Best 100 things to do in South Portland, ME

Pedal Maine’s coast past lighthouses, forts, and harbor views

Watch Maine's colorful sky from a lobster boat while passing lighthouses and Portland's scenic coastline.

Handle lobsters and help reset traps in Casco Bay

Sip local beer and wine and savor fresh Maine oysters during a scenic two-hour harbor cruise.

Sail Casco Bay at sunset with live music and a BYOB vibe

Cruise Casco Bay at sunset past lighthouses, forts, and islands

Cruise Casco Bay on the Joseph S. Kennedy with optional lobster roll add-ons

Relax on a slow cruise for great views of Portland from the water

Relax on a 1.5-hour Casco Bay cruise with views of Portland

Relax on a 1.5-hour Casco Bay happy hour cruise for up to 12 guests

Relax on a Casco Bay sunset cruise with Portland views

1.5-hour Casco Bay mimosa cruise for up to 12 guests

See Casco Bay lighthouses, working boats, and coastal wildlife with live narration

Sail Casco Bay at dusk with lighthouse views and live narration

Explore Portland landmarks and stop at Maine’s oldest lighthouse

Taste Portland craft drinks and local bites aboard a guided trolley

See Portland Harbor lighthouses, forts, and Diamond Pass from the water

Ride an amphibious duck boat through Portland streets and into Casco Bay

Tour Portland by vintage fire engine on a 50-minute narrated ride

See Casco Bay’s lighthouses, forts, and islands from the water

Savor oysters and prosecco on a Casco Bay cruise

Sail Casco Bay at dusk with a local drink and lighthouse views

Trace Portland's past with local beer at three Old Port stops

Taste Portland beer at three breweries with guided van travel between stops