Winston's was recommended to me by my tour guide and it certainly didn't disappoint! From the moment you walk in, you feel like family. The cashier was very attentive and authentic Jamaicans working in the kitchen. Ordered a cheese steak sandwich and side of jerk pork. Both were excellent! One of the best cheesesteaks I've had. Will definitely be visiting there again. read more

This is a carry out restaurant. Service was not very friendly. I ordered a breakfast sandwich with sausage on white bread and the Jamaica me crazy coffee. Sandwich was decent, coffee was not very good to me. This restaurant is located on the water. There are benches and tables in walking distance to enjoy your food. My mom got the blueberry muffin which she seemed to enjoy. read more

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I had an apple chicken sausage sandwich which was good. The place is small so we got ours to go. Server took our orders and when the food came out it was hot. The special coffee was suppose to have kahlua vanilla and more but it. Tasted like plain coffee but after cream and sugar it was ok. They have chips and more . It's on the beach too lol read more

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The food here was quite disappointing, and it's unfortunate as it was recommended by quite a few people. This is a carry-out only restaurant, and they allow you to place orders ahead for pickup. My friend and I walked in and both ordered the oxtail dinner, and I also ordered a side of plantains. The oxtail came with a healthy side of cabbage and rice and peas. The flavor on the oxtail was very bland, and the meat itself was somehow both fatty and tough. The rice and peas, cabbage, and plantain were both okay. I don't see myself coming back again, but if I did, I would stick to the fried chicken, as that seems to be a popular item. read more

Winston's Kitchen - Oxtail dinner - Sandwiches Near Me - Oak Bluffs, Massachusetts

Call in my order for four people. One w a vegetarian. Everyone was very impressed and happy. I'm going back today.

Winston's was highly recommended when we visited the Island, the oxtails to be specific. While reviewing the menu, I became a bit concerned b/c there's so many items on the menu and it ranges from American to Caribbean, I even think I saw enchiladas! Lol But I went with it. We called the order in while we were lounging on the beach for pick up. This is a pick-up only spot as I didn't see anywhere to sit and eat. Items ordered were the Oxtails, Thai Salmon, Blackened Shrimp. My friend that ordered the blackened shrimp was the only one disappointed. The oxtails were amazing and tender. I paid .75 for a side of Jerk sauce. The peas/rice were a bit dry; but the jerk sauce helped. I even had leftovers for the next day. I also got the coffee drink with Vanilla & Bailey's, I think it was called "Jamaican me Crazy" That was a bit disappointing because they just handed us a cup with ice for us to pour ourselves. I was hoping for freshly brewed. read more

Winston's Kitchen - Oxtails from the Daily Menu - Sandwiches Near Me - Oak Bluffs, Massachusetts

Their fish and chips are pretty good. Fish batter was crunchy; would like the fries a little more seasoning.

Wonderful food and customer service experience. Shout out to the chef on the "best fish sandwich ever" per my husband.

Friendly takeout with wonderful food. everything is freshly prepared. Rice & beans with jerk chicken wonderful. Chicken sandwich delish, great BLT and tasty baked goods. read more

For the price and the portions its a great value for your money. The fish and chips is lightly breaded and plenty of fish. Plenty of fries to share with the other meals we had. The coleslaw isn't vinegary . I called ahead and everything was ready to go. It's more of a grab and go . You could do a picnic lunch outside or head to the beach. ( In the summer there's bathrooms around the corner not apart of Winston's ) . read more

Winston's Kitchen - Grilled Cheese on white bread ( not on the menu, but they made it happen) $7 - Sandwiches Near Me - Oak Bluffs, Massachusetts

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PROS: great friendly service, knowledgeable staff, lots of parking, easy to find but also easy to miss as it is a tiny pick-up & go spot, besides their menu items, there are a number of snack/quick eat & desert items to purchase. Their menu has a good variety. The food was okay. I got the Jerk Chicken Sandwich & a garden salad (w/t a pouch dressing) while the husband got Thai Chili Salmon w/t mashed potatoes & green beans. The sandwich, freshly made and tasted okay; salad was perfectly made, husband's salmon was thick, hot and fresh, potatoes and green beans were good. CONS: I must admit, after reading the menu, I was expecting the food to knock me over with flavor goodness, but, it did not. The tzatziki sauce on sandwich was plentiful, but strangely, it did not enhance the sandwich at all. Also, I could barely taste a jerk flavor. The same goes for the salmon, the Thai chili sauce did not enhance the salmon at all. I think they need to add spice directly to the protein instead of letting the sauce do the talking because it did not. Although I said what I said above, I would still go back and try something else as their menu has a lot to choose from and I think they try to provide good food and service. read more

