area was one of those once-in-a-lifetime-feeling activities. If you’re anywhere along the northeast coast, it’s absolutely worth adding to your list.
After our tour, we spent some time walking along the harbor in Gloucester.
We stopped by the Fisherman’s Memorial, which is a really moving tribute to the area’s fishing community, before grabbing a casual lunch in town. We picked up pizza and some honestly insane cannolis from Virgilio’s Bakery — definitely one of those “glad we didn’t skip dessert” moments.
Gloucester itself is a really cute little coastal town. It still feels like a working harbor, but with plenty of spots to wander, eat, and just take in the views.
We also made our way out to the nearby lighthouse area, where there’s a long jetty you can walk out on for ocean views in every direction. The Dog Bar Breakwater Lighthouse sits at the end of it, and walking along the rocks with the waves on both sides was one of those simple but really memorable coastal experiences.
It ended up being a perfect mix of activity and downtime after the whale watching — nothing complicated, just a really nice day by the water.
Salem and Beverly
On our other days based in Rockport, we used it as a launch point to explore a few nearby coastal towns.
In Salem, we wandered through some of the historic areas, including Old Town Hall and the old cemetery. We thought about doing a ghost tour, but decided it might be a bit much for the kids. Even just walking around, there’s a slightly eerie feeling to the town, knowing its history with the Salem witch trials and how heavily that story still shapes the area today.
We grabbed dinner at Boston Burger Company, which ended up being a fun stop — great burgers, but the real standout was the over-the-top milkshakes (the kind you definitely don’t need, but also can’t skip if you see them).
On the drive back toward Rockport, we stopped in Beverly and spent some time at Lynch Park. It’s a really beautiful waterfront park with ocean views, gardens, and plenty of space to just walk around and relax. Of course, we also managed to find a basketball court nearby, which has basically become a running theme on our trips.
Wrap-Up
This part of the Massachusetts coast ended up being one of our favorite slower-paced stretches of the trip.
Between Rockport, whale watching out of Gloucester, and day trips to places like Salem and Beverly, it felt like a really nice mix of coastal towns, history, and easy exploring.
It’s an area that doesn’t require a packed itinerary — you can just pick a town, walk around, eat well, and take in the water views. And honestly, that’s probably what made it so enjoyable for us.
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