Chebeague Island Inn: Maine’s Casco Bay Greek inn

Beaches, kayaking, and relaxation at the tip of New England’s northernmost state.

Escape: They say no man is an island, but, last time we checked, “they” seem to have no problem with man doing some serious relaxing on an island. Chebeague Island, located in Casco Bay, is a short ferry ride from Portland, but at times feels like the edge of the world—a very friendly edge of the world, where the inhabitants wave to each other on the roads regardless of acquaintance (or lack thereof). Aside from a post office/gift shop, a convenience store, and a part-time clam shack, the island is meant to be enjoyed on its own terms. The Chebeague Island Inn is the center from which this warmth radiates. Think an ultra-cozy parlor complete with blazing fireplace; a cocktail menu and bar perfect for quieting corporate demons; and a porch that couldn’t be more picture-perfect.

Unplug: This 1920s Greek Revival inn is really the only game in town when it comes to lodging, and that’s just fine. Retreat into one of its 21 unique guest rooms, furnished with cozy queen beds and a sunny décor that brings the sea inside. Enjoy walks on the island’s many beaches, kayaking, and lots of reading by the fire, broken up by excellent meals at the Inn’s upscale (and a bit pricey) restaurant. (Note: Get the butter-poached lobster. Get it for every meal. Pack as much in as you can; it’s that good.) And to cut down on the distractions, the rooms are sans TVs and landlines. Oh, you’ll relax, all right.

Smartphone Substitute: If you’re worried about becoming too well rested/read, consider rousing yourself for some play. Lawn games are available to all guests, as are L.L.Bean bicycles to take around the island, and a nine-hole golf course abuts the property ($30 fee for guests of the Inn or restaurant). The Inn can arrange kayak tours of the bay, and a ferry trip back to the mainland is well worth it for a tour of the bay on one of the fantastic wooden schooners of Portland Schooner Company ( The island is eminently walkable; a full circuit takes up an afternoon, leaving you plenty hungry for lobster in the evening, and thirsty for the Inn’s popular and addictive Chebang-ade (Double Cross Vodka, pomegranate juice, and lemon juice). Sunsets are best viewed on the porch, with said ade in hand and a plate of the Inn’s mind-blowing Devils on Horseback (those would be blue-cheese-stuffed dates wrapped in bacon).

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The Details: Chebeague Island Inn, 61 South Rd, Chebeague Island, ME (207) 846-5155; Low season rates start at $210, and peak season starts at $370/night based on double occupancy. The Inn offers a wide range of special packages, including Tee Time: two nights’ lodging, gourmet daily breakfast, afternoon tea, nine holes of golf per person per day, and “19th hole” post-round cocktails. WiFi is available and free to use, if you really must.

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