July 31 at 8 a.m. Pick up a pastry and coffee at Standard Baking Co. at 75 Commercial St., then cross the street to the Maine State Pier, where you can have breakfast while overlooking the Portland Harbor .
9 am Stroll along the Commercial Street waterfront, exploring the quays along the way. Stop at the Harbor Fish Market on Custom House Wharf, a local landmark that features on many postcards and calendars. Walk to Portland Pier, home to Luke’s Lobster restaurant and lobster buying station.
11:00 a.m. Take a train ride along the city’s East Parkway and Casco Bay with the Maine Narrow Gauge Railroad Co. 40-minute rides on historic passenger trains depart from the station at 49 Thames St.
12:30 PM Meet at the top of the Old Port and have lunch at Highroller Lobster Co. on Exchange Street, where you can enjoy a fried lobster tail on a stick. Follow it with an ice cream cone from Beal’s on Moulton Street, then walk up Exchange and sit in a shady spot in Post Office Park on the corner of Middle Street, where you might spot a local street performer.
2:00 p.m. Shopping on Exchange Street. Within a few blocks there is something for everyone including Jill McGowan (women’s clothing), Sherman’s Maine Coast Book Shop, Treehouse Toys, Lisa-Marie’s Made in Maine boutique and D. Cole Jewelers. Continue on Fore Street to browse places like Siempre Mas (imported and Maine clothing and jewelry) and Maine Potters Market.
4:00 p.m. Admire the art at one or more of the galleries in the Old Port, including the Fore River Gallery on Market Street or the Greenhut Galleries on Middle Street. Or make art (while having a drink) at the Muse Paintbar on Commercial Street.
5:15 PM Take part in one of Portland’s famous Maine Duck Tours, aboard an amphibious duck. Hour-long tours feature narration about the city’s history and begin near 177 Commercial St. From there, ducks roam the streets of the Old Port and sail into Portland Harbor.
7 p.m. Impossible to throw a baseball in the Old Port without finding a good place for dinner. If you’ve had your fill of seafood, Via Vecchia on Dana Street offers Italian-inspired small plates and al fresco dining. Alternatively, Old Port Sea Grill on Commercial Street offers fresh seafood dishes in an upscale setting.
9 p.m. Catch live music at the Portland House of Music, 25 Temple St. The venue features local and regional bands as well as national artists. In August, have a “funky Monday” with Gina & The Red-Eye Flight Crew, or listen to 90s rock from Hello Newman most Tuesday nights (times vary).
11 p.m. Grab a late-night sweetie with your darling at the Bar of Chocolate, a martini, wine and dessert bar at 38 Wharf St.