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VISIT PORTLAND / 25
ISLAND PERSPECTIVE
PEAKS
A hip, quirky vibe emanates from the thriving artist community on
Portland’s commuter island. Visit shops, cafes, and museums, and
circumnavigate the perimeter by bike or golf cart.
GREAT DIAMOND
Prim and proper, preserving tradition and embracing modern day
grandeur. Diamond Cove, an exclusive private community, has its
own ferry stop, an upscale hotel and fine restaurant.
LITTLE DIAMOND
The younger sibling, it is only slightly more rebellious. No commerce
exists on this quiet island that’s only inhabited during the summer.
BAILEY
Historic and stoic, Bailey’s has been one of the best kept secrets for
250 years. Enjoy a quintessential Maine lunch with panoramic views.
LONG
A vibrant, independent community, sporting one of the best beaches
on the bay. Sparse facilities for visitors, so bring your own bikes or
walk from the ferry landing with beach chairs in tow.
CHEBEAGUE
A throwback to simpler times, Chebeague showcases timeless
charm with its Greek Revival homes and restored 1920’s hotel
adjacent to a 9-hole golf course.
CLIFF
Small, yet mighty, Cliff’s natural beauty speaks for itself. The only
year-round island in Casco Bay with all unpaved roads, much of its
property is in conservation land, protecting its rural atmosphere.
PHOTOS, FROM TOP: COURTESY JAMES CHATMAS/MAINE DRONE; COURTESY CASCO BAY LINES
Casco Bay’s Calendar Islands
dot Portland Harbor
HOP OFF
Casco Bay Lines provides ferry service to seven Casco Bay Islands, including
a short cruise up the coast to Harpswell. Each island has its own distinct
personality—pick the one that’s right for you and start exploring.