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    Lookout Rooftop

    3.1 (360 reviews)
    Closed 11:00 am - 11:30 pm
    Updated 2 months ago

    Lookout Rooftop Photos

    Business Info

    LOOKOUT ROOFTOP ATMOSPHERE

    What's the vibe?
    Moderate noise
    Trendy
    Outdoor seating
    Dogs allowed

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    Recommended Reviews - Lookout Rooftop

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    Olga P.

    Great views, music and atmosphere! Enjoyed a drink before dinner but could've stayed all evening

    overpriced drinks with a view

    The view is the only good part about this place. You go up the elevator and a man just stares at you and doesn't even ask for your id until you realize. The hostess was on FaceTime and also said nothing to us. We proceeded inside and stood in line at the bar. Two people walked up to the bar while we stood in line and were helped before us. So much potential here but terrible service and overpriced small drinks.

    Kinjal S.

    This place shouldn't be popular yet it is probably because of its location and the view. Service is awful.

    View
    Vinicius F.

    The staff is very nice and polite. The view is incredible, you have a panoramic view of Boston and it feels very upscale. The drinks were a bit of a contradiction. Not super tasty, presentation was underwhelming, and I was really surprised how can a $20 dollar drink came in a plastic cup. I can't comprehend. The Call Your Mum cocktail was not super delicious, as the ingredients might suggest, and the citric acid was too much, my lips got a little burned from it. For a rooftop bar of that caliber, I just expected things to be more consistent with the upscale vibe.

    Wine
    Manhthuong P.

    Food is nice. There is not a lot of variety to choose from since I went for brunch, but the foods taste great. Staff are fantastic. It's a nice igloo looking out to the port, giving it a very nice view for a beautiful date, especially at night! Will be back at night for a different feeling!

    Dani S.

    Ranked one of the top five rooftop bars in the city of Boston. Pricey, but well worth the view! I came here for an event, and the view was stunning. There are several areas in the bar. One side has the harbor view and the other side has the view of the city. The bar has a huge variety of cocktails, and wines. We also got a lot of appetizers to share. The food was pretty good. Service was nice. Great place to spend some time at night.

    Watermelon Frose   yum

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    10 months ago

    Amazing place! Service was great as well! The views are stunning day and night definitely would come back here with friends.

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    Page 1 of 9

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    Ask the Community - Lookout Rooftop

    Is there music at night? What vibes?

    There is music although I cannot remember if there was a live DJ when I was there (Wednesday night). It was insanely loud and crowded just FYI! A club atmosphere at night.

    Do they play music in the daytime?

    Yes, top 40 hits and radio like music.

    Can someone with shellfish, peanut & tree nut allergies eat here?

    Yes. My son has all those allergies and was able to eat from the brunch menu

    Do you have to make reservations to go to the rooftop bar?

    Yes

    Do they ID or take fakes?

    Neither me nor anyone in my party were, but that may be a case by case basis. It doesn't matter if you're 21.......

    Can they accommodate for gluten free dietary restrictions? Their online summer menu doesn't mark anything that can possibly be adjusted to gluten free. I'm celiac and just want to know if I can eat safely here

    We have gluten free bread for any of the sandwiches. The truffle fries, tostones, shrimp cocktail, olives, & both salads can all be made gluten free as well.

    Does this place ever stay open past 12am?

    Yes

    Is there a dress code?

    Nope! Not that's publicly posted ! Perhaps, when it's a special or private event. Dress [weather] accordingly or to impressed is your choice.

    Is there a separate charge for entrance or is it the usual pay for what you eat/drink only?

    There was no cover fee when I went there

    Do you serve brunch on the rooftop or is it just drinks?

    Yes. We had a great brunch with a nice view

    Do you have to book a room to access the rooftop bar?

    No, you don't. Although, making reservations for an Igloo is highly recommended.

    View All 16 Questions

    Review Highlights - Lookout Rooftop

    It's a nice igloo looking out to the port, giving it a very nice view for a beautiful date, especially at night!

