Date Night Guide Pt. 2 – Boston

some drinks from bootleg special

Pier 6

Pier 6 checks all the boxes when it comes to date night. It’s right on the water in Charlestown with sweeping views of the city skyline. You can go for just a casual drink at the bar or hang out on their rooftop deck. As you might expect due to the location being right on the water, the menu is heavy on the seafood. Getting fried calamari at a seafood spot is our equivalent of getting a cheese pizza at a pizzeria. Pier 6’s calamari is as good as it gets. It is lightly fried with a nice crunch, and we devoured the plate in minutes. We are also suckers for anything duck, so the duck lollipops were a no brainer. No, these weren’t actually duck-flavored lollipops (but we probably would have tried that too). The duck pops are essentially duck wings where the meat is loosened from the bone and pushed down to the end creating a lollipop-like shape. These were tender and covered in a succulent house made BBQ sauce. Trust us, you can expect everything here to be high quality.

The biggest pro tip is that there is a free water taxi that goes between Pier 6, Tall Ship, and Reel House. So after dinner at Pier 6 you can cruise across the harbor in style over to Tall Ship.

Bootleg Special

Bootleg Special is a little piece of Bourbon Street in Boston. From the second you walk in, you get swept up by the atmosphere. The drink list is robust and filled with all kinds of fun drinks– which just means you will have to come back and try them all (but don’t wait too long because they tend to have a rotating drink menu). The Guava Lamp stole the show for us. With a tequila base plus guava and lime, this was dangerously refreshing and juicy. For food, there are tons of great shared plates to try, from garlic noodles to grilled octopus.

If you are really trying to have a night then there’s really only one way to go (well, technically two) the two signature boils. These boils are what Cajun dreams are made of. For something truly authentic that you won’t be able to find anywhere else in the city, you will not be disappointed with Bootleg Special’s boils (and it’s so much food you’ll probably be unbuttoning your pants after).


Last but certainty not least, Mariel brings the “wow factor” the moment you walk through the door. Located in an old bank, the cement walls are covered in paint which brings the space to life. If you like your drinks on fire, then look no further, because they have endless options. Our personal favorite is the flaming mojito tower. When going to a Cuban place it feels only right to order this. The drinks are strong, tasty, and expensive– but definitely worth it for the experience.

The menu is heavily tapas-based so you don’t have to feel bad about ordering all six of the items you were looking at. You really can’t go wrong here, but the must-try in our opinion is the steak churrasco. This is the definition of “melt in your mouth,” and it will leave you wishing this was a full plate.

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