Courtside
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.
Yolqueria
Whatever your mark of a great brunch is—gooey cinnamon rolls, killer libations, or an outstanding eggs Benny—this Commercial Street gem delivers. With a background in sourcing organic ingredients for Whole Foods, chef-owner Brandon Quesnell brings the same fresh-and-local commitment to Yolqueria’s menu. The food is worth the wait and the patio is worthy of a cocktail. Paloma picantes and cowboy carnitas, anyone? yolqueria.com.
Yellow Door Taqueria
The ingredient combos here are a bit, shall we say, extra: On one recent visit, campechano tacos, a street-food staple, featured Tecate-beer-marinated steak; chorizo, red corn, and bacon hash; cranberry-onion jam; herb goat cheese; and toasted pepitas. Yet the flavors don’t fight, they play—and how!—when loaded onto delicately doughy, house-made tortillas. 2297 Dorchester Ave., Dorchester, MA yellowdoortaqueria.com.
Violet Furxhi, Mario Russo
It’s a good bet any well-heeled lady in town boastfully swinging her locks around is rocking extensions from this talented stylist. Specializing in long-lasting Keratin bonds, Furxhi makes what can be a timely process enjoyable, interspersing lively conversation with details about where she’s placing your new tresses and why. 9 Newbury St., Boston, mariorusso.com.
Viola Lovely
Effortless and immaculate: Those are the adjectives we’d use to describe this South End boutique’s offerings—and, after a trip here, your everyday style. There’s the expert tailoring from Lemaire, whose designs are inspired by the streets of Paris. The soft, California-chic fabrics of Raquel Allegra. And Alumnae’s comfortable yet trendy slip-on leather mules. In fact, every last piece here feels practical enough for a run to the drugstore or a quick flight to Palm Beach, but lovely enough to take you anywhere in the world. 1409 Washington St., Boston, MA violalovely.com.
Ventuno
Think Nantucket’s fresh catch couldn’t possibly get any fresher? Try pairing it with house-made pappardelle or strozzapreti at Ventuno. Consistently excellent since it opened its doors in 2011, this Italian-inspired eatery continues to wow with hearty from-the-sea entrées such as grilled local dayboat scallops and shrimp with black-truffle salsa. And now with the 2019 opening of sister restaurant Pizzeria Gemelle, the team stands poised to dominate the local pizza game, too. ventunorestaurant.com.
Treatment Training Wellness
Who says massages are just for relaxation? Whether you’re feeling a little sore after a particularly hard-core workout or just coping with everyday aches and pains, the talented technicians at this South End wellness center are here to help with a variety of massage techniques tailored to your needs. Calming music, hot-towel compresses for the face, and a beautiful Himalayan salt lamp all add to the ambiance in the treatment room. 142 Berkeley St., Boston, MA treatmenttrainingwellness.com.
The Salty Pig
Chef Michael Bergin certainly whips up a mean pâté en croute and beautifully brined ham, but it’s not just Salty’s eponymous porkers that elevate the almost entirely house-made charcuterie. Bergin knows his way around other animals, including chicken (don’t miss the liver terrine with Madeira gelée!). The meats are perfect for pairing with a top-notch selection of funky cheeses. 130 Dartmouth St., Boston, MA thesaltypig.com.
The Proprietors
Flavor and creativity go hand in hand at this island eatery, where dishes such as mushroom-pâté-slathered focaccia and cheesy fried-green tomatoes set the tone for the most innovative brunch menu in town. Top it off with one or two of the Proprietors’ signature drinks (a sparkling rosé cocktail with vodka, passion fruit, and vanilla, perhaps?), and start your Sunday Funday off right. proprietorsnantucket.com.
The Haven
In Boston’s sea of rowdy, singles-filled Irish bars, this rare Scottish gastropub stands out as unique, friendly, and approachable—just like the ideal date. As its name suggests, the restaurant is an intimate place to get cozy by candlelight with your Tinder match over an extensive, icebreaker-friendly scotch list organized by region, as well as hard-to-find specialties like haggis and Scotland-born deep-fried Mars bars. With so much to talk about, conversation will flow as easily as the Belhaven beer on draft 2 Perkins St., Jamaica Plain, MA thehavenjp.com.
The Coonamessett Inn
After a top-to-bottom 2018 renovation by Lark Hotels brought breezy “modern coastal” décor and integrated technology to every guest room, this old-school Falmouth inn is ready to welcome a new generation of guests. Sip a cocktail on the lushly furnished lakeside patio, groove to live tunes at the on-site music venue, or simply stretch out on the plush king bed after a long day in the sun: Your long-weekend wish is the Coonamessett’s command. thecoonamessett.com.
The Boston Shaker
This Davis Square establishment holds all the accoutrements you need to make one killer cocktail (or six). Swizzle sticks? More than you could swizzle in a lifetime. Recipe books? Your options rival Barnes & Noble. Shark-shaped tiki mugs? Also available in whale variety. And don’t forget about the lauded bitters tasting bar, from which staffers are more than happy to provide samples. Happy drinking, indeed. 69 Holland St., Somerville, MA thebostonshaker.com.
Tasting Counter
Unsurprisingly, this 20-seat setup tucked inside a Somerville warehouse excels at the format for which it’s named. Chef Peter Ungár continually catches us off-guard with ingenious touches prepared inches away—think: pads of mackerel brined in fermented daikon broth and crowned with turnip kimchi and herbs from the restaurant’s living wall. Also unexpected: the recent launch of TC Market (a line of house-made condiments), not to mention news that an à la carte Counter will land at a local food hall this year. 14 Tyler St. , Somerville, MA tastingcounter.com.
SRV
At this South End hot spot inspired by Venetian bacaros, chefs Kevin O’Donnell and Michael Lombardi deliver a singular study in layered flavors and textures: See fried artichoke electrified with tonnato sauce and capers, and the house-made pillows of fontina-stuffed scarpinocc dressed with crunchy almonds. Creative cicchetti shoot in rapid-fire from the kitchen, each dreamier than the last, each designed to pair perfectly with cocktails on the charming patio. 569 Columbus Ave., Boston, MA srvboston.com.
Social Boston Sports
Want to show off your three-pointer, or revel in the schoolyard-era glories of dodgeball? Social Boston Sports has been helping Bostonians tap into their inner jock in nearly every neighborhood in the city since 2010. And don’t worry if you’re not a natural-born athlete: There’s always SBS’s cornhole league. socialbostonsports.com.