These Little-known Islands in Maine Offer a Charming Getaway — With Delicious Seafood and Picturesque Views

Lobster, lighthouses, and quaint scenery await on the Casco Bay islands off the coast of Maine.

Flowers overlooking the water in Casco Bay Islands
Photo: Rebecca Deurlein

From national parks to sandy beaches, Maine is a destination with no shortage of picturesque spots to explore. And off the state's southern coast, on the little-known islands of Casco Bay, even more beauty awaits.

While craggy cliffs and crashing waves dominate the Maine coastline, the delightful islands of Casco Bay — just a boat ride away from Portland — offer a gentler counterpart, with soaring pine, oak, and maple trees, homes nestled among lush gardens, and docks with hammocks peeking out from dense foliage.

It's a version of island life you'll want to explore, but where to begin when the Calendar Islands — so named because there's at least one for every day of the year – are so plentiful? Consider starting with one or more of the habitable islands, where you can spend a day exploring, biking, and swimming.

Here's our guide for easily navigating the Casco Bay islands, where you'll find a range of dining options, bars dotting cobblestone streets, and sleek accommodations.

Take the Mailboat

Houses on the water in Casco Bay Islands
Rebecca Deurlein

The best way to access the islands is via the Casco Bay Lines mailboat, a true working boat that makes deliveries to Little Diamond, Great Diamond, Long, Cliff and Chebeague islands. The boat runs three times a day and drops off (and picks up) at designated stops. It leaves from Maine State Pier in the heart of the waterfront, so your first view will be the scenic city skyline fronted by the Portland Breakwater Light lighthouse jutting from the shoreline.

A sign on dirt path in Casco Bay Islands
Rebecca Deurlein

The captain narrates the trip for passengers, pointing out the unique features of each island as you approach. Green and verdant, the islands are dominated by trees that hide some homes and showcase others. In fact, some houses are best seen from the water, providing a glimpse into the lives of locals you'd never otherwise witness.

At each dock, you have an opportunity to hop off and wander. Or, if it's seclusion you're after, stay at an inn, camp under the stars, or bring the family and rent a private home.

Bike an Island (or Two)

The main town in Casco Bay Islands
Rebecca Deurlein

Summer Feet Cycling offers guided bike tours, providing an inside view of island life with visits to the still-operating one-room schoolhouses and general store with 50-cent coffee.

Load your bike on the mailboat, then pedal around Chebeague Island, a quaint and quiet spot where locals sell vegetables at roadside stands. Perched on a hillside with a green, rolling lawn that disappears into the bay, the sunny Chebeague Island Inn provides a midday respite for lunch on the back porch. Refuel with a salad mounded with lobster or succulent Casco Bay mussels.

Buying flowers in Casco Bay Islands
Rebecca Deurlein

Then, head to Cousins Island, where you can bike from end to end, stopping to take photos of the Cape- and Victorian-style homes, historic churches, estates fronted by manicured lawns, and fields of wild purple lupines stretching toward the sky.

Spend the Night in Portland

Lobster crates in Casco Bay Islands
Rebecca Deurlein

If you're looking for the best of both worlds, explore the islands on a day trip and make Portland your home base. Portland is anchored by a working waterfront laden with bright red buoys and lobster traps stacked in a Jenga-like form.

Pick any street in this walkable city, and you'll find restaurants, bars, shopping, and nightlife. Luke's Lobster is a wooden shanty in the heart of the Old Port, where you can watch lobstermen pull in their bounty while devouring the fruits of their labor. The creamy lobster roll and New England clam chowder are quintessential Maine.

Outdoor dining on a cobblestone street in Casco Bay Islands
Rebecca Deurlein

If you want to dress for dinner, don't miss Evo Kitchen + Bar for artisanal cocktails, locally sourced dishes that rotate daily, and the optional tasting menu with wine pairings.

Stroll the streets and duck into dive bars like Munjoy Hill Tavern, home of the heavy pour. Or, pop in and out of the bars lining the cobblestoned Wharf Street, and enjoy a few drinks at outdoor cafe tables for the best people-watching.

Just a short walk from all the action, retreat to The Francis, a recently renovated historic mansion that now serves as a boutique hotel. It offers spa services, private decks, and freshly made breakfast sandwiches from the adjacent bakery, delivered right to your room.

In other words, with a trip to Portland and Casco Bay, you can both absorb the island vibes and still enjoy the heartbeat of a vibrant, thriving city.

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