INMAN SQUARE. This trendy little coffee house attracts an artsy, eclectic crowd who come to enjoy coffee or tea on a work break or with friends in the morning or evening. 1369 also offers a menu of light fare, including soups, sandwiches, and scones. A perfect place for quiet conversation and catching up with an old friend or for an intimate chat with someone special. Get there early to catch a table, which fill up with students and laptops.

DORCHESTER. This small restaurant makes up for its lack of space by its exceptional New American menu. The offerings are plentiful and feature fresh fish such as monkfish, mussels, grilled salmon, and catfish. The menu also includes chicken, beef, and vegetable entrees. The interior space, with its cheery yellow and exposed brick walls, black and white floor and theatre-style kitchen, invites guests to stay awhile and enjoy the casual environment. Outdoor garden seating available during pleasant weather.

SOUTH END. A lounge that transcends cool, 28's wins high marks thanks to its suave atmosphere, inventive cuisine and superb cocktails. Indeed, whether it's to indulge in tuna tartare, to savor a key lime martini (the lounge, after all, is named after the optimal chilling temperature for martinis), or to listen to the hip soundtrack assembled by that night's DJ, this South Ender is the type of place where hip, young urbanites hold sway. Aesthetically, the space features basic black and white walls, dim lighting and soft, comfortable banquettes.

BACK BAY. 29 Newbury is a trendy café-bar, where socializing is high on everyone's list of priorities. You'll often spot a crowd of local business folks making the most of the hip atmosphere, nursing drinks and expanding their networks. Celebrities have also been known to make appearances. Should you get hungry, sample Japanese spring rolls or fried calamari, and follow with lobster and basil orecchiette or baby rack of lamb.

BACK BAY. While glitz and glam are terms that don't necessarily apply in Boston like they do in a city like, say, New York, there are a few establishments in the former that cater to the discriminating patron's palate. This handsome restaurant and lounge is just such a place, combing sophisticated design elements (LED-lit bars and stairwells, maple ceilings, and weathered brick walls) with fine New American cuisine. True hipsters, though, brush past the folks gathered at the bar or seated in the restaurant and make their way down the stairs to the suave lounge area, where celeb DJs and deep-pocketed VIPs hold sway. NB Tables in the lounge are by reservation only.