Talk about awkward... upon arriving, you're greeted with a sign at the door that tells customers not to listen to what people at the inn are saying about them. The inn and restaurant are on the same property and evidently the owners are feuding. It's rumored one owes the other $750k. Yikes! Our large dining party went there because we were staying at a nearby marina and the dining choices are somewhat limited in that area. Our waiter barely understood English. They don't accommodate for allergies at all, and despite their GF pizza menu option, they didn't actually have it. My husband ordered prime rib which he said was just "ok". I ate the beet salad and had his portobello mushrooms. The bill was a bit steep... $90 per person, but hey- it's Montauk prices I guess. I wouldn't suggest coming here... at least until there whole money debacle is worked out. You can feel the tension in the air which makes for a somewhat edgy dining experience. read more

Kenny's Castaways - Beet salad - Italian Near Me - Montauk, New York

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For the time of year, one of the few places open. Adjacent to our hotel. Across from the water but no water view- just boats in line of sight. Warm, homey feel- live music some nights, locals rave about the pizza here and for good reason. Plenty of options for everyone, and very attentive service. Make sure when you ask for flat water- you say "tap" otherwise it's a $12 bottle of "flat" water - full bar area well stocked with top shelf to tap beer. Priced accordingly- small parking lot shared with the motel. read more

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We must have driven past Kenny's a million times, and my cousins even stayed here at the hotel... but never ate at the restaurant. We just got off a two hour sunset catamaran and wanted somewhere to sit and eat. It was 8:30, we were hungry, and only a party of 11 (not 20+), and I decided to poke in. The host said, no problem, come in, and they set a table for us. With absolutely zero expectations, we sat and saw the menu. Our server Mario took care of drinks and apps straight-away, and indulged the children with some much needed banter. The pizza's looked interesting so we put in a few. We also ordered some apps - shrimp cocktail, calamari, polpo, mamma's meatballs. We rounded out the meal with some salads and tried the bolognese. Everything was great- we really had a nice meal, and could definitely see adding this restaurant to our regular rotation going forward. read more

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The food was generally good, and Mario who took care of us was nice. There is one thing that I must draw attention to. My party was charged for 5 baskets of garlic bread at $7 a plate for a total of $35. Yet, we never ordered this bread. In fact, they were bringing it out to every table at the beginning of the meal as typically happens in similar restaurants. This time, the bread was not complimentary. It was a hidden charge. We did not order any bread nor were we asked if we wanted it. We weren't warned of a charge either. When paying the bill, my party mentioned this issue to Mario, and he just shrugged his shoulders. In the end, we were forced to pay this $35 charge and no rectification was made despite noting our confusion and explaining the situation. One must assume they are doing this to all tables - perhaps some notice the charge, and others don't. Are they trying to cheat their customers? This practice is highly inappropriate and unfair. Further, why bring us out 5 baskets? The restaurant is just picking an arbitrary number and then making customers pay? It's not about the money, it's the principle of it coupled with the fact that it wasn't rectified when a clearly perplexed customer pointed it out. My family comes to Montauk 2-3x per year, and we will not be returning to this restaurant because of this duplicitous practice. Addendum: Regarding your below response. What a joke! When we arrived, there were 2 people in your empty restaurant. Actually, when we saw it was so empty, we paused to wonder about that. In reality, Mario, you never said there was a charge for bread. $35 for bread - ridiculous!! In the end, I leave it up to the future potential customers to decide. read more

Went with a large group. Bartender was lost to start. Appetizers were ok. Ordered the steak, decent. Out of a group of 30. At least 75% of the people that ordered chicken got uncooked chicken. Not undercooked. Uncooked. Would not recommend. read more

Delicious food, amazing service!!! The tuna was delicious. Tiramisu perfect. Will definitely visit there next time we come to Montauk.

