Best 133 things to do in Portland, ME

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

Paddle to Fort Gorges and explore ashore with a Maine-licensed guide

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

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

Reserve camping and paddling gear rentals with limited availability

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

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

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

Paddle with a morning group on Tuesdays or Thursdays

Choose your craft and explore Casco Bay from Portland’s waterfront

Explore Portland’s East End waterfront with gear included

Paddle Portland’s East End waterfront by kayak or stand-up paddleboard

Build core strength with a paddleboard workout on the water

Cruise Portland’s coastline aboard a classic wooden vessel with all-inclusive drinks

Evening views and all-inclusive drinks aboard a 1950s wooden vessel

Cruise Casco Bay with brunch, bottomless mimosas, and included drinks

Private chef dining and drinks aboard a restored Maine lobster boat

A private evening on Casco Bay beneath the setting sun

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