Bernard Toale
Toale wins this year not just for his keen eye but for his moxie. When all five gallery owners at 11 Newbury Street were forced to leave in April because of an outrageous rent hike, all but Toale went across the street to 14 Newbury Street. He boldly chose to move to the South End, adding his adventurous style to a handful of galleries that are trying to turn this area into Boston's version of SoHo. 450 Harrison Ave., Boston, MA .
Micro Plant Studio
Invite a little life into your workspace with help from this South Boston shop, which carries and delivers all things leafy and green (bamboo palm, burro’s tail, Venus flytraps), plus fun pots to display them in. Even better: You can brighten two households with Micro’s “buy to give” initiative, which lets you sponsor a succulent to send to a local essential worker. 365 W. Broadway, Boston, MA 02127, microplantstudio.com.
Tupelo
The reserved atmosphere may be more Cambridge than New Orleans, but Tupelo's southern flavors are right on. Owners Mike Walker and Renee McLeod serve authentic comfort-food classics like creamy pimiento cheese (the caviar of the South), hearty gumbo, and crunchy fried crawfish tails. The crown jewel? Alligator prepped the way God intended: coated in buttermilk batter, hot sauce, and Cajun spices, and piled on a bed of creamy cheddar grits. 1193 Cambridge St., Cambridge, MA 02139, tupelo02139.com.
Louis Boston
Hey, you—in the cargo pants and Chucks. Casualwear is fine for casual moments, but your big client meeting, your anniversary dinner, and for-the-love-of-Christ your best friend's wedding call for something far spiffier. At Louis Boston (go on, it's not as scary as it looks), made-to-measure and ready-to-wear suits from Brioni, Kiton, and Dries Van Noten make dressing up a cinch. Even easier-going ensembles by such names as Neil Barrett and Annapuna put postcollege khakis to shame. 60 Northern Ave., Boston, MA 2110, louisboston.com.
Stel's
With worthy new openings like Flock, Uncle Pete's, and Suneri, this category is getting crowded. But Stel's owners Tina Burgos, Dave Nauyokas, and Jon Callahan keep packing their Newbury digs with an independent-minded collection that's fashion-forward without being too trendy. Personalized service and a unique selection of Rachel Comey, Gary Graham, Tom Scott, and Cardigan threads earn the shop mail-order customers from around the country, many celebrities among them. 334 Newbury St., Boston, MA 2115, .
The Boston Harbor Hotel
This 230-room palace has bragging rights locked up, thanks to its flawless waterfront view from Rowes Wharf. The whole scene—billowing sails, bright blue slices of sky and harbor, and a breathtaking panorama of the cityscape—is straight out of a postcard fantasy (and will even make you forget the chaos of Big Dig construction out front). The interior views aren't too shabby, either: luxuries including a plush spa, gracious suites, experienced concierges, and a terrific restaurant. 70 Rowes Wharf, Boston, MA bhh.com.
Grill 23 & Bar
Let the newcomers show off their newfangled steakhouse specialties; people who really love steak will always return to Boston's exemplar of the genre. Here you'll find dry-aged, bone-in chops and tenderloins that drip with flavor in each juicy bite. The vibe—gold rails, leather banquettes, white-coated waiters—is classic without seeming clubby. 161 Berkeley St., Boston, MA 2116, grill23.com.
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.
Via Mare
Jetting off to the Italian Riviera may not be in the cards just yet, but brunch at Via Mare — Italian for “by the sea” — is nearly as exciting. Showcasing honey-hued shiplap walls, cozy sofa seating, and vintage coastal décor, the restaurant offers American classics dressed up with Italian gusto: Take, for example, the deviled-egg starter prepared with daily-changing ingredients like pesto and pickled shallot, or the breakfast sandwich on a house-made kaiser roll topped with seared mortadella. Sail away at the end of the meal with the budino topped with toffee caramel and decorated with lightly torched triangles of meringue. 17 Broad St., Nantucket, MA 02554, viamarenantucket.com.
Doggieday
Need someone to look after your critters? While you're away, DoggieDay will walk Spot four times a day, clean Fifi's litter box, grab your mail, water your plants, inject your diabetic gerbil with insulin, and taxi Dirk the boa constrictor to the vet—all for a competitive fee. Unlike most services, DoggieDay covers almost all of Greater Boston, and is registered with Pet Sitters International. Future services in the works include dog training at home while you're at work and massage therapy (for your pets, not you). 295 Devonshire St., Boston, MA .
Paws to Consider
Even the bad pun can't keep us away from a pet service this efficient, loving, and dependable. Owner Scot Jones clearly cares for his four-legged commissions with the same passion he does his business, keeping an organized staff of five fully briefed in everything from pet first aid to the fundamentals of TLC. Whether it's cat sitting (litter changes included) or dog walking (rain or shine, 365 days a year), Paws to Consider makes as many visits as you want—and will even care for plants, collect mail, and make veterinarian or grooming runs. 24 Halifax St., Jamaica Plain, MA pawstoconsider.com.
Warren Asnes, Peace of Mind
A couple of years ago, Warren Asnes was a bureaucrat in the state's Office of Human Services. But last year, he decided to become a full-time housewatcher—a move inspired by his musing whether he or the other occupant of a two-family home was responsible for filling the house's boiler. Today he'll tend to the care and feeding of your home while you're away by walking your dog, watering your plants, forwarding your mail, even stocking your refrigerator for your return—all for seven bucks a trip. He comes with references, is fully insured, and is not put off by large numbers of pets: he once baby-sat 34 cats. Newton, MA