This past birthday season was one for the books.

Earlier this year, I knew I wanted to have a real New England summer. It has been so much fun exploring more of this region, and I thought a New England road trip would be the perfect way to celebrate both Max’s birthday and mine.

Since my mother-in-law was flying up from outside Memphis to celebrate Max’s birthday with us, we decided on a Boston → Martha’s Vineyard → Cape Cod → Nantucket adventure. She joined us for the first part of the trip, which made it even more special.

We kicked things off in Boston on July 10. Matt had never been, and neither had my mother-in-law, so it felt like the perfect place to start.

I love Boston so much. I lived there briefly one summer nearly 20 years ago, so being back always brings a little nostalgia. We spent the afternoon doing some classic sightseeing, rode the carousel, walked down to the marina, caught some live music, ate, explored, and generally let Max enjoy the city. He had an absolute ball.

The next morning, we woke up early and headed south to catch the ferry to Martha’s Vineyard.

I had only been to the Vineyard once before, many years ago, and didn’t remember much of it, so it was wonderful to experience it again with my family. We explored Oak Bluffs, wandered through the beautiful scenery, shopped for a few souvenirs, and I finally got the Vineyard sweatshirt I had been wanting.

We also made our way to Edgartown, where we visited the lighthouse and spent time walking around the town. It was such a beautiful day.

I already shared more about Martha’s Vineyard, and Max’s third birthday in this post, so you can click here to see more photos and read about that part of the trip.

After the Vineyard, we headed back to Boston because my mother-in-law was flying home the following day. Before she left, we spent some time in Cambridge, which was especially meaningful for me because I previously studied global journalism at Harvard.

It was so much fun being back on campus and walking around my old stomping grounds. Harvard’s main campus is such a beautiful place, and returning with my family made it feel even more special. The next morning, after dropping my mother-in-law at the airport, the three of us continued on to Cape Cod.

I had never been to Cape Cod before, and we stayed at the most charming little place: the Anchor In Waterfront Lodge. The hotel was incredibly charming and more importantly for us, it was very close to the Nantucket Ferry.

There was a beautiful green courtyard where Max could run around, a lovely pool overlooking the water, and everything felt relaxed and picturesque.

That evening, we walked to dinner and, in one of those wonderfully random small-world moments, I ran into a friend from grad school whom I hadn’t seen in years. Of all places! It was such an unexpected treat.

The next morning was my birthday. We caught an early ferry to Nantucket, a destination that has been on the wishlist.

I put on a dress I absolutely loved, we had a smooth ride over, and then spent the day exploring the island.

And Nantucket? Nantucket is that girl.

The hydrangeas. The houses. The architecture. The landscaping. Everything was just beautiful.

We visited the iconic lighthouse, walked around, took what felt like a million photos, and simply enjoyed being there. It was also funny timing because we happened to visit right around the height of all the conversation about influencers and their impact (positive and negative) on Nantucket that summer. I personally didn’t see much of that while we were there, but it was interesting to be on the island just as  the whole conversation was happening.

More than anything, though, I was just grateful.

Going to Nantucket had been a dream of mine for a long time, and getting to experience it on my birthday with Matt and Max made it incredibly special. Boston, Martha’s Vineyard, Cape Cod, Nantucket, oh my! What a trip.

Such a beautiful way to celebrate another year of life, another year of Max, and our very New England summer.