10 Wildly Romantic Long Island Getaways For Lesbians

Move over LA. Long Island is the new “L Word.”

Sup, babes? What’s that I hear? You need a break from the city? You want to impress your girlfriend and take her somewhere other than a Brooklyn dive bar this weekend? You’re so lucky to have me, your own personal Long Island lezzie tour guide. Long Island isn’t just strip malls and tanning salons (though we are still very proud of that fact.)

This weekend, why not take a break from subways, cover fees, and late nights? How do pine trees, wine, mood lighting, and locally sourced food sound? And while you’re here, you can get a mani-pedi for only $20. Yup!

Or maybe you’re from Long Island and still live here (in which case hit a lez up!) and you are sick of seeing NYC getting all the glory, all the dating guides, and events. You’re tired of taking the LIRR every weekend then being too drunk to take it back and spending $120 to Uber home (like yours truly does on the reg). So why not stay in the motherland this weekend? Invite that snobby Brooklyn lez you’re dating that refuses to leave the city—she needs to see how wonderful Long Island can be! Because both you and I know, this shit is romantic. It’s beautiful. It’s way cheaper than the city. And it’s way underrated!

Let’s start with the North Fork. I know, I know—you associate the North Fork with summer. But in my humble lesbian princess opinion, it is ten times more fabulous in the cold. There is something so ~sexy~ about winter in a summer town. The wineries are less crowded. The locals finally come out of hiding (or their seasonal jobs) and hang out at bars and restaurants. There isn’t any traffic. There’s a chill in the air and fireplaces at almost every winery. There are bed and breakfasts to curl up in. There are adorable little holiday shops to get lost in. Sound good? I present to you 10 romantic date spots on the North Fork.

First up: directions. Take the subway line of your choice to Penn Station and jump on the LIRR. Another option is the Hampton Jitney, or be extra AF and take a car.

1) Love Lane, Mattituck

This is an iconic cute little street situated in Mattituck. I’ve already meticulously planned your date for you because I’m a control freak: start at Lombardi’s Market with an espresso and a muffin. Then buy your bae a sexy new outfit at Mint. Next up, the Love Lane Sweet Shoppe (to save some chocolate for later). Then the most important part: The Village Cheese Shop. I know gouda doesn’t sound that exciting, but trust me, it is their best cheese. Then have the cute girl behind the counter hook you up with a baguette. Doesn’t matter that it’s huge: you’re on a day-cation, you deserve all the carbs. Now, head next door to the Roanoke Tasting Room. Order the Cab Franc if you like red. Try Infinite Possibility if you like white. Eat your snacks, make out, drink, repeat. There’s also board games if you’re into that. I prefer to just get drunk and stuff my face, but to each is own.

2) Lieb Cellars, Cutchogue

A post shared by Lieb Cellars (@liebcellars) on

If you like sparkling rosé, have I got a place for you. This winery has the best sunset view in all of the North Fork. It’s super romantic and intimate. If you want to sit outside by the fire, they provide cute fleece blankets. Plus they have bomb AF meat and cheese platters. I also get queer vibes from the hot girls that work there, but that could just be wishful thinking. This is the perfect place to cuddle up with bae, listen to live music and take in the beautiful view.

3) Eastwind Shoppes, Wading River

If you like little nick-nack shops, consider this your paradise. Holiday tree lightning this Saturday at 6! Boasting over 20 independent shoppes and eateries, this is a seriously cute date spot. Shop for wine, crafts, cheese (am I talking about cheese too much?), jewelry, clothes and more. The carousel is gorgeous and fun AF (yes, I’ve gone on as a grown ass adult. No shame.) It sounds lame, but there is holiday magic in the air here. My top picks are Brezza’s Pizza Kitchen (they have awesome pizza and a local selection of beer and wine.) If you’re like me and could eat cheese for every meal, be sure to check out the Cheese and Spice Market. Order the Euphoria Cheese. The name speaks for itself. You Me and Tea is a quaint little tea shop where you can browse and smell the teas before you choose. The lavender tea is heavenly. My friends and I have also voted the tea shop as having the most queer playlist on earth. Go in and you’ll see what I mean. If you’re into Paint and Sip, The Painted Canvas is super cute. When I went, I just drank and didn’t follow directions, but if you’re a craft lez, this is the place to be.