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We were traveling by ferry around lunch time so we stopped at Winstons to pick up sandwiches for our group of three. The subs were packed with meat, cheese, lettuce, tomato and because we chose the spicy Italian subs lots of peppers! They were a delicious choice. One 12" sub is enough for 2. The staff were friendly with big smiles. Very patient as we decided on the order. There are daily menus and lots of choices from the store. Drinks, desserts, sides. You name it. read more

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This is a hidden gem. No big storefront. It's near the public restrooms. It has plenty of parking. Everyone is friendly. I had an ice coffee but found it weak. I ordered the grilled chicken sandwich and it was delicious! So delicious I ordered another one the next day. The grilled chicken cutlet was marinated and seasoned perfectly. I devoured the sandwich before I could take a picture. Look for their daily specials on Facebook. read more

Winston's Kitchen - Sandwiches Near Me - Oak Bluffs, Massachusetts

My bf really liked the fish and chips. The fish was fresh and cooked with a nice crunch. I got the hotdog with onions I wasn't super hungry. The hot dog was good it came with a brioche buttered bun and some sauce not sure what it was. I say go to experience it. It's also takeout so no seating. Service was quick and efficient. read more

Bottom Line: Satisfying and hearty take out at a great value. After a long travel day my husband and I were searching for a take out spot to get some sandwiches. Lucky us, Winston's Kitchen was the perfect place! We both ended up getting cold subs (Italian and Roast Beef) which were big enough that we could have split one sub. Aside from cold subs, Winston's has hot subs, wraps, and specials throughout the day. They also offer breakfast in the morning. Service was friendly and our order came up quickly. read more

I have had takeout twice from Winston's. I first got steak tips special which was to die for. I went back and they had tomato soup and grilled cheese special. The tomato soup was one of the best I've ever had. This place has the comfort food that makes you feel like you're at home, 10/10 recommend! read more

Winston's Kitchen - Bourbon Steak Tips - Sandwiches Near Me - Oak Bluffs, Massachusetts

The spicy Italian was so delicious. First meal on the island. I would rank it truthfully an 8.6 out of 10. The bread was a little soft but very good the hot pepper relish made it so spicy. But I love spicy things. So very good sandwich read more

Winston's Kitchen - Sandwiches Near Me - Oak Bluffs, Massachusetts

We ordered the jerk chicken wings and oxtail. They just tastes like bbq sauced chicken wings and canned/jarred gravy on the oxtail. And the oxtails were cut so thin.. I would not recommend either of those. read more

Such a great grab and go sandwich shop on the island. And VERY vegetarian friendly. 3 people in my party, including me were vegetarian. You can order any sub, and sub the meat for another veggie. I got the ham and cheese and subbed the ham for avocado, and took the pickles out and replaced those for spinach. And took the olives out. My only complaint is that I asked for no pickles and no olives and got both with addition with the ones I subbed for those. They have a bunch of pastries inside and some ready made containers of food. Large menu so whether you're a vegetarian or not you will find something to eat. Service took a little but also we had 5 sandwiches to make with substitutions and all that. So I get it, otherwise great place and the sandwich was great. No seating but technically you can sit by the water. So it's nice and relaxing. We took them to the cliffs and ate them there but overall I will be returning! read more

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The food is awsome! Service for 15 was spectacular! Chicken, Jerk pork, steamed veg, rice and beans and mashed all went! So good and Lisa a dn Winston were so easy to work with! read more

Food was delicious and reasonably priced Really enjoyed the garlic chicken plate. I will definitely return. so nice to have a takeout restaurant that offers wonderful home-cooked meals. read more

The oxtail is their best recipe, but you won't go wrong with the curry chicken and plantains. They're quick, friendly and have great takeout in a convenient location next to the OB harbor. read more

Food is amazing! Only offers to go and there is nowhere to sit and eat nearby so plan accordingly

Great spot for breakfast, lunch or dinner! Quick, convenient and delicious! Try the Jamaican Jerk Pork dinner!!! Or subs are great too!

