things to do in South Portland, ME

Craft drinks, waterfront views, and Prohibition stories by trolley

Private Casco Bay cruise with a guided Maine oyster tasting

Learn how Maine oysters are raised, then taste them from the water

Follow seasonal migration with an expert guide, local tastings, and comfortable transportation

Sail Kennebunkport with options to relax or take the helm

Launch from Sebago Trails’ private site and paddle for up to 4 hours

Island-hop by sea kayak in Casco Bay with a beach break

Taste fresh oysters and lobster rolls on a Maquoit Bay cruise

Savor Maine flavors on a guided lunch walk, offered June–October at 10:30am

Private lobstering and scenic cruise for up to 6 on Saco Bay

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

Spot whales off Maine with 360-degree views and expert narration

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

Cruise Casco Bay, see oyster farming in action, and taste fresh oysters

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

Explore Maine’s coastal towns, lighthouses, and harbor views privately

Sail into the evening light along Kennebunkport’s rocky coast

Easy evening paddling with Maine guide stories

Reserve camping and paddling gear rentals with limited availability

Create a private scenic or educational outing around Maine's islands

Share local bites and stories with your dog on a short, guided walk in Dock Square

Book a private 6-hour powerboat cruise for up to 6 in Casco Bay

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

Ride a performance RIB to see all seven Portland-area lighthouses in 2 hours