Thursday, July 12, 2012


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.

64 Comments / Post A Comment


I just got as far as "two-story kitchen" and got winded by my immense jealousy.

But this sounds like a lovely vacation. VRBO is the best, especially for things like this.


@bitzy I stopped reading after a few paragraphs and just scrolled, looking at the pictures, thinking, I fucking hate you. I fucking hate you. I fucking hate you.

/living life all wrong.

Beatrix Kiddo

@bitzy I cannot even physically comprehend a two-story kitchen, but I know I want one.


@bitzy Yeah, I can't. I can't read most of these "travel" posts because I know in advance that I'll smolder into a pile of envy. But I clicked this one because the first question was pretty much exactly what was going on when I read the headline!

Um, however? My reaction went from "wtf, who does that" to nearly tearing up when I read the part about "don't nearly get to see each other enough" blah blah because I guess I'm sentimental today? I think I need to rent an island with a bunch of my friends, or something.


@Beatrix Kiddo What does one do with a two-story kitchen? Like, are there two actual floors? Or just one really, really high ceiling?


@ThatWench I was wondering about that two. Doesn't two actual floors seem kind of inconvenient? Like, the purpose of a kitchen is to have everything you need, like, in one room?

I went to vrbo and looked it up, and it seems like just a really high ceiling but I could be wrong.


@bitzy Hi- you're right. It takes up two stories of the house, and there's a little balcony off the den upstairs where you can spy on what's going on in the kitchen. I think there's a picture of it on the real estate site that someone dug up below.


cant get enough!@a

oh! valencia

Sounds absolutely perfect! How large was your group?


@oh! valencia I know! I was like, you cooked for HOW MANY people?


@whizz_dumb I've done this on back-country "hut" trips in Colorado with groups of 12-16. I put hut in quotes because it's more like Luxury Rustique (TM) in the middle of the mountains. But anyway, the group dynamic is super fun, everyone kind of gravitates toward some task and it all goes really smoothly.


@oh! valencia Agreed - HOW MANY IS SOME?! I spent way too long looking for the answer (I know it's more than 12, BUT HOW MANY!?)


@oh! valencia we had 16 souls in total. I think that's what you say about a sea voyage, right?

Reginal T. Squirge

Ctrl+F, "$", Enter

0 results

Hey, tell us about the dollars. That's the whole point of this, right? How much does it cost to rent an island?


@Reginal T. Squirge For real. I, too, want to rent an island. Tell me how much so I can start saving!


$4800 for 3 days.


@Reginal T. Squirge I already did some math!! If it was ~$300 apiece, and we assume that they paid per bedroom and all 11 were filled, that's about $3,300.


@bitzy Aaaaaand beat me to it.

oh! valencia

@OhMarie because some of the 11 rooms had couples

eta the $$$ question was what I was trying to roundly get at with my "how large was your group" Q above.


@OhMarie I wonder if this is it? http://www.vrbo.com/250462

oh! valencia

@parallel-lines that looks like a match!


I just got back from a short getaway at a lake and I feel like a million bucks. It was no private island but sunshine and water are so good for the soul.

sudden but inevitable betrayal

@likethestore I leave tomorrow and I can't wait! Goodbye work! Hello water!


Ahhhhhhhh. I want to do this. This sounds like perfection. One day, when all of my friends have "real jobs" and "vacation days", I will bring this up.


This sounds like an amazing vacation. A bunch of friends and I used to rent a giant converted barn and do pretty much just this, except much cheaper, and in the woods of northern Pennsylvania. The place had about ten bedrooms and a hot tub in the living room. We called it "camping," air quotes included.


@kellyography this sounds very interesting - do you have more info?


@teenie The place is called King's Barn: http://www.kingsbarn.com/


@kellyography This looks awesome! I love vacation homes with 70s/80s furniture.


Oh man, super nostalgic for my family's summer vacations on Fire Island and hucking everything from the ferry to the rental house in a little red wagon. (We did not bring cases of beer.)

(We did bring box wine.)


@anachronistique boxed wine is so perfect for camping! Last summer I did a kayaking trip to a bunch of little islands in Maine and we brought a couple of boxes of bandit and man, did they ever hit the spot.

miss olsen

@parallel-lines How fun! I've been scoping out island-based trips to Maine -- where did you go? How much kayaking was involved?


@miss olsen I went through this company: http://www.mainekayak.com/
And even though I'm not exactly kayak proficient it was really doable and the tour guide was awesome and full of fun facts about the islands. We got to pick wild blueberries and seals swam next to us and at the end of the trip we got fresh lobster--can't recommend them highly enough!


I did a Maine Kayak trip too! It was awesome!


@anachronistique I remember when I first discovered that Ann M. Martin didn't make up the red wagon thing in all her books!


Thimble Islands!! Close family friends have a house on neighboring Governor's Island that's legit registered on the National Historical Sites or Whatever Is a Big Deal for Old Homes Yo Etc Etc Etc. I learned to swim when my uncle threw me off their dock and figured I already knew how (responsible childcare!!) Highly recommend the Thimbles for anyone in the NY/CT area, it's definitely overlooked.


