Lookout Tavern — Restaurant in Oak Bluffs

My girlfriend and I recently visited Martha’s Vineyard and decided to dine at The Lookout Tavern. As servers at high-end restaurants in Orlando, we looked forward to experiencing what the Vineyard offers. While the food certainly didn’t disappoint, the service marred our overall experience.

Upon arrival, we were warmly greeted by the host, Chantelle, who was phenomenal—super bubbly and incredibly personable. Despite arriving four hours early, she accommodated us, allowing us to reserve a spot or return at a specific time. When we returned around 5:30 PM, Chantelle went above and beyond, offering us immediate seating or the option to wait a bit longer for our preferred spot on the upper deck with a view. Her customer service set the tone for what we hoped would be an excellent dining experience.

However, when our server, Maria, finally approached us—after over five minutes—there was no friendly greeting, introduction, or explanation of the menu or the restaurant’s highlights. Instead, we were told, “Do you know what you want?” It was an off-putting start, especially after Chantelle’s warm hospitality.

Despite the lackluster service, the food at The Lookout Tavern was outstanding. My girlfriend ordered the lobster roll, which was nothing short of amazing.

The Lobster Roll:

Generous Portions: The lobster roll was packed with a hearty amount of tender meat, ensuring each bite was satisfying.

Freshness: The lobster was incredibly fresh, reflecting the local New England catch, with a sweet and succulent flavor.

Balanced Flavors: The roll perfectly balanced the lobster's buttery richness and the light seasoning, allowing the lobster's natural taste to shine.

Soft and Buttery Roll: The bread was soft yet held up well, with a buttery exterior that beautifully complemented the lobster filling.

Lightly Dressed: The lobster was dressed with just enough butter to enhance the flavor without overpowering the lobster.

Classic New England Style: The lobster roll stayed true to the traditional New England style, offering an authentic and satisfying taste.

Perfectly Toasted: The roll was toasted to a golden brown, adding a slight crunch that contrasted nicely with the tender lobster meat.

Visually Appealing: The presentation was clean and appealing, and accompanied by homemade potato chips.

Meanwhile, I opted for the tuna melt, which was equally impressive. The bread was perfectly toasted, providing a delightful crunch with each bite. The tuna was rich and flavorful, blended with just the right amount of seasoning and melted cheese. It was comfort food at its best—simple but done exceptionally well.

Unfortunately, the service continued to decline. We waited an excessive amount of time for our check, and when it finally arrived, I was shocked to see a $6 charge for soda water. When I brought this up to Maria, she responded dismissively, saying, “It’s a fountain drink, so I charged you for one.” I mentioned that we both work as servers in Orlando and have never encountered this before. Instead of showing understanding or flexibility, she got even more defensive, saying, “I’ve been to Orlando; they do that everywhere. If you have such a problem with it, I can get my manager?” We were both taken aback by her aggressive attitude.

Ultimately, our server's rudeness and lack of professionalism overshadowed what could have been an exceptional dining experience. Bella tried to end the conversation positively by saying, “Enjoy your night,” but we were disappointed and shocked by the encounter.

The food at The Lookout Tavern is undeniably fantastic, and the location is lovely, but the service—at least from our server—left much to be desired. We would consider returning, but only with the assurance that the service experience would improve...

My friends and I visited the Outlook Traven on 6/30. Our waitress was pleasant and some of the food tasty. I ordered the sirloin tips med well. I received them cooked well done. I sent the plate back and asked for it to be prepared medium well. The plate came out more well done and charred. I asked the waitress to return it and she took it back only to return back stating that the kitchen refused to cook it again. She proactively offered for me to speak with a manager. The young African American woman approached our table and approached me with an attitude asking what I would like to do with my food. I asked if my steak could be prepared medium well, and she responded by saying they could not keep wasting food and if I would like something else. I told her that they would not waste food if her cooks knew how to prepare food as ordered. She said she was not going to go back and forth with me and said I could reorder something else or she could just remove the charge from our ticket. I asked that she remove the charge. She then stated that I could not eat anything from the plate. My response was not a problem. This young lady did not once apologize or make any attempt to make it right. She did not demonstrate any leadership or customer service skills, nor did she express empathy. This is my third time visiting the restaurant and the second time that our group had a very negative interaction with this rude manager. The food was good with the exception of my charred sirloin tips ordered during this visit. But the customer service is 1 on a scale of 1-5. This manager Shekila not have any interactions with the public. Sorry I did it get her name because I would really like this comment to be directed towards her and not the entire management team or staff. Not sure if I will ever return to...

Love Their Lobster Roll!

The Lookout is a must for any island visitor as it's located just across the street from the ferry terminal. Aptly named, it sits perched above Seaview Ave in Oak Bluffs with a wonderful ocean view. To eat here, plan ahead, however, as it is quite popular with wait times easily exceeding one hour. Find a seat at the bar or sushi bar and you'll still get full service.

The restaurant offers a full bar which is evident as you enter; the room is loud, busy, and crowded so if you're looking for something laid back and low-key, this is not the place.

Belly up to a table and start with a specialty drink or cold brew. They've got a wide selection on their raw bar and sushi menus, great soups and sandwiches, and their house chips are delicious.

This review is about their Lobster Rolls. I've had a few across the island and I find I like these the best. They start with the perfect, split-top bun and fill it with fresh, chunky, lobster until it's overflowing with mouth-watering seafood. It's so big, you might consider having a starter and then splitting this with your partner.

The roll comes with their house chips. These chips are good! Seasoned perfectly and served crunchy! I guarantee you'll eat them all and want more.

When you're craving an excellent lobster roll, stop by the Lookout, put your name in and then wander around for a while. It's definitely worth planning a visit!

Why not a 5-star rating from me? They should offer a call ahead seating solution and the dining room is a bit...