I have been trying to figure out how to write this because I don’t want to give you another Martha’s Vineyard travel guide. There are plenty of those, and there are certainly enough social media videos telling you where to eat, what party to attend and which flowing dress you need for whichever event everyone has collectively decided requires white linen that year. I want to tell you what I wish someone had told me before I went. I want to tell you about the Martha’s Vineyard behind the pictures, because I loved the island, I absolutely think you should go, and I also think you should understand what you’re actually going there to experience.

Let me start by saying that I am a researcher, which most of you already know. I don’t really just go places. I read about them first. I had studied the history, looked at maps, researched restaurants and learned about the different towns before I ever arrived. I even managed to squeeze in a visit to Harvard before we headed toward the ferry because we were in Massachusetts, Harvard was there, I had never been, and obviously my children needed Harvard T-shirts. Some people apparently know how to simply go on vacation. I like to add a little educational field trip before the dinner.

Naturally, I also developed goals for Martha’s Vineyard. One of those goals was biking the entire island.

Let me go ahead and clear that up now.

I did a lot of biking. A LOT.

The entire island, however, turned out to be one of those ideas that sounds perfectly reasonable while sitting comfortably at home in Southern California and significantly less reasonable once you are actually on Martha’s Vineyard riding a bicycle. I still believe the goal was beautiful. We simply ran out of time, thigh muscles and perhaps collective enthusiasm.

The funny part is that Martha’s Vineyard wasn’t even on my 2026 Bingo Card. Many of you saw that I had already taken what I considered my once-in-a-lifetime trip earlier this year to South Africa, so when Martha’s Vineyard came up during book club because a friend might have a home available for us to share in August, I dismissed the idea almost immediately. Kalie would be doing too much. I had traveled. I had plans. I was showing restraint.

Then a few weeks later, I casually mentioned the possibility to our family friend Ally, who immediately announced, “We are going.”

I looked at my husband. He looked at me. I shrugged.

Apparently my season of restraint had come to an end.

Somehow the stars aligned, and we ended up going as three very different couples, all connected in one way or another by technology, books, friendship and a love of debating abstract ideas that have absolutely nothing to do with us. We can start dinner discussing whether we like the restaurant and somehow end up debating capitalism, feminism, artificial intelligence, education, parenting or some hypothetical social structure none of us has actually been tasked with fixing. Nobody has requested a white paper. There will be no follow-up meeting. This is simply how we relax.

Which brings me to my first piece of advice: go to Martha’s Vineyard with people you actually like.

I don’t mean people you like taking pictures with. I mean people you genuinely enjoy. People you can sit around a house with when nothing is happening, who can disagree and keep eating and who don’t require a scheduled activity every waking moment. Martha’s Vineyard is a group trip. I could see it being wonderful with family or other couples. A girls’ trip could certainly be fun too, although if the objective includes meeting single men, I personally did not observe enough inventory to justify airfare from California. That is simply one researcher’s field observation. Conduct your own study. Go with people you enjoy when absolutely nothing Instagram-worthy is happening because, surprisingly, those ended up being some of my favorite moments.

Now, before you decide you too need to be on Martha’s Vineyard next August, there are some logistics we need to discuss. Martha’s Vineyard is an island off the coast of Massachusetts, reachable only by boat or plane. There are ferries from several locations, but bringing a car during peak summer season requires planning, particularly in August. Housing is no different. This is not one of those vacations where I recommend waking up in July and deciding Martha’s Vineyard sounds fun for August. If you are seriously thinking about next summer, start looking now.

And my fellow Californians, I should warn you that somewhere between airfare, accommodations, transportation and food, you may look at your spouse and realize you could have gone to Europe.

I am not discouraging you. I believe in informed consent.

We had one midsize SUV for six adults, luggage and several boxes of books. Somehow everything fit. Technically. At one point I was sitting in the third row with luggage, physically holding things in place as we drove toward the ferry. It was neither glamorous nor structurally reassuring, but all six adults and every single book successfully arrived on Martha’s Vineyard.

Once you get there, though, I want you to understand the history because it changes the experience.

There are six towns on Martha’s Vineyard, but Oak Bluffs is probably the one most Black visitors know before arriving because its history is extraordinary. Beginning in the late nineteenth and early twentieth centuries, Black vacationers came to Oak Bluffs during a time when segregation excluded Black families from many American resorts. Over generations, families returned. They bought homes. They built institutions. They created traditions. The Inkwell, Union Chapel, the Cottagers and generations of Black families returning to the same homes and porches aren’t simply charming pieces of Vineyard history. They tell a much larger American story.

