Charlie Boy: A Five Star Addition to the Greenport Waterfront

“If it ain’t broke, don’t fix it,” doesn’t always apply – certainly not in the case of Charlie Boy, a reimagining of Claudio’s Tavern & Grill in Greenport. It’s a vast improvement that manages to stay true to what the tavern was while introducing fresh concepts.

A New York City Italian-style restaurant, Charlie Boy is just one element of an effort by Claudio’s management and Gansevoort Hospitality Group to help revamp the waterfront. Claudio’s Tavern & Grill is now Charlie Boy, while Claudio’s Pizza has become a city-style slice shop called Little Charli. The waterfront eatery once known as Crabby Jerry’s has become a country-style restaurant called Common Country East. Claudio’s Waterfront remains untouched.

“We really felt like thi230-9044.s space would represent Charlie Boy,” Keith Hancock, chief operating officer at Gansevoort Hospitality, said. “We thought it would do well here, and it’s proven. Yeah, it is doing well, yeah, because there’s nothing like this here.”

It played out in a way that truly emphasized what Charlie Boy has to offer. A reservation was set for Dan’s Papers to eat at and review Common Country East, which remains on the dock as Crabby Jerry’s was, but inclement weather prevented Common Country East from opening. Instead, we were offered to dine at Charlie Boy instead.

It was cloudy, and the fog was so thick, you couldn’t even see the end of the Claudio’s dock – almost like a planned day trip to Greenport that weather threatened to ruin. But ruined it was not. In fact, Charlie Boy was more than worth a foggy Sound Avenue drive – you may want to save a rainy summer day just to try it out.

The atmosphere manages to both feel like a quiet East End eatery and a bustling New York City restaurant at the same time. And if the weather is nice, there is still an outdoor eating option at Charlie Boy, overlooking the docks. There is also a fully stocked bar.

Hancock said that he interviewed up to 1,000 people for jobs at Charlie Boy, and settled on roughly 55. This shows, as the staff is incredibly dedicated to the Charlie Boy theme, and equally attentive to their guests. No food or drink took more than five minutes from order to table, and the waitstaff was quick to help with anything.

Drinks

There’s a non-alcoholic drink menu, a wine list, and a cocktail menu. Since there were too many good options, we went with what’s proven at Italian restaurants – an Aperol spritz. It was made beautifully and served in a retro style cocktail glass, and accompanied the food flawlessly.

Appetizers

The lobster toast, served on a piece of bread with Calabrian chili aioli, basil, and shallots, is as if the best lobster roll you’ve ever had was styled like classic avocado toast. It’s savory, meaty, and filling.

The chopped salad could be an entree. Made with shaved Brussels sprouts, banana peppers, grapes, sliced salami, egg, olives, and spicy Colatura vinaigrette, it’s sweet, it’s savory, and it’s got a little bit of a kick. While it’s on the appetizer menu, it could easily be a main course if salads are your thing.

The Boy’s Prawns, large prawns served in balsamic garlic, chili, and olive oil, are a must for shellfish lovers. It’s like if grilled shrimp and lobster were combined, taste-wise. While there’s no shortage of great appetizers on the menu, try to make room to try this.

The standout on the appetizer menu is the Truffle Arancini. A variation of Italian fried rice balls, they’re made with black truffle, melted fontina, and glazed with honey. You may have to consciously stop yourself from gobbling it down so fast to try to enjoy all the flavor – these go down too easily.

Main Course

Charlie Boy offers up to six different kinds of pizza, eight pasta dishes, and five meat dishes for your entree. Filled with Italian classics like eggplant parmigiana, chicken marsala, linguine with clams, cavatelli, and more, we opted to try the White Boy pizza. It’s made with ricotta, mozzarella, parmesan, roasted garlic, lemon zest, thyme, chili flakes, hot honey, and lemon-infused garlic oil. It’s hard to pinpoint the exact flavor, as all of these blend together to create an excellent pizza with a little bit of a kick.

These pizzas can serve one person, so you may want to try multiple if you’re with a crowd.

Dessert

For dessert at Charlie Boy, you can get soft serve ice cream with a number of toppings, mixed berries and whipped cream, or a Nutella pizza. By dessert time, we only had room to try the Nutella pizza. Three simple ingredients, ricotta, Nutella, and marshmallows, make it a memorable choice.

Final Verdict

Rain or shine, romantic date or a day trip with friends, Charlie Boy is unlike any other restaurant in Greenport – and it’s worth paying a visit to this summer.

Five out of five stars.

Charlie Boy is located at 111 Main Street in Greenport and can be reached at 917-230-9044.