Shiki
Most Japanese restaurants around here are either sushi specialists or theatrical hibachi houses. Shiki, a subterranean spot tucked away on a Coolidge Corner side street, is the outlier. Offering a massive selection of traditional small plates—tangy tsukemono pickles, fluffy agedashi tofu, and mushroom-packed, sticky-rice-stuffed squid, along with plenty of sake to pair with them—this spot was designed for the true Japanophile. 9 Babcock St., Brookline, MA shikibrookline.com.
Lolita
A good pickup bar needs two things: a classy atmosphere, and really strong drinks. At Lolita, bartenders pour more than 50 varieties of tequila in a setting more apropos of Dos Equis's Most Interesting Man in the World (as he says, he does not always drink beer) than frat boys. Try the margaritas—they'll make you feel both refined and, let's say, outgoing. 271 Dartmouth St., Boston, MA lolitatequilabars.com.
Drink
Drink is a bar of firsts—the first high-profile craft-cocktail joint in South Boston; the first place that some of the city's top bartenders worked; and, most notably, the first place that many people discover their favorite cocktail. There are usually a few drink suggestions on the board behind the bar, but don't miss out on chatting with the expert mixers, who will design a sipper based on your preferences. 348 Congress St., Boston, MA drinkfortpoint.com.
Pavement Coffeehouse
One of the first places in Boston to offer pour-over and cold-brew coffees, Pavement goes well beyond crafting lattes and cappuccinos (although these are fantastic here, too). From the quality Counter Culture beans and complimentary soy milk at the bar to the strong WiFi connection and inviting tufted couches, this is a true coffeehouse experience, one that both java aficionados and on-the-go professionals will savor. 1096 Boylston St., Boston, MA 2115, pavementcoffeehouse.com.
Sportello
The gleaming, U-shaped bar here is your gateway to Barbara Lynch's homemade pastas (the tagliatelle with Bolognese is a perennial favorite) and sophisticated plates like whole-roasted trout with anchovies and olives. True, this casual trattoria can be pricey for a weeknight meal—especially when Drink, Lynch's downstairs bar, is tempting you with aprés-dinner cocktails—but the return on investment is reliably delicious. 348 Congress St., Boston, MA 2110, sportelloboston.com.
Grotto
A stone's throw from the gold-domed capitol, Grotto is a quietly luxurious refuge for well-to-do Beacon Hill residents looking to escape touristy Charles Street for a light lunch or dinner (a prix fixe is offered daily). And when they want something heartier, there are dishes like house-made ;tagliatelle or beef tenderloin over creamy risotto. But the three words that keep Beacon Hillers—and a lucky few hoi polloi—returning time and time again: banana bread pudding. 37 Bowdoin St., Boston, MA 2114, grottorestaurant.com.
Bergamot
This warm, elegant Somerville bistro was cleverly designed to suit both neighborhood residents and those who travel for a celebratory meal—a nice balance that can be attributed in part to wine director Kai Gagnon's skill in choosing wines for both crowds. His bottle list is lengthy and varied—a veritable tour through Europe—but there are also nearly two-dozen by-the-glass options for those with commitment issues. Most important? The knowledgeable servers to guide you to the perfect selection. 118 Beacon St., Somerville, MA 2143, bergamotrestaurant.com.
Menton
Barbara Lynch's haute-cuisine mecca was an instant sensation when it opened in 2010. The parade of tiny, striking dishes! The feather-light glassware! The prices! And the place has only improved over time, from the stunning prix-fixe menus to the staffers who anticipate your every need. We're not alone in noticing. In February the restaurant became Boston's first Relais & Châteaux property, a distinction reserved for the likes of Eleven Madison Park and the French Laundry. 354 Congress St., Boston, MA 2210, mentonboston.com.
Island Creek Oyster Bar
Chef Jeremy Sewall has a family connection to the best crustaceans around: His cousin Mark is a Maine lobsterman. And the best vehicle for his wares just may be Island Creek's lobster roll. Mixed with créme fraîche, dill pickles, and celery salt, the succulent meat is stuffed into a house-made rosemary-flecked roll and sent out to the table bursting at the seams. Take a moment to savor the stunning visual, because it'll be gone before you can say, "Pass the napkins, please." 500 Commonwealth Ave., Boston, MA 2115, islandcreekoysterbar.com.
Saus
A truly great fry is only as good as the stuff you dip it in. And while we love Heinz as much as the next guy, It's hard to top this ;frites shop's cheddar Duvel sauce, garlicky "Vampire Slayer' aioli, and truffle ketchup—merely a few of the condiments available. Order your cone of hand-cut, cooked-to-order spuds with a deep-fried egg on top, and write us a thank-you note later. 33 Union St., Boston, MA 2108, eatfrites.com.
Rialto
The city's Italian-dining scene skews either reasonably authentic (yet undistinguished), or posh (but not quite legit). Rialto bridges the gap with seasonal, from-scratch cooking (strands of bucatini with lobster and saffron; salumi with house-made ricotta) and attentive, special-occasion-worthy service. Chef Jody Adams's regional menus, which spotlight a different part of Italy every two months, are delightful, especially when paired with the suggested wines. 1 Bennett St., Cambridge, MA 2138, rialto-restaurant.com.
Jo Jo Taipei
One bite of this Allston beauty's crisp, pillowy scallion-and-roast-beef pancakes, and you'll never order those sad, green-flecked cardboard slabs from your local Chinese takeout joint again. Here, it's all authentic Taiwanese dishes—like three-cup cuttlefish, spicy beef-noodle soup, and dry-cooked chicken with three peppers—and none of that greasy cream cheese-stuffed crab rangoon or gloppy General Gao's chicken you get elsewhere. 103 Brighton Ave., Allston, MA 2134, jojotaipei.com.
Sweet Cheeks
Smoked meat, we've long held, is the great equalizer—the one cuisine practically everyone (vegetarians aside) can agree on. For proof, head to chef Tiffani Faison's tribute to Texas. You'll find families with toddlers, hipsters chugging Bud Light Lime, and camera-wielding tourists still buzzing about the Fenway tour—all with a huge grin accented by a smidgen of tangy sauce. The pulled pork is divine, and be sure to order a bucket of fluffy biscuits and a scoop of broccoli casserole. 1381 Boylston St., Boston, MA 2215, sweetcheeksq.com.
Phoenix Landing
It's time to change up your sports-bar rotation. Head to the Phoenix Landing, where soccer—er, football—is almost always on the telly. This pub is Boston's official Liverpool FC clubhouse (the Red Sox's John Henry owns the team). Of course, all fans are welcome here ... as long as they're willing to drink Guinness while belting out, "We'll fight for the boys in Red, We'll fight, we'll fight for Liverpool, The team that Shankly bred." 512 Massachusetts Ave., Cambridge, MA 2118, phoenixlandingbar.com.
Woodward at the Ames
When you're looking for someone to pick up what you're puttin' down, try the Ames hotel's saloon, where a glass-topped bar and stainless steel accents lend an upscale gloss to the robust singles scene. If you're not ready to chat up a Financial District suit, head for the dance floor—or plot your next move while nursing a motivationally named cocktail, such as the "Skip and Go Naked." 1 Court St., Boston, MA 2108, ameshotel.com.