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.
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.
Orleans Inn
As the only waterfront restaurant in town, the Orleans Inn has reason to brag. But humble's the default setting at this 132-year-old spot above Town Cove, which has gone through many an incarnation (boarding house, supply store) to reach its current status as the top place to gaze and graze on the Cape, with a dining room serving up local seafood with stirring vistas. 3 Old Country Rd., Orleans, MA 2653, orleansinn.com.
The Juice Bar
We'll spare all you dogged ice cream testers the brain freeze and bellyache, the stained clothes and the extra pounds: On Nantucket, the only ice cream of consequence is at the Juice Bar. At this sage-green shop, blackberry, peanut butter, mint chocolate chip, and other homemade flavors teeter over enormous, just-baked waffle cones. The only thing not to love is the long line. But the chatty college kids behind the counter are industrious, so your hefty scoop is never too far off. 12 Broad St., Nantucket, MA 2554, .
Mexico Lindo
Assuming the hyperfestive décor at this family-owned joint hasn't already knocked you on your heels, there's no doubt the powerful, wide-ranging flavors will. Surrounded by a rainbow of serapes and folk art furniture, diners are primed with homemade chips and salsa (and usually some high-test margaritas) before getting down to business. Mole is among the strong suits here, as is anything doused with the bright chili verde sauce. Bonus points for solid vegetarian choices, and lunch specials that pack dinnertime heft. 449 Main St., Melrose, MA 02176-3837, .
Bakers' Best Catering
When the only thing the family can agree on is not to sweat over a hot stove, 10-time winner Bakers' Best has got something to satisfy every craving: Dieting Dad will love the grilled vegetable, hummus, and cucumber wrap. Mom will savor the crab cakes with spicy rémoulade on the side. And the kids will fight—good-naturedly, of cours—over who gets second helpings of the cream cheese brownies. 27 Lincoln St., Newton Highlands, MA 2461, bakersbestcatering.com.
Coonamessett Inn
With its glossy, red shingles and gabled roofs, the Coonamessett Inn is the epitome of old Cape Cod, a perfect setting for high-style weddings and anniversaries alike. But you needn't wait for a special occasion: Sunday brunch features an array of delicious classics, from make-your-own omelets and baked salmon with special weekly sauces like beurre blanc or citrus, melon, and mango, to oversized fruit plates and gorgeous renditions of sweet favorites like chocolate mousse and carrot cake. 311 Gifford St., Falmouth, MA 2540, capecodrestaurants.org.
Les Zygomates
The pleasures of wine-drinking diminish considerably when everything a restaurant pours (a) puts you in debt or (b) comes from a vintner or varietal you've never heard of. Cheers, then, to Les Zygomates for its accessible list aimed at connoisseurs on a shoestring. Arranged by color and grape, the menu boasts dozens of wines under $50. There's even a quick-hit guide to bottles that can be had for an Andy Jackson or less, a handy resource for diners who are really pinching pennies. 129 South St., Boston, MA 2111, winebar.com.
L'Espalier
For a modern Boston tea party, head to L'Espalier on a Saturday afternoon, when the Back Bay brownstone is filled with elegant ladies nibbling on pastries and canapés. We recommend Red Riding Hood's Basket: savory tea sandwiches, melt-in-your-mouth scones with crème fraîche, and chocolate-dipped strawberries or Valrhona milk chocolate mousse tarts. The tea, delivered with a graceful flourish, is brewed just so and punctually refilled. You won't want to spill a drop. 744 Boylston St., Boston, MA 2199, lespalier.com.
Jumbo Seafood
If lobster was exclusively meant to be served boiled and dunked in butter, God would not have created ginger and scallions. One mouthful of the crustacean at this Chinatown gem, and you'll rethink the wisdom of the clambake. Equally transcendent are the whole, crispy fish; the jumbo shrimp netted live from an in-house tank and fried in a spicy orange sauce; and the (yes, delightful) Seafood Delight. 5 Hudson St., Boston, MA 2111, jumboseafoodrestaurant.com.
Clear Flour Bread
The crisp, airy baguettes and delicious country loaves are an excellent reason to make this European-style bakery the stop for your daily bread. But it's the cinnamon 'morning buns,' pear-ginger coffee cake, and apricot brioche that make us loyal—nay, slavish—customers. Clear Flour's crowning glory, and on this even the most exacting French pâtissier would have to agree, is their chocolate croissant: diaphanous, buttery, divine. 178 Thorndike St., Brookline, MA 2446, clearflourbread.com.
Sandrine's Bistro
The ambiance seems a touch suburban. But no matter: At Sandrine's, all eyes are on chef Raymond Ost's accessible French classics. Follow a salmon crepe starter with seared sea scallops and mashed potatoes piqued with sauerkraut or the house speciality, an Alsatian tarte flambé. Even the (quelle blaspheme!) meatless options (eggplant and cheese ravioli, stuffed artichoke) are fantastic. 8 Holyoke St., Cambridge, MA 2138, sandrines.com.
Tony Maws, Craigie On Main
Tony Maws is the anticelebrity chef. Undistracted by fame and fortune, he is laser focused on ferreting out the finest ingredients from local farms and transforming them in his cramped Cambridge kitchen into deliciously unexpected dishes like roasted Vermont organic squab with pomegranate-rose gastrique and sour milk panna cotta with candied fennel. Which, of course, is exactly what makes Maws a shining star. 653 Main St., Cambridge, MA 2139, craigieonmain.com.
No. 9 Park
Regulars at No. 9 Park are devoted to the house cocktail for the same reason they are to chef Barbara Lynch's prune-stuffed gnocchi with foie gras: It's simplicity perfected. While similar combos at other establishments tend toward the cloying, the Palmyra balances subtly sweet Rain vodka—made from white corn—with locally picked mint and a squeeze of lime to create an irresistible, always refreshing summertime sipper. 9 Park St., Boston, MA 2108, no9park.com.