While Provincetown, located at the extreme tip of Cape Cod, Mass., is not technically an island, its longstanding status as a gay mecca certainly makes it feel like a secluded land mass.
Open to any and all LGBT people all times of the year, a particularly popular event during the summer season is the annual Bear Week, when "woofs" fill the air and the hairy (but friendly) men sniff out fresh meat. Restaurants run out of food, calorie-free items languish on shelves, and any skinny boys are deemed "chasers." Men of all ages, sizes, and furriness relax, free to wander up and down Commercial Street drifting from the Tea Dance to the cafes.
Start with brunch at Relish; don't miss the cottage egg sandwich and a cupcake (or two). Take your plunder and hike over to Herring Cove, where your breakfast seat has an unobstructed Atlantic view. Once you've gotten your fill, rejoin the hirsute pursuit at the Atlantic House Tea Dance before getting sweaty at Purgatory, a steamy basement club. Then finish the night at Spiritus Pizza. By 2 a.m., the throngs will be ravenous enough that you can order a pie (stick to cheese for simplicity), eat a slice, and trade the rest for cute, furry men's affections -- if that's your thing.
The next day, lounge aimlessly at the Provincetown Inn's pool and in the evening, learn about combustion at a friend-filled bonfire at Race Point Beach, next to the lighthouse. Just be sure to make like that most famous of bears, Smokey: Follow the rules and get a permit in advance.