21 Federal
Much as we enjoy fighting for a bar stool with sunburned tourists and libidinous and over-lubricated college students, we do sometimes crave a slightly more civilized scene. 21 Federal, inside a classic Nantucket 1847 Greek Revival building, features a sophisticated downstairs bar and another cozy one upstairs. In-the-know Nantucketers congregate here for masterfully poured drinks; an award-winning wine list; good-looking, genial bartenders; and a crowd that knows how to have a stylish sort of fun. 21 Federal St., Boston, MA 21federal.com.
New Art Center
In Newton's New Art Center classes, weekend collectors can ponder the age-old question—What Is Art?—then study the intriguing works showcased in the late-1800s Universalist church. Should you find something lacking in any of the canvases, prints, or sculptures, you can improve the view by organizing your own exhibitions: The guest curatorial program lets interested parties help decide what goes on display. 61 Washington Park, Newtonville, MA 2460, newartcenter.org.
Coolidge Corner Theatre
The sad fact is that big corporate multiplexes show big corporate movies. Truly, you are what you screen. Which makes Brookline's Coolidge Corner Theatre an art-house jewel among the plastic giants. This 75-year-old, not-for-profit space boasts a classy schedule of documentary, international, and independent movies. The Coolidge also keeps a hand in the community by hosting readings, live performances, and film festivals. 290 Harvard St., Brookline, MA coolidge.org.
Boston Bowl
Forty-four lanes. Metal bumpers. Affordable prices. A kingpin's dream—and now a bowling reality. The pro shop (yes, this bowling alley has a pro shop) stocks enough balls, bags, and shoes to satisfy amateurs and experts alike. The sprawling entertainment complex also has 12 pool tables, a video-game arcade, and a full service bar, and is open 24/7 (save for Christmas Eve). 820 Morrissey Blvd., Dorchester, MA bostonbowl.com.
Avalon Ballroom
In Boston, the "mists of Avalon" refer not to the foggy shores hiding King Arthur's final resting place, but the dry ice curling around the feet of the club's performers. Whether your taste is for Aimee Mann or Franz Ferdinand, the light show and acoustics in this cavernous ballroom are fantastic—as is its size, which is midway between nosebleed big and sell-out small. 15 Lansdowne St., Boston, MA .
Club Hollywood Boston at Ekco Lounge
Butches and femmes hoist their bottles together here on Saturday nights, when this Chinatown karaoke lounge and dance club becomes the closest thing lesbians have to a downtown clubhouse. Two levels of dance floors offer ample space for the mostly young and urban crowd to get down to electro, house, and hip-hop. Once a month, grrls slip on suits and fedoras (and boys and butches, dresses) for "drag karaoke." 41 Essex St., Boston, MA .
Joey's
Herren of Steve's Ice Cream has won this award. But Steve has sold Steve's to Joey Crugnale, who owns Joey's. And Joey is putting a bit more effort into Joey's than he is into Steve's (also, the lines at Joey's are shorter). Very smooth and light ice cream (Joey says he uses a "fast-whip" process). A make-your-own sundae bar, and chocolate-cinnamon-raisin to boot. 1161 Broadway, Somerville, MA .
Union Street Inn
Though there's a flurry of hotel action on the island (the renovated retro-chic Chapman House, Lark Hotels' sleek new 76 Main), the Union Street Inn continues to define the gold standard for boutique lodging on Nantucket. In addition to Matouk duvets, free WiFi, and made-to-order breakfasts, this stylish inn now boasts freshly decorated rooms and a revamped patio and outdoor space. 7 Union St., Nantucket, MA unioninn.com.
Artcliff Diner
A Vineyard Haven mainstay, the Artcliff Diner is celebrating its 70th anniversary this year. Try the popular almond-crusted French toast; get indulgent with the Green Monster, which loads scrambled eggs, cheese, avocado, and spinach on top of tortilla chips; or go big with the hearty Irish breakfast. Brunch is served daily, and staffers never allow your coffee cup to dip below half full. 39 Beach Rd., Vineyard Haven, MA .
Ocean Edge Resort & Golf Club
At a resort, it's easy to get lost in the shuffle. But not here, where a personal concierge caters to your whims. That's a welcome addition to the Ocean Edge, which has undergone $50 million in renovations to its villas, mansion rooms, and restaurants. So now you get the coddling you'd expect from a boutique hotel, plus smart touches like a fridge stocked with ice cream and all the fixin's for s'mores if you book a villa. 2907 Main St., Brewster, MA oceanedge.com.
Mr. Sid
Is there anything out there more wonderfully old-school than Mr. Sid? The parquet floors; the in-house bar, hair salon, and billiards table; the genteel service—it all feels reminiscent of another time. The clothing itself is as current as it gets, however, with sharp styles from the likes of Ermenegildo Zegna, Brioni, and Scott James, plus a collection of high-end footwear. Men who prefer to go bespoke will appreciate the "made-to-measure" program, which offers custom clothing from a selection of the store's designers. 1211 Centre St., Newton Centre, MA mrsid.com.
5 Corners Kitchen
This French-inspired restaurant is not what you'd expect to find in a quaint seaside town. The feel is trendy but unpretentious; the space is open and airy; and the wine list rivals those you might see in Boston. The food itself is a wonderfully eclectic mix of country cooking and local seafood, with everything from escargots and oysters to bacon cheeseburgers and house-made squid-ink spaghettini represented on the menu. 2 School St., Marblehead, MA 5cornerskitchen.com.
Surroundings
There was a time when anyone on the South Shore interested in fine furnishings had to make the trek up to Boston. But there's no need now. At this lovely one-stop decor shop, you'll find outstanding American lines like Oly and Hickory Chair, French furnishings made by Grange, and accessories by the Vermont-based Simon Pearce. Overwhelmed? Seek out the in-house designer, Bill Barr, who offers complete interiors service. 81 1/2 Fairhaven Rd., Mattapoisett, MA surroundingshome.com.
Bundle of Hope
Clothing, accessories, furniture, and more: Bundle of Hope offers it all, with a delightful variety and a warm personal touch. Leave your kids in the play area while you peruse the high-quality offerings for infants and toddlers; have them try on clothes in the charmingly handpainted dressing room; even let them bring friends along for a tea party. The staff here is more than accommodating, wrapping gifts, making shipments, and setting up baby registries. 146 Front St., Scituate, MA bundleofhope.net.
Wilson Farm
Since the 19th century, the sprawling barn at Wilson Farm has proffered more than 100 varieties of the grower's own fruit, vegetables, herbs, and flowers; fresh-baked breads and pastries; locally made cheeses; and house-made pastas, soups, salads, and more. It's a one-stop shop in the dead of winter, the height of summer, and any time in between. 10 Pleasant St., Lexington, MA 2421, wilsonfarm.com.