You may remember that Matt and I attended a wedding on Shelter Island a few weeks back. For those of you who don’t know, Shelter Island is a swanky little island off the coast of Long Island that is only accessible by ferry. Now y’all already know I’m a planner. While everyone else’s day starts with their first sip of coffee, mine begins when I open my personal calendar and give my daily to-do list a scan. Schedules give me support and lists give me life…it’s just, as Keri Hilson and Timbaland would say, the way I are. However, I’ll be the first one to admit, I dropped the ball when it came to making the necessary arrangements for this trip, so when I finally got around to researching places to stay on Shelter Island I was, simply put, shit out of luck. It was like Goldilocks and the friggen hotel search…this place was too pricey, this place was already full, and this place was too creepy (Airbnb, I love you, but I’m not staying in some old lady’s basement…I’ve seen The Goonies enough times to know better). I was seriously bugging out until I stumbled across the Silver Sands Motel in Greenport, which is one of the towns the ferry to Shelter Island takes off from. The reviews were good and the rates were even better, meaning there had to be a catch, right?
The “catch” is that the Silver Sands Motel is famous—or infamous, depending on your personal feelings on the matter—for its outdated décor and laid-back management style. The interior hasn’t been updated since the 50s, the TV in the room had basic cable only, and wi-fi? Not a chance. But… get this…that’s what they’re going for. Its quirky, retro vibe has actually made it the setting for a ton of movie and magazine shoots over the years, and its lack of technological “prowess” made it the perfect place to disconnect, even if it was only for the few hours of downtime we had here and there. And maybe you’ll think I’m crazy for saying this, but once you get past the lack of aesthetic and slightly musky cabin smell, it was actually quite charming. It was quiet and clean. It had a private beach right there on site, not to mention a beautiful marsh adjacent. Plus, what does everyone always say? Location, location, location! It was only a 5-minute drive to downtown Greenport, as well as about a 15–30 minute ride to some great Long Island vineyards.
While wedding festivities took up most of our Saturday, we arrived early enough Friday evening to set out on a mission for a solid cocktail and some good eats. One of the other motel patrons—who, of note to me, has been coming to Silver Sands for years and couldn’t stop raving about the place—recommended we check out 1943 Pizza Bar . A place with both “pizza” and “bar” in its name? Count me in every time.
Already stoked on the promise of bomb ‘za, little did the Hubs and I know our intended destination would be nestled within the cutest little outdoor plaza in Greenport Village’s Stirling Square. The area, which I came to find out is actually the “courtyard” of the American Beech Hotel, was absolutely beautiful, with rustic string lights; outdoor seating ranging from modern, brightly colored circle chairs to cabana-style sofas; and tons of lush greenery sprinkled throughout, which together gave the whole area a laidback tropical paradise-meets-funky hipster vibe that was, as the kids say, totally Instagram-able. Now, did I take advantage of this? No. I am truly THE WORST blogger ever, but just trust me (and the one photo i snapped below), it was really, really pretty. The focal point was a high-top bar wrapped around a huge (I’m going out on a limb [see what I did there?] based on context clues) Beech tree, aptly named Beech Bar. With two open stools calling our name, we promptly made our way over. OK, maybe a little less promptly on my end, as I was too busy drooling over—but not taking pictures of—all the exterior design and décor touches.
We both ordered a “Lights Out,” a simple cocktail made with rum, pineapple juice, lime juice, and aperol—not my typical drink of choice in September, but I was clearly very taken by the surrounding island-inspired flora. The drink was fine…sweet and boozy, though nothing special, but I appreciated the atmosphere enough that I wasn’t about to write the place off over a run-of-the-mill cocktail. Ravenous by this point, we moved on to dinner at 1943, which was just a few short yards away under another veranda on the perimeter of the plaza.
Now, as I just touched upon, I am a total sucker for a “cute vibe” (ugh, vom, I know), so like with the drink, I had already labeled the night a complete success simply because I was so head over heels about the overall aesthetic. But I kid you not, this was one of the best dining experiences I’ve had in a minute. We started with the goat cheese–stuffed piquillo peppers, which had a smoky char and tangy balsamic drizzle that complemented the goat cheese perfectly. Next up, a custom pizza order crafted via the merging of the minds of two food lovers. If there’s one thing Matt and I can do well together, it’s a food order. Our creation? A white pie with mozzarella and garlic, truffle oil, onion, and spicy fennel sausage.
Just take a minute and let alllll that sink in.
When we could smell the truffle oil before the pizza even got to our table (#facts), we knew we were in for a treat. The mixture of fennel, garlic, onion, and truffle yielded a cozy, luxurious, savory flavor combination that felt like I had literally wrapped my taste buds in a cashmere blanket still warm from the dryer.
We finished off with a cornbread griddlecake with homemade whipped cream for dessert (because vacation, duh) and then waddled our way back to the Silver Sands to tuck in for the night, stopping down at the beach for a few minutes to listen to the waves and take in the stars. All in all, our night in Greenport was one I’ll always look back on fondly, and if you’re ever trying to do the vineyard scene out that way, I highly recommend staying there. Who knows…maybe you’ll even consider the Silver Sands Motel while you’re at it!