Begin with a stroll among the beautiful Spanish Colonial-style buildings of Country Club Plaza, which comprises 15 blocks of upscale shopping and is also home to a pair of superb cultural institutions, The Nelson-Atkins Museum of Art and Kemper Museum of Contemporary Art. At the latter, Café Sebastienne makes an excellent lunch option, serving well-crafted contemporary American food in a sunny atrium setting. Swing by Cucina della Ragazza (a cozy Italian restaurant) and another nearby gay favorite, Cafe Trio, whose sunny outdoor deck affords perfect views of Country Club Plaza.
Just a stone’s throw away, KC’s Westport neighborhood may be the oldest district in the city, but it’s also quite welcoming to people of all walks. Corner Restaurant (a beacon for brunch) is a delicious places to check out. Also located in the area are gay-owned KC institutions and watering holes McCoy’s, The Foundry and Beer Kitchen. If you’re in the mood for shopping, duck in to Wonderland, chock full of clothing and gifts that are full of personality.
From here, head north on Main Street through Midtown (note that you'll pass a couple of popular neighborhood gay bars, Buddies and Sidekicks Saloon, which you might want to keep in mind for later in the evening) and down the hill to the Crossroads Arts District. What was mostly an industrial tract of warehouses has flourished in recent years with art galleries, distinctive shops, and stylish restaurants. To get a feel for the area, browse stores like Birdies, Peggy Noland, Retro Inferno and Studio Dan Meiners.
Closer towards Crown Center (home to Hallmark Cards), the restored 1914 Union Station contains theaters, traveling exhibits, restaurants and Science City interactive museum. Walk north for several blocks on Main and its cross streets until you reach the Interstate 670 underpass - just west of here, at Broadway and West 16th Street, you'll see the stunning new Kauffman Center for the Performing Arts, home to ballet, symphony, opera and more.
If you're seeking an afternoon snack or early evening cocktail, drop by the Kansas City branch of the dishy gay restaurant chain, Hamburger Mary's (it's "Maryoke!" night on Saturdays), or pop inside Mildred's Coffeehouse, which serves great espressos and is a fun stop for people-watching. If you're ready for dinner at this point, Crossroads staples like Extra Virgin, Michael Smith Restaurant and The Rieger are favorite gay-date spots.
Walk just north across the underpass to discover downtown's vibrant Power & Light District, home to more than 50 bars and restaurants. Most of the city's other top gay nightspots are in Midtown and Westport, which are an easy 10-minute drive south. A good places to start is in Westport at the stylish Bistro 303, a great bet for martinis and also an excellent choice for casual but upscale dining. By midnight on a Saturday, most dedicated revelers have found their way to Missie B's, Kansas City's largest and most famous LGBT nightclub.