The Winery at the Pilot House
Lewis Wharf, on the waterfront in the summer. Ritz-Carlton Hotel, 15 Arlington St., Boston, on the Public Garden in the winter., Boston, MA .
Cambridge Boat House
The drinks aren't bad, either. Gerry's Landing Rd., Cambridge, MA .
Chef Chang's House
Where else can you get Peking duck without calling ahead? 1006 Beacon St., Brookline, MA .
The Blacksmith House Bakery & Cafe
Lighter than pound cake, sweeter than brioche, this shop's kuchen—a slightly lemony cake studded with raisins—is a revelation when spread with a little butter while still warm. In good weather you can enjoy it on the bakery's patio. 56 Brattle St., Cambridge, MA .
John Harvard's Brew House
Could be the largest cozy tavern in town. The Old Willy India Pale Ale is heavenly, especially when used to wash down the grilled sausage. 33 Dunster St., Cambridge, MA .
The Sevens Ale House
The only people unhappy with the Sevens are those standing in line when a regular patron walks by them and through the door. Some of the regulars should have their mail delivered here. 77 Charles St., Boston, MA .
Algiers Coffee House
We'll always miss the old subterranean cafe, but we're glad the Algiers is back and better than ever. 40 Brattle Street, Cambridge, MA .
Morton's of Chicago Steak House
You've got to hand it to those Midwesterners: they have a way with red meat. 1 Exeter Plaza, Boston, MA .
May's Cake House
The problem with most birthday cakes is that the better they look— all flowers and scrolls— the worse they taste. May, bless her heart, has solved the dilemma. She compliments her delicate batters with light mousses and whipped creams, then trims with finely sliced fruits. The cakes she creates are beautiful and delicious. And you can afford one— even after the ticket you'll probably get for double-parking on the south edge of Chinatown. 223 Harrison Ave., Boston, MA .
The Union Oyster House
The semi-circular oyster bar has been in continuous operation since 1826, with the likes of Daniel Webster tossing back three dozen Blue Points at one sitting.Yes, it's on the Freedom Trail; yes, it's "America's Oldest Restaurant"; and yes, it's one of "Ye Olde" tourist magnets. But, all the hokum aside, it is simply the best place to get a dozen freshly cracked oysters. 41 Union St., Boston, MA .
Carberry's Bakery and Coffee House
The secret ingredient in Carberry's Danish pastries: almond paste, kneaded into the buttery, flaky dough. They are oversize and come in several flavors, such as sour cherry, cheese, raspberry, and vanilla cream. 74-76 Prospect Street, Cambridge, MA .
Hilliard's House of Candy
The summertime venture of this family candy business is creamy and extra rich. The chocolate chip is the best anywhere. Chewy Turtle Soup is coffee ice cream studded with Hilliard's own chopped-up cashew caramel turtles. 316 Main Street, North Easton, MA .
Bob Smith's Wilderness House
For many Bostonians, summer is a savored moment wedged between the brutal bookends of the New England winter. For skiers, it's an interruption. They're already dreaming of the first snowstorm. Bob Smith's Wilderness House caters to these people—novices and experts alike—because the staff feels their pain. Völkl, Salomon, Rossignol: The employees here know them all and can discuss at length the merits of each brand (and the best slopes to break them in). Custom boot fitting puts the icing on the cake. 1048 Commonwealth Ave., Boston, MA .
Cape Poge Lighthouse Tour
A narrow beach used to connect Chappa-quiddick to Martha's Vineyard, but the sea breached the divide in 2007, and a 300-yard channel now separates thetwo. Don't let that deter you. Take the ferry from Edgartown and spend a day exploring "Chappy," which boasts 1,000 acres of preservation land. Sign up for the Cape Poge Lighthouse Tour, and a guide will pick you up at the ferry, drive you along the beach, and take you up into the lighthouse for sweeping views of the area. thetrustees.org.
Salt House Inn
This is P-town's first boutique hotel, new this spring, and already we're smitten. Each of its rooms, snug and brilliant white, has plush bedding, nautical curiosities hung on the walls, and unique touches we love. WiFi and parking are gratis, as are the homemade breakfasts (try the strawberry-waffle trifle). The owners have big-city hospitality bona fides, but here their concept is relaxed beach chic. 6 Conwell St., Provincetown, MA salthouseinn.com.