Sunday, August 23, 2026

Martha’s Vineyard: More Than a Summer Destination


 There are places you visit, and then there are places you experience.

Martha’s Vineyard is definitely the latter.

My latest Jaunt took me to the Vineyard during one of the island's most culturally vibrant times of the summer. I was there during the Martha's Vineyard African American Film Festival, which meant the island was filled with filmmakers, executives, entrepreneurs, creatives and more than a few familiar faces.

But what stayed with me wasn't simply who was there.

It was the Vineyard itself.

Getting There Is Part of the Experience

I stayed in Falmouth and traveled over by ferry, which gave the trip a rhythm I actually enjoyed.

There's something about traveling by water that signals you've officially left your everyday life behind. The shoreline begins to disappear, the Vineyard comes into view, and suddenly the pace changes. 

Breath taking views. Efficient and friendly customer service aboard the HY-Line Cruises


And that's one of the first things I noticed about Martha's Vineyard: despite everything happening on the island in August, it still manages to feel removed from the mainland.

You have arrived somewhere.


On the afternoon ferry, not many crowds mid-week, and it also provided some savings. Tickets online are encouraged, for making sure you have a seat aboard in the high season, but not necessary in some instances, where people were able to walk up and purchase at the box office. As a note ahead, if you plan to take your car, this is not your ferry. This is a passenger only ferry. And NO parking is allowed at the dock, so I took an uber from my hotel.


Oak Bluffs Has Its Own Energy

Steps away from getting off the Ferry at Oak Bluffs, this AMAZING Restaurant full of life, and authentic Jamaican Cuisine hit the spot. 

Taking the ferry from the Cape to the Vineyard is a fast journey at less than 1 hour, and goes by fast. 

If you've never visited Oak Bluffs, it deserves time beyond simply passing through.

There is history here, but there is also an unmistakable sense of community. Generations of Black families have made Martha's Vineyard part of their summer traditions, particularly around Oak Bluffs and the historic Inkwell Beach.

That history isn't hidden away behind museum doors. You feel it walking through town.

Families. Friends. People greeting people they haven't seen since last summer. Conversations happening on sidewalks and porches. Someone inevitably running into someone they know.

During festival week, add filmmakers, business leaders, actors, artists and entrepreneurs into that mix, and the entire place becomes one enormous intersection of culture and connection.

Time well spent. Relaxation. Business. Shopping. All my favorite things. 

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Until the next Jaunt... Cheers

A little island indulgence. Because every good Jaunt deserves a proper cocktail.


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