A day ‘TRYP’ to Key West (PHOTOS)

It’s not an awful way to spend a Friday that’s supposed to be a workday. Grab a few of your friends, best clients or both. Duck out of the office, hop on a private jet leaving from Sheltair Tampa’s “executive airport” within minutes of parking your car. Let the networking, conversations and cocktails flow—as you fly comfortably, stress-free, to spend a day in the Florida Keys—and still be home by dinner.

Nope. Nothing awful about that. And it’s quite easy, thanks to the fantastic airport in Tampa and private charter flights, such as TRYP Air.

As a person who dreads flying, particularly these days, let me tell you—a private flight is an entirely different experience, and the only way to go.

For our “tryp,” we showed up at Sheltair and, after a short overview of safety measures, we boarded the plane at 10 a.m. and were in Key West in time for an early brunch and bloody Marys, before noon.

Upon arrival, and departure, no check-in. No long line to muddle through for security. No removing your shoes and laptop. No stress. Nobody searches. No hassle.   

Elliot Mintzer, owner and president of MySky Aviation Solutions and TRYP Air, and his team already had it stocked upon arrival. We were able to settle in for a fast flight down to the southernmost point in the United States without a care in the world.

No masks were required. We were allowed to consume alcohol or not; it was our choice. We had an intimate setting where we could talk and laugh loudly, and tell our fellow travelers what to expect upon arrival. Some were experts and had been many times, some had to be schooled about the brilliance of Blue Heaven and the need for Irish car bombs at Irish Kevin’s. All were excited about the adventure, and the short trip there was bubbling over with anticipation.  

When we landed in Key West, we simply left the plane knowing we had to be back at a certain time (because of potential bad weather conditions). The executive airport was further from Duval Street than we wanted to walk, so we arranged for a private bus to carry us off into the wild that is the Conch Republic.

Our first stop was Blue Heaven, which came highly recommended from TBBW publisher and CEO Bridgette Bello, who called it a staple, a “can’t miss” and the best food on the island. Don’t doubt that woman. She knows her Key West destinations well. As predicted, it was excellent.

The food was incredible and, please, if you make it down there, don’t skip the Key lime pie. As a native Floridian, I can tell you, I’ve never had anything like it. Be prepared to share because it’s massive. The lobster grilled cheese was unforgettable and shared, by many. The ordering decisions were not easy to make, but the food was delicious to consume.   

We met some famous Key West roosters—I’m sure one was named Hemingway—who are also a part of the fabric of the island. We saw the swing, although we weren’t brave enough to take it on with clients in tow—but we imagined the fun that could be had. We were a little surprised by the “cash only” bar that stood between us and our table, but we made the most of it, thanks to some advanced planning.

Upon our bellies being swollen and full, we began the trek over to Irish Kevin’s, another Key West institution. If you make it to the Keys, regardless of how you get there, and you don’t visit Irish Kevin’s, did you really go to the Keys? The answer is no.

After some lively entertainment, both from the live performer and the other patrons, Team Tampa (of course) won the Irish Car Bomb challenge and moved on to a few more spots, including Captain Tony’s, Sloppy Joe’s and the Hog’s Breath Saloon—until it was time to head back to the airport.

Another easy flight back to Tampa and we landed, smoothly and safely, having had the time of our lives and watched, as the sun went down on an amazing day.

It’s all in a day’s work at TBBW.

For more: www.flytryp.com

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