How To Survive A Day Of Wine Tastings On Long Island

Here’s how to have the perfect day drinking wine on the North Fork, so you can focus on managing your chaotic friend group instead of debating where to go for dinner.
How To Survive A Day Of Wine Tastings On Long Island image

photo credit: Anne Cruz

The difference between a wine-tasting outing that inspires fun dinner party stories and one that ends in a shared hangover and animosity is preparation. You’ll need a filling meal, appointments at a few wineries where you can sip a nice chilled glass of pinot gris on a comfy Adirondack chair or plush banquette, and something more substantial than a cheese plate for dinner. 

Trying to find restaurants on top of all of your North Fork winery research can be a bit draining, so we’ve planned the perfect itinerary to help you fill in the gaps between tastings. Here’s how to have a delicious, wine-filled day on Long Island, that starts with a breakfast featuring brown sugar bacon, takes you to a Barbie-meets-cottagecore garden where you can try a dozen different types of rosé, and ends with a seafood feast by the water.


photo credit: Madison Fender



$$$$Perfect For:People WatchingBreakfastBrunch
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There are two reasons why you should make a reservation at Bruce & Son in Greenport: first, to get some food in your stomach before consuming any alcohol. And second, to mentally prepare yourself for a day of clinking glasses and hearing someone murder the pronunciation of “gewürztraminer.”

If your ideal breakfast is actually dessert, their hotcakes are loaded up with peach butter, maple syrup, dried berries, and seeds for some crunch. For a more protein-forward meal, the egg sandwich has thick slabs of sugar bacon for the ultimate savory-sweet combo. If you have some time to kill between brunch and your first tasting, Main Street has lots of antique and gift shops prime for browsing. 


Since you're probably going to be drinking a wide variety of wine throughout the day, it’s best to start with something lighter or sparkling, since the bolder flavors of reds can linger and affect your taste buds. To follow this very scientific advice, go to Sparkling Pointe—they only make effervescent wines, so you won’t throw off your palette for the rest of the day. There’s a nice patio where you can sip your flute of bubbly, or you can seek refuge in their large, air-conditioned tasting room if it’s already way too hot at 11am.


Croteaux has a wide roster of rosé to choose from, so everyone from your aunt who has a WSET certification to your cousin who just turned 21 can find something to enjoy. The shaded outdoor garden and comfy, quilted picnic benches are also an ideal spot to park yourself for a leisurely lunch, since they have more substantial food options than just charcuterie boards. 

Get an order of lobster roll sliders and a basket of beach fries to keep you fueled up for managing the fragile diplomacy of friend groups colliding or hanging out with your mom. Just don’t be surprised if you’re tempted to buy a cute branded sweatshirt and $30 candle in a rosé-induced haze.


Ev & Em is one of the newer wineries in the North Fork, and their large indoor space and covered patio are great for when it starts raining or you’re a little too toasted from lounging outside all day. The flights here are very solid for their $35 price point, and the staff is more than happy to chat enthusiastically about tasting notes without seeming too pretentious or overbearing. If you want just a single glass, the light pinot noir is a great chilled red if you’re the type of person that refuses to drink white wine even when it’s 100 degrees outside.


photo credit: Madison Fender



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Keep the party going after your last tasting by having dinner at Claudio’s in Greenport. Grab a table by the windows or on the covered outdoor deck before the sun starts to dip. That way, your herb breadcrumb-crusted fluke will arrive as you’re bathed in the glorious light you can only get when hanging out at dusk near a body of water. 

There’s lots of seafood here, so order some North Fork oysters and littleneck clams to share as you watch boats ferry back and forth from Shelter Island. If by this point you’ve exhausted most of your small talk topics with your winery companions, you can always debate which bottles to open when you get back to the AirBnB and which ones you want to cellar.

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