Overview of Casco Bay Islands
Lobster, lighthouses, and quaint scenery await on the Casco Bay islands off the coast of Maine.
From national parks to sandy beaches, Maine is a destination with no shortage of picturesque spots to explore. Moreover, 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; however, where to begin when the Calendar Islands — so named because there’s at least one for every day of the year — are so plentiful? Consequently, 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, rich with dining options, bars dotting cobblestone streets, and sleek accommodations.
Take the Mailboat
The best way to access the islands is via the Casco Bay Lines mailboat, a true working vessel that makes deliveries to Little Diamond, Great Diamond, Long, Cliff, and Chebeague islands. The boat runs three times a day, dropping off (and picking up) at designated stops. It departs from Maine State Pier in the heart of the waterfront, providing a scenic view of the city skyline with the Portland Breakwater Light lighthouse jutting from the shoreline.
The captain narrates the trip for passengers, pointing out unique features of each island as you approach. Green and verdant, the islands are dominated by trees that hide some homes while showcasing others. Some houses are best viewed from the water, offering a glimpse into the lives of locals you’d never otherwise witness.
At each dock, you have the opportunity to hop off and wander. Or, if seclusion is what you seek, consider staying at an inn, camping under the stars, or renting a private home for the family.
Bike an Island (or Two)
Summer Feet Cycling offers guided bike tours, providing an inside view of island life with visits to still-operating one-room schoolhouses and quaint general stores selling 50-cent coffee.
Load your bike on the mailboat and pedal around Chebeague Island, a peaceful area where locals sell vegetables at roadside stands. The sunny Chebeague Island Inn provides a delightful lunchtime respite on the back porch, with dishes featuring fresh lobster salad or succulent Casco Bay mussels.
Next, 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, and estates fronted by manicured lawns, as well as fields of wild purple lupines stretching toward the sky.
Spend the Night in Portland
If you’re looking for the best of both worlds, explore the islands on a day trip while making Portland your home base. Portland boasts a working waterfront laden with bright red buoys and lobster traps stacked in a Jenga-like fashion.
Pick any street in this walkable city, and you’ll discover a variety of restaurants, bars, shopping, and vibrant nightlife options. Luke’s Lobster is a charming wooden shanty in the heart of the Old Port, where you can watch lobstermen pull in their bounty while savoring the fruits of their labor. The creamy lobster roll and New England clam chowder are quintessential Maine dishes not to be missed.
If you wish to dress for a memorable dining experience, don’t miss Evo Kitchen + Bar for artisanal cocktails, locally sourced dishes that rotate daily, and an optional tasting menu with wine pairings.
Stroll the streets and duck into local dive bars like Munjoy Hill Tavern, known for its generous pours. Alternatively, enjoy drinks at outdoor cafe tables along cobblestoned Wharf Street for excellent people-watching opportunities.
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 directly to your room.
In summary, a trip to Portland and the Casco Bay islands allows you to absorb the island vibes while enjoying the vibrant heartbeat of a thriving city.
