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With restrictions down, Tampa man is up for being guide to Cuba

“The only place you’ll see cars rambling around like this is Cuba,” Steve Rupert says of his 1940 Chevrolet Deluxe in Ybor City. Rupert, a professional mediator in Tampa, has created a second life traveling to Cuba with tour groups of five to 20 people.


“The only place you’ll see cars rambling around like this is Cuba,” Steve Rupert says of his 1940 Chevrolet Deluxe in Ybor City. Rupert, a professional mediator in Tampa, has created a second life traveling to Cuba with tour groups of five to 20 people.


His mediation practice pays the bills. But Steve Rupert's longtime hobby might finally bloom into a legitimate business.

Since 1997, Rupert, 54, has been an unofficial guide for friends and acquaintances seeking to visit Cuba. The government still bans tourist trips. But Rupert became an expert in exemptions that let Americans visit legally for business and humanitarian missions.

With President Barack Obama relaxing travel restrictions, travel to Cuba by Americans is expected to boom. Rupert obtained a federal "people-to-people" license to sponsor cultural exchange trips for individuals and small groups.

He partners with travel agents to promote a variety of tours on the website Rupert talked recently with the St. Petersburg Times about political pushback on his early Cuba ventures, the complexities of travel rules and a possible tourist boomlet for the area from new flights to Havana from Tampa International.

How did you get interested in going to Cuba?

It intrigued me that there was an island just off Florida and I wasn't able to go. I'm allowed to go to North Korea or Iran without restrictions.

I got a humanitarian travel license from the Treasury Department in 1997 and went to a hospital in Havana with computers, antibiotics and asthma inhalers.

I could only carry so much, so I started bringing other people with suitcases to make it worthwhile. The license was designed for aid groups. The Cubans and government people here kept asking, "Who's your group?" I had to find some vehicle to continue.

How did that work out?

I wrote a story for Creative Loafing that got on the Internet. All of a sudden I was getting calls from California, New York, everywhere for the Cuba guy from Tampa. One was from the U.S.-Cuba Sister Cities Association. Mobile, Ala., established the first one with Havana.

I went to see (then-Tampa Mayor) Dick Greco, but feelings in Tampa were still white hot. I talked to the Port of Tampa, and they treated me like I was radioactive. But the Port of Manatee welcomed me with open arms. We did a sister city with a place called Manati in 2002.

I took groups — doctors, teachers — for cultural exchanges. We've gone to hospitals, schools, retirement homes, orphanages. Then, President Bush shut down people-to-people and sister city exchanges in 2003.

How has that changed since President Obama loosened the restrictions?

I can license any American with a passport to travel to Cuba for cultural exchange. This is not about tourism. You can't just go to drink cocktails on the beach. But if you want to enjoy the culture and happen to have a good time, come on down.

What qualifies as a cultural exchange?

I took some photographers in June. They'd shoot pictures in the morning, then go to art galleries and photograph indoors when the light was too bright. They stayed in seventh-floor apartments overlooking the port that are owned by an 86-year-old woman, a historian. She told them what it was like living in the old city in the '50s.

Every time, we've stayed in private houses with Cuban families. I can do history tours, music. I'm taking five architects in November. It's like going back in time. The buildings are old. The cars are old. There's no neon flashing anywhere. You see a '56 Chevy buzz by; it's like a time warp.

The federal licensing rules can be confusing. You can set up tour programs but can't sell them, right?

Everything is complicated about Cuba. I can't sell you a ticket for the airline trip or hotel. You need a travel service provider (a specially licensed travel agent).

Can local businesses benefit from out-of-towners flying through Tampa International to Cuba?

I think these new flights have the possibility for being an economic boom. Any time you bring people to your city, it's a plus.

Let's fill the hotel rooms, get them into the restaurants. I'll take them down to Ybor City. This is a Cuban city right in America. There are a few streets in Ybor where you can picture life from 100 years ago.

Contact Steve Huettel at or (813) 226-3384.

With restrictions down, Tampa man is up for being guide to Cuba 10/09/11 [Last modified: Sunday, October 9, 2011 6:00pm]
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