Carmen
Okay, so one of Carmen's chefs, Merwin Casey, hails from Ireland. But he cooks Italian better than many of his North End neighbors. Casey tweaks standard dishes just enough to make them exciting again. Witness his porcini-stuffed crespelle topped with a proper Bolognese and the perfect seared halibut splashed with salsa verde. That means delicious green sauce in English—and Irish. 33 North Square, Boston, MA carmenboston.com.
Oak Bar
There could be a raging nor'easter outside, but inside this legend in the Fairmont Copley Plaza, it's always 70 degrees, with the sun setting over the Indian Ocean and the whack of a distant cricket wicket audible over the veldt. Every detail here speaks civilization—from the golden elephant heads holding up the bar rail to the crisp service of the gold-vested bartenders. The generous martinis, on the other hand, whisper pure decadence. 138 St. James Ave., Boston, MA oaklongbarkitchen.com.
Ocean Edge Resort & Golf Club
After a long drive across the bridge, sometimes all you want is to sit back, relax, and not touch your car keys again for the weekend. That’s possible at Ocean Edge, where guests at the Mansion have access to the private Bay Pines beach and everyone can enjoy pickleball and tennis courts, multiple pools, a spa, and a private 18-hole golf course. Plus, if you do need a change of scenery, the resort is just minutes from Nickerson State Park and the Cape Cod Rail Trail. 2907 Main St., Brewster, MA 02631, oceanedge.com.
The Liberty Hotel
Built into the former Charles Street jail, the Liberty was designed to cleverly highlight the original building's mid-19th-century monumentality. Despite its jailhouse origins, the hotel's rooms are captivating (in a good way), with floor-to-ceiling windows and plenty of amenities. There's also complimentary yoga on Saturdays and bicycles for touring around Beacon Hill. Skipping either would be criminal. 215 Charles St., Boston, MA 02114, libertyhotel.com.
Torbert MacDonald State Park
No need for hiking boots and day packs at this nexus of nature and urbanity. A stroll through Medford's Torbert MacDonald State Park provides ample fodder for urban birders, with sightings of red-tail hawks common. And though the stresses of the daily grind are just a few steps away, the sweeping views of the Mystic River and winding walking paths will make them feel a world away. 4253 Mystic Valley Pkwy., Medford, MA 02155, .
Savenor's Cambridge
"What's for dinner?" Ask that question to the butchers at this family-owned nose-to-tail institution, and you'll get plenty of inspiration. Perhaps they could butterfly a veal breast so it's stuffing-ready? Or maybe you'd prefer a few prime dry-aged steaks for the grill? From pasture-raised Berkshire pork to organic Giannone chicken, you'll find only the best cuts—and the best advice—behind the counter. 92 Kirkland St., Cambridge, MA 02138, savenorsmarket.com.
The New World Tavern
Clio and Uni alum Johnny Sheehan has taken his talents south, to a funky tavern in downtown Plymouth. Here, friends catch up over spicy Sichuan ramen; bar snacks like yuzu-glazed pig tails and crispy chickpeas dusted with ras al hanout; and an extensive charcuterie selection. Sheehan's creativity works well with the three dozen craft beers on draft and more than 100 bottled brews from around the globe. It's a new world in Plymouth, indeed. 56 Main St., Plymouth, MA 02360, thenewworldtavern.com.
Linnea Tangorra
Linnea Tangorra and her staff of three can help both brides who know exactly what they want and those who have no clue. Services range from soup-to-nuts planning to hourly consulting with no minimums. Tangorra is quick to respond in any situation, whether she's answering your late-night e-mails, fielding your future mother-in-law's incessant questions or averting weather-related reception disasters with a well-orchestrated plan B. Tangorra Wedding Planning, 251 Newbury St., Boston, MA 2116, linneatangorra.com.
Linnea Tangorra
Linnea Tangorra and her staff of three can help both brides who know exactly what they want and those who have no clue. Services range from soup-to-nuts planning to hourly consulting with no minimums. Tangorra is quick to respond in any situation, whether she's answering your late-night e-mails, fielding your future mother-in-law's incessant questions or averting weather-related reception disasters with a well-orchestrated plan B. Tangorra Wedding Planning, 251 Newbury St., Boston, MA 2116, linneatangorra.com.
Toro
What's as rich as Toro's cheese plate, has as much flavor as its olive oil-roasted Brussels sprouts, and is as undeniably saucy as its patatas bravas? The neighborhood designers and artists, in-the-know real estate movers and shakers, and local restaurateurs who—without fail, seven nights a week—flock to chef-owner Ken Oringer's no-reservations hot spot from happy hour till closing time. Rubbing elbows with such characters over cava at the raucous bar makes waiting for a table seem like a perk, not a burden. 1704 Washington St., Boston, MA .
Audubon Circle
There aren't many places where Asian pot stickers, pork schnitzel, and lobster rolls happily coexist on a menu, but Audubon's eclectic mix of global and American comfort food simply works. The dimly lit spot on a nondescript section of Beacon Street is the perfect hideaway—and after throwing back a couple of BBC Steel Rail brews and snacking on grilled bread dunked in a silky white-bean purée, you'll be glad you're in on the secret. 838 Beacon St., Boston, MA 2115, auduboncircle.us.
Charles G. Crones
Crone's father began the J.A. Sanborn Company forty-nine years ago at 28 Merchants Row (next door to Quincy Market), and it's still flourishing. "We go out of our way to buy the best," Crones told us. "We buy whole fish off the boats, and cut them here. You can always find a good selection." If you dine at the Ritz, or at St. Botolph Street, you're eating Sanborn selections, and Crones will even mail fresh lobsters for you. J.A. Sanborn Company, 28 Merchants Row, Boston, MA .
Gypsy
Want proof that cobblestoned Nantucket is no longer just a quaint and quiet haven of whaling lore and preppies on vacation? Look no further than the designer-filled boutique Gypsy. Catherine Malandrino frocks, by turns sassy and sexy, hang next to cutout Chloé tops, palm-print Celine slacks, lower-than-low-cut True Religion jeans, and Lucite heels. Not exactly sailing gear, but hey, since when must fashion bow to function? 47 Main St., 2nd floor, Nantucket, MA .
Sharrock's English Bakery
Forget "English muffins" and get a hold of the original article. These crumpets are filling enough for a decent breakfast (and, if you have the power to skip butter, they're fat- and cholesterol-free), yet light enough to leave plenty of room for lunch. Ex-pat Brits swear they're the only "real" crumpets this side of the Atlantic. If mail order's not your bag, the bakers also market their goods under the Trader Joe's label (at all Trader Joe's stores in the area). 1649 Wheeler St., North Dighton, MA .
The Barn Bowl & Bistro
Great food and “bowling for everyone,” as its mission states (pop-up rails, please!), make the Barn Bowl & Bistro an ideal hangout for families with kids of all ages, especially on those days when the island’s socked in by rain. And unlike most bowling alleys, you won’t find any tacky Formica lounge furniture here — just comfy sofas and even a place for an ice bucket. This is the Vineyard, after all. 13 Uncas Ave., Oak Bluffs, MA 02557, thebarnmv.com.