Arrive at LaGuardia Airport in NY and take the M60 bus to the 125th Street station, where you can catch the A train to Columbus Circle.
Check in at the Salisbury Hotel on West 57th Street, a simple, affordable hotel with large rooms two block from the outdoor adventures of Central Park, and seven blocks east from the gay bars of Hell's Kitchen.
Drop off your bags and walk west to Bike and Roll Bicycle Rental, where you can rent bicycles-including mountain and tandem bikes-with helmet, lock, and map for rates starting at 14USD per hour. This is one of the best ways to see the over 800 acres of the park. Be aware that there will be many hawkers trying to rent unlicensed bikes; Bike and Roll is the only company with a license, so stick with them.
After the bike tour, drop off your bikes and hop on the subway downtown to 7th Avenue in Chelsea for lunch at Elmo's, a gay-owned restaurant in the middle of this well-known LGBT neighborhood serving modern American food-try the bison burger or watermelon-mozzarella salad-in a bright, retro interior. The basement of the restaurant turns into a lounge cabaret at night, so if you like the vibe, come back for the after-dark scene.
From here a short walk west will take you to the High Line, one of the most original and popular urban walking spots in Manhattan. Built on a repurposed section of abandoned elevated railway, this stretch of about a mile and a half is creatively landscaped and guaranteed to be an airy, refreshing experience. The southern exit of the High Line brings you out just a few blocks north of the West Village, a perfect way to continue your urban hike through the landmarks of this historic gay neighborhood.
Have a drink at The Stonewall Inn or Julius', admire the sculptures in Christopher Park commemorating the birth of the gay rights movement, or stroll along the Christopher St. Pier, once a famous gay cruising spot and today a gathering place for LGBT youth. For happy hour head to lesbian favorite the Cubbyhole Bar on West 12th Street, where the kitschy décor, upbeat bartenders, and cheap beer on draft are the perfect setting to mingle with the many locals who call this their drinking spot. It's a small space, so best suited to groups of four or less.
Dinner should be seven blocks south at Annisa-which means "women" in Arabic-one of the best restaurants in the city. Lesbian-owned and operated, Chef Anita Lo serves an inventive French-Asian fusion menu while her partner Jennifer Scism runs the front of house. The menu changes seasonally, but the chef has a particularly genius touch with fish, so order it if available. From here it's a short trip uptown on the 1 train to Columbus Circle and back to the hotel.