8 a.m. Pick up a pastry and coffee from Standard Baking Co. at 75 Commercial St., then head across the street to the Maine State Pier, where you can have breakfast while gazing out into Portland Harbor.
9 a.m. Stroll along the working waterfront on Commercial Street, exploring the wharves along the way. Stop in at Harbor Fish Market on Custom House Wharf, a local landmark that’s on many a postcard and calendar. Walk to Portland Pier, home of Luke’s Lobster restaurant and its lobster buying station.
11 a.m. Take a train ride along the city’s Eastern Promenade and Casco Bay with the Maine Narrow Gauge Railroad Co. The 40-minute rides on historic passenger trains leave from the station at 49 Thames St.
12:30 p.m. Head to the top of the Old Port and get lunch at The Highroller Lobster Co. on Exchange Street, where you can get a fried lobster tail on a stick. Follow it up with an ice cream cone from Beal’s on Moulton Street, then walk with it back up Exchange and take a seat in a shady spot in Post Office Park at the corner of Middle Street, where you might catch a local street performer.
2 p.m. Go shopping on Exchange Street. In a just a couple blocks, there’s something for everyone, including Jill McGowan (woman’s clothing), Sherman’s Maine Coast Book Shop, Treehouse Toys, Lisa-Marie’s Made in Maine boutique and D. Cole Jewelers. Continue onto Fore Street to browse places like Siempre Mas (imported and Maine clothing and jewelry) and Maine Potters Market.
4 p.m. Take in art at one or more of the Old Port’s galleries, including Fore River Gallery on Market Street or Greenhut Galleries on Middle Street. Or make some art (while having a drink) at Muse Paintbar on Commercial Street.
5:15 p.m. Take one of Portland’s famous Maine Duck Tours, aboard an amphibious duck boat. The one-hour tours feature narration about the city’s history and start near 177 Commercial St. From there, the duck boats travel Old Port streets as well as cruise around Portland Harbor.
7 p.m. You can’t throw a baseball in the Old Port without hitting a good spot for dinner. If you’ve had your fill of seafood, Via Vecchia on Dana Street offers Italian-inspired small plates and outdoor dining. If not, Old Port Sea Grill on Commercial Street offers food fresh seafood in an upscale setting.
9 p.m. Catch some live music at Portland House of Music, 25 Temple St. The place features local and regional bands as well as national acts. In August, spend a “Funky Monday” with Gina & The Red-Eye Flight Crew, or hear Hello Newman’s ’90s rock on most Tuesday nights (showtimes vary).
11 p.m. Have a late-night sweet with your sweetie at The Bar of Chocolate, a martini, wine and dessert bar at 38 Wharf St.
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