Things To DoThings To Do
Portland Head LightPortland Head Light
Most photographed lighthouse in the world! It is in the center of Fort Williams Park so plan on enjoying as long of a walk throughout the picturesque grounds of the park. There are so many directions to go. Fun for dogs, too! Perfect place to capture picture perfect moments against a backdrop of Casco Bay!
Spring Point Ledge LighthouseSpring Point Ledge Lighthouse
We always take our guests here because you get to walk all the way out to the lighthouse on massive stones. Wear comfortable shoes! Many choose to walk it barefoot, too. Either way, get some epic photos!
Inn by the SeaInn by the Sea
Benny, Jet, Christina and Tom are regulars here. Pet-friendly, including dog menu! The human food and drinks are sensational. Walk their idyllic path to the stunning beach and enjoy a scenic, sandy stroll by the sea.
Top of the EastTop of the East
We go here for special occasions. Beautiful vantage point for drinks above Portland.
Old PortOld Port
Lots of shops, restaurants, cafes. Spend time walking! Wonderful boutique shops, art galleries and more! Some of our faves are Danforth (artisan metal), Edgecomb Potters, D.Cole, the bar at the Regency Hotel, Standard Baking, the Green Elephant (yummy vegan lunch/dinner) and our favorite bar, Blythe & Burrows. The Old Port is also where you catch the ferry to Great Diamond Island.
Peaks IslandPeaks Island
Enjoy a ride on the Casco Bay Ferry line to Peak's island. Visit Cairn Beach (the rock-stacking beach), sometimes called Prayer Point, where visitors build little stone towers called cairns.
Diamond's Edge Restaurant and MarinaDiamond's Edge Restaurant and Marina
This is THE restaurant on the island. Sit outside and overlook the bay while dining! (This is where "Just Married" brunch takes place on August 30th)
the Crown Jewel (on Great Diamond Island)the Crown Jewel (on Great Diamond Island)
Call now / in advance for reservations because it is 1 of the 2 restaurants on Great Diamond Island. Cute place that gets packed, so be sure to get yourself a reservation if you want to check it out while you're on the island.
Kayaking, paddle boarding, bicycling on Great Diamond Island or Casco BayKayaking, paddle boarding, bicycling on Great Diamond Island or Casco Bay
The Inn at Diamond Cove has 30 bikes, 2 kayaks, 3 paddle boards--first come first serve on the island--plus there are plenty rental places on the Portland side of Casco Bay.
Sea Glass BeachSea Glass Beach
Speckled AxSpeckled Ax
Tom's fave coffee shop in Portland.
Black Point InnBlack Point Inn
Classic dining overlooking Scarborough beach which you can cross the street to walk along the sprawling coastline beach.
Bard CoffeeBard Coffee
Our second fave coffee place in Portland.
Longfellow BooksLongfellow Books
We love shopping for books here.