    Mentioned in 46 reviews

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    Gray’s Hall

    Gray’s Hall

    4.9
    (52 reviews)
    1.3 mi

    You must order the kale salad. I am not a kale salad person, yet I have dined here three times in…read morethe last week to eat the kale salad and am already planning my next visit. You know when you're eating a kale salad and the pieces are too big and you're kind of cramming them into your mouth and then the salad dressing is all over your face? This is NOT that salad! The kale is perfectly chopped so you can enjoy it with just your fork as you talk to your friend/spouse/date or just read your book. The dressing is such perfection, and the perfect amount, no gloopiness here! Crunchy breadcrumbs add magical texture and then there's a shower of finely grated gouda cheese on top. Have you ever read a good book and as you're reading it, you're so into it that you don't want it to end? So you slow down your reading speed to make it last a little longer? That's how I feel about this salad. There are other delicious items on the menu, I saw someone eating the burger that looked so good, I also want to try the Brussels but the call of the salad siren is too strong. Everyone is super welcoming and friendly, especially Catherine, and the kitchen team even shared the dressing recipe with me. Excellent wine list, casual and cozy space with twinkle lights, a lot of bar/counter seating, great date spot. Also attached/sister company to American Provisions I believe (great spot in Southie for sandwiches, cheeses, wines, pastries, rare food items).

    This is one of those spots that I want to keep on the down low because I don't want it to become…read moretoo popular...but I have to give Gray's Hall their flowers. I absolutely ADORE this place. It's one of my top 3 places in all of Boston. The vibes, the food, the wine, the prices, EVERYTHING is 10/10. This is one of those places where I feel at peace because I feel like my money was 100% well-spent. The prices are fair, and I don't feel like I'm being taken advantage of. And the FOOD, the food is exquisite. My favorite time to go is on Tuesdays for the $1 oyster deal, definitely my favorite $1 oyster deal in the city. They mostly have small plates and a few large plates, but you seriously can't go wrong with anything on the menu. And the wine options, amazinggggggg. Gray's is a true gem!

    Photos
    Steak Frites + Orange Wine!
    Steak Frites + Orange Wine!
    $1 oysters on Tuesdays! The best!
    $1 oysters on Tuesdays! The best!
    Gray’s Hall

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    The Playwright

    The Playwright

    2.9
    (58 reviews)
    1.3 mi

    Came here for dinner for the first time with a couple of friends. Hubby and I ordered their…read morebuffalo loaded fries, a spicy chicken burger, pressed veggie melt, and a couple of drinks. Total came out to approximately $80 (not including tip). What's Hot - Menu. Pretty good variety. There's something for everyone, including vegans (for the most part). Specifically for vegans, they do not appear to have vegan cheese. They recently added loaded fries to their menu. - Quality. We tried their buffalo loaded fries, which definitely a good kick of spiciness. There was a good amount of buffalo mozzarella cheese and chicken. Their fries are slightly crispy on the outside, soft and tender on the inside. I really enjoyed my pressed veggie sandwich. There were whole veggies, such as broccoli, with a good amount of cheese melted between all the veggies. I liked that it was not a mashed patty. The sourdough bread was not tart (which I prefer), soft, and not too greasy. No skimping on the ingredients either. Their mozzarella bites appetizer is good, not overly breaded, and cheesy/stringy. All of us enjoyed our meals. - Service. We showed up without reservations on a Friday night when it was cold and rainy, and they were able to seat us right away. We tried several other restaurants before getting here, and we would have had to wait at least one hour, because we did not have reservations, even though those restaurants clearly had open tables. Our waitress was helpful. She answered all questions she had and was able to provide us contextual helpful info (i.e., what she's tried from the menu, what she liked and why, flavor level, etc...). She paid attention to detail. One of our friends hates pickles and specifically asked for no pickles with his burger. This may seem like a minor detail, but if a staffer cannot pay attention to detail in the service industry, that is not a good indication. - Price. Good value for money, especially given the quality of food and portions. - Portions. Good amount and enough to get one full on one dish. - Location. Conveniently located in downtown Boston around many other shops and restaurants. - Layout. At the front, there's a pretty large bar area, including high tables and chairs, with booths and smaller tables towards the back. They appear to be able to accommodate large groups and smaller parties, including individuals. What's Not - Acoustics. It's pretty loud inside and sound carries very easily, so it's difficult to carry a conversation. Final Answer Worth returning.

    I got two cocktails from here and loved both! The "down cape" was very pretty and tasty. I also…read moreenjoyed the "starstruck" drink. The restaurant is very large and has plenty of seating. The servers and bartenders are all very nice. My only complaint is that some of the things on the menu are not actually available. I tried to order a sangria but no luck.

    Photos
    The Playwright
    PW nachos
    PW nachos
    Buffalo loaded fries

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    Buffalo loaded fries

    Lookout Rooftop - bars - Updated June 2026

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