Charlie Boy — Restaurant in Town of Southold

We recently visited this restaurant and initially enjoyed sitting outdoors — until it suddenly began to rain. We quickly ran inside to avoid getting soaked, expecting at least a bit of understanding or help from the staff. Unfortunately, that was not the case.

While trying to find shelter, my son was served his pasta and we sat him at the first available table so he could eat without his food getting cold. Shockingly, the manager approached us and asked him to get up — claiming that the table was reserved for guests expected 20 minutes later. Not only was this unnecessary, it was incredibly tone-deaf given the situation and showed a complete lack of hospitality and flexibility.

The manager showed zero initiative to help or accommodate us during the rain, and instead chose to prioritize a reservation far in the future over the comfort of a family already dining and clearly in distress. His lack of experience and poor judgment were obvious and disappointing.

To make matters worse, the overall service was cold and inattentive. One particular staff member, a woman with a long-sleeved tattoo, was especially dismissive. Her attitude matched the manager’s — indifferent and unwelcoming.

In a service-based industry, kindness, adaptability, and empathy go a long way — and sadly, this place had none of it. We won’t be returning, and I would not recommend this restaurant to anyone expecting even...

This Memorial Day weekend, I had the pleasure of dining at this cozy establishment, and I was thoroughly impressed with both the ambiance and the menu offerings. The service at Charlie Boy was commendable. Our server was attentive ensuring our glasses were never empty. The staff seemed genuinely enthusiastic about the menu, which added a personal touch to the dining experience.

Now, let's get to the highlight: the food. The menu features a variety of options that would please even the pickiest of eaters. The truffle arancioni were such an incredible upgrade from your typical rice ball. The lobster toast was delicious and left us wanting more. For the main course, I opted for the grilled branzino, which was simply outstanding. It was cooked to perfection, flaky and delicious. My husband chose the chicken cutlet and said it was better than any he has had. Did I mention he’s the pickiest eater ever!!!

It’s a must-visit when you’re in Greenport. I can’t wait to return and explore more of what their menu...

My friends and I went to Charlie Boy over the weekend and thought the food was decent, but the portion sizes were extremely small. Oddly, our party of six was told we could only order two pizzas for the table, which seemed arbitrary, but we went with it. We were also warned that the pizzas might take a while, but the timing was worse than expected: by the time one friend got her pizza, everyone else had already finished eating. On top of that, the presentation was strange—they served the pizza on top of an old tomato can instead of a proper rack. When the check came, there was no checkbook or pen, just a loose receipt, and we had to use a random crayon to sign it. Overall, the food was fine, but the service, pacing, and presentation could use...