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A Well-Heeled Horse Racing Fan’s Guide to the Kentucky Derby

As the thoroughbreds head into the first leg of the Triple Crown, the sport of kings should be enjoyed like... well, a King or Queen.

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They don’t call horse racing the “Sport of Kings” for nothing.

Sure, everybody’s betting on the same pot of gold—that’s literally the meaning of “parimutuel“—but to truly enjoy horse racing at its finest, it helps to be ultra-wealthy.

The reason? Unless you’re an owner or a degenerate gambler, horse racing isn’t just about the hefty payouts for wins, places, and shows (and exactas, trifectas, and pick-sixes); it’s about the overall experience. And while the underdressed gawkers stand trackside, waiving their rolled up programs like makeshift riding crops, chomping on overpriced hotdogs and guzzling cheap beer, the ones who really get the best view will be sitting far, far away, in the lap of luxury. That experience will include a billowing cigar, an expertly crafted cocktail—a Mint Julep, maybe—and the highest-quality cuisine available.

So while the rest of the internet is bleating on about what funny hat to wear or which horse will earn a gambler $4.34, RealClearLife has dug deep to provide you with the best overall experiences on each leg of the Triple Crown and beyond.

Billionaire's Guide to Horse Racing
The famed spires at at Churchill Downs on Kentucky Derby Day May 5, 2007 in Louisville. (A. Messerschmidt/Getty Images)

 

Kentucky Derby (May 6)
And You’re Off: If you’ve ever had the pleasure of visiting Louisville, Kentucky (pronounced LOO-vull by the natives), you are no doubt aware of just how much sports mean to this city. For one, there’s the college basketball scene. There’s also the Louisville Slugger bat factory and museum, which has been feeding hungry hitters in the majors for decades. And of course, there’s Churchill Downs, the famed horse racetrack, where the Kentucky Derby is run annually.
The Inside Scoop: With the Derby right around the corner, a distinguished aficionado really needs to work connections to find the best luxury options onsite, as most are probably unofficially sold out. But just like Saratoga (see below), Churchill Downs has enough cachet in and of itself to offer patrons an incredible experience—wealthy or not—anywhere on the track’s grounds. At the moment, the only luxury ticket package still available is the balcony area of the Stakes Room. What comes with that package? Premium open bar from 8 a.m. to 6 p.m., gourmet food buffets from 11 a.m. to 4 p.m., and everything one needs to put his or her money on the right horse in the right race. Tickets start at $5,000/person (reserve one here).
Secret Sauce: Show up two days early and grab tickets to the Fillies & Lilies Party at the Kentucky Derby Museum, which will feature live music from country great Clint Black. VIP ticket-holders get access to a premium open bar; private bourbon lounge (hopefully, they have some Pappy Van Winkle); heavy appetizers; a reserved table for four in the second row; and private cocktail servers. General Admission tickets go for $599 a pop. But you know you want VIP access. That’ll cost $999/person. Reserve a spot here.

Billionaire's Guide to Horse Racing
The field heads into the first turn during the 141st Running of the Preakness Stakes at Pimlico Race Course on May 21, 2016 in Baltimore, Maryland. (Rob Carr/Getty Images)

 

Preakness Stakes (May 20)
And You’re Off: Just a few weeks after the Derby, there’s the opportunity to jet over to Pimlico Race Course in Baltimore, Maryland, home of the Preakness Stakes—or the second leg of the coveted Triple Crown (the last horse to accomplish the rare feat was American Pharoah in 2015). Although the most happening party’s in the infield—the area between the oval track and the track itself—unless you want your finest clothes to be ruined (or get waterlogged, in the event of inclement weather), it’s best to look for a dryer, more esteemed solution like the one we’ve mapped out below.
The Inside Scoop: While you sip at your bourbon-based Black-eyed Susan, the official cocktail of the Preakness, it’s best to hold down the fort at the Turfside Terrace, which is the best value and view for the money. Running $450 per person for the day, the ticket includes trackside seating under an awning, with full view of the home stretch and finish line (there are also two Jumbotrons, in case the spectator in front is 6-foot-9). The deal also includes a gourmet luncheon, beer and wine, a souvenir program, live entertainment, and of course, access to private betting machines. For more information, click here.
Secret Sauce: A more refined visitor doesn’t have to avoid infield just because of the more liberal attire and libation options. If you do wander into the party, there are some cleaner, less pedestrian options to enjoy. The VIP-like Mug & Vine Lounge tickets cost $155 per person, and get you in front of the live entertainment in a private corral (country stalwart Sam Hunt co-headlines), with added amenities such as wine, private restroom trailers, and jumbo screens. Order tickets here.