Black people created a place where we could experience leisure.

That sounds so ordinary now that it is easy to miss how extraordinary it was. They came to swim. They sat on porches. They visited friends. Their children played. They ate. They talked. They dressed up. They rested. Then they returned the following summer and did it again.

Eventually, repetition became tradition. Tradition became culture. Children became adults and brought their own children. Houses stayed in families. Friendships crossed generations. A vacation destination became something much more complicated and beautiful: a place where people belonged.

You feel that history differently once you’re standing there.

But please don’t go all the way to Martha’s Vineyard and only see Oak Bluffs.

I loved Oak Bluffs, but Edgartown was absolutely fabulous, and I was actually very glad our Airbnb was closer to that side of the island. We could ride our bikes into town, wander through the shops and sit near the harbor watching all this boating life happening around us. I know almost nothing about boats, but that has never stopped me from enjoying expensive ones. Edgartown is polished in that old New England way: white captain’s homes, beautiful boutiques, hydrangeas, restaurants and boats clearly belonging to people operating in a different tax bracket.

The rest of the island changes again as you move through Vineyard Haven, West Tisbury, Chilmark and Aquinnah, home to the Wampanoag Tribe of Gay Head, whose relationship with the island predates all of the vacation culture most visitors associate with Martha’s Vineyard today. We managed to catch the sunset at Menemsha Beach one evening, and although we weren’t there nearly long enough, I still think about it. My point is simply this: the island rewards curiosity.

Now let us discuss the Martha’s Vineyard you have actually been seeing on Instagram.

The fabulous part is, in fact, fabulous.

I am not going to return home and rewrite history as though I flew across the country in August searching for solitude and a wooden bench. I packed the dresses. We went to beautiful hosted events. We ate wonderful food. We drank very good cocktails. We met fascinating and important people and ran into enough celebrities that eventually our group developed a silent system of looking across the room at one another to confirm, Yes, that is who you think it is.

Occasionally everyone else knew exactly who someone was while I smiled politely and made a mental note to ask for an explanation later. Nobody screamed. Nobody pointed. We are grown adults with home training.

And yes, I took pictures. Many of them. I am not traveling 2,600 miles across the country, paying August-on-Martha’s-Vineyard prices and then suddenly developing a moral objection to photography. Absolutely not. If the dress is good, the hydrangeas are blooming and the lighting is right, everyone may need to wait a moment. I can contemplate the historical significance and commercialization of Black leisure while simultaneously believing my husband has not quite captured the outfit yet.

I contain multitudes.

There really is something extraordinary about seeing so many accomplished Black people simply enjoying themselves, at dinner, on the beach, walking through town, sitting on porches. I could spend an afternoon contemplating the historical significance of Black land ownership in Oak Bluffs and still spend the evening deciding which earrings worked better with my dress. These things are not in conflict. We are allowed range.

And August is genuinely packed. The African American Film Festival gets enormous attention, but there are also books, fashion, HBCU and Divine Nine gatherings, music, dinners and cultural programming throughout the summer. So yes, there is plenty to do.

However, this is where Instagram has committed a small act of fraud.

The Reels don’t show you the logistics.

Martha’s Vineyard in August can be difficult to navigate. Restaurant reservations can be hard to get. You will stand in lines. You may wait a very long time for coffee. Transportation can become an entire group discussion. That beautiful woman you watched gracefully enter a fabulous restaurant in a fifteen-second Reel may have spent the previous forty-five minutes trying to figure out how she was getting there.

Instagram simply began filming after that part.

This is why renting bikes was one of the best decisions we made. Pack the dresses, certainly, but also pack shorts and sneakers. Buy groceries. Be prepared to cook at the house. Leave room for plans to change.

Most mornings we sat around drinking coffee and figuring out what we wanted to do that day. Mine usually had a small shot of coffee liqueur in it because apparently Vacation Kalie decided ordinary coffee was unnecessarily restrictive. There was something wonderful about sitting there with my slightly enhanced morning beverage while six adults attempted to create a plan that was entirely dependent on weather, bicycles, bus schedules, restaurant availability and our collective ability to leave the house at the agreed-upon time.

The island will humble an itinerary.

And this is where Martha’s Vineyard surprised me.

When I think back now, the things I miss most aren’t necessarily what I was most excited about beforehand. I miss riding our bikes into town with entirely too much confidence in our athletic abilities. I miss the bookstores and grocery runs and sitting at bars talking to people we had met five minutes earlier as though we had known each other for years.

