Farther afield, the charms of Mackinac Island draw the couple all the way to Michigan’s Upper Peninsula from time to time. Limited to transportation by horse-and-buggy, bicycle or foot, Mackinac’s historic architecture, bustling downtown area and world-famous fudge all do their part toward making the trip worthwhile.
Wherever Chris and Kathy wind up cruising, they’re not shy about putting hours on the Dauntless’s engine. Chris says they average 120 to 150 hours in a six-month season, easily. “We have the 350 [Mercury] Verado on it and couldn’t ask for anything better,” Chris says. “Great speed, agility, all the other pieces that go along with it. And the 150-gallon fuel capacity gives us a very, very long range. That helps make it a well-rounded boat.”
The O’Shaughnessys keep their boat at Marina Shores in Portage, Indiana, which is just a quick 5 miles from their home. “It’s great: You get off work at 4:30 or 5:00 and head down to the dock, get on the boat and go,” Chris says. “There’s no excuse not to be boating when the weather’s nice.”
Their good friends Bob and Lori McKean often join them on impromptu outings. They cite the Stray Dog restaurant in New Buffalo as a favorite hangout, a place to soak up harbor views from an upper deck. More often, though, you’ll find the two couples more directly engaged with the water.
“Bob and Lori are a big part of our boating life. We spend as much time together as we can,” Chris says. “We basically take turns: our boat, their boat. It’s a great friendship.”
“No day is the same,” Kathy adds. “We’ll go exploring, or go 2 or 3 miles offshore and drop anchor and relax.”
Chris and Kathy also enjoy making overnight trips to Chicago, where they’ll keep the Dauntless at Burnham Harbor and stay with friends in the city. Everywhere they go, they seem to meet fellow Whaler owners who share their enthusiasm.
In part, it’s because Chris wears his love on his sleeve—literally. “I have almost every Whaler shirt you can buy,” he says with a grin. “Mugs, coolers… People think I’m a rep for the brand. Even the back window on our truck has a decal.”
They welcome the attention it draws. “Whaler guys are really the best. You see another Whaler owner or boat, and you can count on an hour-long conversation right there,” Chris says.
The O’Shaughnessys have been customers of B&E Marine since 2008, when they purchased their first Whaler, and have nothing but praise for the dealership. “Our sales rep, Terry Belue, is phenomenal. He does everything he can to make the buying experience—well, maybe ‘fun’ isn’t the right word, but he goes the extra steps,” Chris says, laughing.
A tour of the Boston Whaler manufacturing facility in Edgewater, Florida, was another highlight of the process. “Really neat to see where the magic happens!” they agree.
Florida showed the couple a good time all around. They took the 270 Dauntless to Boca Raton before cruising down to Miami and checking out the sunny beaches of Key Biscayne. “We’re so used to being up on Lake Michigan, it was great to do some open-water boating,” Kathy says.
Wherever their next adventure takes them, they’re sure to embrace it with open arms. And if those arms happen to be clothed in a Whaler shirt, all the better.