Billionaire's Guide to Horse Racing
The field loads into the starting gate for 148th running of the Belmont Stakes in Hempstead, NY. (Joshua Sarner/Icon Sportswire via Getty Images)

 

Belmont Stakes (June 10)
And You’re Off: The last stop on the Triple Crown locomotive is the Belmont Stakes, which takes place on Long Island in Elmont, New York. Of course, New York City is too close by not to do a run-through, and there are countless ways to enjoy the Big Apple in the summer: We’d suggest a Yankees game or Hamilton on Broadway, but there are countless other options. There’s also loads to do out on Long Island as well, including exploring the North Fork wine region and of course, the Hamptons. But a plan is essential for race day, as traffic could easily put a damper on the day if the travel-time is underestimated.
The Inside Scoop: There are quite a few options for luxury accommodations at the track itself, but your best bet is the ultra-exclusive, third-floor luxury suites tied to the temperature-controlled Diamond Room at North Shore Terrace. Ascending a private escalator, you’ll get premium views of the track below in an air-conditioned box (handy in a humid New York City summer). This also comes with access to a number of additional amenities, including a fully stocked bar, live entertainment, celebrity chef, jockey meet-and-greets, and other perks. This’ll run about $1,100/person.
Secret Sauce: If you want to rock out the night before the big race, we’d suggest catching Mike DelGuidice & Big Shot, who are playing the track and all your favorite Billy Joel hits. Why the recommendation to watch a cover band? The catch here is that DelGuidice is actually on tour with the real Billy Joel, who heard his tribute band and hired him. (If you want to make it a really long weekend, you can catch the real Billy Joel at MSG on June 6.)

Billionaire's Guide to Horse Racing
Arrogate No. 1, ridden by Mike Smith, wins the Travers Stakes on Travers Stakes Day at Saratoga Race Course on August 27, 2016 in Saratoga Springs, New York. (Dan Heary/Eclipse Sportswire/Getty Images)

 

Saratoga (July 21–Sept. 4)
And You’re Off: About 3.5 hours north of New York City, Saratoga Springs is a quaint upstate New York town—not so dissimilar from some of the higher-end resort locales on Long Island (save for the lack of beaches). Once known for its mineral spas and itinerant summer residents, Saratoga now caters almost exclusively to the upscale, many of whom have moved there year-round. The town’s biggest draw, besides Skidmore College, is Saratoga Race Course, which opened in 1863, and is one of the oldest horse racing tracks in the country. The top race of the year is the Travers, which occurs several weeks after the third leg of the Triple Crown is over, and usually includes the Derby winner among the top-level competitors.
The Inside Scoop: This writer is a little biased here, having grown up in Saratoga, but that gives RealClearLife an edge: An insider’s knowledge of all the secret spots. For those that wish to get the all-in experience, suggest checking out real estate in the area (either buying or renting a house immediately), or checking into one of the luxury hotels (the majestic, 19th-century Adelphi Hotel in downtown Saratoga, will reopen July 1 after extensive renovations). For the best experience at the track itself—really, regardless of income level—RCL‘s suggestion is to inquire about box seating. The track still has that “classic” feel (think: Fenway Park or Wrigley Field), so a visitor needs to experience it firsthand to get the full experience. It has the best line of sight to the action … at least among the best-dressed folks. There’s  table service, TV monitors, and maybe even a little visit from Lady Luck. (For those looking for a little more privacy, there’s always the luxury suites.)
Special Sauce: Make sure not to miss breakfast at the track. It’s not such a big secret anymore, but it’s still worth the experience. More here. If you’re a fan of celebrity sightings, we’d suggest grabbing some bar real estate after hours at 9 Maple Ave., a jazz club that has a sprawling whiskey and martini menu. On the weekends, though, it can get crowded, and Travers weekend, it’ll be shoulder-to-shoulder.

Billionaire's Guide to Horse Racing
(Courtesy of Del Mar)

 

Breeders’ Cup (Nov. 3-4)
And You’re Off: Although technically not part of the Triple Crown circuit, the Breeders’ Cup attracts the top talent from around the globe and usually features the recent Triple Crown (or leg) winners. The two-day event tends to shift around from track to track on an annual basis, and this year, Del Mar Racetrack in Del Mar, California, has the honors. Aside from the beautiful, always-summer weather in California, Del Mar itself has quite a bit to offer guests of a certain ilk.
The Inside Scoop: A rep at the track told RCL that the height of luxury for Breeders’ Cup weekend can be had at Del Mar’s Trackside Chalet, which runs about $2,000 per person. At the chalet, patrons will get unrestricted views of the race—and a separate outside viewing platform—reserved seating in a climate-controlled area, gourmet food and beverages (upgrade that to an open bar for $200), and jockey appearances.
Secret Sauce: For those who want to jump on next year’s Kentucky Derby, make sure to catch the Del Mar Futurity, which will help predict the following year’s racers. Check out the track’s stakes schedule here.

To get in the mood, watch the running of last year’s Kentucky Derby below.