Top Sunset Cruise Routes in Portland, Maine
Sunset Cruise Route #1: Long Island to Fort Gorges
Kick off your evening just off the northwestern shore of Long Island, where you can ease along the coast, taking in the quiet charm of weathered cabins and working piers. From there, head south through Hussey Sound, where the view opens up to the Atlantic and the light starts to shift.
Cruise between Great Diamond and Peaks Island, where historic homes perch on rocky cliffs and sailboats bob in the mooring fields. Then wrap up your route near Fort Gorges, perfectly positioned for a golden-hour photo with the Portland skyline glowing in the background.
It’s peaceful, scenic, and packed with everything you want in a Portland Maine sunset — all on your own schedule.
Sunset Cruise Route #2: Fort Gorges, Fort Scammel, Portland Head
Head out across Casco Bay toward one of Maine’s most iconic sights: Portland Head Light. Cruise past the rugged cliffs of Fort Williams Park as the sun begins to dip, casting a golden glow on the lighthouse and headlands.
From there, swing past historic Fort Scammel on House Island, then make your way up into Portland Harbor, where the working waterfront meets the city skyline.
This route blends classic Maine scenery with a front-row seat to the rhythm of the harbor — perfect for a private Portland Maine sunset cruise with just the right mix of adventure and calm.
Sunset Cruise Route #3: Falmouth Foreside to Portland Head
If you enjoy a slow cruise through mooring fields, checking out a mix of working boats and weekend cruisers, this route’s for you. Start near the Falmouth Town Landing, then wind your way past Handy Boat, hugging the shoreline lined with classic coastal estates, summer cottages, and boats.
From there, drift past Mackworth Island and into the upper reaches of Portland Harbor, where the harbor traffic starts to pick up and the skyline comes into view. The setting sun reflects off the water, lighting up the hulls and rooftops around you. It’s a great mix of quiet waters, active coastline, and unbeatable views — perfect for soaking in a Maine sunset from your own boat.
