A local islanders guide to visiting Casco Bay, Maine

A Local’s Guide to Casco Bay, Maine: From Cliff Island to Hidden Gems

I grew up on Cliff Island, Maine — a speck of land on the edge of Casco Bay, just far enough from Portland to feel like its own world. My parents were the teachers at the island’s one-room schoolhouse, and I was one of five students. We shared the same classroom, from kindergarteners to eighth graders, all of us bundled up in winter sweaters or bare-legged in the summer breeze.

In the winter, the island emptied out. The summer folks vanished, and the year-round population shrank to just a couple dozen. Snow turned the island into a frozen playground. I used to sled down the hill near the firehouse, the ocean wind freezing my cheeks. In the summer, the island pulsed with life again — boats filled the harbor, kids chased each other down the beach paths, and I’d fish off the dock for mackerel with a handline, hauling them in one after another under the setting sun.

These days, I’m one of the summer people. But Casco Bay still feels like home. Whether you’re visiting for a day, a week, or a season, here’s a local’s guide to exploring one of Maine’s most magical places.

🗺️ What is Casco Bay?

Casco Bay is a stretch of the Atlantic Ocean off the southern coast of Maine, dotted with over 200 islands — many of them uninhabited, others with tight-knit communities and summer cottages. It’s known as the Calendar Islands because there were once said to be one for each day of the year.

Some are connected to the mainland by bridges or ferries, while others are only accessible by private boat. Here’s a quick rundown of the ones worth knowing:

🏝️ The Islands You Should Know

Cliff Island

• The last stop on the Casco Bay Lines ferry, Cliff feels the most remote.

• Horseshoe-shaped, quiet, with sandy beaches and a tight-knit vibe.

• Bring a bike or walking shoes. No shops, just a small store (sometimes open), and lots of natural beauty.

• Must do: Walk the perimeter road at sunset. Fish off the dock. Say hello to the year-rounders.

Chebeague Island

• The largest populated island in Casco Bay.

• More amenities — a golf course, a hotel, beaches, and a couple of restaurants.

• Must do: Grab lunch at the Chebeague Island Inn, then explore the shoreline on foot.

Great Diamond Island

• More developed and popular with vacationers.

• Home to Diamond Cove, a former military base turned resort.

• Must do: Visit the artists’ galleries and dine by the water.

Peaks Island

• The most accessible and tourist-friendly, just a 20-minute ferry ride from Portland.

• Known for its artsy community, WWII museum, and biking loops around the island.

• Must do: Rent bikes. Visit the Umbrella Cover Museum (yes, that’s real). Get ice cream at Down Front.

Long Island

• Quiet and more residential, with wide beaches and wooded trails.

• Fewer tourists than Peaks, more locals.

• Must do: Explore South Beach or paddle a kayak around the shore.

Bailey & Orr’s Islands (Drive-on)

• Technically part of Casco Bay but connected by road, so easier access.

• Gorgeous coastal views, lobster shacks, and classic Maine charm.

• Must do: Visit Lands End on Bailey Island, eat lobster rolls at Cook’s Lobster & Ale House.

🛥️ Getting Around

• The Casco Bay Lines ferry is your lifeline — running year-round to the main islands.

• For adventurers: rent a kayak, take a mail boat tour, or charter a sailboat.

• No car? No problem. Most islands are walkable or bikeable.

🌊 What to Do

• Swim at Sandy Beach (Cliff Island) or Echo Bay (Peaks)

• Catch mackerel or striper off the rocks

• Explore old WWII forts hidden on the islands

• Watch lobstermen haul traps in the early morning

• Have a bonfire on the beach under a sky full of stars

🌅 Final Thoughts

Casco Bay isn’t about flashy attractions or packed itineraries. It’s about quiet mornings, salt air, and the kind of stillness you don’t find many places anymore. Whether you’re sitting on a dock eating a lobster roll or biking the back roads of Peaks Island, it’s hard not to feel connected to something simple and timeless.

And if you ever make it out to Cliff, wave to the schoolhouse — you might hear echoes of five kids laughing as they walk down to the dock, waiting for the ferry to bring the rest of the world back in.

Planning a trip? I can help you pick which island suits your vibe — just ask.