Why you go there: It's fast, it's easy, and tex-mex is probably the best of the best in food genres. This is very casual, I go here on Sunday lunches or weekday dinners, you don't feel uncomfortable in sweats. Go with friends or a casual date. Plus the service is surprisingly good in the Braintree location. Eg Tara and Elliot
What you order: Where do I start? On Mondays you can get 2 for 1 fajitas, thats more or less a must. Chicken crispers are a lock if you want to have the most delish meal of your life and get about 2000 calories. My buddy dubbed these 'donut chicken". Beers are cheap and tall. Burgers are solid. Honestly, order anything.
How much you spend: Thats the best part, app, 2 entrees, 4 drinks = under $60, Chilis tops in regards to bang for your buck
4.) The Fours
Why you go there: Hang out with friends and grab a bite to eat. Pretty good sports bar, so you can watch a game. Good after work crowd, always packed, Quincy location in particular. Food, for what it is, is awsome.
What you order: You have to start with the buffalo chicken nachos. #1 appetizer I have ever had, could almost be a meal. The Johnny Kelly chicken sandwich is my favorite, but my people say the Bobby Orr is the best on the menu, I've actually never had it. STAY AWAY from the salads here, bland and the pieces of lettuce are as big as your head.
How much you spend: Great deal on the food... The beers and drinks are where they make their money. App, 2 sandwiches, a bunch of beers because you'll be watching sports, and maybe a cocktail = $80
3.) Abby Park
Why you go there: Awsome ambience... really nice inside, good tables, good bar. Right in east Milton square next to some chinese food restaurant. I was there a week ago and sat next to a blind date, seemed like a good date spot (not that i was spying on them).. So its middle of the road in regards to "Fancyness" if thats a word...
What you order: The flat breads are good... Calamari was worth it.. Sandwiches are really good, I got the Monte Cristo last time I went, which was like eating a pancake with ham, in a good way.. There are only 3 entrees on the menu, so I have never got one, the limited entrees may not be a bad thing, it's kind of trying to be swanky and modern, so it works
How much you spend: This really depends on what way you go with it, some sandwiches are cheap, some are oddly expensive, pizza and apps are reasonable, so I'll estimate here... app, entree and sangy, desert (because of date factor) and 4 drinks = $65
2.) Union Brew House
Why you go there: This is one of my fave's for a few reasons, outdoor seasonal seating, casual, bar type atmosphere and bar food, but it's also kind of cozy, fireplace etc. Add that to a Beer Club they offer (you can get your own plaque for trying 99 beers, great marketing) and thats why I like it. Any occasion except a "date date"
What you order: You can get a crazy amount of draft and bottled specialty beers from all over the world, so ask the bartender for a suggestion and you're off.... All the pizzas are delicious.. The quesadillas are superb.. and they have comfort food specials like mac and cheese fried bites... not your healthiest choice, but funnest maybe
How much you spend: Food is a little pricey for bar food... The beers are through the roof but worth it.. You and a buddy, a couple pizzas and an app, coupled with weird belgian ales = $80/hour
1.) Abe & Louies
Why you go there: Special occasion, big date, delicious food, sit outside on Boylston, you name it... I know it isn't south shore, but when it comes to giving top 5 restaurants, I can't name mine and not include this spot
What you order: Listen closely, DO NOT DEVIATE. Start with Jumbo Crab Meat Cocktail, follow with Steak and Seafood, 10 oz fillet and 1 lb lobster (come on, you only live once) handcut potatoes for a side, Sam Adams, New York style cheesecake... Best meal of your life
How much you spend: $200 or so, bring the AMEX