Let the Games Begin

The biggest and best spectator sports events are draped in rich traditions, but many of those crashed to a halt during the 2020 pandemic season. For instance, the first Saturday in May has belonged to the Kentucky Derby since 1875, making it the longest continuously held major sporting event in the United States—until last year, when the “Run for the Roses” was first postponed, then held without fans, devoid of all the pomp, circumstance, and fancy hats. The Masters was similarly pushed back and held fanless, leaving the world’s best golfers befuddled when they reflexively turned to wave at crowds before remembering they were all alone.

Now sports are back, and travel is returning at a blistering rate. All options from safaris to Machu Picchu are high priorities, with travelers realizing that life is short, the future uncertain, and those “someday I want to see that” moments are better not put off. This is especially true for sports, which has so many “musts,” and some that are held just every two or four years.

Sports travel is about a lot more than just getting a coveted ticket. Most events are bookended with parties, festivals, sightseeing, and entertainment that make the actual 60 minutes of action even more special. In the case of the Derby, it is days of balls, VIP stable and bourbon tours, the Kentucky Oaks the day before, after-parties, and milliner visits that make the trip so much more than the two-minute sprint.

Former TV sportscaster turned luxury travel adviser Chad Clark made a multiyear pilgrimage to personally see every top event or championship in every major sport worldwide, from the Rugby World Cup in South Africa to the Olympics to Heavyweight Championship bouts, the Masters, Wimbledon, and eclectic events like Siena’s Palio alongside the World Series, Final Four, and Super Bowl. Now his eponymous Chad Clark Travel Ventures (chadclarktravel.com), a Virtuoso agency in Phoenix, helps clients enjoy these in high style, and he has very strong opinions.

“Football is America’s most popular sport, so the Super Bowl is on top of many bucket lists,” he explains, “but it’s not even in my top 10. It’s so corporate, so expensive, and your team probably is not playing. I prefer events that are not just two teams, where half the audience always leaves bummed out.

“For the World Series or NBA Finals, you really want to go to Game Seven, but most years there is no Game Seven. The events that go on for days or weeks and draw international crowds are much more fun. That’s why I love the Olympics (Summer or Winter), and I’d put the Kentucky Derby, Masters, Monaco Grand Prix, and Royal Ascot in my top five, but it’s so hard to pick. The Indy 500, FIFA World Cup, and Rugby World Cup are tremendous as well.

“But whichever you do, plan on being in town two to three days early because that’s when all the fun happens: the galas, the strawberries and cream. The first time I went to the Indy 500 I missed a lot by not going early. You also need access to the VIP or behind-the-scenes events, to be on a yacht in Monaco and attend the Ferrari party—that’s what makes it amazing. When I plan a trip for clients, I do it as if I were going myself,” says Clark, “Whatever the event, once the horn sounds to start the game, your trip is essentially over.”

Location may also drive an event up your short list. If you dream of the Super Bowl, wait for a marquee host like New Orleans or Phoenix, rather than far removed venues like Dallas or New Jersey’s Meadowlands. If you love tennis, Wimbledon is the ultimate, but if you have always dreamed of visiting the Great Barrier Reef, maybe the Australian Open is a better Grand Slam event for you. “When the World Cup was in South Africa, clients used it as a reason to see Victoria Falls or go on safari,” says Duane Penner, vice president of Roadtrips (roadtrips.com), a luxury sporting event travel specialist. “I always tell people that the real excitement is all the events around the event. Seeing sports live is spectacular but running into a past legend of the game at a restaurant, or staying in the same hotel as the team, that’s the story you are going to be telling for years.”

Fans may have a favorite sport, but the most fun events might be outside your box—you don’t need to have ever seen a race to get swallowed up in the feverish fun of the Derby or Grand Prix. There are travel specialists who do nothing but high-end sports travel, and these are their most popular events.

KENTUCKY DERBY

Takes Place: Late April

When to Book: The previous April

The Saturday Derby caps a two-week festival and two full days of hoopla at Churchill Downs. Friday is Kentucky Oaks day, just as festive as race day, with the same hats and fancy attire but featuring a different signature cocktail: the vodka-based Oaks Lily (Derby Day is all about Mint Juleps). Most luxury packages include the same seats for both days, so the Oaks is a good dry run. There are several days of private balls beforehand, plus after-parties, the most important of which includes the championship presentation inside the museum at Churchill Downs. Specialists can provide tickets to all of these, as well as local tours, and race-day access to one of several private in-track hospitality lounges with their own betting windows, food, and free-flowing adult beverages.

Alternative: Clark highly recommends the races at England’s Royal Ascot, which have similar fancy dress and an electric atmosphere. “For the well-heeled, it is just a fantastic event, and it’s the best time to be in the UK. You also have the Chelsea Flower Show, the Henley Royal Regatta for rowing, and the Wimbledon Tennis Championships.”

OLYMPICS

Takes Place: Every two years

When to Book: One year out

It’s relatively easy to get tickets and accommodations through specialists, so it’s worth waiting for a great venue. Fewer Americans may be interested in the 2022 Beijing Winter Games than, say, 2026 when they will be held in Milan and Cortina, combining the world’s biggest sports gathering with universally beloved Italian travel, including a great ski vacation option. The spectator-free 2020 Tokyo Summer Games would have been a fantastic trip, but there’s another world-class luxury travel destination to look forward to in 2024, when the Olympics revisit Paris after 100 years. “You can add on cultural tours as well as culinary delights,” says Chris Pronger, president of Well Inspired Travels (wellinspiredtravels.com), a top provider of VIP access for Protravel International’s Global Travel Collection. Pronger is a Canadian former professional ice hockey defenseman who was a senior adviser of hockey operations for the Florida Panthers of the National Hockey League.

MONACO GRAND PRIX

Takes Place: Late May/early June

When to Book: As little as a month out

The entire municipality is transformed into a big fancy party. There are two strategies: Stay in the city and drink it in 24/7 or stay outside, in Cannes or Cap Ferrat, and split the festivities with escapist luxury. “Clients could be a guest of team Ferrari with pit seating at Red Bull Paddocks, but we also have exclusive access to The Automobile Club of Monaco that is a transformed art studio overlooking more of the course than any other vantage point,” says Sandy Garcia of Protravel International (protravelinc.com). “For the Amber Lounge invite-only party, we simply slip an invitation under our clients’ doors and they get to take part in the most exclusive party of the year. There is no experience during the Grand Prix that we cannot gain access to.”

Alternative: “The combination of a sporting event and a destination is big now, and we are seeing more and more interest in the Singapore Grand Prix. The food and hospitality there are off the charts,” says Roadtrips’ Penner.

INDIANAPOLIS 500

Takes Place: End of May

When to Book: Several months ahead

Averaging over 300,000 fans, the Indy 500 is the most attended single-day spectator sporting event on Earth and caps a nearly month-long run-up of special events and big-name concerts. After more than 100 years, the city handles the surge surprisingly well, and both good tickets and top hotel rooms are available with advance planning. VIP options include pit passes, garage visits, and the chance to take laps on the famous oval in a pace car or actual Indy car with a driver who has raced here, paired with hospitality suites near the finish line (vital, as it is often very hot in the grandstands). Alternative: France’s 24 Hours of Le Mans, popularized in the hit 2019 film Ford vs. Ferrari.