Tourism Jobs We're Totally Jealous Of

Our dream gigs include everything from schooner captain to certified spook master.

Valerie Fraser Luesse

I’ve never forgotten the hotdog boat, even after all these years. There I was on the beach, enjoying my allotted 2-hour break during a sales meeting on Florida's Captiva Island, when I looked up to see a boat cruising along in the shallow water, running parallel to the beach. And on that boat was a grill, a cooler, and a hotdog vendor/boat captain.  Sunbathers would wade out to the boat, cash in hand, and purchase their refreshments.

It’s not so much the hotdog boat I remember as the vendor—Captain Hotdog, if you will. He seemed to come from a different universe than my sales meeting crowd, with our 2-hour breaks and conference rooms and PowerPoint presentations. Captain Hotdog was very tan and very chill. His job was to cruise along in gorgeous water and make hungry tourists happy with the simplest of offerings: a hotdog, a bag of chips, and a Coke. And in return, they handed him money. I can’t think of a more pleasant way to make a relaxing buck.

The truth is that there are many enviable (not to mention colorful) jobs in the travel industry. Here are just a few we’ve run across lately:

Mississippi Gulf Coast Schooner Captain (Biloxi, Mississippi)

The Maritime & Seafood Museum has two authentic replicas of Biloxi’s long-ago oystering schooners, dubbed the “White Winged Queens.” The lucky captains get to go to “the office” aboard the Glenn L. Swetman and the Mike Sekul, where they sail happy tourists about.

Trail Boss Lady (Fort Worth, Texas)

Only Fort Worth’s Stockyards National Historic District has a twice-daily cattle drive, called The Fort Worth Herd. But if you’re expecting to see a cowboy out front leading the way, you’ll be surprised. Trail Boss Kristin Jaworski leads and oversees The Herd. She’s the first woman in this role, which entails managing everything from horses to Texas Longhorns to people as she helps develop educational programs and enhance media relations for the city.

Sand Sculptor (Key West)

In "the Conch Republic," you'll find Casa Marina, a Waldorf Astoria Resort, where a resident award-winning sand sculptor oversees sculpting workshops. What guests wouldn’t love a staff member who can help them sculpt a life-sized dog or an extreme sand castle?

Certified Spook Master (New Orleans)

At the Hilton New Orleans Riverside, the resident Spook Master can give you tips and tricks for getting your spine chilled in the Big Easy—everything from ghost tours (like the Voodoo & Cemetery Tour) and haunted houses to best costume parties around the city.

Gelataia (Dunwoody, Georgia)

What’s a gelataia? Basically, the creative director of ice cream. Former Atlanta Journal Constitution dining critic Meredith Ford scored this sweet gig at Novo Cucina, an Atlanta area restaurant whose menu includes gelato artigianale (handcrafted gelati and sorbetti made from scratch with fresh, whole ingredients). Novo Cucina combines traditional Italian gelato-making with such American flavors as Banana Pudding and Thin Mint.

Resident Historian (St. Augustine, Florida)

The Collector Luxury Inn & Gardens, made up of seven guest houses that date back to 1790, has a resident historian who can tell you all about past guests (way past, as in Mark Twain and Sinclair Lewis); share inside intel on the original inhabitants; and arrange private tours of historic St. Augustine.

Treetop Quest Operations Manager (Georgia/Mississippi)

Jackie “Peanut” Mileson spends her workdays helping guests climb trees—first completing all the safety checks, then getting guests into their harnesses and up to speed on the equipment, and then . . . Jackie’s literally up a tree.

Chief Getaway Officer (Charleston, South Carolina)

The HarbourView Inn's “CGO” coordinates unique experiences for guests—from picnics at historic plantations to bar crawls, sunset cruises, golf outings, and fitness classes.