Lake Michigan, the behemoth freshwater lake sitting between Wisconsin and Michigan has been tempting adventurers for decades. From paddleboards to kayaks, it’s a challenge just waiting to be tackled.

The lake’s record wave height is 23 feet, and this summer water temperatures were rarely above 70 degrees. The weather in the area, largely controlled by the lake, can change at the drop of a hat—a fact bordering cities have learned to live with.

Every year, groups of people train for months in order to cross Lake Michigan, preparing in gyms, in water, at home, and wherever they can, but more often than not, they don’t make it.

This August, Andrew Pritchard, Jeff Guy, Kwin Morris, Joe Lorenz, and J Mueller formed Stand Up for the Great Lakes, a paddling initiative that focused around benefitting the Great Lakes. The group hoped to raise $10,000 to donate to the Alliance for the Great Lakes. They made it to $7,385.

They didn’t make it far into the water, either. When the group was getting ready to paddle out, they were giving themselves about a three-week window to accomplish the feat. Unfortunately, they never had the chance to set out onto the water.

The plan grew when a few of the guys came up with the idea last December, and eventually more joined in. They had spent the year training and preparing for the paddle, as well as figuring out what charity to involve. Their main motivators were the physical challenge of crossing the 60 miles of freshwater, and standing up—literally—for something that mattered to them: preserving the Great Lakes. Pritchard and the rest of the gang are from Traverse City, a scenic town that overlooks Lake Michigan and is home to a number of pristine beaches and sand dunes. It’s no wonder the guys have a thing for the lake.

“The entire west coast [of Michigan] is stunningly beautiful. We have the huge lake stretching to the horizon, you want it to stay that beautiful forever,” Pritchard said. “You only have to spend a little time on these lakes to see the impact that we have as human beings.”

For many who attempt to make the trek across the lake, charities and other causes are tied into the journey. In July 2013, a trio that included two brothers—Craig and Trent Masselink, and friend Ginny Melby—crossed the lake by paddleboard. They worked to raise money for Restore International, a charity working to improve human rights and educational opportunities in Uganda, India, and Somalia.

The group was successful in their 80-mile trek, and took a route that was different than the one the Stand Up for the Great Lakes boys had been planning. The three paddlers took turns on one board, taking breaks on their escort boat every 30 minutes, which could have been a vital part of their success.

The biggest aspect of their success, and anyone else’s who makes the attempt, is the weather. On any given day, Lake Michigan can churn out waves that can hit the six-foot mark, no problem. Lake Michigan has a surface area of 22,300 square miles, is 118 miles wide at its widest point and has an average depth of 279 feet. In order to safely make the trek across the lake, the weather must be utterly perfect, and perfect for more than a day. In a region where one day is 80 degrees and sunny, and the next is 60 and raining, finding this window is tough.

For the guys at Stand Up for the Great Lakes, it was all about the wind and the temperatures. They were hoping for wind around 10 knots, which is about 11 miles per hour, mild temperatures, and waves that were as small as they could get them.

Another attempt was made this past August by Jesse Hieb, of Milwaukee. He was turned back after 17 hours of paddling because of eight- to 10-foot waves.

What is the recipe for a successful paddle across Lake Michigan? Four members of the Chicago Area Sea Kayakers Association—Tom Bamonte, Bill Burton, Sarah Hartman, and Haris Subačius—boiled it down to a few points after they successfully kayaked from Chicago, Illinois to St. Joseph, Michigan in 2010. The 60-mile paddle was sprung on them when waiting for the perfect weather window, and the opportunity to go had to be taken immediately.

When grand ventures such as crossing one of the largest freshwater bodies on the planet via a piece of plastic are being planned, there’s obviously an immense amount of preparation and information that needs to go into the plan itself. The kayakers of CASKA who crossed Lake Michigan were extremely well equipped with gear, food, provisions, spare paddles, and plenty of options for emergencies. They were ready, physically, and had been training all year. They were ready mentally as well, “We began our planning by accepting that we might never launch. This was not a ‘we’re going to do this regardless’ mission,” they wrote in a post on the CASKA website.

In addition to planning, they attributed their successes to their strengths and weaknesses playing off of each other, their motivation, each person’s personal responsibility, their caution, and of course, their luck.

More than any expensive gear, any sponsors, any amount of donations, or any quality of escort boat, it is luck that makes a difficult paddle like this possible. The guys at Stand Up for the Great Lakes were prepared. “Everyone is very active and involved in sports and watersports,” Pritchard said before the planned paddle. “We’re all very similar and prepared for what the lake can dish out.”

Being prepared for the lake isn’t enough, it’s also being prepared to be patient, and allowing for months-long windows instead of a few weeks, and even then, the lake can always change at the drop of a hat—or a paddle.

Images courtesy of Stand Up for the Great Lakes/John A. Gessner Photography