Randy Rosen grew up boating the multifaceted waters of South Florida. So when he bought his 240 Outrage in 2005, it was his chance to pass along his love of the water to his son. “I consider myself lucky to do this, to go boating—and wanted to impart this enjoyment of boating on to my son, Jonathan,” Randy says. “And I really believe I have. Boating keeps the family together.”

It keeps friends together, too, or at least gives them lots of fun things to do. Randy met Rocco Ferrara at work many years ago, and soon they were carpooling to the office and spending time together outside of work. Even after Rocco moved on to another company, they remained close friends. Their children practically grew up together, becoming inseparable friends in the process. Sons Jonathan and Alex, now 19 and 20, still enjoy the friendship that began when both were barely toddlers.

The 240 Outrage has become the hub of activity for all four men. The Rosens keep their boat in Miami, and Randy calls Biscayne Bay “our waterway.” With idyllic destinations like Sand Key and Elliott Key (the northernmost islands of the Florida Keys) within cruising distance, it’s quite a waterway indeed.

Randy’s father, Harold, introduced him to the boating lifestyle in his early teens. In the years prior, Harold had been a classic “type A” workaholic: an entrepreneur who owned a local business and worked long hours, including many weekends.

This changed when Harold was terribly injured in an accident that nearly cost him his life. The life-changing moment forever altered his view on what was really important. Taking stock of his life from the vantage point of a hospital bed, the elder Rosen “decided to wake up and enjoy life with his family and friends,” Randy says. “My father jumped right into boating, he went right for it,” Randy remembers, starting out with a 30-foot cruiser. It didn’t take long for the family to trade up to a 43-foot double cabin, and most weekends would find the entire Rosen clan out on Biscayne Bay, with frequent overnights at Elliot or Sand Key.

Every summer, the Rosens would embark on a two-week adventure, cruising lazily through the many small islands of the Bahamas. For Randy, his own annual trip to the Bahamas with the two boys and his friend recreate those trips of his youth. Randy learned indelible life lessons from his dad’s experiences, passing these and his love of the water to his own son. “From my perspective, everything in life is a balance. You have to want to play just as much as you want to work. You work to support your family, but you play to enjoy your family.”

Most often, Randy, Rocco and the boys would take the Outrage on day trips around the bay and to the upper Keys. But in the summer of 2006, the fathers began to cast about for a big adventure. They were looking for more than just a day trip, and the annual Boston Whaler Bimini Rendezvous made for the perfect escape. Carrying on the annual tradition, this year the foursome will make their seventh trip to the Bahamas.

The group’s first trip across the Atlantic Ocean was memorably wild. Facing 5-foot, 6-inch waves, everyone but Randy was holding on for dear life. And yet, being in the Whaler and surrounded by fellow Whaler owners, they felt safe. Gripping the wheel for stability, Randy felt he had the best seat in the house.

Fishing the plentiful waters encircling the Bahamas has always been a highlight of these annual offshore journeys. Both sons still talk about that first fishing excursion. “The non-stop fishing”—i.e., catching—”was a big deal for the boys,” Randy says. “They were just 13 and 14.” Yellowtail tuna is the primary catch, but two years in a row Jonathan boated sharks—an experience which is thrilling for boys of any age. Besides fishing, they love heading over to one of the main Bahamian islands to satisfy a taste for conch salad, a national staple. They also enjoy pulling the boat up to the stingray-filled waters in a protected cove. There they spend the day roughhousing, swimming and playing ball in the shallow, crystal-clear expanse.

They’re bound to go snorkeling, too. The waters are protected and incredibly clear, and casual swimmers can enjoy a variety of underwater sites. Last summer, Jonathan goaded Randy into joining him in clambering up on a partially submerged shipwreck and leaping off together into the waters below. “That’ll be the last time I ever do that,” Randy says with a laugh. “I didn’t realize how much I had cut myself up on the wreck until later.” It’s a good bet that the younger Rosen will find some way to challenge his father on an upcoming trip.

The girls in the Rosen and Ferrara families grew up together as best friends, as well. And while Randy’s high-school senior daughter, Hannah, asks every year about the trip, she says she understands it’s a “guys-only thing.”

Each year the annual guys’ trip creates its own special memories, but it’s always about camaraderie more than anything else. It doesn’t get better than boating together, enjoying an impossibly good tasting meal after being in the sun and on the water all day, and then resting up to do it all over again the next day. How long do the foursome intend to continue their once-a-year guys trip? Randy laughs, “As long as the boat holds out, and the kids want to go!”

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