Charles Kropke is on a quest to bring back paradise lost.

Longing for the era of swashbuckling ships and island-hopping seaplanes, the 48-year-old entrepreneur has set his sights on bringing new life to the former Miami Beach-based Windjammer Barefoot Cruises, the iconic Chalk’s Ocean Airways and the historic, shuttered Belleview Biltmore Hotel on the Gulf Coast.

He’s finding the effort costly and challenging, but says he believes the end result will pay off.

“When things are worthwhile, when there is something that’s worth pursuing, you give it another round,” said Kropke, whose office is adjacent to the Biltmore Hotel in Coral Gables.

The next round for his version of Windjammer — called Windjammer Sailing Adventures — starts Sunday in Grenada, when passengers will board a ship that once belonged to the original company.

That outfit stopped sailing in 2007 after running into financial problems, leaving some customers stranded, others out thousands of dollars and many heartbroken.

“It’s like losing a part of your life when you’ve been sailing that long,” said Linda Reisdorf, a Panama City resident who sailed on the old ships more than 25 times.

She and many of her fellow former passengers were heading to the Caribbean late in the week for a reunion with each other and the Mandalay, a 58-passenger vessel that Kropke bought earlier this year.

Though he never sailed on a Windjammer cruise, Kropke said he had his eye on the family-owned company even when it was operating. Once the company folded, he bought old furniture and paintings at a 2008 auction, and began planning a comeback.

Last July, he went to a gathering of old Windjammer fans called Jammerfest and met Cynthia Greenway, a businesswoman with more than 20 cruises behind her, and Sylvester Dzomeku, a former Windjammer captain. They liked his plan to start a new Windjammer company and, by December, had signed an agreement to start the business. Within weeks, they had bought the ship after Kropke assembled a group of private investors to come up with the approximately $5 million needed to purchase and refurbish it.

“That was not our business plan,” said Greenway, now president. “Sylvester and I were going to come work in the office, do a business plan, get advertising and investors in order. And the Mandalay became available to us. We said, ‘We better do this.’”

Kropke said his goal is to eventually have 8-10 tall ships in the Caribbean. But in the meantime, he and his team are trying to get the word out about the venture through Facebook, old Windjammer partners, travel agencies, advertising and databases for his other businesses.

He is a co-owner of tour operator Dragonfly Expeditions, which focuses on the Caribbean and southern half of Florida, and co-owner and co-founder of several other tourism-related companies.And Kropke is leading a trip in October as a test run to become a tour outfit affiliated with Jimmy Buffett’s Margaritaville, which he believes could also direct customers to the ships.

The key, he said, is finding the right customers for Windjammer Sailing Adventures.

“There’s no waterslide or Putt-Putt golf or shows or anything,” he said. “The pool is jump off the side of the ship and come up the ladder. So it doesn’t fit everyone. But when it does fit somebody, it feels like they just found their dreams.”

He said there’s also the old mistrust to overcome from former passengers who lost money.

Meg Phillips, a longtime Windjammer cruiser who is sailing on Sunday, said some of her fellow enthusiasts are taking a wait-and-see approach. But others, like friends who are sailing with her next week, couldn’t wait to return.

“We don’t expect everything to be perfect and we never have,” said Phillips, of Virginia. “Even on the old Windjammer Barefoot Cruises, things were never perfect.”

Kropke has found that, in his line of work, few things are perfect. But he is rarely cowed, said Eleanor Goldstein, his co-author on the book South Beach: Stories of a Renaissance. That book was the firstpublished by Tropic Moon Press, another venture Kropke started.

“No challenge is too big for Charles,” said Goldstein, of Delray Beach. “No matter what you talk to him about, if he has a problem, he says, ‘I’ll figure it out.’ I think that’s probably his favorite phrase.”

Next to figure out: relaunching Chalk’s Ocean Airways, the commuter seaplane operation between Miami’s Watson Island and Bimini that went out of business after a 2005 crash into Government Cut that killed all 20 aboard.

While he’s been interested in the airline since before the tragedy, he didn’t have any stake in it until a couple of years ago. That’s when he bought the name — which he admits is just a “token” — but he is now looking at possible plane purchases and has put together a team that can move to action when he’s ready to start a company.

Kropke said he wouldn’t look to compete with commuter airlines but to raise the level of service (and prices) and offer service to hard-to-reach islands in the Bahamas, Florida Keys and, one day, Cuba.

The timing to get that project off the ground could be soon, he says, or could be a couple years out. He expects the initial cost to be around $2 million.

With two Miami partners, architect Richard Heisenbottle and real estate developer Hector Torres, he’s alsoworking to purchase and restore the historic Belleview Biltmore Hotel near Clearwater, a process that is expected to wrap up by September.

The group signed a purchase agreement for the world’s largest wooden lodging on March 31 that allowed for six months of due diligence; they are still working through that phase and tweaking plans. The group hasn’t disclosed financial details.

A native of Maryland, Kropke moved to the Fort Myers area when he was still a child and grew up exploring the state.

“I came to understand that there was a lot more to Florida than a lot of people know about, all kinds of beautiful places and undiscovered stories,” he said.

While Kropke said he realizes his latest efforts seem rooted deeply in the past, his goal is to preserve what makes Florida, the Bahamas and the Caribbean special.

“It’s not about looking back,” he said. “It’s basically about looking forward and taking the things that were most important from the past and giving them a new opportunity.”