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Questions for Someone Who Recently Rented a Private Island

Last weekend, to celebrate my 40th birthday, some friends and I rented a house on Pot Island, a tiny and humorously named land mass in Connecticut’s Thimble Islands. We thoroughly enjoyed ourselves.

You did what? Exactly who the hell do you think you are?

No seriously, I’m just some guy. But you discover, when embarking on this sort of project, that if you combine a large group of people, the result is some serious purchasing power! We each threw in somewhere around three hundred bucks. (They haven’t told me what the exact figure was, because, well, it was my birthday.) We stayed from Friday to Monday. We cooked all of our own meals and mixed all of our own drinks.

You cooked for that many people? Were the logistics a drag?

A few of my friends are so good at this stuff that they should consider doing it for a living. There were a lot of spreadsheets and grocery lists involved. On the drive up we went to Costco, and then to a normal grocery, and then to a liquor store. From the island we ended up calling a Connecticut package store that, amazingly, delivered directly to our dock, for the sundries that we had forgotten to buy, and for ice, which one can never have quite enough of.

Is Pot Island the headquarters for NORML or something?

While we did get quite a few good laughs out of the name of the place, as well as nearby Stony Creek and Weed Beach (seriously) I can assure you that we didn’t rent this place to get stoned on the porch. I looked on VRBO and selected Connecticut and “more than 12 persons” from the dropdown box. Pot Island was the first result. It’s about a two-hour drive from Manhattan, traffic permitting. It is a lovely place that I don’t think a lot of New Yorkers know about. Most of us are still grinning a few days later. 

All that being said, the majority of Pot Island is currently for sale, and if NORML or High Times were to purchase it for their corporate retreats, I think that would make a good deal of sense.

So what does a person do on Pot Island?

Not a whole lot, frankly. If you’re the sort of active vacationer who prefers to learn a language or ride horses or play a lot of tennis, then god love you but pick a different destination. I’m not that sort of person, and neither are most of my overworked and child-rearing friends. There were two big decks, a field, rocks for scrambling upon, a beach, and four kayaks. There was a dock to leap from, and there was the ocean, salty enough that you could lie on your back and float without waves knocking you in the sinuses. There was a literal knotty-pine rec room, complete with ping pong and pool tables. There was scrabble and poker. There was nautical bric-a-brac everywhere, ship’s wheels, maps and charts, and a library of books about seafaring. There was no Wi-Fi, but our cell phones worked, for the most part. There was a beautiful two-story kitchen full of Le Creuset enamelware and a gas stove with eight burners, and also multiple barbecue grills. We made burgers and dogs, steaks and chimichurri, a bolognese, some half-assed stuff for the vegetarians among us, some fabulous breakfasts, and a birthday cake. There was a bar, which we stocked with an embarrassment of liquors.

There was a lot of staring at a fixed point on the horizon. There was also a lot of laughing. There was a lot of deejaying for one another with an iPhone dock. And there was a whole lot of bullshitting late at night, which was great because I don’t get to see the people who came nearly as often as I would like.


Did you say ping pong? Are you any good at that game?

You guys, as it turns out, I am so good at that game.

Also a pool table?

I’d prefer not to discuss the pool table. I’m pretty sure it was warped or something.

And kayaks? How did that turn out?

They can be intimidating at first. Trying to get into the damn thing with a beer belly leads to a lot of unintended physical comedy. Then you push yourself away from the beach with a gentle shove of the paddle, and it’s like you’re levitating. The craft just barely breaks the surface of the water. Paddling can be a little tough on the upper body, but when you get tired of rotating your shoulders you can just lay the paddle down on your beer belly and stare up at the clouds. We would hop around from island to island, just breezily checking stuff out. There was one bizarre little island, which we christened Zombie Island (the whole area is ripe for a setting as a teenage sex-horror film) and when I paddled out there with my ladyfriend we both got thoroughly creeped out. Why would someone build this, we wondered, just a house, up on stilts, on about 1000 square feet of rock jutting from the sea. We argued about what could be inside, and my guess was a big stack of dirty magazines and a dartboard. As we were turning away I noticed a black crane, or egret or something that was about three feet of elegant neck and long graceful legs, just gorgeous. I turned to mention it to my ladyfriend, just as she tilted at the wrong angle and suddenly dropped face first into the water. I paddled furiously to reach her, but it turned out that she was standing on a rock and was only waist-high in the water. I collected her paddle, she did an elegant maneuver to get back into the boat, and off we went.

How many bedrooms are we talking about?

The house that we rented, a nineteenth-century former bed and breakfast, had eleven. There are three stories in total, and the second floor has the master bedroom, which we took to calling the Presidential Suite, and which had three rooms, one with bed, one with tub, and one with shower and toilet. Several other large bedrooms were on the second floor as well. The third floor had most of the sleeping space, with smaller rooms, where we mostly put the single people. We imagined that there would be some wacky erotic hijinks between our friends creeping from room to room in the night, but I’m not sure if that actually happened because, as the birthday boy, I was happily snoring in the shameful and enormous master.

Did you look into the history of the place at all?

We did. After the trip, one guest sent the group an email titled “Pot Island: From Captain Kidd to the Fat Men’s Drinking Club.” There are amazing stories of adventures and waspy drama: Captain Kidd supposedly buried some treasure in a cave on the island, which we were too lazy to look for. Even better, in the 1880s the island was occupied by a fat man’s club, which I’m pretty sure I would be invited to join if it existed today. They would fill a natural cistern in the rock with thirty-five feet of boozy punch, and wouldn’t leave until it was gone.

Yeah yeah, but something must have sucked about all of this. What sucked?

Hmm. There were bugs. For that we had spray. There was heat. For that we had breezes. There was some occasional ennui and hurt feelings, as there are in all places on the Earth. There was no air conditioning, which I would normally be the first person to complain about, but it didn’t bother me on Pot Island.

But uh yeah, it wasn’t all gin and tonics and lazy games of Frisbee. Electricity came from a propane-powered generator which the owner assured us was whisper quiet, but which actually sounded like a lawnmower turned upside down. The genny was only for use a few hours a day, so we would run it for an hour or two in the morning and then for a few more hours after the sun went down. This was actually kind of a revelation to me: how much, in good times, one actually does not need power. In the coming global-warming apocalypse, I imagine we will all be quite familiar with this. But I guess we will also become familiar with the pleasures of lighting via candles, which makes everyone look more attractive than they actually are.

There was also the matter of getting that many people, and their provisions and gear, out to the house. Our ferry captain was visibly annoyed at the amount of shit that we brought with us, and then we were annoyed when we realized how far we had to hump all of that stuff from the dock to the house. I was sweating, swearing, and wearing flip flops as I carted potatoes, pancake mix, and cases of beer in a hand-trolley up a massive rock to reach the porch.

But into every perfect weekend, a little nonsense must fall, I suppose. And really, there is no way you came here to listen to me complaining about any of this.

So what’s the takeaway from all of this leisure?

It was one of those experiences that doesn’t make you sad to think about, even on those slightly melancholy final few hours when you’re packing and hauling hard-carts back to the dock, and if you’re like me, you’re obsessing about whether you’ll ever see the view from the porch again.

Forty years old. How many left? Impossible to say. But I know that my friends and I spent at least one weekend correctly.

Brian Pritchett is a writer and a web producer in Brooklyn.

Photos by Noel Proffitt, Melinda Fought, Todd Eaton, and Carrie Noteboom.


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