We were looking for a place to enjoy dinner on a rainy Tuesday evening in Montauk. We were 6 guests of the motel (Kenny's Tipperary Inn) and due to the weather we decided to stay local, and this restaurant is attached to this motel. We took a look at the menu ahead of time, items were pricey even by NYC standards, but it was convenient and we decided to give it a try. Upon arrival we were lead by Mario to a "special" table in the room with all the windows. They took our drink order which were served promptly, along with a choice of sparkling or Montauk water. We decided to try a few appetizers...calamari, Montauk Tartara, and a Margarita Pizza. Everything was fresh and tasty. The only complaint was that the calamari portion was significantly less than most, but it was delicious, tender, hot and crispy! Our entrees were somewhat varied, 2 Lamb Chop(s), 1 Chicken Milanese (that was split) and an appetizer of Mama's Meatballs to accompany a dinner portion of linguine with clam sauce, that was also to be shared by one couple. Our entrees were slow to come out. We received the chicken and lamb chops entrees first. One couple waited and waited for the meatballs and linguine to arrive until we finally said something and a few minutes later the meatballs came out and then a plate with linguine that was not fully cooked. We had already spoken to them earlier about service being unusually slow and they offered a round of drinks on the house to apologize for the delay. Now with dishes for two guests being inedible they obviously comped the two dishes and offered another round of drinks and dessert and coffees on the house. At this point we were told that they were understaffed, two people hadn't showed up that day. We wished they had shared that early on. All in all, the food was delicious that was served properly. We were there for a long 3 hours. I would have given them a 5 star review if things had gone better or perhaps if they been more honest about their situation. read more

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We decided to come in for a drink after walking around our neighborhood one summer evening. Bartender was friendly and helpful. We got snacky and ordered the margarita pizza. Worth every penny. Dough was soft and flavorful. Sauce was simple and sweet. Can't wait to try more things from the menu. read more

My boyfriend and I got out to Montauk late in the evening and were starving. We haven't been out this way in awhile but decided to take a chance on Kenny's. I'm so happy we did! I first called to make sure the kitchen was still opened and was told not to worry, come on over. We were thrilled. My boyfriend is a diabetic and his sugar was getting very low. That sat us immediately and Mario served us warm bread with olive oil and a medley of olives. We then ordered the Mozzarella Napolitano appetizer, which was delicious. My boyfriend had the chicken parm with pasta and I had the beet salad which I added chicken too. We were both very happy with our meals and the portions were huge. We couldn't even finish them. However Mario was kind enough to treat us to dessert, crème brûlée and limoncello sorbet. Somehow we found the room to enjoy both of them. I also ordered a cocktail, grey goose watermelon basil fizz. I'll be making this at home for sure! We got to talking to Mario about the restaurant and learned they took over the restaurant only a few years ago and renovated it from the back of the kitchen through the front of house. They have indoor and outdoor seating and if you're in the mood for pizza, they have a brick oven. They were even showing another customer the brick oven when we were leaving. Mario and the entire staff were so nice and accommodating and the food was wonderful. We'll definitely be back! Sorry we didn't take pictures, we were too busy enjoying everything. read more

It's a dump. Food is overpriced for what you get. How they can manage to make a pizza taste both rubbery and burned, I don't know. The owner, Mario, is a rude jerk. We don't care if you're the owner or not, Mario. read more

Absolutely one of the most delicious meals my wife and I have had in years. Mario is so warm and friendly. Spent time getting to know us, new customers. We enjoyed every minute of our evening dining on Italian cheese, slivered truffle, caramelized onion pizza, savory meatballs, classic but better than classic chicken parmigiana. We can't wait to go back! read more

Drinks and appetizers were good. Entrees however we're a big miss. Salmon slapped over some rice with NO flavor, linguine in white clam sauce had clams but no sauce (you should have enough left to dunk some bread in!), chicken Milanese was dried out, pizza was ok. At a time when most restaurants ask if any one in your party has any allergies the menu states NO substitutions and the dishes are way overpriced for how they're prepared. Cannot recommend. read more

