Digital City Boston (www.digitalcity.com/boston)
A simple way to sort through the cultural offerings on any given day, Digital City Boston does all the little things right. A single movie page, for instance, tells you when and where a film is playing, and gives a synopsis, a critic's review, and a chance to submit your own rating. The dining area constantly updates the top 10 users' choices; it's also easy to search for restaurants by location, price range, or name.
Kendall Square Cinema
Culture and film buffs thank the celluloid gods for this place to see all the idiosyncratic flicks that get reviewed in The New Yorker and The New York Times. Still the sole straddler of the art house/multiplex genres, it offers a great selection on nine screens and in many languages. Great snacks too: real biscotti and cappuccino, and birdbath-size containers of high-quality popcorn. All this and gumfree floors. One Kendall Square, Cambridge, MA .
Club Cafe
One of the few gay bars you can go to where your friends— male and female, gay and straight— can all have a good time. Whether in a group or with a friend this is the best bet for a good time. The weekend can turn into a meat market, but the atmosphere is friendly enough that you feel comfortable approaching that cute someone in the baseball hat. 209 Columbus Ave., Boston, MA .
Dar Williams
Just off tour with folk legend Joan Baez, Dar Williams is now home in Belchertown savoring the critical success of her latest CD, Mortal City. When Williams originally moved to western Massachusetts from New York, she got a job with the Boston Opera Company and aspired to become a playwright or to direct operas. But the call of the coffeehouse was too strong, and Williams's modern folk style soon drew a following that recognized a new talent on the rise.
Mitchell Gold + Bob Williams
Contemporary doesn't have to mean mod. Mitchell Gold + Bob Williams gets this, and sells a mix of retro furnishings alongside pieces with cleaner, more classical lines. There are sophisticated neutrals and playful colors, accent pillows and striking lamps, even stylish "seating" for your pet. Best of all, many of the items we like most are affordable. 142 Berkeley St., Boston, MA mgbwhome.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 .
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.
Pazzo
This welcome newcomer was opened last year by the owners of the popular Nantucket spot Lola 41. Lamb meatballs with hummus and yogurt sauce, and white bean purée topped with crispy ham make for excellent starters, followed by the house specialty main course: a traditional Moroccan tagine for two, served in a clay pot. The refreshing libations—try the "Pazzo Freeze," an after-dinner drink made with homemade lemon sorbet and limoncello—are the perfect complement to the hearty Mediterranean fare. 130 Pleasant St., Nantucket, MA 2554, pazzonantucket.com.
Water Street
Why choose among made-to-order omelets, eggs Benedict, and malted Belgian waffles when you can have it all? The superlative Sunday brunch at Water Street, the Harbor View Hotel's on-site restaurant, features a veritable smorgasbord of everyone's favorites: savory carving-station roasts, a raw bar stocked with oysters and fresh seafood salads, and a dessert table showcasing profiteroles that proliferate beyond your wildest fantasies. 131 North Water St., Edgartown, MA 2539, harbor-view.com.
Olivia Rose Children's Boutique
There are kids so adorable they make clothes look cute, and then there are clothes so cute they make kids look adorable. This shop has plenty of the latter, with Baby Lulu tangerine plaid capris, New Potatoes red wagon—covered jumpers, and Mulberribush polos. These clothes will withstand any childhood adventure until your little one outgrows them. 1945 Ocean St., Marshfield, MA oliviarosechildrensboutique.com.
Giblees
You gotta love a 50-year-old clothier—on Route 114 in Danvers, of all places—that carries cool Ben Sherman shirts. Giblees does, along with suits, sportswear, shoes, and accessories from designers such as Hugo Boss, Zegna, Brioni, Alden, Bruno Magli, and more. The courteous staff will guide you to the racks in your particular price range, whatever that may be. 85 Andover St., Danvers, MA giblees.com.
Cabot's Ice Cream & Restaurant
This family-owned ice cream parlor is a flashback to the '50s, but what better era to find a real New England ice cream frappe? Here they've perfected the art, with three straw-bending scoops of ice cream blended in a tall frosty frappe glass (five scoops for the extra-thick variety). Your choice of nine flavors, including mocha, black raspberry, mint, and cherry, or mixed with strawberries, banana, or pineapple. 743 Washington St., Newtonville, MA .
Tremont India Pale Ale
Used to be this hophead's delight was available only on the occasional tap at, say, F.J.Doyle's in Jamaica Plan. As of April, though, the good people at the Tremont Brewery, way over in Charlestown, started running product through their million-dollar bottling line. The ale is alty, extremely well-hopped and just the right shade of light copper. By now, it should be flying off the shelves at your neighborhood's finest packy.
Tir Na Nog
Its name means "Land of Eternal Youth" in Gaelic, but this smallish bar in Union Square hosts both young and old. Proprietors Robert Elliot and Patsy Wheelan run a welcoming pub, where those with a brogue out-number those without. Patsy's band Zozimus (starring Billy Bulger's son Brendan, on fiddle) rocks the house on weekends, and during Sunday seisiunsan Irish gentleman can sing an old folk song to the respectful silence of the whole room. Tasty food is available; parking is easy. 366A Somerville Ave., Somerville, MA .
The Bristol Lounge
Stripped down to its raw form, a martini is just a stiff belt of gin, which any jamoke can pull off a no-name bottle in an alley. So how to judge? Presentation and accouterments. The white-jacketed waiter at the plushy-not-stuffy Bristol pours each traditional martini tableside from its own chilled shaker with not one, not two, but three meaty olives. Utterly civilized. Keep in mind, while the martini is traditional, the $9 price tag is a tad nouveau. Four Seasons Hotel, 200 Boylston St., Boston, MA .