things to do in South Portland, ME

Trace Portland's harbor defenses and shipbuilding history at three lighthouse stops

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

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

Private White Mountains Day Trip for Scenery, History, and Mountain Views

A private evening on Casco Bay beneath the setting sun

Rent a kayak, canoe, or paddleboard for up to 24 hours

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

Make your time on the water your own with a personalized private charter

Walk Kennebunkport’s historic gardens with a local home gardener

Sail Maine’s coast in a small group of 6 or fewer

Enjoy eight hours on the water with a choice of power pontoon boats.

Ride a 14-passenger RIB for lighthouses, forts, and wildlife in Casco Bay

Cruise Casco Bay, shuck fresh oysters, and finish at a local lobster shack

Sit back and enjoy the scenic route to a Maine seaside village

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

Tour Bar Harbor and Acadia in a private vehicle from Portland

Cruise Portland’s coast for islands, lighthouses, and waterfront views

Paddle through autumn color with local river stories

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

Reserve the boat for an intimate Maine coast sail with your own group

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

Walk Kennebunkport’s historic district with a local guide

Haul lobster traps and explore Maine's shoreline by private boat

Sip local flavors and uncover Portland stories aboard a guided trolley