Foundation Lounge
We've never understood the phrase "so hip it hurts." A bikini wax—now that hurts. But a night spent amid lacquered wood and PYTs, drinking mango martinis while dipping into small plates of Japanese zensai and nodding along to high-rent house DJs? There's nothing painful about that. 499 Commonwealth Ave., Boston, MA 2215, .
Wonder Bar
Who needs comfort food when you have comfort drink? Lurking beneath the floorboards of the stiff-backed, black-attired glam scene at the Wonder Bar is a comfortable lounge downstairs. It has enveloping booths and sofas and a TV playing sports du jour. The jazz wafts down from upstairs; the pretense, fortunately, does not. 186 Harvard Ave., Allston, MA .
Tie: Bim Skala Bim and The Allstonians
Two acts ostensibly playing the same style, but each with a unique sound. The former's catchier doubletimes tunes rocket you from your seat; the latters more sluggish, sparse style digs a deep groove. Plus, you have to love the 'Stonians endearing tribal loyalty: "Living in Allston is the final word!"
Galley Beach
For the ultimate drink with a view, head to this chichi waterfront lounge, plant your feet firmly in the sand, and try a Moscow Mule or a North Shore (made with local 888 cranberry vodka). Sip and repeat until the sun sets, then retire to the dining room for lobster tail and a veal chop, prepared by the new executive chef, Neil Ferguson. 54 Jefferson Ave., Nantucket, MA galleybeach.net.
Natale's
Natale's is the place to go for high-end men's clothing south of the city. Everything in the store is tailor-made with only the finest wools and fabrics; staffers pride themselves on their ability to help you create a custom wardrobe designed precisely for your needs; and a lifetime of alterations is guaranteed. 171 Washington St., Norwell, MA natalesclothing.com.
Straight Wharf
A gorgeous waterfront location, impeccable service, creative New England fare from chef Gabriel Frasca—Straight Wharf has it all. Particularly notable are the signature clam bake—buttery lobster and chorizo over sweet corn and clams—and the flaky, baked-to-order strawberry galette with house-made buttermilk ice cream. 6 Harbor Square, Nantucket, MA 2554, straightwharfrestaurant.com.
Sultan's Kitchen
Why single out what is already probably Boston's only Turkish restaurant? Because there are some who work downtown and still haven't had one of their kebab sandwiches for lunch. Give 'em a shot: only your breath will suffer. 72 Broad St., Boston, MA .
Bob the Chef's
If you can beat two eggs, your choice of breakfast meat, hot bread, grits or home fries, juice, and coffee for five bucks, let us know. Don't miss what may be the best sweet-potato pie in the city. 604 Columbia Ave., Boston, MA .
Formaggio
Hard to believe the best cup of coffee and best deli exist side by side in a converted parking garage across the river, but that's the way it is. Great cheeses, breads, and meats, along with off-the-wall specialties like pesto, ratatouille, and a strange house policy of no mayonnaise (only mustard or butter). The Garage, 36 Boylston St., Harvard Square, MA .
Deli-Sound
Deli-Sound on Commonwealth Avenue in Allston has a cake which is flown in special form New York and costs only 65 cents. If you get bored with oral gratification, you can tickle your aural fancy with any of the eight-track stereo tapes also available for sale at Deli-Sound. Commonwealth Ave., Boston, MA .
Southwest Corridor Park
Looking for a place to stretch your legs? At this 4.7-mile, 52-acre linear park, you'll find dedicated bicycling and jogging paths for the hardy, basketball and tennis courts for the sporty, and jungle gyms and skate parks for the kiddies. 38 New Heath St., Jamaica Plain, MA 02130, swcpc.org.
Hilton's Tent City
This equipment emporium, which moved from the West End to Central this year, stocks all the camping gear, boots, backpacks, and tents you need for your next rugged hike in the White Mountains. Including one remnant of the original location: a wall of trail maps and postcards. 565 Massachusetts Ave., Cambridge, MA 02114, hiltonstentcity.com.
Blue Dry Goods
The menswear shop of your yacht-club dreams exists in Concord Center (naturally), where you’ll find all the gear necessary for a Nantucket weekend or a day on the links—from little boys’ blazers to cuff links to a massive selection of Vineyard Vines pants and coats. 16 Walden St., Concord, MA 01742, bluedrygoods.com.
Lexington Venue
In a world of plush megaplexes with cushy seats and cocktails, there’s still room for classic cinemas like Lexington Venue, with its healthy mix of indie flicks and new releases. Screen your movie of choice, then stroll to Rancatore’s for ice cream. 1794 Massachusetts Ave., Lexington, MA 02420, .
Elisabeth Accardi, Upon a Star Events
If your precious tot longs for a Wizard of Oz–themed hayride or a Lego Minecraft–inspired bash, call Elisabeth Accardi. The bubbly former actress has brought childhood fairy tales to life for 17 years, including a soiree for a former president’s daughter. uponastar.net.