Street & Co. 33 Wharf St.; 207/775-0887; dinner for two $50. Mediterranean-style dishes are served in a brick-walled room with copper-topped tables and herbs dangling from the ceiling. The perfectly flaky bluefish, served with sugar snap peas, is delicious.
Fore Street 288 Fore St.; 207/775-2717; dinner for two $60. This is another venture of Street & Co.'s Dana Street, in an old warehouse where tanks were repaired during World War II. It's big, hip, and hearty: dishes such as the three-inch-thick spit-roasted pork loin are so sought after that it's a good idea to make reservations two weeks in advance.
Perfetto 28 Exchange St.; 207/828-0001; dinner for two $65. The melon green walls, lava lamps, and black-tiled bar seemed too far-out for Portland when the dining room opened five years ago, but now it's the mainstay of the restaurant scene. Go for the baked sweet native haddock with sticky rice and asparagus coulis.
Aubergine Bistro & Wine Bar 555 Congress St.; 207/874-0680; dinner for two $52. Everything here is checkered in black and white: the floors, the napkins, the waiters. Try the brioche-crusted trout fillet.
Harraseeket Inn 162 Main St., Freeport; 800/342-6423 or 207/865-9377; brunch for two $34. Take the 15-mile drive to Freeport to indulge in seafood ragoût or crêpes stuffed with lobster in a dining room that overlooks English-style gardens. Then walk it off at Freeport's 110 outlet stores.
portland island life
The archipelago of glacial islands in Casco Bay were nicknamed the Calendar Islands because some groggy explorer counted 365 of them. In reality there are 180 Casco Bay Islands, many inhabited by gulls and cormorants. Some of the islands have intriguing names such as Junk of Pork (what it looked like) and Pound of Tea (what it sold for), but the three to visit are Peaks Island (the closest to Portland), Long Island (the most beautiful beach), and Great Chebeague Island (the one with the old-style summer hotel).
The best way to see the islands is to take the Casco Bay Lines' Mailboat Run (Commercial and Franklin Sts.; 207/774-7871), a three-hour narrated tour. Steaming off on the bumblebee-colored Maquoit, you can look back on Portland's red-brick Old Port. You'll probably pass a Russian container ship called the Indropiou, and as you approach one of the islands you're likely to see kids roll down on skateboards to meet the ferry and help Mom haul home groceries.
Peaks Island (population 1,200 in winter, 4,500 in summer) is just a 20-minute trip from Portland. The ferry unloads near Jones Landing (207/766-5542), a restaurant whose porch is packed in the summer with diners wearing lobster bibs and tapping their feet to live music—swing bands, jazz groups, even the Portland Symphony. Rent a tandem bike from Brad Burkholder at Brad's Recycled Bike Shop (take a left from the dock; 115 Island Ave.; 207/766-5631).
Less populated is Long Island, known for a protected, white-sand cove called Singing Sands Beach. From the ferry landing, it's a 15-minute hike.
Most of the islands' summer hotels have long since burned to the ground or fallen into disrepair. The one remaining is the Chebeague Inn (South Rd.; 207/846-5155; doubles from $90) on Great Chebeague Island, one of the last stops on the tour. Its 150-foot-long wraparound porch overlooks the ocean in back and a nine-hole golf course in the front. This place is at the far end of the island from the Casco dock, but innkeeper Dick Bowden runs a limousine service for guests. The hotel also has the best restaurant on the island, serving seafood bought daily on the docks.