If they ever make a movie about Jordan and Matt’s seagoing adventures, it might be called Planners of the Caribbean.
Five years ago, the couple were hardcore Midwestern landlubbers. Today, they live aboard their Leopard 40 as they cruise the Caribbean islands searching for the perfect dive while continuing to work full-time. It’s a wild and free life made possible by Jordan and Matt’s commitment to planning and organization.
“I’m all about organization and efficiency,” says Jordan. “I think that really helps us achieve both the fun part of life and keep up with our professions.”
A New Way of Life
In 2015, Matt, a software engineer, and Jordan, an actuarial consultant, lived and worked in Chicago. They were successful and happy. But something was missing. Things began to crystalize when Jordan came across a blog post.
“It was about this young couple with a dog who took a year off work, bought a sailboat, and sailed around the Caribbean,” says Jordan. “I just really loved it. From that point, I was like, yes, we should do this. I’ve always been really into scuba diving, so that love of being underwater is what sparked sailing as something we would enjoy doing.”
The couple spent more than two years refining their vision of full-time adventure. They considered buying an RV but eventually decided that a sailboat would better serve their desired lifestyle. It afforded them the living space they wanted, allowed them access to exotic locations around the world, and provided the perfect platform to pursue their underwater passions.
“I love hiking and diving, says Matt. “But given a choice, I’ll always choose diving.”
There was just one hitch with Jordan and Matt’s grand vision. Neither Jordan nor Matt had ever sailed. That reality kept Matt from fully committing to the high seas.
Jordan immediately devised a plan to address this challenge. She found a week-long live-aboard teaching cruise in the British Virgin Islands, where she and Matt got a taste of the sailing life and learned basic seamanship on a Leopard catamaran.
With Matt now fully onboard, the couple opened a spreadsheet and began comparison shopping for a boat. These meticulous planners and analysts ultimately chose a Leopard for its sensible, efficient design.
Choosing Leopard Catamarans
“We looked at a ton of boats, and I just kept coming back to Leopard because everything is logical,” says Matt. “The layout, from where the helm is to where the winches are – everything on it made sense. We’d step on other boats, and I’d be like, this doesn’t make sense. Some of those other layouts were actually confusing to me.
Adds Jordan: “We liked how the engines were placed, and we liked the way the bathroom was set up. We liked how the anchor comes out of the boat more in the center, versus in front of the trampoline. It was just the way it was laid out and organized.”
Matt and Jordan bought a Leopard 40 in late 2018 and moved on board in January 2019, two-and-a-half years after they first considered going to sea.
Hard Work Pays Off
Anyone looking for a pair of sailing bums should cruise right past Jordan and Matt. This couple is, by their own description, “very intentional” about their days. They work and play with purpose. Both Matt and Jordan were able to take their jobs along on their adventure, which makes for some unusual workplace moments.
“I’ve done Zoom calls while she’s motoring the boat down through the Exumas,” says Matt with a laugh.
When they aren’t working, Matt and Jordan are relentlessly exploring above and below the ocean’s surface.
“We’re not people who stay at an anchorage [very long],” says Jordan. “We get somewhere, and we’re like, okay, where are all the snorkel and diving sites we need to hit? Anything on land? Then we get up at sunrise the next morning and head out to the next spot. We are just always trying to see and experience as much as we can. We never really stayed anywhere more than a couple of days up until literally when COVID forced us to.”
Jordan and Matt’s experience – the places they’ve seen, the people they’ve met, the skills they’ve learned – has given the couple something they value above any material possession – personal growth.
“You’ve got to push yourself to be uncomfortable a little bit all the time,” says Jordan. “You make yourself grow by constantly going outside your comfort zone. A boat does that for you.”
