Just like the Kentucky Derby that's held up the road, The Pendennis Club is a true classic. Named to the National Register of Historic places, this private, member's only club has been in operation since 1881, and moved into its current, 78,000 square-foot clubhouse in 1928. Inside, you'll find a historic ballroom on the third floor, two bars, a barber shop, library, athletic facilities, and plenty of marble, natural walnut, and red-carpeted and teak wood floors. Need more motivation? The Pendennis was also the birthplace of the Old Fashioned, making it quite possibly the birthplace of the modern cocktail itself.
It might be hard to get in, but if you're a cigar lover, it's well worth it. The Vertigo Club is a private place for enjoying fine cigars — and maybe even some poker — in the company of like-minded individuals. Included in your membership is a temperature and humidity-controlled Spanish Cedar cigar locker with your own key and name plate, a subscription to Cigar Aficionado, 7-day-a-week access via key card, free Wi-Fi, access to exclusive trips and events, and, optionally, your own custom-tailored smoking jacket. The downside? membership is limited to just 150 and is only offered by invitation — so good luck, and be sure to invite us for a smoke if you make it in. [Scouted by Sam]