Portland’s charm lies in its authenticity – it is among the oldest surviving urban working waterfronts in the United States.

Its compact downtown combines wharves and chandleries with a vibrant shopping, arts, and restaurant scene.

Becky’s Diner

Traditional diner food on Hobson’s wharf. Becky’s is on the waterfront (although you won’t see the water from the booths inside) and the business was started to serve fisherman (as shown by its 4 am opening time). Breakfast is served all day along with excellent lobster rolls and chowder. www.beckysdiner.com

390 Commercial Street, 4:00 am – 10 pm daily. No reservations. From the Regency: turn left outside the hotel onto Milk Street, 1 1/2 blocks to Exchange Street, turning left on Exchange. Walk to Fore Street, then right on Fore Street, left onto Dana Street, and right on Commercial. Walk 5 long blocks on Commercial to Becky’s, on the water side; 0.6 miles/20 minutes (or 3 minutes by cab).

The Crooked Mile

Old Port sandwich shop serving breakfast and lunch since 2003. Sandwiches, salads, wraps, latte concoctions, and espresso drinks featuring Carrabassett coffee.

Monday – Friday 7:30 am – 5 pm. Phone: 207-772-8708. Step out the front door of the Portland Regency Hotel and Spa and look to your right.

http://thecrookedmilecafe.com

Duckfat Cafe

Before he won on “Chopped,” classically trained Rob Evans presided over Hugo’s, for which he won the James Beard Best Chef in the Northeast award among other accolades. Rob and his wife Nancy now live and work on a farm west of Portland that supplies ingredients for their small and casual place, Duckfat. (So named as the frites are cooked, Belgian-style, in rendered duck fat…which tastes unbelievably better than it sounds.) Features panini, including the tuna melt named one of the best sandwiches in America by Esquire magazine, soups, salads, and charcuterie. http://www.duckfat.com

43 Middle Street, 11 am – 9 pm daily. No reservations. From the Regency: turn right outside the hotel, then an immediate left onto Silver Street. Walk one block to Middle Street, turning right. Walk 4 1/2 blocks, crossing Franklin (aka Route 1-alt), to Duckfat on the left; 0.3 miles/10 minutes.

Flatbread Company

Dine indoors or out on wood-fired pizzas made from organic and locally grown ingredients. A community fixture, Flatbread donates a portion of every Tuesday evening’s sales to local nonprofit organizations. No reservations.

72 Commercial Street, 11:30 am – 9 pm daily. From the Regency: turn right coming out of the hotel, then an immediate right on Silver Street. Continue straight ahead, crossing Commercial Street. Walk another 2 1/2 blocks to Flatbread on your right.

Five Fifty-Five

Steve and Michelle Corry have worked at some of the most renowned restaurants in the country, and 555 has been featured in almost every food and wine magazine. Truffled lobster mac and cheese is a house specialty, and Steve is 2013 Maine Restaurant Association chef of the year. www.fivefifty-five.com

555 Congress Street, 5 – 10 pm daily. Phone: 207-761-0555. From the Regency: outside the hotel, make a slight left and immediately turn right, walking up Market Street. Walk 4 blocks to Congress Street, then 6 blocks to 555; 0.6 miles/20 minutes (or 3 minutes by cab if you want to avoid the occasional hobo on Congress).

Fore Street

Sam Hayward is another über-celebrated local chef and key driver of the sustainable, locally sourced restaurant movement in Maine. Fore Street has won a boatload of national awards. It has great ambiance and a huge open kitchen. Well worth a visit if you can get a reservation (i.e., call right now), if somewhat less sublime than in the years before Sam got famous. The downstairs bread company, Standard Baking, was started as a way to supply the restaurant with superb crusty bread, which is as great as ever. www.forestreet.biz

288 Fore Street, 5:50-10 pm daily. Phone: 207-775-2717. From the Regency: turn right outside the hotel, walking a block to Pearl Street. Turn right on Pearl, then cross the street and turn left onto Fore Street. Continue walking about 400 feet to the restaurant; 0.2 miles/7 minutes.

