Martha’s Vineyard – A Pleasant Surprise

To quote the great Joseline Hernandez, my year of travel, was more about quality not quantity. I did not do nearly as much traveling as I typically do. I only used my passport twice this year and I only went to one new country! However, I do feel like I went on some really nice and big trips this year. I was able to visit both Napa Valley (read about it here) and Martha’s Vineyard, places I thought I would not be able to afford until I was much older!

I fell in love with Martha’s Vineyard as a teen after watching a movie called The Inkwell. It is a 90’s film, with a young Jada Pinkett Smith and it was set in this sleepy beach town. She would ride around on her bike, through long pathways with huge weeping willow trees and jump off beach piers and catch lobster. It was such an idyllic setting. As with most things in life that I enjoy, turns out it is a very expensive place to vacation and visit.

Martha’s Vineyard is an island off the coast of Massachusetts. It’s a very affluent summer colony, President Obama even owned a home there. You may even can catch a glimpse of Oprah, Jay-Z and Beyonce there in the warmer months on enormous yacht’s. And if you’re thinking about purchasing a home there prices start around two million. I’m hoping you get the vibe right..?

Getting Around

To get to Martha’s, you can fly there directly or into Boston International Airport. From the airport you can catch a private bus that takes you directly to the ferry port, Steamship Authority. The bus and the ferry tickets are very convenient and inexpensive. I highly recommended to book tickets in advance – especially in the summer. On the ferry, I actually met an amazing woman named Kindra who used to live there! I spent my whole first day there with her and she was so knowledgeable about the island. Just an absolute gem! I swear that solo travelers are never really alone – the universe always surrounds me with amazing people on my trips.

The viineyard is split up into six towns. Edgartown, Oaks Bluffs, Chilmark, Vineyard Haven, West Tisbury and Aquinnah. The island is around 22 miles long and takes 45 mins to drive from one end to the other. You can bring along a car on the ferry or rent one when you get there. During my time at Martha’s I rented a bike for riding around the area I stayed in and used the public bus to visit other towns. Each town actually has its own vibe, which is very unique considering that Martha’s Vineyard is so small!

Edgartown definitely had more of a fancy, expensive vibe going on. Oaks Bluff and Vineyard Haven were the most similar to me, very lively with a lot of restaurants and bars. Chilmark, Aquinnah and West Tisbury are kind of rural-ish compared to the other cities.

What I Did in Martha’s Vineyard

I did not do a ton of research on Martha’s Vineyard before my arrival. Of course, I knew that my room and food were going to be very expensive. I also knew that it was a popular summer vacation for African American’s starting in the mid 1950s. However, I did not know that the island was originally inhabited by Native Americans, the Wampanoag Tribe. It’s actually close to 4,000 of them that still live on the island! Many of the natives live around Aquinnah, which was one of my favorite parts of the island. It has many unique stores and restaurants that lead up to gorgeous views at the top of Gay Head Cliffs.

For my visit, I stayed in Oaks Bluff in the cutest Victorian bed and breakfast, The Narraganset House. I had it saved on my Pinterest for years and was so excited to stay there. The house was in a perfect location, walking distance to the main streets and just about everything. It’s also close to a gorgeous bike trail, that I rode around every day. I would ride up and down the coast, stopping at the beaches and enjoying the ocean breeze. And of course, taking hundreds of photographs of all the beautiful and unique mansions that I would ride past.

Oaks Bluff is also full of picturesque Victorian homes and smaller versions know as gingerbread houses! It’s actually around 300 of them in a village that is right off the main street. Most of the gingerbread homes were built in the 1800s and it’s even a museum for one of the first that I was able to visit during my stay. When they were originally build they were around $200-$500, now they are close to $1 million, crazy right?

I wish that I could write about all the different new cuisines that I tried, but I mostly ate seafood – lobster in particular. I ate steam lobsters with butter, lobster rolls, lobster ceviche, lobster bisque, lobster macaroni and cheese, a chef salad made with lobster. Clearly, I was in lobster heaven. I did skip out on lobster for breakfast and tried Biscuits, which is the number one breakfast restaurant on the island. Breakfast restaurants never really excite me, it was just ok to me. I did run across a Jamaican carry-out restaurant that was pretty tasty though!

Final Thoughts

Martha’s Vineyard truly surprised me! Before arriving there, I thought it would be full of pretentious, unfriendly people who acted cold on a warm island. Even though it does live up to its hype, it feels like a place that the residents care about and just want to maintain is heritage and beauty. The African American presence is definitely felt there and probably a bit more because I was visiting during Juneteenth weekend. I definitely plan on visiting again in the future and would recommend it as a nice domestic getaway! It’s really some amazing beaches and places to visit in the states. It turns out that we don’t always need our passports.