Excellent Yard Plate! Their version of Oxtails is unique and I recommend. Enough food for two people'. read more

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We love Winston's!!!!! Chicken parm sub & grilled cheese/tomato soup will blow you away. Whatever we order is always fresh and delicious. read more

Great stop for beach sandwiches. Fully loaded. Great flavor. Parking. Awesome location in OB. Highly recommend. read more

Winston's Kitchen - Turkey Sammy - Sandwiches Near Me - Oak Bluffs, Massachusetts

A hidden gem -- we got off the ferry at vineyard haven, took bus 13 to the first stop in oak bluffs and this was the little shop we decided to stop at. We were one of the very few people there around 11:00 and although we waited about 20 minutes for our food, it was well worth it. We sat by the docks while waiting and then went to the park across the street to eat our amazing food. Very big portion sizes for the price so we were satisfied! Great service and fantastic start to the day! There also are gluten free options! read more

Winston's Kitchen - entrance from the harbor - Sandwiches Near Me - Oak Bluffs, Massachusetts

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Not good. I ordered the jerk chicken plate. The chicken was extremely dry, they smothered it with a horrible jerk sauce on the plate. It was just grilled chicken with that store bought too sweet, not enough heat jerk sauce. The rice and beans were bland, absolutely no flavor. The other side was cabbage. Once again no taste. It didn't even have a cabbage taste. I'm thinking it was there all week. I didn't finish the plate. Another couple before us also complained. They were West Indian and they definitely didn't approve. read more

20 full minutes waiting for utterly tasteless egg sandwiches on barely toasted bread. No butter, no salt, no love and you forgot the cheese. The woman taking my order clearly didn't want to be there and got 100% of our orders wrong. Coffee was pretty good. I don't get these reviews. You can easily do better right nearby. read more

Stopped by for the sandwiches and ended up getting a pulled pork dinner. The food is so good and they give you SO much of it. Service was quick and prices were reasonable. We sat and ate on some benches nearby. Was perfect. read more

Winston's Kitchen - Pulled Shredded BBQ Pork Dinner - Sandwiches Near Me - Oak Bluffs, Massachusetts

Great lunch! We were very impressed with both sandwiches on the way to the beach. We had a pulled pork sandwich and Italian sub and both were tasty. While waiting for our lunch we saw them cooking the orders and the jerk chicken. It all looked amazing and fresh. Definitely check this place out if in the area. read more

Acceptable cheesesteak for a non-Philly place. Prices aren't ridiculous. Comfy deli feel amidst the land of foo foo yuppie food

Wow! Steak sub was loaded, as well as the spicy Italian sub. Chicken salad with walnut & cranberries was fresh on homemade bread. Greek salad was full of ingredients. Staff was personable & prompt. Great sub rolls. Wish I lived close by because the rice & beans with BBQ pork looked amazing!! read more

Fantastic option for year round and summer folks. Wonderful group of people and great food. Thank you!

Small little take out restaurant on the water. Sandwiches are massive. Could hardly bite the sandwich it was so big. Should have split one that's for sure. Super nice person on the register. Did not try any of the specials. read more

Best sandwiches on the island. They are always big enough for two. Roast beef/ steak sandwich is fantastic, and so is the chicken sandwich! NO SEATING. It's pick-up only but right on the water with plenty of park benches with a view. They are fast and always GREAT!! Staff is always friendly and helpful. We've been here many times over several years - same consistent awesomeness! read more

This exceeded expectations especially for the reasonable prices. The breakfast sandwich I got was sooo good - real egg and bacon, not the fake egg patty a lot of other cafes have. The iced coffee they have was also very good and fresh tasting. Can't wait to go back! read more

Excellent selection of tasty items. Friendly staff. Right on the Oak Bluffs harbor with great views.

I gave Winston's Kitchen another try and I'm glad I did. I ordered a Cheeseburger and fries. It was not a skimpy burger pattie...it was substantial and it was delicious. I'll be back. Again, glad I gave them another try. read more