Best 163 things to do in South Portland, ME

Sail Kennebunkport with options to relax or take the helm

Sail into the evening light along Kennebunkport’s rocky coast

See Portland's coast during New England's fall color season

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

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

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

Craft drinks, waterfront views, and Prohibition stories by trolley

Taste Portland’s food scene from a trolley, with lunch, drinks, and neighborhood views

Pair fresh oysters and prosecco with Portland coastal views

Taste local flavors while exploring Maine’s historic coastal lighthouses

Paddle Casco Bay at sunset with a quick SUP lesson and licensed guide

Build Part I skills and practice an open-water crossing in Casco Bay

Paddle Portland’s waterfront on a slow-paced, family-friendly sea kayak tour

Learn capsize recovery skills in a 3-hour sea kayak lesson

Build sea kayaking skills in a small-group lesson on Casco Bay

Join a Monday evening kayak or paddleboard race at East End Beach

Paddle with a morning group on Tuesdays or Thursdays

Build core strength with a paddleboard workout on the water

Private Casco Bay cruise with a guided Maine oyster tasting

Private coastal sunset cruise with oyster tasting and room for your own drinks

Sail to Wood Island and tour inside the lighthouse and keeper’s house

Sail Saco Bay and tour Wood Island Lighthouse from tower to Keeper's House

Fish the Saco River on a private fly-fishing charter for up to 2 guests

Cruise Casco Bay at sunset on a classic Maine-built powerboat