Sailors and distance power cruisers are prone to say “getting there is half the fun” as they justify the inordinate amount of time it sometimes takes to get somewhere they’d really like to be sooner. There’s pleasure and value in any boating adventure from the moment you leave the dock, but sometimes it’s just better—and safer—to be able to get to your destination quicker.

That calculus eventually caught up with Tom Dill. The retired energy business CEO, lifelong boater and inveterate cruiser is making the transition from a Fleming 55 to the new triple-outboard Back Cove 39O. Rather than downsizing, Dill and his wife are more “quicksizing.” Their cruising patterns have changed, and they want to reach their favorite destinations faster from their base in Fort Myers, Florida, without sacrificing comfort and convenience.

Dill grew up in the St. Louis area, earning his boating chops on Table Rock Lake and Lake of the Ozarks. He’s owned boats most of his life.

“Like most trawler people, I was a sailboat owner,” he says. He did a two-year cruise on a 41-foot Hans Christian out of Texas in the early ’90s. When the time came to sell it, he intended to buy another sailboat, but ended up with a 46-foot Viking convertible. His cruising windows were limited to a week or two, but he explored Florida, the East Coast, Texas and points south. In 2007, he bought a 36-foot Grady-White with triple 250s, which he fished and cruised. From there, it was on to the Fleming.

The three-stateroom Fleming 55 is an iconic cruising yacht, often cited by trawler owners as one of their dream rides. When the Dills bought theirs, they had time for longer cruises.

“We put probably more than 12,000 miles on the boat, and another 2,000 or 3,000 with my buddies,” Dill says. “We could spend between four and six weeks, sometimes two months aboard. Early on, we were cruising the Bahamas, Florida, and we even took her down to the Virgins.

“If I were spending six weeks aboard, there’s no other boat I’d rather be on, especially with a fair amount of open water,” he adds. “But our cruising is evolving back into three-week trips, and we’ve found we don’t really need all that space. We don’t need a third stateroom. Guests stay no more than a week.”

Transit time to their favorite haunts has become a serious consideration. They enjoy the Exumas, and the trip from Fort Myers on the Fleming could be two or three days each way at 10 knots, leaving just a few days at their destination.

Back Cove says the 39O will cruise at 34 knots with the triple 400-hp Mercury Verados, but even at 25 knots, the Dills are cutting their run time in half. The outboards also will reduce noise and vibration.

Dill also likes the Back Cove because a cruising couple sometimes needs a little separation.

“You have to have that space,” he says. “We had that on the Fleming. With the Back Cove 39, with the lower and upper salons, we each have our own space to do our own thing.”

Other considerations also played into their choice to buy the Back Cove. On the Fleming, they typically would air out the boat during the day and air condition the master at night. Generators are uncommon on outboard boats, but their 39O will be equipped with a 9-kW generator to power the air conditioning at night so they can stick to plan.

With no engine room, the 39O has excellent stowage aft, but with the outboards, carrying a RIB is not an option. Dill hearkens back to his days with the Grady, when if the couple wanted to go to the beach, they just pushed in close, trimmed the motors, and set bow and stern anchors. He adds that these days, instead of spending 10 percent of their time in marinas and the rest on the hook, they’re spending 70 or 80 percent in the marina anyway. They may buy a stowable soft-bottom dinghy down the road.

They keep a small Grady outside their house, and are taking delivery on the Back Cove in November. Dill is clearly thrilled about the new direction in the couple’s cruising lifestyle.

“We had the time to go anywhere we wanted to go,” he says. “It just took a lot longer on the Fleming. It was just time to move to a smaller, faster boat.”