It’s the biggest city in Maine, a bustling urban center with a historic core. Old Port is chock-full of 19th-century brick buildings that now house chic boutiques, local shops, taverns, cafes, and trendy restaurants. Yet the former shipping and trading center, set on a peninsula poking into Casco Bay, still maintains its hardworking, unpretentious soul.
STAY HERE: Great location and service draw a loyal following to the Hilton Garden Inn Downtown Waterfront (65 Commercial St., 207-780-0780, www
.hiltongardeninn3.hilton.com, most summer rates in the $200-$300 range), within walking distance of shops, restaurants, and attractions. Contemporary rooms have soothing neutral palettes, granite and tile baths, and lush linens. The staff is welcoming and knowledgeable, and it’s family-friendly (there’s an indoor pool) and pet-friendly too.
CULTURAL PURSUITS: The Portland Museum of Art (7 Congress Square, 207-775-6148, www.portlandmuseum.org, adults $12, ages 13-17 $6, 12 and under free), housed in three architecturally significant buildings, boasts one of the finest mid-size collections of art in New England, including an impressive number of Winslow Homer graphics. Stroll through Old Port for a look at 19th-century red-brick buildings, home to chic boutiques, taverns, and restaurants. For a deeper peek into Portland’s past, join the Maine Historical Society’s Old Port Walking Tour (489 Congress St., 207-774-1822, www.mainehistory.org, adults $10). The society also offers tours of the Wadsworth-Longfellow House (see above, adults $12, students $10, age 5 and under free). We love the Old Port Culinary Walking Tour (223 Commercial St., 207-233-7485, www.mainefoodietours.com, $45) that combines a bit of history with a look at today’s top Maine-made products and strong locavore movement.
START YOUR DAY: The laid-back, slightly funky Local 188 (685 Congress St., 207-761-7909, www.local188.com, $7-$11), with a large, open kitchen, mix-and-match tables and chairs, and local art, is a weekend brunch hot spot. Impossibly fluffy pancakes, well-seasoned egg scrambles, and the house-made, thick-sliced bacon are memorable, and the $6 bloody Mary, made with hot pepper-infused vodka, was one of the best we’ve had.
BEST BISTRO: If we had only one dinner to eat in Portland, it would probably be at Petite Jacqueline (190 State St., 207-553-7044, www.bistropj.com, entrees $13-$23), a lively, intimate restaurant serving French country cuisine with creativity and care. The pleasures are cumulative: Start with the charcuterie platter with house-made meats and pates or the signature onion soup topped with gooey gruyere cheese, followed by traditional steak frites or the complex and tasty boeuf bourguignon.
TREAT YOURSELF: Mount Desert Ice Cream (51 Exchange St., 207-210-3432, www.mdiic.com) has won oodles of awards for its ultra-creamy confections. Whoopie pies rule in Maine — it’s the official state treat — and you’ll find some of the best at Two Fat Cats Bakery (47 India St., 207-347-5144, www.twofatcatsbakery.com). If your taste buds lean more to salty, crunchy, make a beeline to Duckfat (43 Middle St., 207-774-8080, www.duckfat.com) for their wickedly good, hand-cut, local Maine potatoes fried twice in duck fat.
LOCAL WATERING HOLE: Gritty McDuff’s (396 Fore St., 207-772-2739, www.grittys.com) was Maine’s first brew pub to open after Prohibition, and remains a favorite hangout. Grab a stool at the copper-topped bar or one of the wooden tables, where conversation and beer flow easily. There’s always a good selection of their small-batch, English-style ales and the grub is decent (try the ale-battered chicken served on grilled garlic toast with bacon, the meatloaf, or the local haddock fish and chips, $9.99-$10.99).
SEAFARING FUN: Join a local lobsterman as he hauls up his traps on Casco Bay. You’ll learn plenty about Maine’s favorite crustacean, and see Civil War forts, lighthouses, and pretty coastline scenery on the 90-minute Lucky Catch cruise (Long Wharf, 207-761-0941, www.luckycatch.com, adults $25, ages 13-18 $20, 2-12 $15).