Trevi Cafe and Wine Bar
Yes, it’s nestled within the tourist mecca of Mashpee Commons. No matter: Once you step into Trevi, you might as well be on a European vacation with your secret paramour. There’s an expansive covered terrace overlooking a soothing backlit fountain, a vast menu of global wines, and a list of generously poured cocktails (the Trevi Tini is our favorite). 25 Market St., Mashpee, MA 02649, trevicafe.com.
Doretta Taverna & Raw Bar
When Doretta popped onto the scene, Michael Schlow fans puzzled over the uncharacteristically conservative menu—especially when compared with the fresh takes offered at nearby Pelekasis, Brendan Pelley's mod-Greek pop-up. So Schlow did what any pro would do: Once Pelley's temporary gig ended, he scooped him up as chef de cuisine. Together, they're a Hellenic dream team, slinging a perfectly calibrated mix of impeccable classics (charry lamb chops) and restless stunners (saganaki fondue with Sichuan peppercorns). 79 Park Plaza, Boston, MA 02116, dorettaboston.com.
Oak Long Bar + Kitchen
We escape into a hotel bar when we want to feel like visitors in our own city. And there's no grander way to see Boston than by sidling up to the gilded bar at the century-old Fairmont Copley Plaza. Take a seat under the soaring ceilings and sip a stiff gin martini or an oversize pour of pinot while the world passes by. 138 St. James Ave., Boston, MA 02116, oaklongbarkitchen.com.
The Times Bar and Restaurant
To hell with baked beans. Clam chowder is Boston's crowning food—not potato, not flour, but clam. That's a distinction understood at the Times, an otherwise largely undistinguished beer hall within a stone's kick of the waterfront. Each spoonful of the chowder here is heaped with clams so fresh they carry a signature nip of sand and the odd crunch of shell. It's dense but not gluey, and the flavor is emphatically shellfish. Other chowders boast fancier bisques or gourmet crackers, but this barroom stew wins out on the strength of the defining mollusk. 112 Broad St., Boston, MA timesirishpub.com.
Silvertone Bar & Grill
There are perhaps no greater late-night food cravings than for French fries or macaroni and cheese. Fortunately for Boston barhoppers, Silvertone serves mean versions of both in its soothingly dark subterranean bar and lounge. Slip down the stairs and settle into a booth to order from a menu filled with a mix of comfort food and gourmet dishes, served quickly and efficiently by the casual, friendly staff. The full bar means that those who still have the aptitude for one last tipple can wash down their BLTs with an ice-cold draft. What's more, the location (smack-dab in the middle of the newly trendy Ladder District) makes Silvertone an easy addiction to indulge. 69 Bromfield St., Boston, MA silvertonedowntown.com.
Grill 23 & Bar
Great steaks are only the tip of the iceberg at Grill 23. Sure, executive chef Jay Murray has a knack for cooking red meat, but the other dishes on the menu, including Chilean sea bass and grilled stuffed lobsters, are just as delicious as the marbled prime rib, steak au poivre, and filet mignon. The meats are made still better with the addition of such tasty side dishes as the decadent truffled macaroni and cheese or crispy hash browns. Settle into a table in the cavernous downstairs dining room to sip giant martinis and cut into porterhouse steaks with the high rollers, or book an upstairs private dining room for a more intimate dinner. Either way, the service is impeccable and the steaks, superb. 161 Berkeley St., Boston, MA grill23.com.
Brad Duncan Skin Care
From the outside, it's easy to mistake Brad Duncan Skin Care for a physical therapist's office. But once you ring the bell and descend the stairs, you'll find yourself in Zenlike subterranean digs. Duncan's skin-care mecca focuses on anti-aging corrective facials that leave skin clearer and tighter. He specializes in intense (though surprisingly painless) pore extractions and enzyme-based exfoliation. He's also friendly, serene, and possesses the type of complexion we've envied since ninth grade. 530 Tremont St., Boston, MA 2116, .
Grill 23 & Bar
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.
Small Planet Bar and Grill
Eclectic props and great people watching can keep you entertained if the date turns out to be a bore, and the excellent vegetable burgers can save the evening if your new friend turns out to be a vegetarian. 565 Boylston St., Boston, MA .
Uni Sashimi Bar
You won't find a single fried clam on the menu at Uni, Ken Oringer's tiny sashimi bar. Instead, head chef Youji Iwakura serves delicacies like octopus (with yellow pepper juice, black mint, and Vietnamese coriander) and hamachi (with sea urchin, yuzu, onion seeds, and radishes), flown in daily from Japan. Grab a seat at the marble bar and let the chefs use their imagination. 370 Commonwealth Ave., Boston, MA unisashimibar.com.
Turner Fisheries Restaurant & Bar
Experimentation may be the spice of fine dining, but chowder demands tradition. To heretics inclined to load their chowder with corn, carrots, or—God forbid—Baileys Irish Cream, we say: Move west. Real Bostonians demand their chowder like Turner's. That is, dense with clams, not flour; well stocked with potatoes; flavored with the merest hint of smoked pork; and awash in aromatic cream. Westin Copley Place Hotel, 10 Huntington Ave., Boston, MA turnersboston.com.
Union Bar and Grille
Not quite a year old, Union has managed to root itself so deeply into South End culture, you'd think it has been around for decades. What's the secret? We suspect it has something to do with co-owner Jeff Gates' genial nature, executive sous chef Josh Steinberg's steady hand with mostly local ingredients, and bartenders who know their way around the many bottles they shake, chill, and pour with such profound dexterity. Or maybe it's simply Union's mix of unpretentiousness and sophistication. Whatever the draw, few who drop into Union can resist coming back—and fewer still believe it isn't here to stay. 1357 Washington St., Boston, MA unionrestaurant.com.
Lyceum Bar & Grill
Smack dab in the middle of history-drenched Salem, you'll find Lyceum Bar & Grill—famous not only for a contemporary lunch and dinner menu that mixes global cuisines, but as the very spot from which Alexander Graham Bell made his first long-distance phone call. If that's not enough to lure you in, the Sunday brunch menu ought to be—for delicate lobster-filled crepes served with leeks and sun-dried tomato cream, maple-cured ham and cheese sandwiches with onion marmalade, and classic eggs Benedict. 43 Church St., Salem, MA .
The bar at Turner Fisheries
Locals, foreigns, and domestics—a smorgasboard. Copley Place, Boston, MA .
Grill 23 & Bar
The steaks, like everything else off the grill, are great. But the service and the fin de siècle setting at Grill 23 make you feel as though this really is the Hub and you are a proper Bostonian. 161 Berkeley St., Boston, MA .