The Madonna Queen of the Universe Shrine
It's strange to refer to a 35-foot-tall sculpture as a "hidden" gem, but this bronze-and-copper marvel (originally created by Italian-Jewish sculptor Arrigo Minerbi in tribute to the Catholic order that harbored him during the Holocaust) seems to inhabit a world of its own from its hillside Orient Heights perch. Those who make the pilgrimage will be rewarded with breathtaking city views—and handy proximity to Belle Isle for an après-awe lobster roll. 150 Orient Ave., East Boston, MA 02128, .
Trina's Starlite Lounge
The H-word may be ill defined—something about young, vaguely cool people having fun in a place where you're not. Unless you happen to be at Trina's. Equal parts dive bar, cocktail lounge, diner, and comfort-food joint, it has the type of lived-in authenticity the you-know-whats can't resist. 3 Beacon St., Somerville, MA 02143, trinastarlitelounge.com.
Audubon Circle
Boston is full of places to grab a beer, a greasy burger, or wings on the cheap. But for a brew and tasty bites that won't cause a morning-after food hangover, sidle up to a barstool—or cozy banquette—at Audubon Circle. The crispy duck salad with sage vinaigrette, the pork schnitzel with pickled onion, the chévre cheesecake—this is the kind of inspired fare that convinces you to sit back and order another Fisherman's Ale...and another. 838 Beacon St., Boston, MA 2115, audubocircle.com.
Oleana
Oleana's candelit garden feels a world away from the bustle of Cambridge. Tucked at a table under the vine-laden trellis, you could easily be in the Greek isles, Turkey, or Morocco. Ana Sortun's eclectic Mediterranean food—don't miss the fried haloumi and the flambéed asparagus—won't necessarily help you pin down a particular region. But wherever the experience takes you, we're sure you won't want to leave. 134 Hampshire St., Cambridge, MA oleanarestaurant.com.
Mistral
Unlike at many chichi restaurants, chef-owner Jamie Mammano's entire critically acclaimed menu is served at Mistral's bar until quite late, freeing barflies to sidle up to that sexy someone without having to forgo their real beloveds: the beef tenderloin pizza with mashed potato and white truffle oil, or the glistening, Asian-spiced tuna tartare. 223 Columbus Ave., Boston, MA mistralbistro.com.
88 Supermarket
This is where shoppers from both the 'burbs and Chinatown buy their lime leaves, shrimp balls, bok choy, and soy "pork," in a Star Market-sized store crammed with tidy isles of Asian goods. Bilingual signs and a friendly staff make 88 accessible to the uninitiated; 10 minutes of wandering, and you'll be ready to fire up the wok. No wok? Buy it here. 50 Herald St., Boston, MA .
Charlie's Kitchen
The contagious only-in-a-karaoke-bar camaraderie at Charlie's has crooners of all ages forgoing television remotes in favor of their own version of American Idol. During the always entertaining Tuesday night ham-fests, gleefully off-key patrons cover everything from frizzy '80s power ballads such as "Don't Stop Believin'' to campy oldies like Peggy Lee's "Fever." There's no prize for the best cover at this diner-bar; thankfully, there are no incoherent ramblings from Paula Abdul, either. 10 Eliot St., Cambridge, MA 2138, charlieskitchen.com.
The Wauwinet
This is the place to truly get away from it all. Located on the idyllic (and blissfully quiet) northern side of Nantucket, here you can indulge in an Atlantic seaweed wrap or wildflower-and-herb-infusedmassage at the spa, get refined with port and cheese in the library, explore the quaint town of 'Sconset on bikes, or simply relax on the hotel's private beaches. And if you're for some reason missing the crush of day-tripping tourists, you can hop the complimentary water taxi to downtown Nantucket. 120 Wauwinet Road, Nantucket, MA 2584, wauwinet.com.
Truro Beach
This gorgeously untarnished world of sweeping dunes and fresh Atlantic air is about as idyllic as nature gets. That may seem to be true of many Cape shorelines, but this one stands out from others for its spectacular and endless stretches of perfectly undisturbed white sand. With nary a touch of human architecture for miles, this slip of coast also provides a view of the sunrise that approaches the sublime. Rte. 6, Truro, MA .
Silhouette Cocktail Lounge
The recipe for a superlative dive bar is simple: cheap drinks, good music, and a feeling of belonging for every sad sap who saunters in. The Silhouette Lounge delivers all of these ingredients, with a few grubby-but-great enhancements: dartboards, free popcorn, and stools so tattered they look like they've endured a natural disaster. If you're looking for panache, look elsewhere. If you're looking to drink away the blues and talk to strangers, sidle up to the bar at 'the Sil.' 200 Brighton Ave., Allston, MA 2134, .
Soul Cake
COURTESY OF SOUL CAKE If you need another excuse to get married, look no further than Soul Cake’s Instagram. A casual scroll reveals masterpiece after masterpiece, thanks to pastry chef Gayoung Kim’s myriad textures and toppings: monstera leaf plastered to a pink-marble surface, blue watercolor fondant interrupted by flashes of gold, and sugar peonies placed by the bucketful. But of course, looks alone do not a wedding cake make—not only are Kim’s creations gorgeous, they’re also can’t-put-it-down good. Why double-tap when you could order one IRL? Woburn, MA 01801, soulcakeshop.com.
The Porches Inn
Fleeing the city seems an idyllic notion, until you find yourself bunking down among doily-strewn antiques and overpowering potpourri at a B&B advertising bucolic "charm." A rare exception is the Porches Inn, set in a row of renovated multi-colored Victorians in North Adams. Its 50-odd rooms are done up in modern décor and feature high-speed Internet and smart service. Out back are a pool and sauna; out front, the stylish Mass MoCA complex. Those still craving a little countrification can kick back in one of the dozens of rocking chairs that sit on the inn's verandas. 231 River St., North Adams, MA 2147, porches.com.
Artepicure
Armed with the diplomacy and precision that come only from years of European-training—and a tricked-out kitchen sporting the latest sous vide accoutrements—chef Mark DesLauriers helps novices and gourmets alike sidle up to the stove with confidence. New this year: couples’ cooking classes ($170 per duo) on Friday evenings. Woo that special someone over a meal of roast duck breast with warm shallot dressing, red-wine-braised duck leg and pan-seared foie gras with vegetables roasted in duck fat, and chocolate pot de crème. One Fitchburg St., Somerville, MA 2143, artepicure.com.
Limelight
There are two kinds of karaoke-goers: traditionalists "just in it for the music" and Axl-style mike hogs. Limelight suits both. More than 5,000 songs provide variety, and an always appreciative, largely tipsy audience supplies the right amount of Idol-esque egging on. (Those suffering from stage fright can "Sweet Child o' Mine" it up in private studios modeled on clubs in Tokyo, where subtitled singing is practically a professional sport.) The food may be greasy and the drinks can be weak, but never having to share stage time with "Sister Christian"-loving frat boys is more than a fair exchange. 204 Tremont St., Boston, MA limelightboston.com.
Water Garden, Larz Anderson Park
Visiting this idyllic, sheltered enclave is something like stepping into a Georges Seurat painting. It wouldn't be surprising to see ladies with parasols strolling around the pond, seeking shade under the willows, or daydreaming on the footbridge. With such out-and-out tranquility just minutes from the crowds of the city, Larz Anderson Park is an ideal spot to relax, stretch out on the grass, and spread out a feast. There are even grills and tables. At the end of the day, when the sunset reflects off the water and slides through the trees, you'll feel as though you've entered an entirely different era. Newton St., Brookline, MA .