Very nice place , great bar. The octopus app was unbelievable. We tried 2 different Pizza & great. Lasagna was absolutely delicious. Great home made sauce. Teramasu , chocolate martinis , gelato. Home made meatballs like a Momma . We left very full & very happy. The owner and his brother made us feel like family. A must go to restaurant. read more

Kenny's Castaways - Yum - Italian Near Me - Montauk, New York

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Staff was super friendly and food was good! Enjoyed a pasta dish. A good casual Italian dining option. Typical Italian dining atmosphere. read more

Kenny's Castaways - Parpadelle Bolognese - Italian Near Me - Montauk, New York

My husband and I came across Kenny's Castaways on a recent October weekend trip to Montauk. The restaurant was packed on Saturday night, so we went back on Sunday. The atmosphere and food is fabulous. Our experience was heighten by the personal attention we received from the Owners, Mario and Anthony. The service provided was stellar!! The appetizers and entree's were abundant and tasted like it came out of my grandma's kitchen, very flavorful! Kenny's Castaways will be a food destination when we are in Montauk. See you in the Spring! Joe & Rexanne read more

Every restaurant in Montauk was jammed so we kept looking. When we walked in here we were the only customers,which made me nervous. We both ordered linguine w clam sauce which my friend tries at each italian restaurant. We both agreed it was terrific and friend said it was the best she ever had. Giant chunks of fresh, tenderized clams on every forkful. Oh and by the time we left the place was pretty filled up with locals. No views so tourists were scarce. read more

The least you could do is make a pizza for $25 that is big enough to fit the box you sell it in. And the crust taste burnt!

Ate at this wonderful restaurant tonight and was so lucky to have picked it. Service was excellent, food was like home cooked by a italian grand mother. A true piece of heaven. We had meatballs, chicken parma, and penne vodka. All fabulous. Try Kenny's you'll be smiling for the night. read more

Our first reaction was that the prices were high but then we saw the size of the dishes and knew we had tomorrow's dinner as well! We shared the grilled Octopus starter and it was exceptional and even though we both had plenty, we still had leftovers The chickpea purée on the plate gave the "pulpo" a great flavor. My chicken parmigiana was very good and huge. My wife had the pappardelle with a meaty bolognese sauce that was enough for three people. The atmosphere is nice and relaxed and we were not rushed. Very enjoyable dining experience. read more

I don't really like to post bad reviews and frankly, I held off for a long time, but I was going over some notes that I took of this place when my family visited Montauk in late June, and I got reminded all over again why reviews matter. My family and in-laws were staying at a nearby hotel and we decided to order to food from Kenny's. We had a fairly large contingent of kids, so our order mainly consisted of pizzas, but we also got some calamari, eggplant, and something that caught my eye, Watermelon salad. First thing that should have sent up a warning flag. My wife made the initial call and had some simple questions for the person on the other end of the phone. That person was unbelievably rude, and the answer for most of the simple questions were "LOOK AT THE MENU." However, we powered through because our kids and rest of group were hungry, and managed to put the order in. So the one thing they don't mention when you LOOK AT THE MENU, is the size of the pizzas. Starting at $22, you would figure that they are your standard size, wouldn't you? So we ordered two pizzas thinking they would be enough for the kids. When we went to go pick up the food, this place has a very slick move....they put the pizzas in larger boxes, so that you believe there's an 18 inch pizza in there. Certainly two of those pizzas would be enough for the kids. Like DUMMIES, we never bothered to check the pizzas in the boxes. When we got back to our hotel and opened up the pizza boxes, what a surprise to see the pizza were very slightly larger versions of personal pizzas. Really? We paid what equates to $50 for two personal pizzas that were no where near enough to feed what we expected them to feed had they been the normal size. This was kind of upsetting. Well ok then, they are probably going to be the best tasting pizzas we've EVER had, right? Nope...they were very doughy, and did not get the amount of time they needed in the pizza oven. We had to throw them in our own oven at the hotel to cook them thoroughly and make them slightly more crispy. The eggplant we ordered, not so good. Not sliced thin enough and had a bit of a rubbery texture. Two bright spots. The calamari was actually cooked to perfection and came with a really good sauce. The watermelon salad was about the best I've ever had, if I'm being totally honest, which of course, I am. It's a shame that a few good items were overshadowed by rudeness, overpriced and undercooked pizza, and ridiculously high prices. If they are still in the area when we go back next year, I may go back just for the watermelon salad. Beyond that, no dice. read more

