Harbor Nights: Moonlit Memories on the Mary Lloyd

In her heartwarming narrative,  Annelise Mendelman invites readers into a cherished childhood tradition. Growing up on the picturesque shores of Long Island's east end, Annelise, alongside her sister Kaylee and best friend Mali, celebrated the end of each summer with a sleepover on the historic Mary Lloyd—a restored 1939 Elco wood motor yacht. This annual adventure was filled with laughter, bioluminescent swims, and youthful exploration in Sag Harbor. Through her vivid recounting, Annelise captures the essence of a coastal childhood and the unbreakable bond of friendship forged on the gentle waves of Gardiner's Bay. Enjoy the story! 

A Childhood Tradition: Sleepovers On The Water
By Annelise Mendelman

There are many fond memories I cherish having grown up on the beautiful east end of Long Island; school beach days, family kayaking trips, annual fish fries and clam bakes. But one of my favorite childhood traditions was the yearly sleepover I would have with my sister, Kaylee, and our best friend, Mali, on Mali’s boat! This wasn’t just any boat either, it was the Mary Lloyd. The Mary Lloyd is a 30ft 1939 Elco wood motor yacht, which was restored by Mali’s dad. She is an absolute classic beauty.

The Mary Lloyd

My sister, Kaylee, and I have been best friends with Mali since her family moved here from Wales waaay back when we were elementary school kids. After many playdates, sleepovers, and gymnastics classes, we three were inseparable.

Kaylee (left), Mali (center), and Annelise (myself, right), and Mali’s little brother Frank (back) in 2013

At some point we started the tradition of having a sleepover on the Mary Lloyd every summer, usually before school started. My sister and I would pack up our bags of pajamas, towels, and YA books, and excitedly await the sight of the familiar gray minivan which would whisk us away to our destination.

Setting out on our journey bright and early, the Mary Lloyd would carry us across the calm blue waters under the hot summer sun as we listened to the radio and watched the wake cascade out from the stern. Our destination: Sag Harbor. The Mary Lloyd would amble along out of the harbor entrance and into the expansive Gardiner’s Bay. The three of us would be fervently waving at all the passing vessels, screeching with glee at our victories when our fellow boaters waved back.

The stunning view exiting Three Mile Harbor into Gardiner’s Bay

Eventually, the Mary Lloyd would round the bend of Cedar Point and Sag Harbor would come into view. With the salty breeze whipping our hair, we’d pull up to the wharf practically jumping overboard with anticipation. After receiving the go-ahead from Mali’s parents, the three of us would dash up the docks and into the town.

Bustling streets filled with the sounds of flip flops slapping concrete mixed with lively music and a cacophony of people chatting and laughing. Mali, Kaylee, and I would pace up the sidewalk expertly dodging leashed dogs and unleashed children. We would pop into our favorite stores, browsing but buying nothing. From marveling at expensive jewelry to playing with knick knacks in the toy store, eventually we would make our way to either of the two best places in Sag Harbor: Buddha Berry or Yummylicious. I’m not sure if you can tell from their names, but they are a frozen yogurt shop and an ice cream shop respectively. Imagine the unbridled joy coursing through our veins at the sight of a sweet treat usually inaccessible to our driver-licenseless selves. Of course, we happily indulged every time. 

Mali and Kaylee goofing around in a restaurant in Sag Harbor

After filling our cups with sweet frozen cream and too many toppings, we’d meander down to the small beach beneath the windmill to watch the sunset. Smelling like sunscreen and salt, melted ice cream on our tongues, we’d splash around in the shallow sandy water as the warm remnants of sunlight fell beneath the horizon.

The sunset as seen from the cabin of Mary Lloyd

The sunset seen off starboard of the Mary Lloyd

But! This was only the end of the first act! We still had much more sleepover to have! After our jaunt through Sag Harbor, it was time to return to our homeport. In the dimming twilight, we boarded the Mary Lloyd and set off once again. 

Annelise (me) relaxing on the bow of the Mary Lloyd during an evening cruise

The trek home was usually a slow uneventful cruise along placid black waters under a twilight sky. But one time was different. When speaking with Kaylee and Mali before writing this blog post, they reminded me of one year’s spectacular view on the trip back. Picture this: you’re sat aboard the bow of the Mary Lloyd, towels spread beneath you topped with bread and cheese to snack on. The warm wind wisps past you as you feel the waves slowly rock the boat. The rumble of the engine fills your ears as you feel it pushing the boat through the water. It’s nighttime, but the sky is not entirely dark. You look out into the distance and see the sky lighting up in different shades of white, blue, and purple. Lightning flashes every few seconds, casting magnificent shadows on the towering clouds of the dry storm. You stare at the ginormous storm cell that oddly seems so small in the distance. The lightning dances across the moist air, the flashing capturing its instant leaps and pirouettes in your eyes. You and your fellow boaters watch the storm in awe, only occasionally breaking the mirrored silence of the storm with gasps of wonder. This is the kind of experience that reminds you why we love to go boating. Cruising on our small but strong vessel, facing down the majesty of mother nature, we humbly continued our journey back home.

