On Friday, July 10th, my husband, Max, and I traveled to Boston to meet up with my MIL, Kristina. It was the start of what would become an incredible 5 days of traveling New England. It was my first time back in Boston since 2013, and it was everyone else’s first time there, so we were all excited to explore this historic city. In Boston, we stayed at the Home2 Suites in the South Bay area. Kristina chose this hotel for its proximity to a variety of amenities and shopping, its spacious rooms, and its kitchenette. This hotel was going to be our home base until Monday the 13th, so we all appreciated the extra room and the ability to store all the treats we accumulated throughout the weekend.

It was already late Friday afternoon when we started exploring, and we spent most of the time at Quincy Market trying and buying treats, Faneuil Hall, and just taking in the people and sights in downtown. Since we were headed to Martha’s Vineyard early the next day, we didn’t want to stay out too late.

Saturday morning we woke up at 5:30 to get ready to celebrate Max’s 3rd birthday at Martha’s Vineyard. I’m still not over the fact that he is now 3. Time is going by so fast! The itinerary for the day was to catch the 8 am ferry to the Vineyard and catch the 5 pm ferry back. The last time I was there was in 2013 for a day trip as well, and I recalled having 7 hours on the island as sufficient. And it was!

 
Here is everything we did.

We took the Seastreak ferry from New Bedford to Martha’s Vineyard’s Oak Bluff. Oak Bluffs sits on the northeastern shore of Martha’s Vineyard and stands out as one of the island’s most historic and lively towns. It is full of history and seaside charm, famous for the iconic Flying Horses Carousel, which is the oldest continuously operating carousel in the United States. The town is also known for its colorful Victorian Gingerbread Cottages, a busy harbor, beautiful beaches, and a downtown area where you can easily walk between local shops and restaurants. 

 

We rode the Flying Horses Carousel, which is the oldest continuously operating carousel in the United States. The carousel is right next to the ferry, and it opens at 10 am, so we were able to ride it before it got too busy. Highly recommend doing this early in the day. According to the website, it was built in 1876 and “it is one of only two Dare carousels that still exist.” Max loved it!
 

After that, we walked over to the Gingerbread Houses. According to Boston Magazine, the 318 Gingerbread Cottages first appeared in the 1800s as simple summer homes for Methodist families who came to religious camp meetings. These cottages were built to take the place of canvas tents. Over time, they became known for their bright Carpenter Gothic style and detailed gingerbread trim. Today, they are a National Historic Landmark and one of Martha’s Vineyard’s favorite sights. Most of the cottages are still privately owned, and many have stayed in the same families for generations.

Lucky for us, it was hydrangea season, and they were in full bloom! The amount of hydreageas everywhere was hard to believe. The sheer volume and size of them is the stuff of dreams. I am not kidding when I say I have about 100 photos of hydrangeas in my phone.

Just when I thought our Vinyard experience couldn’t get any better, we stumbled upon a wonderful vintage, antique, and thrift market (one of my favorite surprises of the day!) This is the only picture I have of the market, but I have over on my Instagram.

For the second part of the day, we jumped on the bus and made our way to Edgartown where we explored the iconic stores and walked to the beach to see our first lighthouse of the trip. I also finally got a Vineyard sweater!

Edgartown, founded in 1671, was the first colonial settlement on Martha’s Vineyard and later grew into one of the world’s most successful whaling ports. Source. It has a different vibe than Oak Bluffs, and is wonderful and charming in its own way. We loved admiring the historical homes and loved visiting the lighthouse. 

My favorite photos of the day were taken at the beach and by the lighthouse. Max has always loved the ocean, and I think his favorite moments were riding the historic carousel and searching for seashells along the shore.

When we got back to Boston that evening, we had birthday cake, sang “Happy Birthday,” and watched him open all the thoughtful gifts from family and friends. We really appreciate everyone’s love and generosity. Thank you for making his third birthday so special.

The presents were wonderful, and he is still enjoying them. But I believe the best gifts we can give him are moments like these: toes in the sand, salty ocean air, shared adventures, and memories that will stay with our family long after the toys are put away.