The Publick House
Sometimes a cozy haunt, sometimes a party den, the imported-beer mecca is consistently the square's best bet for elbow bending (and rubbing). 1648 Beacon St., Brookline, MA 2445, .
Ice House
You'll probably be underwhelmed by the squat, nothing-special exterior, but trust us when we say your reaction to chef Job Yacubian's Mediterranean cuisine will be quite the opposite. In fact, it's the whole diamond-in-the-rough appeal that makes the BYOB meals her—spring pea pudding, potato gnocchi in Parmesan broth, bacon-wrapped yellowfin—so spectacular. Judging by how hard it is to get a reservation and Bittersweet's celebrity clientele, it's safe to say this ever-changing West Tisbury spot (formerly the Red Cat, then Ice House) has hit its stride. 688 State Rd., West Tisbury, MA 2568, .
The Coach House
The Coach House has always beckoned diners with its open-air seating and Edgartown Harbor views. Now there's another reason to eat at this harbor-view spot: New chef Joshua Hollinger (formerly of Manhattan's Tribeca Grill) has taken over the kitchen and revamped its lunch and dinner menus. But his real triumph is the Sunday brunch. Delicacies like sushi and boutique chocolates join an already impressive menu of berried French toast, eggs Benedict, and myriad savory salads. You may even find yourself forgoing the vista of passing sailboats to stare at the buffet instead. 131 North Water St., Edgartown, MA 2539, harbor-view.com.
The Publick House
Think of the Publick House less as a bar, and more as a library stocked with craft Belgians. You’ll even get an education, thanks to beer-nerd staffers. 1648 Beacon St., Washington Square, MA 2445, thepublickhousebeerbar.com.
Haley House
This nonprofit bakery-café serves up superb fooddon’t miss the jerk-chicken grilled cheesewith a side of good citizenship (and free WiFi). 12 Dade St., Roxbury, MA 2119, haleyhouse.org.
Area Four
To find espresso this good—hot and potent, with a nutty crema—served sans withering disdain is a rare thing indeed. 500 Technology Sq., Kendall Square, MA 2139, areafour.com.
Boarding House
Like sitting on a South End patio, you'll see everyone during weekend brunch here. People-watching aside, the covered, fenced-in Federal Street terrace is also a cool and shady spot to take in Seth and Angela Raynor's outstanding service and locally sourced fare. Go sweet on pillowy house-made brioche doughnuts and soufflé pancakes, or ease into the day with a savory grilled pizzetta topped with fontina, arugula, and prosciutto. Whichever way you go, the BoHo's classic bloody mary is a must. 12 Federal St., Nantucket, MA 2554, boardinghousenantucket.com.
The Publick House
At Brookline's artisan-suds mecca, a vintage Son Volt tour tee will get you further with the aging hipster crowd than any designer finery; let it slip that you grow your own hops, and you might very well seal the deal. 1648 Beacon St., Brookline, MA 2445, .
House of Slam
In the beginning, there was House of Siam's Chicken with Basil, and it was the best. Subsequent visits introduced us to their pad thai, which gives Jae's a run for its money, and interesting seafood dishes such as Diamond Mine, consisting of sea scallops, bamboo shoots, and baby corn in a hot chili sauce. The food is consistently excellent: everything is very fresh and cooked to order, with most dishes leaning toward spicy but easily modified with a request. 542 Columbus Ave., Boston, MA .
The Custom House
Boston musician Fran Sheehan has put together an extensive, well-priced list at this North Shore establishment. 9 Atlantic Ave., Marblehead, MA .
House of Blues
Live gospel music in a mini-museum of folk art, and a Southern-style buffet that includes eggs, fried catfish, breakfast meats, biscuits, fruit salad, and bread pudding. It's a revival meeting cum dining experience that simultaneously satisfies body and soul. 96 Winthrop St., Cambridge, MA .
Sparrow House
The 17th and 21st centuries merge seamlessly in this part-museum, part-gallery that sits inside a Colonial-era landmark. Three times each season, Sparrow House holds free shows featuring American artists such as oil painter Marlee Brewster Brockmann and pastel artist Anne Heywood; available year-round are unique handicrafts—ceramic bowls, silver jewelry, polished wooden utensils—by contemporary American craftsmen. 42 Summer St., Plymouth, MA 2360, sparrowhouse.com.