Twelve rolls into our research, it seemed there was no escaping the Bun Situation: perfectly sweet meat marred by stale, soggy, cold, dinky, or too-hearty bread. Then we tried Belle Isle's roll. The buttery, griddle-crisped hot dog bun brilliantly holds its own against the tender tail, knuckle, and claw meat stuffed inside. One Main St., Winthrop, MA 2128, belleisleseafood.com.
What separates a smaller shop like American Provisions from a typical grocery store is its personality, from the handwritten signs suggesting wines to match each cheese to the handcarved bottle openers (crafted by a customer) for sale. And then there's the quality—grocers here carefully select all of the wines, olive oils, and cured meats on offer, so there's never a doubt that what you're bringing home is top-notch. 613 E. Broadway, South Boston, MA americanprovisions.com.
You can't call yourself a Bostonian until you've whiled away a Sunday morning nibbling a sticky bun at Flour. Regulars know to arrive early, before the hopeful hordes of sugar babies queue up for owner Joanne Chang's homemade Oreo cookies and berry bread pudding. Daily specials keep the counter lineup feeling fresh and for those after-dinner cravings, the South End location sells sweets until 9 p.m. 1595 Washington St., Boston, MA 2118, flourbakery.com.
Rolling furniture, textured wood-grain walls, Kobe burgers: Few spots in bookish Cambridge offer West Coast atmosphere like the Middlesex. What burst onto the scene with a flurry of red-roped parties last fall has slipped into the role of a comfortably hip nightspot frequented by artsy, playful types willing to form their own semicircles of gray faux-suede seats. 315 Massachusetts Ave., Cambridge, MA middlesexlounge.us/.
Do not order your own entrée here—the portions are enormous. Not in the mood to share? Well, don't say we didn't warn you. Heavy on garlic and olive oil and served still in the pan, Jimmy's pastas—linguine ;puttanesca, frutti del mare—are so good you might just eat the whole thing yourself. And that might hurt. Owner Jimmy Cippola doesn't take reservations, so expect to wait in line (even if you're Bill Clinton). 32 Kennebec Ave, Oak Bluffs, MA 2557, .
If you're investing in a three-months'-income heirloom, you want to work with someone who understands your vision—and your budget. Cynthia Pischdotchian ditched an engineering career to pursue her bejeweled dreams and bring precision to a timeless art form. Today she works out of a Gothically appointed Newbury Street studio, designing one-of-a-kind jewelry both modern and art deco-inspired. She'll also repurpose existing pieces, transforming Grandmother's diamond clip-ons into your newest wardrobe staple. 45 Newbury St., Boston, MA 02116, cynthiabritt.com.
Husband-and-wife team TJ and Hadley Douglas wrote the book (literally) on Progressive Shelving, their innovative, palate-broadening system that organizes wines by body rather than region or grape. The shop’s whole culture, really, is forward-thinking—see: its Clink Progressively education series, which hosted a virtual Juneteenth panel about issues facing Black winemakers, or its new Wine Studies Award for Students of Color, which will send ambitious oenophiles through wine school and connect them to paid internships. 303 Columbus Ave., Boston, MA 02116, theurbangrape.com.
It’s great fun whiling away a night with friends at this charmingly quirky Quincy newcomer. Sip on a well-curated lineup of craft beers and creative cocktails—such as the Count Dracula, smoky mezcal with Campari, raspberry cacao, and mole bitters—while sharing bites of chef Ashley Gaboriault’s globally inspired comfort food: say, a crispy fried-chicken sandwich topped with kimchi, and not-quite-mozzarella sticks stuffed with Cajun risotto. idlehourquincy.com.
The perpetually overwhelmed will find relief in the care of the errand-vanquishing team at Fini. Need your car detailed, your trip to Reykjavik arranged, and the cable guy dealt with, but have more pressing things eating up your day? Hoping to deck out your stoop with the neighborhood’s spookiest Halloween decorations but don’t have the time (or the eye for artificial cobwebs)? The pros at Fini, who’ve been doing this for 15 years now, have your back. 665 Beacon St., Boston, MA finiconcierge.com.
Rather than fill your Instagram feed with impossible-to-achieve abs and “detoxifying” weight-loss teas, why not fill it with news you can actually use in the gym or at home? Somerville gym Achieve Fitness’s social community of almost 500,000 followers get valuable advice on living a healthy lifestyle. And if you still have questions, they’ll answer them via their story for the benefit of all. 42 Merriam St., Somerville, MA achievefitnessboston.com.
Nineteenth-century urban planning may have transformed an ocean inlet into the Back Bay neighborhood, but about 150 years later, inspired chef Michael Serpa is still filling it with (fabulous) Mediterranean-inspired fish: sea bream, whole-roasted and sauced with parsley, mint, and oregano; swordfish with champagne mango and rose harissa; and salmon crudo augmenting towers of oysters and crab salad. A whip-smart wine list—including a nice pool of reds—pays equal attention to terroir. 50 Gloucester St., Boston, MA selectboston.com.
Boasting expertise in architecture and interiors, Stern McCafferty delivers a powerful design punch to every home it touches, breathing new life into old spaces and building from the ground up with equal aplomb. For proof, consider the 1905 Cambridge abode the firm remodeled with a new two-story atrium, wrapped in oversize windows and Cor-Ten steel. 46 Waltham St., Boston, MA 02118, sternmccafferty.com.
Just off the north side of Moody Street, Waltham’s restaurant row, sits this slice of Havana heaven. During the Cuban eatery’s bustling brunch, crêpes stuffed with slow-roasted pork are washed down with guava-mint mimosas and other hairs of particularly delightful dogs. The Spanish Colonial–inspired digs sport artsy Cuban movie posters, overhead mambo beats lend as much pep as the fresh-brewed Umbria coffee, and warm servers make this hacienda a home. 663 Main St., Waltham, MA 02451, gustazo-cubancafe.com.
This basement-level bakery is part of Frank DePasquale's North End culinary empire, and yet somehow everything about it screams old-world charm. From the tiny space, bakers churn out umami-rich olive-studded loaves and prosciutto-stuffed baguettes that are served at DePasquale's restaurants and, if you're lucky, with your next plate of home-cooked pasta. 241 Hanover St., Boston, MA 02113, briccopanetteria.com.
After a sweeping $50 million upgrade, Hotel Commonwealth is in a league of its own. In addition to 96 sleek new guest rooms, the Kenmore Square gem now boasts a Red Sox-themed luxury suite and private event space overlooking Fenway Park. Add in three of the city's hottest dining and drinking spots—including Eastern Standard, which also serves up gourmet room service—and you have a home run. 500 Commonwealth Ave., Boston, MA 02215, hotelcommonwealth.com.