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 .
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, .
"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.
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.
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.
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.
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 .
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/.
Best: Lauren Rauschenbach, aka Mrs. Henri Rauschenbach. Indicted on charges of shilling for jailed financier Carmen Elio, the ape Cod senator gallantly laid the blame for his predicament on his wife's expensive tastes. "My wife was, you know, prodding me a bit," Rauschenbach said. "My wife comes from a family with dollars. You know, Lauren's the only one of the daughters that's married to a guy who's making 30 beans a year." Even Better: Teresa Heinz, aka Mrs. John Kerry. See Best Quote.
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
This companion to the long-running National Public Radio show extends the lunacy that you hear on the air every Saturday. The centerpiece of Click and Clack's home page is "Time Kill Central," which includes features like the Hate Mail Generator (which can churn out letters to lousy mechanics) and the Daily Didactic Diversion, a trivia contest. You can also print out your own traffic tickets—like a "Blue Hair Offense" for people who can't see over the wheel and rive 35 mph in a 65 mph zone.
A stalwart in Boston since 1959, the gallery managed to not just survive but thrive this past year thanks to live and online shows that brought legends and locals together. See: works from modern-art icon Josef Albers, contemporary star Jenny Holzer, and Mike Glier, whose paintings are inspired by birdsong in the Public Garden. The gallery even hosted its annual AIDS Benefit Auction around the holidays virtually, with all proceeds going to the Dimock Center’s pediatric and family programs 10 Newbury St., Back Bay, MA 02116, krakowwitkingallery.com.
Street art in Boston got a thrilling new addition this past May with Quiñonez’s Look to Your Elders, a vibrant painting on the side of Grove Hall pot shop Pure Oasis depicting a woman and young man surrounded by Caribbean plants and Indigenous patterns. A heartfelt nod to Boston’s generations of Caribbean and Afro-Latino residents, the piece is more than just a mural: It’s a stop-you-in-your-tracks work of art that has turned the spot into a must-visit. 430 Blue Hill Ave., Dorchester, MA 02121, marka27.com.
There's always something that catches our eye at this contemporary gallery inside the Back Bay's Church of the Covenant. Now celebrating its 40th year, Naga prefers to showcase work by locals, such as Peter Vanderwarker's stunning landscape photography and Gerry Bergstein's mixed-media agglomerations on panels. The other thing the artists all have in common? They hit the sweet spot of challenging the mind while creating images that you can immerse yourself in for years. 67 Newbury St., Boston, MA 02116, gallerynaga.com.
Every time we walk into this avant-garde Harrison Avenue gallery, we fall in love with yet another up-and-coming video artist, painter, or sculptor. 450 Harrison Ave., Boston, MA 02118, carrollandsons.net.