UPPER KEYS — It’s been smooth sailing for retired U.S. Navy SEAL Joe Mastrangelo. It’s because he runs a “tight ship” aboard his 22-foot boat called the Dutch Treat, on which he teaches fellow veterans, active duty personnel and the county’s first responders how to navigate the high seas through his nonprofit Veteran Sailing Association.

Mastrangelo has taught about 165 honorably discharged veterans and law enforcement officers how to sail at no cost since late 2016.

Looking ahead, he plans to teach and certify through the American Sailing Association at least 10 more vets by the end of the year, which is heavily dependent on donated funds.

There are a few different courses to choose from that span three to five days. Mastrangelo also teaches more advanced-level classes, if students already have some background in sailing. After completing on-the-water training, students are expected to pass a written exam.

Vets do have to pay for their own transportation and board.

“We are struggling financially just to keep these guys sailing. I cover all of the materials and expenses to get these guys out there. Every dime goes toward taking veterans sailing,” Mastrangelo said. “I’ve been extremely fortunate that certain people have heard about his organization and have donated. I’m doing what I can. It takes a lot to keep this thing running. I’ve applied for grants, but they don’t always come to fruition.”

It’s over the billowing sails and the promise of a high seas adventure that Mastrangelo connects with other veterans.

“It’s veterans helping veterans, the way it should be,” he said.

Purple Heart recipient Dan Lama, who served in the U.S. Army’s 25th Infantry Division in Iraq, completed his ASA 101 keelboat and 103 coastal cruising sailing certifications last week with Mastrangelo. He’s learned how to prevail in the sails.

“You have to know what you are doing, and why you are doing it,” he said. Much like life, this applies to sailing, he said.

“I ran 30 nautical miles yesterday with Dan,” Mastrangelo said. “Dan’s nephew wants to sail across the Atlantic and make a living off the ocean, and maybe he’ll go with him.”

Before they set sail, Mastrangelo said they spent hours preparing and cleaning hulls. He spends 40 to 50 hours per week on operations beyond teaching vets to sail.

“If there is a mechanical issue, we go past sunset. If not, we usually start at 9 a.m. and go until about 6 p.m.,” Mastrangelo said.

“We’ve been jamming,” he added. “We have a whole military base in Key West and in Homestead.”

Veteran Sailing Association’s operations haven’t slowed during the COVID-19 pandemic. His Facebook page is covered with success stories of veterans who have passed the class over the last few years.

“It’s been smooth sailing for me. I’m a Navy frogman. I’m going to get it done and I’ve been very fortunate,” Mastrangelo said.

Veteran Sailing Association is located at 90791 Old Highway in Casa Mar Village. For more information, visit veteransailing.com. It can also be found on Facebook under the same name. Mastrangelo can be reached at 305-619-3433.