For Kelly Callahan, life has no boundaries as he lives in beautiful Southwest Florida, enjoying the four catamaran sailboats he puts out for charter from the Island Gypsy Marina on the Isles of Capri.

Kelly and his wife, Sharon, are proud of the business they've built up for eight years now and enjoy being on the water.

But this story isn't about his love of the water, but his love for throwing off the traditional norms and taking a chance.

Kelly's two work vehicles are M35 "deuce and a half" heavy-duty military cargo vehicles.

"I knew he was looking for a truck, but when he pulled up with this, my jaw nearly hit the floor," said Sharon. "I just couldn't believe it, but he loves his big toys."

The 2 ½ ton diesel-powered vehicle has the reputation for being a versatile workhorse for the military over several decades. You can't miss either of the trucks. Both are the standard military green and are quite impressive to see as they roll down the road.

Kelly's first foray into purchasing this style of vehicle saw him come home with the standard cargo-bed configuration. The second acquisition was another M35 with a shop-van body in place of the standard cargo bed. Kelly refers to it as just that his "shop on wheels," as it carries tools, parts and other equipment necessary to keep his fleet in top-notch condition.

The Kellys have worked in the restaurant-service business for years. When they first met eight years ago, Kelly was living on his 42-foot sailboat on Capri. One day, another captain asked Kelly and Sharon to cover for him while he took a two-week vacation.

That was the start of their own venture as entrepreneurs. They began their own charter business when their friend retired to Texas.

Today, Cool Beans Cruises runs four boats – three 33-foot catamarans, and a 42-foot Maine Cat catamaran out of the Capri marina.

Kelly still likes to take his Jeep off-roading to Colorado in September, but Sharon still prefers her Lexus or Mercedes to the big green trucks that Kelly loves.

You can look them up at for a great time on the water and maybe Kelly will let you catch a picture of his big green machines.

More information

Cool Beans Cruises, 292 Capri Blvd., Naples, call 239-777-0020 or visit

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