4) Jedediah Hawkins, Jamesport

A post shared by Jennifer Ann (@jpn1010jpn10) on

Ugh. Ever been to a place so perfect for couples, you kind of want to die? This is the perfect bed and breakfast to relax, connect, and f*ck your brains out in. There are beautiful gardens, an art gallery, a delicious restaurant, and charming rooms. The best part is the authentic speakeasy in the basement. You can’t go wrong with their seasonal cocktails and the fries are to die for. When things get too hot and heavy in the Speakeasy, head upstairs to your room.

IDK who this girl is but she slays.

5) Main Road

One of the most famous roads on Long Island, Main Road is loaded with wineries and restaurants. In addition to getting your booze on, be sure to stop in The Christmas Shoppe, which is a true winter wonderland. The Northfork Chocolate Company will blow your mind with their chocolate covered pretzels and local art display. If you can handle more sweets, Junda’s Pastry Shop’s cookies are life-changing.

6) Sound Ave

A post shared by Justin Pellegrino (@jtpelle) on

Sound Ave is the Mecca of romantic holiday cuteness, and will be one of the most gorgeous roads you will ever drive on. Start on Sound Ave in Riverhead and drive all day. You will pass tons of wineries, open fields, farms, and animals (!!!).

7) Grana Trattoria Antica , Jamesport

Ya’ll…I’m getting emotional just thinking about this restaurant. My instagram caption says it all. Grana serves up all organic and locally sourced ingredients and handmade pasta. I think it is the best Italian in New York. And I’ve eaten at a sh*t-ton of Italian restaurants; pasta is basically my number one hobby next to masturbating. Be sure to make a reservation. This place is small and intimate– it fills up quick. I know their website looks ratchet but trust me on this.

8) Orient State Park, Orient 

A post shared by Lynne (@photomom1956) on

Easily one of the most beautiful places I’ve been to. This drive will take your breath away. I think it’s even more beautiful in the winter because there is a slight melancholy in the air. What can I say? I’m such a Jenny Schecter.

9) Custer Institue and Observatory, Southold

A post shared by Connor Rogers (@crogers426) on


Custer Observatory gets my pick for most unique date. Every Saturday, they are open for planet and star observation through their state of the art telescopes. You can legit see the craters on the moon! They usually have some sort of event accompanying the observation hours, like a food or beer tasting. Check their website for upcoming winter events.

10) Greenport Village, Greenport 

Greenport is my favorite Long Island town, hands down. Here is your perfect date mapped out by a princess dyke: start at American Beech for cocktails. I know its winter, but order a Garden Party (watermelon, mint and vodka). Trust me on this. If you’re staying the night, American Beech is also a hotel. Wink wink. Next up is Brix and Rye speakeasy. No sign– I promise you’re in the right place. Go down the stairs. No menu– just tell the bartender what you like and they’ll hook you TF up. Now that you’ve got a buzz, head to The Times Vintage to $hop. They have some seriously amazing designer vintage. You gotta do some searching though. Are you hungry? Good, ’cause the restaurants in Greenport are LIFE. Lucharito’s is definitely a town favorite with celeb customers like Gigi Hadid. It’s usually too crowded to touch in the summer, but in the winter you should breeze right in. Get the fried jalapeños. If you’re in the mood for Italian, try 1943. Their pizza will bring tears to your eyes. After that, warm up with a coffee at Aldo’s.

I promise you Long Island will charm the pants off of you and your date. So much so that you might want to extend your day-cation, so here are some B&Bs.

What Do You Think?

Leave a Reply

Your email address will not be published. Required fields are marked *