Planning a group dinner is hard. You need a place that’s big, that’s fun, and maybe more importantly, that has a waitstaff that won’t curse you out when you ask for eight separate checks. Which brings us to one of the biggest ethical dilemmas of the modern age: if you know you’ll be splitting the bill evenly, do you take advantage of the situation and order the most expensive thing on the menu? We can’t help you with that one - you’re the one who’s going to have to live with yourself after forcing each of your closest friends to pay for 1/8th of your truffle burger with uni mayo. But what we can do is tell you where to go. Here are 15 places in Boston that’ll make just about any group happy (at least until the check comes).
This guide is presented in partnership with MINI - so you can spend less time picking a great restaurant, and more time on the things that matter. Like the people you’re eating with.
You probably don’t have a smoker big enough to roast an entire pig on the porch of your third-floor triple-decker apartment. But you know who does? Pagu. And if you have 10 friends, you can go there and have your own suckling pig roast for $500. Even if that’s not your thing, this place in Central Square has a big menu with small plates you won’t find anywhere else, like squid ink bao and curry crab croquetas.
For a long time in your life, “group dinner” was probably synonymous with pizza. First there were all the pizza parties you went to when you were a kid, and then came the free pizza at literally every student activity in college. Even now, there are the sad conference room pizzas that make your quarterly corporate trust exercises barely tolerable. This is still the ideal food for sharing, but you deserve something better. Like the pizza at Area Four in Kendall Square. Grab a beer flight in this big, airy sit-down space and share a clam and bacon pie. Or three.
What’s the opposite of a sensory deprivation chamber? If there isn’t already a name for it, let’s go with Hojoko. Come to this Fenway izakaya and play Pac-Man, take in the completely random movie playing on a loop in the back, and order tons of Japanese barbecue bites and tiki drinks. And whatever you do, definitely split the wasabi roulette - a hamachi roll that’s hiding a secret that some lucky person in your group will discover. Because what’s the point in group dining if one of you isn’t going to unwittingly be destroyed by a piece of sushi?
The Sinclair in Harvard Square has an upscale gastropub and a major live music venue under the same roof, so you can make a whole night out of this place. The small plates are reliably great - we like the ginger lime brussels sprouts and the burrata with smoked beets - and the cocktails are always interesting. If you don’t have tickets to the show, just start buying drinks for everyone at the bar. Eventually, someone will either return your generosity with a ticket, or get too drunk to use theirs.
The food at this Asian fusion spot in the Fenway is very good. But you can get good food at lots of places. We’re pretty sure, though, that there’s only one place where you can get a seven-serving rum punch served in a treasure chest. Make sure there are several orders of the crispy chili potatoes on the table to soak it all up.
The dining room in this Downtown Crossing spot is big enough to host an entire steamship’s worth of robber barons and oil tycoons - and it looks the part. The opulent rooms are cool enough that you’d be happy just to sit with a scotch, but you should also try the small plates (we like the honey walnut shrimp). Save this place for when you want a fancy but fun night out.
Someone in the group wants Indian, another wants a burger, and someone’s new significant other says they’re “just having drinks.” You can satisfy everyone at this place in Central Square, which specializes in global tapas - meaning you can have a fried chicken sandwich, biryani, pasta alla vodka, and a caviar sandwich all in the same meal. Definitely check out the cocktails too - especially the one served inside a grapefruit, which is helpfully labeled on the menu as “The One in the Grapefruit.”
Yes, Legal Sea Foods is a chain, and yes, you’ve probably already had the chowder hundreds of times in your life. But sometimes places become institutions for good reasons. And at the flagship Legal Harborside in the Seaport, you can at least be sure that you’re not getting the same Legal’s experience you’d find at locations in malls up and down the East Coast. This place has three different levels, each with their own menus. If you have guests in town, the rooftop has some of the best views in the city.
There’s only one way to do a group dinner right at this Italian spot in Cambridge - ask for the giant wooden table in the middle of the room and pretend you’re hosting a medieval banquet. Just please order the bucatini and try not to call your server a wench or give anyone the black death.
This Kenmore Square restaurant is a great place for big brasserie standards like mussels and ribeye steaks, and has a bar that’s the perfect place to sip on a shaken egg white cocktail. It’s also nearly the size of a European train station, so it will fit all of your friends. Don’t forget to dramatically waive a handkerchief out the window of your Lyft like you’re leaving to fight the Great War after you finish the crab legs.
Should you and your friends order one of each kind of shellfish on the menu at this Kenmore Square classic, line them up on the table, and pretend to do the opening number from the Spongebob musical? The answer is, unequivocally, yes. You should also get the crispy oyster sliders and the cod with mustard spaetzle. This is one of our favorite restaurants in the city, with a big space that can easily accommodate your crew.
Some of the Liberty Hotel’s novelty may have worn off since it opened up in 2007, but it’s still pretty cool that the restaurant inside is housed in what used to be a 19th Century jail. The pizzas are creative, the handmade breads are perfect for sharing, the wine list hits every price point, and you won’t have to Andy Dufresne your way out of there at the end of the meal.
It’s a historically-documented fact that no one had more fun than the American expats in 1920s Paris. You missed it, that sucks, and you won’t be going to 1920s Paris any time soon, but as a consolation you should check out Gaslight in the South End. It’s all there: the French food, the globe lighting, the white-tiled walls, and the silver bar. Grab some friends and split the shellfish platter. Or if your group is six or more, let the restaurant customize a menu for your table. This isn’t the 1920s, but you also don’t have to worry about Spanish flu, so you’ve got that going for you.
The good news about doing a group dinner at a small plates place is that you get to order everything on the menu. The bad news is that you might only get one bite of each thing. Luckily, this place in Harvard Square also has an excellent cocktail menu, so you can handle your conflicted emotions that way. Get the rabbit, the tuna crudo, and the barrel-aged cocktail. This is a big, fun restaurant that’s almost always buzzing.
If the weather’s nice, definitely sit on the shaded patio out front of this comfort food spot in Jamaica Plain. If it isn’t, there’s still plenty of room for your group inside, along with the added bonus of being closer to the kitchen so that you and your friends can be treated to mac and cheese aromatherapy. The big bar along the side of the dining room also has a great collection of craft beer taps, so get after that, too.