Taft & Rinlaub's Cruising Guide to the Maine Coast is a bit dismissive of Chandler Cove, which is bounded by Great Chebeague Island to the north and east, Little Chebeague Island to the west, and Long Island to the south. The guide complains that the cove is a bit too large and deep to be comfortable in anything but settled weather, but fails to note it is almost perfectly situated as a short-notice get-away hidey hole for people (like me) who keep boats in and around the city of Portland. Many times I have hopped aboard Lunacy very late in the afternoon, cast off her mooring, and have wafted north into Chandler for the night on the remnant of the day's southwest sea breeze. In the cove's upper bight there is perfect protection against any northerly nastiness, plus there are always more than a few empty moorings available. Most of these are plenty stout enough to stand up to any southerly wind you are likely to meet during the summer, even if you're sailing a 21,000-pound tank like Lunacy.
I anchored out in Chandler Cove, just east of Little Chebeague, for the first time during my recent Mini Solo Cruise. The wind was flat-out westerly, so the smaller Chebeague offered better protection than the larger one. Plus, I wasn't quite in a "pick-up-a-mooring" sort of mood. I dropped the hook in 30 feet of water at low tide (or about 40 feet at high tide), which is a little bit deep, but not too bad.
After working my way through a short punch list of boat chores the following day (including my temporary Gamage damage repairs), I went ashore to explore the island itself.
Unlike Great Chebeague Island, which is thick with both fancy summer houses and lesser permanent residences and enjoys year-round ferry service into downtown Portland, Little Chebeague is currently uninhabited. It is, however, often visited. During the summer, there is a steady stream of camp cruisers who paddle, sail, or motor out in small craft and pitch tents just behind the gravel beach on the island's east side. The beach itself is a real treasure trove if, like me, you are a connoisseur of beach stones. There is a pronounced tidal swale running through the heart of the beach and just either side of this you can find some interesting specimens.
On marching inland you'll find there are many ruined houses. As with beach stones, I am a great connoisseur of these. In my youth I spent many happy hours sailing a styrofoam Sea Snark from island to island in the mouth of the Kennebec River exploring ruined summer homes. So, again, I felt very much as though I'd stumbled across some treasure here.
Unlike the ruined houses of my youth, which were entirely uncategorized, most of those on Little Chebeague are now neatly labelled and historicized with plaques that give the names of the wealthy merchants and professionals who built and summered in them way back when.
Little Chebeague also once had a grand hotel on it, but this (as seems to have been common with shoreside hotels in Maine during the late 19th century) burned to the ground and little trace of it remains. Fortunately, no lives were lost in the blaze. Ironically, during World War II the U.S. Navy inhabited the island and, among other things, gave lessons in firefighting. This is what the very large rusty steel box on the island's east side (the most prominent landmark, by far, for anyone examining the island from Chandler Cove) was used for.
If you do hike inland on Little Chebeague, be warned that there is lots of poison ivy and more than a few ticks. Stick to the trails, wear bug spray, and do a careful tick check after returning to your boat.
While anchored off Little Chebeague, I also encountered some cool birds. In the late morning, as I worked on my list of jobs, I saw a bald eagle sweep by overhead. That evening some osprey came out and fished successfully for fish in the cove. The following morning my spreaders were alive with swallows.