With a harbor, four major rivers, and three man-made channels, eating and drinking on the water in Boston should be easy. But thanks to 50 years of poor urban planning and maybe a fear of pirates, there are shockingly few places where you can grab a drink and some decent food while fending off seagulls. We’ll probably have a lot more options in a few years when the Back Bay sinks (think of all the great canalside patios on Newbury!) but for now, these are Boston’s 10 best spots for eating and drinking on the water.
Update June 10th 2020: After months of being closed, Boston restaurants have been allowed to reopen. Check out the list of Boston Restaurants Reopened For Outdoor Dining for up-to-date info.
the outdoor spots
If camping were allowed on the Esplanade, we’d pitch a tent next to the Owl’s Nest all summer so we’d never have to leave. Sure, we wouldn’t have the best personal hygiene, but who cares about a few deer ticks when you have beers from one of the city’s best breweries and rotating food at your tent flap? Don’t let summer slip away until you’ve spent at least one evening here as the sun sets on the Charles.
We now have an entire neighborhood that derives its name from the fact that it sits on the harbor. And yet, there are still only a handful of waterfront places in the Seaport, most of which each are either corporate chains or tourist traps. Legal’s Harborside is both of those things, but that doesn’t mean it’s not good. Whether you’re outside on the ground-floor pier where the traditional Legal’s menu is served, or on the roof where the focus is on sushi and raw bar items, you’ll have fun and have direct views of the fish pier in one direction and the harbor islands in the other.
Despite being the approximate size of a Saudi prince’s yacht, it can be hard to get into Legal’s during the summer (and close to impossible to get one of the outdoor tables). Luckily, Temazcal is right next door. The modern Mexican food menu here is more than good enough to complement the real reason you’re here: an excellent selection of mezcal and tequila that you’ll work your way through while the sea breeze blows through the dining room. Be strategically generous and buy a few rounds for the people around you, too - one of them might have pulled up to the restaurant on one of the boats that’s tied up out front, and that’s a good friend to have.
Admittedly, swimming on the beach at Castle Island isn’t great. There’s mud, overgrown seagrass, and half-empty tins of chew buried in the sand. But sitting by the water with a lobster roll and a box of whole-belly fried clams from Sullivan’s is pretty much the best beach experience you can have inside 128.
Belle Isle is only about one football field away from the city border, and yet it feels like it’s a world apart (well, except for the planes taking off and landing so close to you that you might be able to read the in-flight magazine in someone’s seatback). This classic New England seafood shack makes one of Boston’s biggest and best lobster rolls to go with some outstanding fried shellfish, and you can eat it all on picnic tables that overlook what looks like a little North Shore harbor.
You are coming to ReelHouse first and foremost for the view, there’s no question about that. But when the view is legitimately stunning like it is here - a straight shot across the harbor to where the city is lit up like Atlantis - there’s no shame in that. And while there’s nothing to get too excited about on the seafood-heavy menu, you’re really here to drink under the sun and watch the sailboats and ferries on the harbor. Split some oysters and avocado toast to keep you going while you order another drink.
If Epcot added a New England-themed restaurant, it would look a lot like the Barking Crab, considering how stuffed it is with maritime kitsch. This is a tourist trap in a prime location, so it doesn’t have to try too hard, and you might find an uncooked clump of flour in your chowder. But, man - that location. Sitting on the deck here feels like sitting on the deck of a ship that’s just come into port, and there are few better places to grab an outdoor drink than here, with the waters of Fort Point Channel right underneath you and the skyline right next to you.
The patio at Lolita is just a little ways down the channel from the Barking Crab, but unless you prefer a view of mailvans loading up with Pottery Barn catalogs over the downtown skyline, the vista isn’t quite as good. The tacos, however, will keep you happy as you order margaritas at the outdoor bar.
The Charlestown and Everett shorelines of the Mystic River are covered with enough smokestacks, gas tanks, and abandoned piers to film a zombie apocalypse movie. But River Bar in Assembly Row is located in such a spot that, not only does the Mystic not look like a dystopian hellscape of urban decay, it looks downright pleasant. The American bar menu is a little hit or miss, but get some drinks and the crispy chicken sandwich. With fire pits, trees strung with lights, and views of boats tying up on the river and kids flying kites, you’ll have a good time.
OK, we’re admittedly stretching the meaning of “on the water” here. While you are right next to the harbor at this Australian spot in Eastie, you’re also next to a lot of 18-wheelers, a couple of rusting piers, and possibly some industrial waste. But you don’t have to eat the waste. Instead, you can eat some fantastic meat pies while you sit on an adirondack chair and play Jenga. This is a great place to either hang out for an afternoon and play corn hole, or engage in your recurring role-playing fantasy where you’re a corrupt longshoreman who smuggles drugs into Boston for a mysterious supplier known only as “The Accountant.”