Hidden Gem in montauk! Had a great Italian meal here with my family. Friendly staff. Real Italian food. Will def be back

It was a lucky night when we found Kenny's. We were looking for an authentic Italian restaurant and we found it. The food was amazing service incredible. Mario was a joy and the Best host ever. I have been in the restaurant business I should know great service. The restaurant was warm and welcoming and we will be back next year. We also recommended kennys to 10 people back at our hotel. Thank you Mario for a great evening. read more

Very friendly and attentive staff. the owner makes a point of greeting and and speaking with diners throughout the restaurant. Nice personal touch. We had the Tartufata and the San Danielle Pizzas and both were amazing! The meatballs and the calamari were fabulous as well. The Zeppole dessert is a must have. Highly recommend. read more

the place itself it quite nice the vibe is nice and the staff is very kind and accommodative. we ordered the watermelon salad and it was OUTSTANDING! the food came quickly and we never had to ask the waitress for any help at all she checked in on us multiple times which i really appreciate. there house bread which has garlic and olive oil was truly a treat. we ordered the margarita pizza and it had a great cheese pull and a TO DIE FOR crunch. my only issue with the pizza is that it wasn't fully cut and we had to cut it ourselves. for dessert the crème brûlée was wonderful and the mint was truly the cherry on top. there is something going on with the Tipperary Inn and this restaurant but despite that i think it is a nice place to try and you should stop by for a meal. especially if your staying at the Tipperary Inn. It's close by and easy meal. I really recommend this place. read more

Awful. The online prices are VERY DIFFERENT from what you're charged when in there. Plus I know Mario, no bueno.

Food was great, service was excellent. Only reason I can't give 5 stars is the price. Prices were very high even for montauk. Still would recommend read more

Best kept secret in Montauk. Superb dining experience from cocktails, appetizers entrees and desserts. Mario the owner was so accommodating so are the staff. Definitely coming back!!! I'm a local, 5 stars for me... read more

Extremely rude staff. Showed up with 6 adults and 3 children and the restaurant was completely empty aside from one couple. Showed us a table that sat 6 and said this was the best he could do. The best he can do? So we left and loaded everyone back in the cars. As we were pulling out, the couple that was inside was leaving. I rolled down the window and asked them how the food was and they said horrible and had to send it back. Can't wait to see what this restaurant will be next year after they close down. read more

Loved the food ... loved the atmosphere...and loved the history provided by Mario!!! Thank you for making our first experience, at your place, a great one!!! To all, it's definitely a must when in Montauk!!! sandy and friends! read more

Behind one of the infamous revolving doors of Montauk, a new business ought to be putting their best foot forward in their first (and likely last) season but this place fell woefully short. We were seated right away as the place was empty, which is no surprise given the service, but we were initially seated at a table set for six with a party of nine and ended up dragging a second round table over ourselves to fit everyone. The wine list had maybe 25 options. We selected two, a white and a red, and BOTH were out of stock. A white was automatically substituted and we were charged the extra $5 for the subbed bottle. Sorry, but if your stock doesn't match your menu, you eat the difference. Post beverages we ordered appetizers. Calamari was crispy and came with multiple dipping sauces, tasty but nothing special. The shrimp cocktail were sizeable and cooked well, but served in a glass full to the top with arugula and the cocktail sauce was stirred into the lettuce making it impossible to use as a sauce. We came with two small children to a venue that is attached to a hotel and previously was home to two different family friendly restaurants and were given no children's menu, no children's option, and the children were literally not acknowledged with so much as a hello, let alone a beverage, even after we ordered multiple bottles of wine and appetizers making it clear we would be a sizeable check. As for the meals, the chicken parm was nothing you couldn't get at a local pizzeria and when we requested garlic and oil instead of marinara on the pasta we were told "the chef doesn't offer substitutions but you can order an additional side" for a $31 single piece of inadequately pounded thick chicken. The penne a la vodka was a favorite of the toddler who ate most of it since there were no children's meals. Service was slow despite most tables being empty, and half of the entrees arrived several minutes ahead of the other half, followed by the salads which arrived after entrees. Overall a wildly disappointing experience but one that certainly won't be repeated as this place probably won't see October. read more

