Visiting Long Island: That Time I Traveled The Longest Island In The Shortest Amount Of Time

When you think of vacation destinations in the US, I bet Long Island doesn't really come to mind. And there's a reason why: There hasn't been an actual tourist draw... until now. I was able to be part of a small group of people taken to soak up everything Long Island has to offer, as guinea pigs for the Long Island Convention and Visitors Bureau and Sports Commission (we shall call them LICVB for short, yes?)

The trip was made possible by the amazing people at LICVB, along with the stellar New York branch of The Brandman Agency. Five of us (four chatty girls and one brave guy — the executive rep from Brandman) spent the better part of four days traveling in a van that really became our mobile home (we logged lots of hours in that sucker... some awake, some asleep, lots in laughter and song), visiting spot after spot, meeting person after person, before crashing at a new hotel (sometimes a castle) every night. It was a jam-packed, dizzy-headed trip. And when you spend that much time with a small amount of people in an enclosed space, you really hope you'll like each other.

We got lucky.

Y'all, Long Island is big. So many islands...and shores...and forks... It's a massive place! Yes, I realize it tells you that in the name, but still. And here's the thing — there really is something for everyone on Long Island.

If you're a US history buff, you need to get yourself to Sands Point Preserve on the original Guggenheim Estate (a.k.a. 'East Egg' of F. Scott Fitzgerald's The Great Gatsby). Touring that old mansion makes you feel like you need a Champagne coupe in one hand and a dance partner in the other. In Oyster Bay, you can tour the 'Summer Whitehouse' of Teddy Roosevelt... with Theodore Roosevelt, himself. (Or his impersonator, rather.) And if you're lucky, like we were, you can go grab a beer with Teddy after his shift and play Cards Against Humanity in the Oyster Bay Brewing Company (whose Grapefruit IPA is stellar, by the way). And then on the North Shore, you could visit the Brewster House where American patriot Caleb Brewster spied on British soldiers during the Revolutionary War.

But when it comes to history, I tend to perk up when the subject turns to music, so I particularly loved walking through The Jazz Loft in Stony Brook after we left Brewster House. It was a tiny house filled to the brim with all things jazz. Walking through that room with VP (and killer jazz musician, in his own right) Ray Anderson was like taking a master class. Anderson loves what he does, and his energy is contagious.

There's also a great deal of shopping to do on Long Island. If you're a mall person, Roosevelt Field Mall is the largest they have, and their Macy's cosmetic area alone rivals Sephora. If you're more of a local, small business shopper, Stony Brook Village Center is just so adorable and quaint. And if you go, you have to visit Brew Cheese they have a fantastic cheese selection and a wide variety of local craft beers. There were a ton of places just like that all along Long Island.

In fact, most every town we visited had a rich culture of locally sourced ingredients. I had the best espresso of my life at the cutest lunch spot, Love Lane Kitchen in Mattituck (North Fork). The coffee was local and from North Fork Roasting Co. and one of my only regrets from this trip is not hunting down a bag to bring home. One of the best domestic sparkling wines I've tasted also came from Mattituck/North Fork in the most unexpected of places, Harbes Family Farm. (This is also where I tasted the best ever Honeycrisp apple, grown right there in the soil beneath my feet, as well as a darn good apple cider doughnut.) Harbes Vineyard Blanc de Blancs is the sole reason why I checked my bag on the trip back. I bought myself a birthday present bottle of bubbly after stumbling across a surprise wine room past the pumpkins and apples. (It's a gift.)

If food is a big reason why you travel, then it should be said that one of the best meals of my life came on the first day of travel from chef Michael Psilakis (whom we had the privilege of meeting) at MP Taverna in Roslyn. Chef P does modern Greek cuisine, and he does it right. They gave us a prix fixe tasting menu and I cannot recall a time where I was fed as well. The bulgur salad with pomegranate, fennel, and olives alone is worth the trip. But while you're there you may as well have their perfectly grilled octopus. And their impeccably fried calamari. Also their baklava. How he managed to make something oftentimes cloying, be so inviting with every bite, is beyond my comprehension. It was so good, in fact, that they boxed some up for me that served as my birthday breakfast in bed the following morning. Because who doesn't love the sound of "birthday breakfast-in-bed baklava?

And then there was Jerry and the Mermaid in Riverhead that served as lunch before we fed fish and pet a sitcom cast of precious penguins at the Long Island Aquarium around the corner. Jerry and the Mermaid took me completely by surprise. With their giant, laminated menus and walls bestrewn with beach art, it's almost as if they don't want you to know they make the best lemon-butter grouper and chicken wings. The grouper dish was a special, but the wings are "Jerry's Famous Wings" and Jerry himself will not tell you the ingredients he uses in his sauce. Even if you guess some of them — like I suspect I did — he chooses to pretend you didn't. He's earned the right to be that proud, because those wings were the perfect combination of sticky, sweet, and spicy.

My favorite part of the trip, which really deserves more than a couple sentences, was paddleboarding with Mokuloa Paddle Tribe in Oakdale. It was the first time I had ever paddleboarded, and being out on that still water, with the sun dipping in front of me and new friends all around me, was a moment and a feeling I will never forget. It's a powerful sensation being up there on that board — manning your own ship. And the people of Mokuloa were the warmest, most down to earth, and just downright coolest people.

Ohhh, right: the castle. So we kind of stayed in a castle our last night. Oheka Castle in Huntington, to be exact. The story and history of Oheka deserves its own article, but trust me when I say it is magnificent in every possible way. It's also the castle in Taylor Swift's "Blank Space" music video, the location where Kevin Jonas got married, and also where several films and television shows have been filmed. Not to mention the fact that the original owner, Otto Kahn, is the actual inspiration for the Monopoly Man. (That's his face on the board game box, y'all!)

We stayed in great spots every night, such as Danfords Hotel and Marina in Port Jefferson (quaint beachy spot, serious shower game, and my room had a private terrace right on the water) and Montauk Yacht Club (great restaurant, luxurious room on the water, easy to get lost in the tub and the bed), but it's really not fair to those guys to put a castle stay at the end of it all.

The people of Long Island are very proud of who they are and where they come from, and you can feel that in every word they say. It was so inspiring. And while I probably wouldn't recommend touring the entire place in four days, I would recommend touring it. There's a certain charm to Long Island that still, as I write this, is pulling me towards it. Every face was smiling. Every smile was rich. Every handshake was firm and genuine. If their job was to convince me that Long Island is a place to be seen, then job well done!