"I had confidence because I'd been boating on the Mississippi since I was 16—but I also had respect for the water, so I brought along another captain who was familiar with the locks and dams and marinas as a backup," John says.

"This was my boat and I wanted to be the one to take it in and out of each and every dock and lock, but I wanted someone along who could instruct me on how to do things better," he adds, noting that the largest boat he'd docked prior to that was 28 feet. "At my first docking, I backed our 55-foot boat into a 42-foot slip with six inches or less on either side, and with about 250 people watching on that holiday weekend. I figured if I could do that, I could dock anywhere!"

John says that the trip allowed him to see a different part of the Mississippi River than what he knew and loved growing up. "I had no idea how beautiful the Mississippi was up north. It was a recreational paradise with sandy beaches on both sides even though we were in flood water season," he says.

And he learned what he needed to know, taking the boat through 40 or so locks and almost as many slips and marinas. In Pensacola, Florida, they brought in a different captain to guide them through the offshore portion of their trip. "Dana Freed was a great coach," John says. "We went across the Gulf down to Naples. It was my first offshore trip as captain and it was far more intense than I had imagined. Dana took us through a thunderstorm and some rough water. I also began learning how to use all of the electronics, radar and charts."

As John and his family headed toward Miami, René got sick. They docked in Fort Lauderdale and flew home where she was diagnosed with terminal cancer. John and René were able to take a few short trips on the boat with the kids and grandkids while they were based in Boynton Beach, where René was taking part in a clinical trial.

"The kids and I are very blessed to have those memories," John says. John has continued to share his love of boating with his family, first with his four kids and nine grandkids and more recently with his fiancée Lynn, who has two children and three grandchildren and who also lost her long-time spouse, Tom, years ago to cancer.

A lawyer, real estate broker and businessman, John carries two smartphones, an iPad and two laptops on every trip and works from Rock 'N Roll each day. "You don't have to wait until you retire to have fun," he says. He is based in Las Vegas but has a client base that spans the United States and internationally.

John and Lynn do several one- to two-week trips a year, spending a total of two to four months on the water in a given year. "Lynn was never a boater, but she loves it now and is truly a great boater," John says.

Lynn says, "Boating on Rock 'N Roll has reminded me how important it is to keep an open mind in order to experience life to the fullest. Anyone can become a boater at any age." "But it is like riding a bike," John says. "You can't learn by talking about it. You have to do it."

They have traveled more than 10,000 miles as their own captain and crew in the last few years. "We've seen some of the most beautiful places in the United States and Canada," Lynn says. One trip took them from Florida, up to all of the Great Lakes and back to New York City and then to Boston before heading back to Fort Lauderdale; another from Fort Lauderdale to Bar Harbor, Maine, and back; another across Florida through Lake Okeechobee; and several to the Bahamas.

Along the way, they've learned so much from the boating community. "There are many great resources: America's Great Loop Cruisers' Association (AGLCA), the Waterway Guides, paper and electronic maps, and charts," John says. "Bluewater Books and Charts in Fort Lauderdale is one of the best resources.

However, the best information comes from the fellow boaters on and around the docks. They can tell you things that you won't find on the chart. When it comes to what you want to avoid, local knowledge is essential. They can tell where it is safe to anchor for the night, when water conditions are changing, and where to find the best restaurants."

Once, when heading toward the Welland Canal, going from Lake Ontario to Lake Erie, they met a couple who had a houseboat in the marina. John mentioned their plans to take a cab to see Niagara Falls and the couple offered the use of their truck. "We were dumbfounded," John says. "But while this is an extreme example, we've learned that boaters really are a community eager to share and willing to help others."

The Trent-Severn Waterway is one of John and Lynn's all-time favorite boating experiences. "The Big Chute is better than expected and east of the Big Chute is The Waubic, a restaurant and marina accessible only by water, which will always be one of our boating highlights," Lynn says. "That trip was far more than we ever expected and The Waubic restaurant experience is magnified because of the hospitality of [owners] George and Jennifer Fleet and their family."

Who knows where the water will take them next? They would like to do some Rock 'N Roll trips up the East Coast, exploring some the locations they have previously enjoyed as touch and go spots, including St. Augustine, Georgia and the Carolinas, as well as the Great Lakes. And they definitely anticipate many more trips to the Bahamas. The Virgin Islands and Cuba are also possibilities. "We rarely plan more than a few weeks out due to my work commitments, which take priority. We just watch the weather and then we go when and where we can," John says—and he thinks everyone ought to follow the same philosophy.

John and Lynn look forward to seeing you at a MarineMax rendezvous, raft-up or docktail event. If you are interested in hearing more of their Rock 'N Roll adventures, John can be reached at jor@oreillylawgroup.com.

WRITTEN BY JAIME LACKEY