My granddaughter and I came to this place because it was close and we were hungry. JACKPOT!! Food was delicious, staff was kind and considerate, and very attentive. Watermelon salad was to die for, Margherita pizza, shrimp cocktail yum! Crème brûlée and hazelnut gelato for desert! So good! Ate too fast to take pi's! read more

The drink's were fabulous and the food and atmosphere was lovely highly recommend!!!

Nothing to write home about! We had the lobster bisque, it had a weird taste to it. Not to our liking. Also had chicken parmigiana with spaghetti. We didn't care for that either. Chicken was tasteless needed cheese in the breadcrumbs. They didn't serve grated cheese. We also had the beet salad which was good. The pulpo (octopus) was ok like I said nothing to write home about. The bread and olives they brought to the table was awesome, but that's it. We had gelato for dessert. We won't be back. read more

If someone in your party has a food allergy, don't bother going. We checked before going to see if they could accommodate. The response was...this isn't the place for you. They could care less. Can't comment on the food since we were tuned off by the careless response we got from the person who answered the phone. Solid way to represent your business. Any professional operation knows how to adjust their menu. It's not difficult. read more

I was very impressed with this authentic Italian restaurant. Greeted by the owner who was honest about seating capacity and asked us to wait about ten minutes as he didn't want to over lburden his staff. When we were seated the service was excellent and the food arrived on time. Food was well prepared and largely homemade. I rarely review restaurants but thought I would give this place the thumbs up. read more

I'm not sure what some of the negative reviews are about. Had dinner here tonight And we were very happy with the service and the food.It was refreshing to find this place as I find most of the restaurants in Montauk have the same menus. The food here is absolutely delicious and the service was excellent and its a different menu from the other restaurants. Their desserts are amazing. We were very pleased with the whole dining experience at Kenny's Castaways. It's a higher scale restaurant. read more

First time there...food was good but was so disappointed when I received the check. I was charged $52 for 2 bowls of pasta with butter for my kids. When I asked the server why I was charged for a penne vodka I was informed that they do not do modifications to the menu and penne vodka was the closest thing to what we ordered. Had he told me that when I ordered it I would have just gotten a pizza for the kids. Needless to say I won't be going back there. Highly disappointed. read more

Kenny's opened one month ago after being closed for two years for renovations and then Covid. We happened upon it on our recent visit to Montauk. We had a drink at the bar and talked to its new owner who is experienced in running restaurants. We returned the next night for dinner. It is elegant for Montauk with white tablecloths, outstanding service, an attractive decor, and both inside and outside dining. We had pasta dishes which were delicious, and a very nice white wine. If you are looking for someplace special in Montauk, near the harbor, we highly recommend Kenny's Castaways. read more

My husband and i ate at this restaurant every weekend from Memorial Day weekend till the end of October. When walking by one day we stopped in just to check it out and the owner Mario showed us around. From that moment we knew we would be regulars ! Mario was so personable! He made us feel like we were coming home to Sunday dinner with family. Of course since we enjoy eating at the bar we met the bartender Hailee...best bartender in Montauk by far! Somehow remembers everyone after the first visit and makes the best cocktail! Always a smile no matter how busy she is VERY rare in Montauk The food is excellent! Made with the freshest ingredients and authentic Can't wait to be back Memorial day weekend next year! Hoping this restaurant is here to stay! read more

My wife and I had dinner there Tonight the service couldn't of been any better the owner is a gentleman and the food is absolutely fantastic