The Dog Bar/65 Main
Folks who come to this beloved local watering hole enjoy its outdoor patio and live music on weekends, and get an added bonus: They can walk into the adjoining restaurant, 65 Main, and pair the town's best burger with, say, a pint from Cape Ann Brewing Company. 65 Main St., Gloucester, MA dogbarcapeann.com.
Mirbeau Inn & Spa
Sipping wine on a blanket by the cranberry bogs is so much more relaxing than sitting in traffic on the Bourne Bridge, isn’t it? With three restaurants, easy access to two golf courses, and a spa, the South Shore’s version of a turreted French manor is a welcome respite before the Cape Cod fray. plymouth.mirbeau.com.
Arthur & Pat's
Arthur & Pat's, in the words of one sage local, "doesn't cater to the fancy-pants crowd." And indeed, the restaurant's worn exterior, wooden signs, and random rock soundtrack are unabashedly down-home. But if those details create a misperception of slapdash management, it's immediately cleared up by the glorious grub. We're talking fluffy pancakes with piles of berries; eggs Benedict with real crab; crispy, greaseless fried clams; bottomless cups of strong, hot coffee. After your meal, you may feel tempted to undo your belt—and given the easygoing air, it'd almost be acceptable to do so. 239 Ocean St., Marshfield, MA 2050, .
East Coast Grill & Raw Bar
Some Sunday mornings require a little time spent catching up with our favorite sister, bloody mary. And the best place to find her in these parts is at the East Coast Grill. The bloody mary bar here goes beyond the traditional to offer tipplers a choice of ingredients—citrus squeezes, herbs, spices, vegetables, and hot sauces—to add to their base of vodka and tomato juice. From there you can get to the next order of business: pulling up to a hearty plate of grilled sausages, tropical fruit pancakes, a fluffy avocado—black bean—salsa omelet, cornbread-crusted French toast, and the Sunday paper. 1271 Cambridge St., Cambridge, MA eastcoastgrill.net.
Helena's
Refreshingly chic silhouettes from Olian, Ripe, Paper Denim, and Inca Mama are enough to recommend Helena's. So are the racks of nonmaternity styles, which include tees by Johnny Was and trapeze tops by Tulle that can be repurposed by those with baby bumps (instantly dressing up, say, a pair of Gap Maternity stretch pants). What puts Helena's over the top, however, is its location, flanked by like-minded businesses Wild Child (see above) and Isis Maternity. In one fell swoop, moms-to-be can purchase a come-hither cocktail dress, sign up for a prenatal yoga class, and test-drive the stroller of the moment. 397 Massachusetts Ave., Arlington, MA 2474, .
The Giftsmith at Brookline Booksmith
What do you get the person who has everything? The answer: Something from this Brookline standout, which offers an eclectic array of present-worthy goods without an ounce of the stuffiness or predictability that plagues some of the other gift shops around. The large selection — which, thanks to a shop expansion, has grown exponentially over the past couple of years — no doubt includes something for everyone on your list: Clark + Hopkins artisanal pepper sauces, floral tea towels from Rifle Paper Co., and organic flower-growing kits from the Urban Agriculture Co. are just the tip of the gift-giving iceberg. 279 Harvard St., Brookline, MA 02446, brooklinebooksmith.com/browse-gifts.
Roux
This saucy bed-and-breakfast brings a splash of urban charm to the outermost Cape. Rooms are painted bright colors—no staid New England décor here. The food stands out, too: At breakfast, dig into treats like caramelized-onion-and-shiitake clafoutis; by night, mingle with eclectic guests over gratis wine and snacks. 210 Bradford St., Provincetown, MA 02633, rouxprovincetown.com.
BCYF Mirabella Pool
Each summer, city dwellers of all stripes—sunbathing nonnas, bronzed Adonises, giddy teens—flock to this urban oasis, making it one of the top people-watching spots in town. Not to mention one of the best bargains: A season pass costs a mere $20. In other words, a whole lot less than a trip to the Cape. 475 Commercial St., Boston, MA 02109, boston.gov/community-centers.
Mirbeau Inn & Spa
Why escape to the Cape for the weekend when you can unwind right in your own backyard? A weekend at this French-style manor can include slurping local oysters in the elegant on-site restaurant; indulging in a seaweed wrap at the 16,500-square-foot marquee spa; or simply relaxing by the fireplace in one of the cozy guest rooms. 35 Landmark Dr., Plymouth, MA 02360, plymouth.mirbeau.com.
Matt Murphy's
Some might scoff that Matt Murphy's perennially wins this award because, well, there aren't exactly Irish restaurants on every corner of this largely Irish town. That probably just means they haven't tasted the sausage, beans, and mashed potatoes with a hint of anise. Or sipped a perfect pint of Guinness while devouring fish and chips wrapped in the morning paper and accompanied by chunky, homemade ketchup. This Brookline Village hideaway is still an unadorned pub experience: good people (Jason Waddleton is one of the friendliest waiters in the Boston area), live seisiuns, or sessions of traditional Irish music, and food that's proud to call itself—dare we call it—Irish cuisine. 14 Harvard St., Brookline Village, MA mattmurphyspub.com.
December Thieves
When Lana Barakat decided to rethink her two Beacon Hill clothing-and-gift boutiques, she envisioned one store catering to home décor and another specializing in apparel and accessories. This divide-and-conquer strategy created more room for something Boston has been sorely lacking: high-end women’s footwear. Handcrafted by European and American designers, Barakat’s collection includes everything from metallic leather boots with an offset heel to cheetah-print loafers to sneakers with a velvet knot tie—perfect for navigating the cobblestones in style as you stroll up Charles to check out what other treasures await at the December Thieves home store. 51 Charles St., Boston, MA decemberthieves.com.
K. Kerkorian Weddings & Events
For more than a decade, we’ve watched Kristyn Kerkorian climb the ladder of local event planning, following along as she went from helming catering sales at the Colonnade Hotel to throwing parties for the Red Sox to launching her own wedding-planning firm in 2017. But it’s not just the BU alum’s prestigious pedigree — or the fact that she successfully executed eight COVID-era celebrations — that stands out to us. We’re equally taken by her calming, down-to-earth demeanor (a godsend for anxious brides and grooms) and undeniable gift for design, evident in each meticulous tablescape, escort-card display, and floral arrangement she helps envision. kkerkorianevents.com.
Lanes Bowl & Bistro
Not every day on the Cape can be sunny and 72 degrees (shocking, we know). When the weather's lousy, head to this multipurpose Mashpee complex, which opened this past winter. There's bowling, a variety of brick-oven pizzas, and a huge selection of New England brews. If the clouds part, hit the outdoor bar for bocce and live music. 9 Greene St., Mashpee, MA lanesbowlandbistro.com.
The Lobster Trap
The golden whole-belly fried clams are worth an impromptu day trip. Add in the Buzzards Bay and Back River vistas, the newly built bar stocked with local brews, and the overstuffed lobster roll served on buttery brioche (yes, brioche), and what you've got is, quite simply, one of the Cape's best casual seafood joints. 290 Shore Road, Bourne, MA 2532, lobstertrap.net.
White Elephant
Leave your car on the Cape. Nantucket’s iconic harborfront resort, and its well-appointed rooms, are no more than 10 minutes from anyplace you’d want to go: Young’s for bikes, the Juice Bar for ice cream, the beach and ferry, too. And if you’re looking for the best on-island massage, you don’t even have to leave the building. 50 Easton St., Nantucket, MA 02554, whiteelephanthotel.com.