Martha’s Vineyard is one of the best places to go if you want a relaxing vacation without a hefty itinerary. On my first visit, I kept things fairly simple and focused on exploring without trying to do everything at once. I spent time walking around and letting the island set the pace instead of rushing. These are a handful of my favorite things I got into while I was there, and for a beginner, these are easy, straightforward experiences. If it’s your first time, this is a solid starting point.

1. Visit Edgartown Harbor Lighthouse

The lighthouse is just a ten minute walk from town and it’s right along the water with sailboats drifting in the background. It’s an easy stop, and it could be quick, but I don’t recommend rushing. If the weather is on your side, then it’s a beautiful place to just hang out. You could even make it a full beach day. Additionally, the walk to the lighthouse through the residential area is very charming, so I would plan to take your time whichever day you plan to do the lighthouse.

2. Experience Beautiful Views Aquinnah Cliffs Overlook

The Aquinnah Cliffs are stunning. These layered cliffs drop into the ocean in a way that reminds me of my time in San Diego or on the Pacific Coast Highway. It’s one of the most striking views on Martha’s Vineyard, and after you hang for a bit at the overlook, you can walk down to the beach and spend the day there as well. To me, it’s absolutely worth the drive if you’re staying in Oak Bluffs.

3. See the Gingerbread Houses

Formally known as the Camp Meeting Association, these cottages look like a storybook. Keep in mind that people actually live in them, and I was happy to know that some of them are Black-owned. They were built in the 1900s and passed down through generations, as Martha’s Vineyard became a popular summer vacation destination. Black families made it an annual tradition to return, as this was historically a peaceful reprieve from segregation.

Because it’s residential, it’s rather quiet, and I went in the off season, so it was even quieter. I was virtually strolling the neighborhood alone, but it gave me a wonderful opportunity to take in all the bright colors, intricate trim, and tiny details that give each one its own personality. It’s a fairly quick walk through the neighborhood, and you can access an entrance from Circuit Ave.

4. Spend Time at Inkwell Beach

Like the rest of the island for Black people, Inkwell Beach has quite a bit of history. It has always been a place of gathering and community, especially for Black travelers visiting the island year after year. Beyond that, it’s just a nice beach. It’s easy to access, close to everything, and perfect for relaxing by the water. I love a nice and quiet beach day, so I took my book and blanket and stretched out for three or four hours totally uninterrupted.

5. Walk Circuit Avenue

Circuit Ave is where people generally hang, especially if you’re staying in Oak Bluffs. This is where you’ll find the shops, some good food spots, and cute things to do like the arcade or the carousel ride.

If you’re curious about what to eat, then check my food guide here. For a casual meal, try burgers at Fat Ronnies, and if you’re looking for a sit-down vibe, try The Sweet Life Cafe.