My favorite moment may have been setting up champagne and caviar on a bench behind the police station, watching the sunset and toasting with old friends and people we just me. There was no exclusive event, no photographer and nobody had sponsored the bench. It was simply champagne, caviar and people enjoying one another.

I realize champagne and caviar may not sound like my strongest evidence for embracing simplicity, but work with me.

Somehow that bench feels more representative of Martha’s Vineyard to me now than some of the far more impressive rooms we entered.

Mostly, though, I miss the five people I was there with.

We’re all friends back home in Southern California. We’ll see each other again. We’ll have dinner. Our husbands will talk about technology. We will inevitably debate education, AI, capitalism or some other societal issue none of us has been personally commissioned to resolve.

But we will never have those exact days again.

We will never again be those six people sitting in that particular house on an August morning drinking coffee, mine slightly fortified, trying to figure out what we felt like doing. We won’t have that exact bike ride, dinner, sunset, bench or conversation with the stranger beside us at the bar. We won’t have that particular version of ourselves again either.

And somewhere in there, without realizing it, Martha’s Vineyard changed my definition of luxury.

I arrived thinking the luxury was obvious. The beautiful homes. The boats. The restaurants. The history. The dresses. The parties. The people. The invitations. The access.

And listen, I remain deeply committed to excellent food, attractive surroundings and a good invitation. We do not need to become different people to learn a lesson.

But the real luxury was time.

Time to ride a bike without really needing to get anywhere. Time to sit over coffee in the morning discussing what we might do. Time to stand in line long enough to actually talk to the person beside you. Time to wander into a bookstore. Time to watch the sunset. Time to sit on a bench with champagne and caviar because somehow that made perfect sense. Time to have long conversations with friends without someone needing to pick up a child, answer an email, get home for bedtime or prepare for tomorrow.

And perhaps that is why I’ve been thinking differently about the argument that social media has ruined Martha’s Vineyard.

I don’t think it has.

Social media introduced a new generation of Black people to a history we should know. It allowed people who may never have heard about Oak Bluffs or the Inkwell to see Black families occupying beautiful spaces and understand that we have been doing so for generations. I don’t believe the answer to discovering something wonderful is immediately closing the gate behind us.

What concerns me more is what happens when corporate America discovers that thousands of educated, successful and influential Black consumers are gathering in one place.

Because corporate America has rarely encountered a beautiful cultural tradition and thought, You know what? Let’s leave that alone.

Suddenly there are sponsorships, activations, branded dinners, photographers, videographers and content creators everywhere. Every gathering becomes content. Every restaurant becomes somewhere to be seen. At one point I watched people sit at a highly sought-after bar for what seemed like hours, ordering almost nothing, apparently hoping someone famous might walk through the door.

And I remember thinking: you spent all this money and traveled all this way to Martha’s Vineyard, and now you’re sitting here waiting for someone more interesting to arrive?

Meanwhile, you’re already on Martha’s Vineyard.

There has to be a balance. I took the pictures too. I attended the events. I loved the restaurants, clothes and parties. I am certainly not suggesting we arrive in sackcloth and surrender our phones at the ferry terminal. I enjoyed all of it.

I just hope we don’t become so focused on being seen on Martha’s Vineyard that we miss what generations of Black families made special about being there in the first place.

They had time to simply be.

I hope to take my children back one day. I want them to swim at the Inkwell and understand why that beach matters, learn about the Wampanoag people whose history on the island came long before ours, and understand that they belong in beautiful places without needing to accomplish anything while they’re there. They can read a book, eat ice cream, sit on a porch, watch the boats and, because they are my children and there are still standards, look reasonably while doing it.

So yes, go to Martha’s Vineyard.

Go for the film festival. Go for the books. Go during HBCU Legacy Week or Greek Week. Go for the music. Go during Juneteenth. Put on the beautiful dress. Attend the fabulous dinner. Take the picture. There is nothing wrong with enjoying any of it.

But leave some room for the island to interrupt your plans.

Rent the bike. Buy the groceries. Talk to the stranger. Explore beyond Oak Bluffs. Sit on the porch. Find the sunset. Drink the coffee, or improve it slightly because you’re on vacation. Spend an unreasonable amount of time talking about absolutely nothing with people you love.

Because after all the research I did before Martha’s Vineyard, the thing I didn’t understand until I got there was that the greatest luxury the island gave me wasn’t access to something exclusive.

It was access to something increasingly rare.

Time.

And maybe that’s why generations of families keep going back.

Always Have, Always Will ~ Kalie