things to do in South Portland, ME

Explore the Kennebunks on your own schedule, with your ride delivered to you

Paddle Casco Bay to explore a Civil War-era fort

Sail Kennebunkport at midday with a local captain, public or private

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

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

Cruise the Gulf of Maine with small-group whale watching and 360° views

Rent a kayak or SUP at East End Beach for an easy 1-hour waterfront paddle

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

Sail longer and see more of Saco Bay on a half-day trip

Sail into the evening with a small-group sunset cruise

Sail Portland Harbor with your own snacks and drinks

Sail Portland Harbor at golden hour with room for your favorite snacks and drinks

Cruise Maine's coast aboard the classic Calista Ann

Cruise Maine’s rugged coastline with an optional lobster roll meal

See how oysters are grown and taste them fresh from the water

Pair fresh oysters and prosecco with Portland coastal views

Sip wine on a 90-minute Kennebunkport sail with a sommelier-led tasting

Learn recreational kayaking while exploring Sebago Lake’s streams and Jordan Bay

Paddle Casco Bay at sunset with a relaxed, beginner-friendly guided tour

Learn about Maine lobsters while cruising Casco Bay's island waters

Paddle Sebago Lake’s coves, islands, and shoreline at your own pace

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

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

Paddle sheltered harbor waters and visit Goat Island's historic lighthouse