Regatta Inn
Thanks to a recent renovation, this centrally located Federal-style building has all of the history but none of the outdated décor. The inn's eight guest rooms boast luxe amenities, including Frette and Matouk linens and marble bathrooms. But perhaps the most compelling reason to stay is new innkeeper Lyn Francis's already-legendary breakfast of such staples as warm muffins and house-made granola. 78 Centre St., Nantucket, MA 02554, theregattainn.com.
Millie's
With strong drinks, panoramic ocean views, and a shoes-optional vibe, Millie's has all the makings of the perfect island beach bar. Here longtime locals happily commingle with the weekenders, thanks to plenty of barstools and an excellent rum-based house drink, the Madaket Mystery. Top-notch nibbles such as local fish tacos and fried clam po' boys encourage the revelry to continue long after that pretty sunset fades into memory. 326 Madaket Rd., Nantucket, MA 02382, milliesnantucket.com.
C Salt Wine Bar & Grille
In the land of beach bars and clam shacks, C Salt is a breath of fresh (salt) air. This tiny house looks more like a ski chalet than an oyster bar, but the locals who pack the dining room don't let that distract them. From an open kitchen, chef Jonathan Philips turns out root-beer-braised short ribs and a spicy tuna tartar tostada with avocado-cilantro aioli worth bottling. The clincher: the coldest, stiffest martini we've ever enjoyed. 75 Davis Straits, Falmouth, MA 02540, csaltfalmouth.com.
The Citgo Sign
Photograph by Mariel Tenney Hitching your sense of self to a big ol' oil company's logo might seem like a manifestation of corporate personhood, but the sign advertising the Venezuelan energy outfit Citgo, which towers over Kenmore Square, provides a quick way for people to situate themselves in Boston. Not only does its design make it one of those rare neon signs that looks good when the sun's shining, Fenway Park and its Instagram-ready tableaux are just a stroll away. Kenmore Square, Boston, MA 02215, .
The Sinclair
With top-notch bookings (courtesy of promoters Bowery Boston) and the city's best-designed concert experience, the Sinclair is the House of Blues, only more intimate; the Paradise, without poles obstructing the sightlines; the Middle East downstairs, with a balcony and style. And no other venue can sustain this level of buzz, with surprises like Converse's weeklong run headlined by Passion Pit, Slayer, the Replacements, and Chance the Rapper this past spring. 52 Church St., Cambridge, MA 02138, sinclaircambridge.com.
Courtside
Photograph courtesy of Istockphoto Karaoke at this Cambridge dive can be a Darwinian proposition—despite Courtside's rec-room feel, every singer's out for herself on Thursdays, Fridays, and Saturdays. But that's part of the fun. Lubricated by cheap pitchers of beer and egged on by crowds that only get feistier as the night wears on, singers who take Courtside's "stage" revel in their four-ish minutes of glory, leaving the next person itching to try to win over the room with even larger antics. 291 Cambridge St., Cambridge, MA 02141, courtsidekaraoke.com.
Pawsh Dog Boutique & Salon
Cue the puparazzi! The expert groomers at this newly expanded Back Bay salon have styled Tom and Gisele’s furry family members, among other celeb canines, and they’ll clean and clip your pooch with the same level of care and attention to detail. Want to make Fido feel even more special? Pick up a few organic treats and toys in the on-site boutique while he gets spruced up. 31 Gloucester St., Boston, 02115, pawshboston.com.
Shepard
A stock of syrups, infusions, and other mixology gimmicks is unnecessary when your way with the classics is so sound. Such is the case at Shepard, where bar manager Nic Mansur mixes one mean Manhattan, among other elegant, restrained cocktails. Factor in the Francophile wine list and eclectic array of apéritifs, and you’ll want to spend the entire evening at the bar, away from the dining room din. One Shepard St., Cambridge, MA 02138, shepardcooks.com.
Red’s Best
Sure, you know your halibut is local, but do you know which fisherman, vessel, and port it came from? Or exactly how it was caught? Thanks to its network of regional anglers—and some cutting-edge tracking technology—Red’s Best can label every pristine piece of monkfish, skate wing, and hake in its case with such precision. Boston Public Market, 100 Hanover St., Boston, MA 02108, redsbest.com.
Buk Kyung
Homestyle hospitality is the draw at this Union Square mainstay, with gratis accompaniments like crunchy daikon, spicy kimchi, and pickled cucumbers complementing huge platters of ddukbokki, tender kalbi, and bibimbap. The restaurant also serves up Chinese-influenced house specialties (Buk Kyung means “Beijing” in Korean) not found at most other local spots, including jajangmyeon, chewy noodles coated in a thick and savory sauce. 9A Union Square, Somerville, MA 02143, bukkyungrestaurant.com.
Todd Maul, Cafe Artscience
From left: Karen Akunowicz, Katie Gilarde, Todd Maul, Meghan Thompson, and Tiffani Faison. / Photograph by Jason Grow, styling by Laura Dillon/Team Imagine a boozy amuse-bouche of scotch, inhaled as a plume of smoke. Or a mai tai that actually grows stronger thanks to rum-soaked banana leaves lining the walls of your tiki glass. Armed with gadgets like a centrifuge and Le Whaf, an invention that turns liquids into vapors, Todd Maul has created a cocktail program that’s as much kitchen chemistry as it is adult playground. 650 E. Kendall St., Cambridge, MA 02142, cafeartscience.com.
Sonsie
We know what you’re thinking: With all the seafood joints in Boston, you landed on Sonsie? Stifle your preconceptions for a moment, because when it comes to the classics, it’s all about execution. And that’s where this al fresco hot spot outdoes its competition: with a just-viscous-enough lunch-menu chowder showcasing plump clams and tender Yukon Gold cubes. And, yeah, the people-watching is pretty great. 327 Newbury St., Boston, MA 02115, sonsieboston.com.
Giulia
This lovable Porter Square trattoria specializes in subtlety, right down to its dim lighting, intimate ambiance, and exposed-brick walls. The straightforward dishes—delicate house-made gelato and hand-rolled pastas with simple sauces, almost all available with a dusting of shaved truffles—are best accompanied by one of the restaurant’s dozens of regional wines. 1682 Massachusetts Ave., Cambridge, MA 02138, giuliarestaurant.com.
Bantam
When Dana Masterpolo and Michelle da Silva introduced Wunderkind to Boston drinkers four years ago, the dry, fruit-forward drink helped usher in a New England cider revival. These days, the small but mighty outfit reliably offers at least seven different ferments on draft every weekend in its taproom, and three year-round blends are available in cans, including in new markets such as New York and Chicago. 40 Merriam St., Somerville, MA 02143, bantamcider.com.
The Bancroft
We’ll take ours with extra onion strings: a leaning tower of burgers from the Bancroft. / Photograph by Jim Brueckner, styling by Monica Mariano/Ennis It’s worth a trip to the ’burbs for chef Mario Capone’s towering lunchtime burger, a study in pure, beefy excess. Made with a high percentage of prime chuck, each juicy 8-ounce patty is sandwiched between a just-squishy-enough brioche bun and complemented by crispy fried onion strings, house-made ketchup, and a mantle of molten Vermont cave-aged cheddar. 15 3rd Ave., Burlington, MA 01803, the-bancroft.com.