A beautiful sunset over Gardiner’s Bay

Arrival back home in Three Mile Harbor would beget a whole new wave of excitement. As the Mary Lloyd surreptitiously weaved through the mooring field populated by sleeping ships, Mali, Kaylee and I would prepare for the penultimate portion of our yearly tradition: the nighttime swim. Bouncing from port to starboard, hyped up on too much sugar, we would impatiently wait for Mali’s dad to anchor the boat, cut the engine, and set the swim ladder. With the whole world around us asleep and quiet, we could only make out the silhouettes of our surroundings in the dim moonlight. A light breeze directed all the vessels around in the same elegant waltz, muted moonlight scattered across ripples on the water, and the inky black shadows of the treeline blended with the dark sky. 

“Alright girls, go ahead!” That’s all we needed to hear. Scrambling up to the bow of the boat, a trail of discarded clothes in our wake, we’d stand proudly in our bathing suits ready to take the plunge. One, two, three! And we would be briefly flying before crashing blithely into the water below. Completely submerged, if I stretched out a leg I could feel the long seaweed growing from deep below tickle my skin. I kicked powerfully, breaching the surface of the harbor exhilarated and full of laughter. The cheers of three young girls would echo between the shores of the harbor. Swinging our arms in wide circles beneath the surface, we would watch with unbridled joy as the water lit up in a myriad of colors. Moon jellies! If you’ve never had the opportunity to witness bioluminescence in person, it is certainly a bucket-list experience. 

Kaylee (left) and Annelise (myself, right) pretending to be sharks while swimming in Three Mile Harbor at night

The moon jellies are present in Three Mile Harbor every summer, they are non-stinging (at least for humans) and you can pick them up with bare hands. Around August every year when the water temperatures are super warm, they light up with rainbow bioluminescence. It’s hard to describe the beauty of them, even harder to photograph. Picture a clear, cylindrical blob of jelly, with small stripes of rainbows zipping up from one end to the other. Now picture a harbor absolutely full of them. When we jumped into the harbor, it was like landing in a melty bowl of jello. Treading the warm salty water, each kick lit up a swath of glowing rainbow in its wake. 

The three of us were endlessly entertained by the glowing jellyfish, we would compete to see who could swing their arms to create the biggest glowing trail. Cupping our hands under the water and bringing them to the surface would produce a handful of soft glowing goo… which, after admiring, we would promptly throw at each other. After much splashing, diving, and shouting in glee, we would rest our tired bodies and calmly float on our backs together. Staring up at the stars dotting the black expanse of sky, feeling the soft breeze across our faces, while the warm harbor water embraced us from behind in a gelatinous hug. Ears muffled beneath the water, only the sound of your own breathing was clear, the slight movements of others felt through ripples in the water. A sea of luminous stars mirrored above and beneath us, it was like we were floating amidst the universe itself. Eventually, someone would break the silence and we would fall into a gentle conversation while slowly treading the quiescent water.

The three of us jumping off the Mary Lloyd into Three Mile Harbor during the day in 2014

The three of us jumping off the Mary Lloyd into Three Mile Harbor two years later in 2016

The hours have long passed midnight by now on our trip. The next, and final part of the sleepover tradition was (of course) actually sleeping. The transition usually occurred deliberately slow, with us dragging our feet climbing up the swim ladder and back on board. We would take turns rinsing down in the cramped cabin shower and changing into our fuzzy pajamas. While the three of us would get ready for bed and choose which bunk to sleep on, the exhaustion from the day would catch up to us. In the end, we would settle into our bunks, flip off the lights, and get cozy under the blankets. With bellies full of ice cream and minds full of memories, we’d be lulled to sleep by the calm bobbing of the tide and sounds of the waves lapping against the hull.

I hope this story inspires you and reminds you why we choose to become boaters. It’s all about the love of the water. If you’ve never been before, I highly encourage you to visit Three Mile Harbor in East Hampton. The harbor is always beautiful and fun, with transient moorings and a watersports area; there's even a fireworks show in July every year! Also, the Mary Lloyd does charters, if you’re interested in cruising on the boat that holds many of my fondest memories, check out their website: www.marylloydboatcharters.com.

Mali (left), Her dad, Scott (middle, in the captain’s chair), and Annelise (myself, right) on a Mary Lloyd charter for my cousin’s birthday.

Don’t forget to enjoy what you have in the moment, relish the little things, and make memories that will last for a lifetime! Happy boating!

Mali (left), Annelise (myself, center), and Kaylee (right) on my 21st birthday

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