Embrace the bustle and glamour of the expansive dining room at this Back Bay red-meat temple. Take in the pillars, ornate ceilings, and suited-up servers, then tuck into a juicy 20-ounce bone-in rib-eye with sides like duck-fat-fried hash browns and bacon-laced Brussels sprouts, plus some of the finest martinis in town. 161 Berkeley St., Boston, MA 2116, grill23.com.
Boston has no shortage of outdoor dining options, but for our money, none is as transporting as the backyard terrace at Oleana. It's a fairyland of flora and fauna—swags of crawling green draped over wooden trellises, fruit trees burgeoning with ripe fruit, flowers of every variety waving in the summer breeze. That's more than most of us needed to set the scene for a relaxing meal—so when chef Ana Sortun tosses in her soothing and exotic Mediterranean menu, it's just glorious gravy. 134 Hampshire St., Cambridge, MA oleanarestaurant.com.
Despite its metropolitan moniker, this year-round treat shop brims with local flavor. The homemade ice cream is churned out in myriad varieties, including velvety black raspberry, cake batter, and mint chocolate chip; this year the creamery also debuted zesty gelato in hazelnut, tiramisu, and amaretto. And because it stays open until midnight during the summer, you can drop in for a cone after dinner, then come back for a fresh-baked brownie, cookie, or pie to enjoy as a bedtime snack. 26 Housatonic St., Lenox, MA 1230, sococreamery.com.
You won’t find a more inventive cocktail program: GrandTen’s liquor license requires staff to create every ingredient on the menu from the distillery’s base spirits—from peach brandy to a vermouth-like "vermaro." But despite its extreme dedication to craft, this bar is a snobbery-free zone. 383 Dorchester Ave., Boston, MA 02127, grandten.com.
In kitchen design, conceiving the proper layout is half the battle. We’d trust the Divine Design team to lead the charge any day: The Wellesley firm—which also boasts a stunning showroom in Boston—once revamped a local space by swapping a restrictive peninsula for a granite-topped island with storage and seating. Multiple locations. 180 Linden St., Wellesley, MA 02482, divinedesignbuild.com.
Perched 33 stories above the city with glass walls overlooking the Custom House Tower, the State Room is a blank canvas with personalization options galore. Chef David Blessing, meanwhile, serves up customized menus that are as breathtaking as the views—think tuna poke in mini cones and adorable s’mores tartlets. 60 State St., Boston, MA longwoodevents.com.
There’s no better place to hang out when the sun’s out, so grab a cone at J.P. Licks, find a comfy bench, and enjoy some of the best people-watching and outdoor performances on this side of the Red Line.
In a world choking on Black Eyed Peas, this cluttered basement shop is a refuge for the lonely few who still cling to the classics. The R&B, soul, and blues vinyl selection is simply astounding, and the music-obsessed staffers are excellent navigators to little-known high notes. 645 Massachusetts Ave., Cambridge, MA 2139, .
It's the thought that counts, but too often pricey flower arrangements arrive as if no thought went into them at all. Not so in Hallie Krachevsky's shop, where she lovingly assembles seasonal blossoms—many of them local—into mini masterpieces. And the store's good in a pinch: none of that "I need 24 hours!" business here. 248 Huron Ave., Cambridge, MA 2138, .
Fabulously flattering cosmetics for almost any skin tone, Bobbi Brown recognized what most lines didn't— that most complexions have yellow undertones, not pink. The line is comprised of subtle, simple to wear, and simple to apply makeup that makes you look natural, rested, and almost bare-faced. The Mall at Chesnut Hill, 199 Boylston St., Chestnut Hill, MA .
Calypso's colorful yet put-together offerings prove once and for all that there is life after gray. Renowned for its clothing and accessories in luxurious fabrics and hues of amethyst, saffron, tourmaline, and fuschia, the bohemian, hippy-chic styling of this shop make it the best place for those who like to stand out from the crowd. 115 Newbury Street, Boston, MA calypsostbarth.com/.
Ever wonder why the church once outlawed chocolate as too sensual? Airlifted weekly from the little chocolate gnomes in Zurich, delectable with the finest cream, butter, and milk chocolate, these are the kind of chocolates you eat so slowly that they melt in your hand long before they get to your mouth. 230 Newbury St., Boston, MA .
The elegantly appointed changing areas and owner Lyudmila Sletkova's painstaking workmanship evoke a bygone era. They also ensure that, whether you've gone a touch brideorexic or decided to don Mom's '70s-era gown, Sletkova can nip your dress into shape without any skimpy-curtain indecency. 268 Newbury St., Boston, MA bestfitinc.com.
Finger sandwiches, Scottish cones, Viennese pastries, English tea breads, pots of preserves, genuine tea caddies, and service stops at 4:30 p.m. on the dot. Hotel GM Robin Brown's standards are strict—as befits a bloke from Grantham, Lincolnshire. 200 Boylston St., Boston, MA .
You hear him everywhere—on the Common, in the subway station, on the street—and he's got a great tone. But all he whistles is the first few bars of "Yankee Doodle." With a little variety in the repertoire, this guy could be the Jean-Pierre Rampal of the mouth.