One Hundred Days of Summer

06/02/2015 10:31 am ET | Updated Jun 01, 2016

From the second I existed as a twinkle in my old man's eye, I called Martha's Vineyard home. Granted, a true islander has every right to crucify me by that statement. When I call the Vineyard home, I mean spending a quarter of my life on the island, missing the days of dark, cold nights and bitter weather of the fall, winter, and spring.

My sad reality: I live as a summer-er amongst Islanders. Not even worthy of the title "wash-ashore," my roots exist in Shrewsbury, Massachusetts circa Christmas Day 1994. I never truly embraced my Masshole roots until I stepped foot at Boston College in the fall of my freshman year.

The kids from Minnesota and California stood in awe at how fast I spoke. I said the word "wicked" as if I never read a book in my life. I drank Dunkins with more cream than actual coffee. Barstool remains my top news source. Hell, I accept Tom Brady as my Lord and savior.

Cali and the Mid-West kids had their lake-houses and hiking trips. I laughed at that. In my mind, my summers possessed no rival. Nothing matched a Vineyard summer. Putting the clocks on rewind for a moment, I remember a typical trip to the magical place across Falmouth I never quite pronounced correctly: Mark's Vineyard, not Martha's Vineyard. My older brother, Mark, proved quite the smart-ass from a young age, telling me he owned the whole island. I ate it up though, happy to tag along for the ride.

Crossing over the Bourne Bridge from 495-West meant donuts and my mom playing James Taylor non-stop over the radio's cassette player. Our family made sure to beat traffic, waking up at 6 or 7 am to catch the 9 am Island Queen ferry. The process of packing up the Nissan Quest at the brink of dawn never grew old. Sure the inside smelt like puke, but if it sent me across the Nantucket Sound, the Quest belonged in that special group next to The Land Before Time and my Jason Varitek signed Sox hat.

My brothers and cousins spent our days soaking in the sun on Jetty Beach in Oak Bluffs. We called ourselves "cool" strictly based on the number of hermit crabs we caught from our parent's fishing nets. Specie consisted of trading fruit-by-the-foot and an argument or two erupted within the first few innings of beach wiffle-ball. A good day ended with a ride on America's oldest carousel, The Flying Horses, immediately after a home-cooked meal on my grandparent's porch. The perfect day meant traveling "up-island" to Aquinnah for a day of body-surfing, Chilmark Chocolates, and the occasional Native-American history lesson.

Sadly, we all grow up. We outgrew those Old Navy shorts and trekked through those excruciatingly, awkward days of middle school. Before you know it, your cousins leave for college. Left behind in the ashes of your innocence, life turns into a Stevie Nix song in the blink of eye leaving you wondering where the time goes. Those trips to The Flying Horses got old. Ice Cream never quite tasted the same and, with nobody to play wiffle-ball with, I grew bored. Things got real. With college looming quick and tuition skyrocketing, I needed a job. Money no longer grew on trees.

A night out turned into house parties in Katama or beach bonfires with co-workers by the banks of Lucy-Vincent. Countless memories of 4 am taxi rides ended waking up at 11 am the next morning, ready to start all over again. We sang throwback Backstreet Boys lyrics on Edgartown's lighthouse beach and ventured into town to grab some late-night food over at the Quarterdeck, losing a flip-flop or two along the way. Life felt perfect. I had a great group of friends and enough money to fuel a ride that accelerated faster each second.

Fast-forward to today. I crashed.

A few rejected internships later and a Boston College junior washes ashore Martha's Vineyard for the next three months. Here we go. My curtain call of childhood: the last summer of retail at Vineyard Vines before I start wearing the ties I once sold for good. Working for the self-conscious, pink whale has its perks. Sure I resemble and easter-egg or a fruit salad much less a 20 year old. But hey, I earn money emphasizing the good life to customers, expected to know the island's hot spots like the back of my hand. "Every Day Should Feel This Good." Live heaven on earth, plain and simple: Nothing beats that.

Looking for a beach, golf course, bar, or even your occasional sports rant? Look no further. Living on your own as a college student with an island full of distractions keeps a kid busy.

For the next one hundred days of summer, I invite you to pull up a beach chair and light a stogie in honor of my last hoorah. Watch the sun set over Menemsha harbor, cookout on Norton Point for the Fourth, and split a gaucho steak over by Sharky's Cantina. Sit at the bar with me, watch a late-night Sox game or even stop by the Oak Bluff Vineyard Vines for a coozie. Throw a wad of cash my way and I promise to get the most out of your day's 24 hours.