Island Adventure Anyone?A half-dozen islands are served by the downtown ferries.
A key element behind Portland's global appeal is how seamlessly it melds an urban setting with the outdoors. And nowhere is that more evident than when you board a ferry from downtown to explore the islands of Casco Bay.
Ferries depart regularly from the Casco Bay Lines terminal at the intersection of Commercial and Franklin streets. A half-dozen islands are served by the ferries, with the most frequent service — and the most popular destination — being Peaks Island.
"I love to send people to Peaks," says tea shop owner Sarah Richards. "It's a special experience, and so quaint and lovely. I particularly love that when you get off the boat and you just take a right and follow trails through the woods … you end up at this little cemetery. That part of the island is my favorite. It's magical."
Those harboring a bit more ambition can undertake a small hike around the island. It's a little over three miles following the island's perimeter. On the backshore you'll see an open, rocky shoreline and a glinting sea. In the leafy, grassy harbor side, dollhouse-like Victorian cottages line narrow, tree-lined lanes. Walking the island is a great way to pass an hour or two, and you can reward your virtue with a pint of tasty ale at the Inn on Peaks Island while awaiting the ferry home.
If Peaks Island whets your appetite for island life, you can hop on the three-hour mail boat run to Cliff Island, the most distant of the Casco Bay inhabited islands. When nearing Cliff, watch for Chandler's Cove (ask a deckhand to point it out). Those large buoys dotting the cove? They mark one of four kelp farms operated by Tollef Olson. Taking the mail boat run is a "prime opportunity, and a pleasant way to pass a few hours," says Olson.
If you'd prefer to not be beholden to ferry schedules yet still want a taste of the sea, head up to Munjoy Hill, home to Sarah Richards' tea shop. That tower on the hill like an inverted ice cream cone? That's the Portland Observatory, built in 1807 and once used to watch for arriving ships. (Flags would be arrayed to let the city know which boats were coming in. Think of it as a proto-Twitter.) The unique, handsome building is now a museum. If the flags are flying, it's open to the public and well worth scrambling to the cupola for a panoramic view of harbor and city.
Closer to the water's edge there's the Eastern Promenade Trail, which loops along the northern edge of Munjoy Hill then tracks along the harbor on an old rail line before finishing up at the Casco Bay Lines, right at the edge of the historic Old Port.