Fuji

Sushi bar and Japanese steak house, around the corner from the Regency on “the” popular street in the Old Port. Hopping busy during the summer; be prepared to wait at the bar. www.fujimaine.com

29 Exchange Street, 11:30 am – 9:30 pm daily. Phone: 207-773-2900, reservations not required (but suggested for hibachi grill tables of 3+). From the Regency: turn left outside the hotel, walking a block and a half to Exchange Street. Fuji is on the corner; 282 feet/2 minutes.

J’s Oyster

Waterfront, downmarket, old-school hangout since 1977, and finally smoke-free. Oysters prepared every way you can think of, as well as burgers, clams, and lobster. “A place that I loved within two seconds of walking in the door…I wanted to move in upstairs,” said Anthony Bourdain when he came with No Reservations to film an episode in Portland. No reservations, no website.

5 Portland Pier, 11:30 am – 11:30 pm daily. From the Regency: turn right coming out of the hotel, then take an immediate right onto Silver Street. Continue straight ahead, crossing Commercial Street, onto the pier; 0.1 miles/5 minutes.

The North Point

Patés, sweet crepes, gourment cheese & meat selections (espoisses de Burgundy and sopressata, for example) are featured at this new wine bar across the street from the Portland Regency Hotel and Spa. 35 Silver Street, 11 am – midnight daily. Happy hour Mon – Fri from 4 to 6 pm, featuring wines at $4 per glass, beer at $3 per glass. Phone: 207-899-3779. From the hotel, turn right and cross to the east side of Silver Street. http://northpointportland.com

Paciarino

Opened in December 2008 by Fabiana de Savino and Enrico Barbiero, who moved their family to Portland from Milan without knowing a soul before they arrived. Assortment of antipasti, Italian wines, and handmade pastas; “tender ravioli are stuffed with sweet local shrimp and haddock, and his spaghetti is hand-stretched and perfectly cooked,” says the New York Times. Casual atmosphere; paciarino means a favorite dish that your grandmother prepares especially for you. www.paciarino.com 

470 Fore Street, lunch 11:30 am –  2 pm except Sunday; dinner 6 – 9 pm. Phone: 207-774-3500. From the Regency: turn left outside the hotel onto Milk Street, 1 1/2 blocks to Exchange Street, turning left on Exchange. Walk to Fore Street, make a right on Fore Street, and walk until you cross Union Street. Paciarono will be on your left just past the Portland Harbor Hotel; 0.3 miles/10 minutes.

Sonny’s

Chef Jay Villani serves up an eclectic menu of locally sourced ingredients with a Cuban twist. Located in a historic former bank building on fun and funky Exchange Street, right around the corner from the Regency. www.sonnysportland.com

83 Exchange Street, open daily. Lunch 11:3 – 3:00, dinner from 5 pm. Phone: 207-772-7774. From the Regency: turn left outside the hotel, walking a block and a half to
Exchange Street. Make a right, walk another block and a half to Sonny’s; 0.1 miles/5 minutes.

Street & Co.

Anthony Bourdain was less kind to Street & Co., which hasn’t hurt business one iota. Specializing in fresh seafood and a bustling, convivial atmosphere, Street and Co. was a pioneer in Portland’s restaurant scene and still is a favorite destination for locals and tourists alike. www.streetandcompany.net

33 Wharf Street, 5:30-9:00 daily. Reservations are useful in the summer, but a third of the tables are kept aside for walk-in customers. Phone: 207-775-0887. From the Regency: turn left outside the hotel onto Milk Street, 1 1/2 blocks to Exchange Street, turning left on Exchange. Walk to Fore Street, then right on Fore Street and the next left onto Dana; 0.2 miles/7 minutes.

Vignola Cinque Terre

Another first-rate farm-to-table restaurant (one of the nation’s top 10, according to Relish magazine). Executive chef Lee Skawinksi presents carefully selected cheese plates and Italian dishes such as Maine lobster ravioli with San Marzano tomatoes, brandy, porcini, shallots, fresh cream and tarragon butter; and Zuppa di Pesce with Maine mussels, scallops, lobster, potatoes, fennel, San Marzano tomato and Harissa brodo. http://www.vignolamaine.com

10 Dana Street, daily from 5 pm. Phone: 207-772-1330. From the Regency: turn left outside the hotel onto Milk Street, 1 1/2 blocks to Exchange Street, turning left on Exchange. Walk to Fore Street, then right on Fore Street and the next left onto Dana; 0.1 miles/5 minutes.