Martha's Vineyard
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Right in Edgartown, you'll find some lovely, gay-friendly accommodations, including the Shiverick Inn, a grand Second Empire mansion whose romantic rooms have sumptuous Victorian bedding and antiques, and the Hob Knob Inn, a handsome and well-run 18-room Gothic Revival property with unfussy but attractive furnishings reminiscent of an English country house.

Just south of Edgartown, with a fantastic location on Katama Beach, the Winnetu Oceanside Resort makes for a delightful retreat, especially if you've got kids in tow - in fact, this is one of the best gay-friendly, family-oriented properties on the East Coast. The property consists of a luxury inn with one- to four-bedroom suites as well as a cluster of three- to five-bedroom town homes. The resort offers dozens of diversions to keep you busy, from bike tours to whale-watching trips, and there's a world-class tennis facility on-site. Also, Winnetu's restaurant, Lure, serves some of the most inventive seafood fare on the island, such as butter-poached lobster with soft cornbread, roasted corn, and fava beans. This upscale resort draws mostly families with kids in summer, but it's more of a couples destination during the mellower spring and fall shoulder seasons.

Outdoors enthusiasts should stick to the western side of Martha’s Vineyard (referred to locally as Up-Island). Here you can sample fresh lobster dockside in the picturesque fishing village of Menemsha (a great place to stop for a casual seafood lunch - just try one of the restaurants on the pier), or admire ocean views from the lighthouse and multihued clay cliffs at Aquinnah (formerly known as Gay Head). Below the Gay Head cliffs you will find, appropriately, a popular nude beach with a moderate following among gays and lesbians - when you hit the beach, turn right, and walk all the way to the end (about 30 minutes). A tip: If you'd like to check the scene out in advance, drop some change into one of the coin-operated magnifying lenses near the base of the lighthouse - it's the closest you'll come to a peep show on Martha's Vineyard.

In the Up-Island community of West Tisbury, set back on a wooded property slightly off the beaten path, you'll find the island's most opulent gay-owned property, Lambert's Cove Inn. Innkeepers Scott Jones and I. Kell Hicklin have restored what had been a somewhat dowdy country hotel into a sophisticated boutique inn with smartly furnished rooms set among three buildings. Amenities include DVD/CD players, high-speed Internet, and plush Egyptian cotton linens, and some rooms have private screened-in porches. A sunken pool in back is the perfect place to while away a hot afternoon. And in the evening, the inn's elegant dining room serves outstanding contemporary American fare, such as braised veal cheeks with sweet corn, English pea risotto, and a Madeira wine reduction. It's the definitive venue for a relaxing Martha's Vineyard hideaway.

Andrew Collins is the author of Fodor's Gay Guide to the USA and as well as numerous other guidebooks.