What You’re Missing About the Hamptons’ Best Greek Restaurant, Calissa

If all you know about Calissa in Water Mill is the celebrity-packed VIP section, you might be missing the big picture. The real star is the food. Calissa is the best Greek food in the Hamptons – confidently classic, casually chic – just what I’m looking for in a Hamptons dinner. 

Thankfully, Calissa is not a reincarnation or reinvention. The focus is on execution and quality, not ego and look-what-we-can-do. It’s a classic for a reason.

I may not be a food critic, but my fiancé is a private chef (actually, she’s “THE” private chef), so you already know how well we eat. That is to say, we had an incredible meal at Calissa, and I don’t think enough people are talking about how phenomenal the restaurant is.

I’ve seen the many sides of Calissa: been in the VIP, taken shots with Ja Rule, attended private events on the meadow grounds. Love it – the space and the team and the vibe – the Hamptons needs this energy. But, and I’m not trying to get political here, Calissa’s restaurant is the real hero. Excellent food that is, thankfully, 5,040 miles* away from another “upscale American-Italian.” Opa!

*the distance from JFK to Mykonos.

A few quick notes: We hit the fish hard, but when in Water Mill, eat as the Greeks do. Also, if your party is more than a date or you’re just experiencing extreme hunger, the “For the Table Menu” looked awesome. The lobster pasta especially had me planning my next visit.

Calissa is no Summer tryst—the elegant restaurant is open year-round, which is a serious badge of honor in the Hamptons—and we’re here for it. 

COCKTAILS

Cocktails like these will give you a reason to use the word mixology. We’re not cocktail people (tequila + soda + lime, repeat), but our drinks were fantastic and not syrupy sweet. Proof the cocktail service is impressive: we ordered a second round! Calissa doesn’t put jewelry in the cocktails because she is not a Pick Me Restaurant. 

I recommend the Gypsy Kiss. Bright, airy and – this is a good thing – with just a touch of red pepper, you can taste the capsaicin! It was so good that I didn’t even mind that it was in a coup!

AWARD-WINNING WINELIST

Calissa’s wine list is exceptional but not overwhelming, beautifully curated by its in-house sommelier (also an owner). It has won the Award of Excellence from Wine Spectator and highlights wine from the Mediterranean, local varietals, rare selections from Greece, and, of course, large bottles ready for the whole table. 

Mediterranean selections, native varietals, and rare picks from Greece, and large format bottles ideal for celebrations. 

MEZZE

I promised myself I wouldn’t… but our starters were A-mezze-ing. Do not forget the Mezze. The pita is still warm! Also—and this is huge—there are more than enough pitas. Take notes, Mexican restaurants. Seriously, these pitas are soaking up that fancy EEVO from the Crudo. Working overtime. 

Red Pepper dip – spicy feta – crazy feta move over! This is real Greek.

Tatziki with cucumbers was great (duh)

Fava Beans with capers – better than hummus? Silkier for sure.

The Best Greek Salad in the Hamptons

This Greek Salad is elite. Elevated by great ingredients and timeless flavors. High-quality feta, you’ll taste the difference. A diner Greek Salad, this is not – we don’t need lettuce. I won the rock-paper-scissors, so I got to drink the last bit of the salad dressing – is this bad etiquette? Should I have let my bride-to-be win?

APPETIZERS

VIPs come for the vibe, we came for the crudo. Get the full Crudo suite because you love yourself. It’s bold to plate a dish so simply—it demands excellent quality and belief in the flavor. If you’re just going to get one: stay local, get the Montauk Fluke.

If you really love yourself, get the Saganaki – fried cheese with honey and lemon. Could have eaten two. It’s crazy to think that it’s gluten-free. Seriously, I almost didn’t mention this so gluten-enjoyers won’t scoff. 

The crispy octopus was the highlight for my fiancé, whose opinions are much discerning than mine. It’s super briny with a substantial bite, like the texture of a perfect scallop. Don’t skip it if you think that Octopus is tough, not when it’s cooked correctly. 

The Keftedes are a diplomatic option great for less adventurous eaters, but they should not be picked over the octopus. Don’t worry if you’re concerned about having ordered fish—the octopus is crispy and substantial in a way fish, to me, almost never is.

ENTREE

Luckily, we listened to our server’s suggestion of the Dorade, a Greek fish. Delicate, crispy, perfectly cooked. I love the extra-crunchy skin, and the watercress salad was great, a simple palate cleanser.

My fiancé reminds me that the margin for error when cooking fish is much slimmer than when cooking other proteins. ”Just like that, it’s overcooked,” with no fat to keep it juicy. So, it’s no easy feat when you have fish this tender and delicious.

SIDES

I’m an American…ask me about the sides! The Gigante Beans were almost like gnocchi, and I was surprised by how good the red saucy base was. I took this home and am actually going to eat it for lunch the day after I finish writing this. The Leek Rice was simple and clean, paired perfectly with the fish.

DESSERT

We’re not dessert people, per se, but the House-Whipped Yogurt can convert me. It’s sweetened with honey and fruit, but mostly smooth and creamy—almost like sweet whipped cream. It’s not your breakfast yogurt, by a long shot. The Baklava will always be a fan favorite. 

NIGHT CAP

Uzo is a bit like smoking a candy cane, but in a really cool Greek Marlboro man way. 

EXCEPTIONAL SERVICE

Service was a standout. Sometimes, you feel like you’re getting in and out, but we felt right at home – Robson even hooked us up with fresh pita to go. Our server, Evan, was the best. Super attentive and knowledgeable, but didn’t make me feel stupid asking if Sancerre was a brand of wine, a region, or a grape.

I have to mention how impressed I have been by the ownership group behind the restaurant – they are hospitality people, taking care of their guests is in their bones. It should be no surprise that a restaurant this elegant, welcoming, and beautiful is partially women-owned. Not to slight co-owner James, who makes you feel like an old friend when he checks in on tables (also, a great DJ), but, for me, the intangible feminine energy that pervades Calissa plays a significant role in the ambiance and aesthetic of the restaurant.