As anyone who travels knows, you can meet the most interesting people when you BreakAway from your daily grind. Today’s proof arrived in the form of Bob & Jen Westerfield.  

While beaching at scenic Trunk Bay, this handsome couple strolled by with grins on their faces and pink drinks in their hands. They paused to admire AllBoy and CurlyGirl body-surfing (it’s common that the kids break the ice) and we began to chat. Soon the sun was moving across the sky. And I learned all about “The Dart Vacation.” Wow.

Bob & Jen, vagabonds & entrepreneurs.

The concept is simple: Every year on January 1, they throw a dart at a US map—and that random landing becomes a vacation target. No exceptions. No rejections. They are five-for-five in five years. So far, this courageous twist of destiny has taken them to…

Marsh Islands, California
Happy, Texas
Zuul, New Mexico
Two Buttes, Colorado (population 45)
Superior, Nebraska

Next year, they will circle their wagons at Circle, Montana. (What goes around comes around?) And like this year’s vacation in Nebraska, the next outing will include their twin sons, now age 1.

They MUST spend some quality time in the place the dart landed. No matter what. That’s not always easy: In the case of Marsh Island, California—which is actually a game reserve with no humans—they had to court a local car dealer and attorney to take them out in a boat.

The price for this slice of bliss and chance? One case of beer.

Once en route or in the area, they do allow themselves to meander, get lost, and see the sights that speak to them. Those broadminded guidelines have taken them to the likes of New Orleans and Wrigley Field. And though their list may not make Conde Nast’s Top Ten lists, they describe each place as fun, appealing, and beautiful.

No wonder they make friends wherever they go, and have even made the front page of a local newspaper—along with their twins and rented Winnebago.

You can’t make this stuff up.

Nor can you concoct the many connections we found within less time than it takes a pelican to find a decent supper.

They vacation at Lake Superior too (on the other side). They also have kinfolk in Brookings, South Dakota (OMG!). And they are also self-employed and hacking their own rules.  In their case, hard work is balanced by frequent and extreme outings of all kinds.  

Sabbatical? Radical? NOT! This spirited couple wins the award for Most Radical Escape Artists.