I'd love to do this with a group of friends, but mine are currently in a spot where they can never get time off or are broke constantly. So, I'm going to be taking a little trip by myself soon which I am kind of nervous about. :X


@Statham I took a trip by myself to Cuba last year cuz nobody else could go AND IT WAS AMAZING it was soooo good. just so good. you'll have fun! bring lots of books! (I didn't even get through one of mine though)


@redheaded&crazie I'm only going over a state for a few days, just to get away and relax. I'm going to bring a few books even though the place I'm staying has a library according to their website. (What if they only have 10,000 copies of the works of Dan Brown?)


@Statham When do you go? What kind of place are you staying in? I am in the same boat, and I want to just go somewhere, so I am psyching myself up to just commit to a plan and go.


@redonion I haven't gone yet. But I plan to in the next month or so. I want to go to a Bed & Breakfast since they provide a meal, and if you look around enough, you can find some with added perks. Like, some will let you bring a pet, or they'll give you a card for gas money. Or, they might just have a really nice library with tea and deserts.


Kayaking is THE BEST. We used to have kayaks when I lived on a lake when I was teenager. So many good times. We also had a paddle boat! And a regular boat, though we didn't use that as much.


@Megano! In a lake, yes. In the ocean not so much.




@Megano! It was just pictures! Of sharks chasing kayaks.


At the springs I used to go to in North Florida, there is a place called Rum Island. That is all.


@stuffisthings North Florida Springs are GORGEOUS & super cold!! Wakulla Springs, DeLeon Springs. Just the freshest, coldest, swimming water ever! You really do feel amazing after swimming in that all day!

rianne marie

@stuffisthings I refute your statement that it's the coldest swimming water ever. Not if you can stay in it all day.
(says the crazy lady who swims in the northern bits of Lake Superior)


I like this dude, and his idea of a fun vacation.


this sounds like so much fun! so this is where the multicity pin-up is gonna be held? (or whatever way cooler name it's being called?)

Faintly Macabre

@redheaded&crazie Pincushion?


@Faintly Macabre YEP THATS IT!


@redheaded&crazie OH! I see you and I are on the same wavelength, even though I got there 4 days too late. But I'm in if you are.


Oooh, I've never heard of VRBO and am now enthralled with this idea of renting a cabin with a bunch of my dear friends.

Do my fellow 'Pinners have any other destination recommendations, maybe closer to the Midwest? Pigeon Forge/Gatlinburg, TN has always been a guilty pleasure vacation for me. I love it in all its cheesy glory.


@aproprose I just went to Pigeon Forge/Gatlinburg earlier this summer, and I adored it! My friends and I were camping in the national park and we just planned an overnight in Pigeon Forge, which was clearly the wrong thing and we just had no idea. We are already planning to go back and do it up right. I also want to try hitting the NC side of the park and include a stay in Asheville.


@aproprose My family rented a big house on the North Shore of Oahu one Christmas through VRBO and it was amazing (the vacay too, but I meant the VRBO-ing). Very painless/legit and you get access to some crazy awesome places you would not be able to get to if you stick to hotels.


@redonion I grew up in rural western NC and pretty much spent most of youth at the Folk School and it is so awesomely fun! Admittedly I haven't lived there since I graduated high school in '96 so I don't know about pricing, but I do still go to contra dances whenever I'm back. It's about 2.5 hours from Asheville so it would be a whole different trip but the area is really pretty. If you stay in Asheville be ready to eat because YUM. Be sure to eat at Early Girl, but unfortunately expect a wait...


More people read "whisper quiet" in Dr. Nick's voice than me, right?

Ahh I want to do this so much. I love me an exploration, big-city, nightlife vacation, but sometimes I also just really want to quietly lie in the sun next to a body of water.


@cosmia I can barely read the words "whisper quiet" without yelling it Juice-Loosener style. Which, seeing as how I share an office, is not a great impulse to have.


The porch. THE PORCH.


@SuperGogo yeahhhh it's alright i guess if you like afternoon naps with a cool breeze slightly rocking your chair back and forth, rum&coke in hand while birds chirp around you, drifting awake every so often to stare dreamily into the distance, the seemingly never-ending stretch of gently rolling water providing endless inspiration for your all your hopes and dreams


Here is a beach/island/woods/cabin beverage that is the best beverage: tinto de verano. You take a bottle of cheap red wine (preferably something juicy) and combine it with a bottle of sparkling lemonade and some fat wedges of lemon & lime. You can drink it forever on the beach/in the woods/on your steamy back porch overlooking your garbage alley.

LE Correia

I daydream about being forty. I really do. And when I do, it's this.

I will remember Pot Island the next time someone's birthday party is six people talking about work and Reddit with no food anywhere. I'll remember Pot Island when all of the friends-of-friends crawl out of the mud to ask What's Your Boyfriend's Name? I'll fall into a reverie and tell myself that soon enough we'll be forty. We will know how to grill, we'll have read all the books, and we'll have $5000 to go celebrate in the ocean.


I do believe we've found our location for the National Pinup!


@Xanthophyllippa Never mind; RH&C got there first. :D

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