Punta Gorda Herald – February 2015

Cuba Ripe For Travel

Steve Rupert has traveled the world. But to him, there’s no place quite like Cuba.

“I have been to countries that were supposed to be our allies, and they spit on you,” he said. “When Obama announced the (thawing of relations) with Cuba, I went there and people were hugging me. They love Americans.”

Rupert has sponsored legal trips to Cuba for years. The Tampa resident — possibly Florida’s only negotiator of malpractice suits who is not a lawyer — has been picking up some good income taking groups of from six to 20 people to the magical island. But, for him, it’s not about the money.

He loves the island. Heck, he even married a Cuban lady he met while on a sister city mission for Manatee County.

Rupert says while normalization of relations with Cuba will be months or even a couple of years away — especially with the mood of the current Congress — cultural exchange trips are fairly easy to arrange. He has taken engineers, architects, students and media on seven-day trips that cost about $2,000.

“The biggest cost is the airline ticket,” he said, noting Cuba has huge influence in ticket costs.

He follows all the rules — mentioning that there is no day-long lounging on the beach with a beer in your hand.

“This is not a tourism trip. That is still against regulations, and I do everything legal,” he said.

His trips are planned to allow participants to truly experience the Cuban culture. And it all starts by staying in a private bed and breakfast with a Cuban family — not in a big hotel. He hires guides who speak English and, he said, are very friendly.

Most of his clients are retirees and “bucket-listers.” But he also often takes media groups, especially for shorter trips, which can be arranged for a little less money.

Rupert said there are a number of reasons to want to go to Cuba.

First, it is perhaps the only country with no American footprint.

“There are no chain restaurants,” he said.

The streets present a feast of sights for visitors and photographers. Laundry hangs on the lines and ’50s and’60s American cars are the normal means of transportation.

“The only American thing you will see is maybe a ’57 Chevy going down the road,” he said.

Second, there is virtually no crime.

“Japan is the only country that comes close to Cuba for having no crime,” he said. “A woman can walk down a dark street at night with $1,000 in her pocket and not worry about a thing.”

And, if you like to dance, this is the place.

“These people have a natural ability to dance. They come out of the womb dancing,” he said. “You’ll see a 2-year-old little girl on the street and when she hears music she begins to dance with that rhythm that they all have.”

Salsa and Merengue are two popular forms of music but something new — called reggaeton, is catching on.

“It is a mix of reggae and hip-hop,” he said. “Surprisingly, the government is giving some leeway to these musicians to be critical in their music. As long as they don’t get carried away, they can sing about (issues) and troubles.”

Rupert’s trip package includes the visa, air and board. All you need is a passport, a love for adventure or a thirst to see Cuba — before it all changes. Check it out at cubatraveladventure.com or call him at 813-263-6300.

Take me with you.

John Hackworth is editor of the Sun newspapers. You can email him at