Mark Reinhardt lives as a ‘gypsea’ by sailing around the world

As Mark Reinhardt started getting older, he really didn’t want to become a burden for his children. A self-employed entrepreneur for most of his life, Mark didn’t have a big pension or even a large Social Security check to rely on to meet his financial needs.

Consequently, Mark researched ways for him to live frugally while enjoying some sense of adventure, and he opted for a life at sea.

“Once you buy a boat and live out on the anchor, not in a marina, it is a lot more cost-effective way of living,” he explained.

Mark started his adventure in November 2022 with a goal of sailing around the world.

“That has been a dream of mine my whole life,” he explained. “I attempted to do it when I was 30. But, I wasn’t prepared in any way, nor had the right equipment, experiences or finances. So, here I am, 35 years later; but, this time I am well prepared.”

When people ask Mark what his favorite place to visit has been, he always responds by telling them it’s the next place he is going.

“The Caribbean was awesome. I did a whole chain of islands in the Caribbean by sailing all the way from Grenada to St. Thomas to the Dominican Republic and Jamacia,” he explained. “Right now, I am in the San Blas Islands of Panama.

“It’s like going back in time. There is no internet, no electricity and no running water,” he added. “There are 50,000 Guna natives who live in paradise on the island. They all live on hammocks in little huts, just like it was for the last 200 years.”

Drawn to the water

Mark grew up in Orlando, but left Florida in his 30s to go sailing for five years before starting a family and moving back to Clermont, Fla., to raise his two children. Today, he has six grandchildren.

One of his most persistent dreams has been to sail around the world. To prepare for the adventure, Mark bought his most recent sailboat, named Gypsea, about 10 years ago and moved back onto the water when he was around 55 years old.

“I got tired of chasing success, so to speak,” he admitted. “I have been a serial entrepreneur my whole life, but never really hit a home run in business.

“I was always driven to succeed, but it wasn’t just about money. My ego needed that feeling of success,” he added. “When I figured out I didn’t need to be successful in that way, that’s when this whole simple life of sailing materialized.”

His business experience is vast in that Mark has owned a grocery store, landscape company, restaurant, bar, trucking company, repair shop and even worked as a grading contractor.

“I’m more of an opportunistic entrepreneur. I see an opportunity to do something and just go after it,” said Mark. “My problem is that I’m not the guy you want to run your business. I like getting businesses off the ground. But, once they become successful, I get bored. I figured that out way too late.”

The siren call of sailing

When Mark moved back onto water 10 years ago, he purchased a 39-foot Ericson sailboat. He used that for nearly four years before Hurricane Irma wiped it out.

“It was an amazing journey in itself in how I went from zero to where I am today on a 50-foot Endeavour sailboat,” said Mark. “It started as a 43-foot boat, but I took it to Guatemala and extended it by nine feet by building a big platform so I could walk down to the water’s edge.

“I’m a big snorkeler diver and it was hard getting in and out of the boat,” he explained. “I installed a ramp on back of the boat to help me, for which I got ridiculed on a cruising website I frequent. But, I have traveled 5,000 miles with it and nobody has died. I consider myself a nay-slayer.”

Growing up on a lake, Mark has been around water most of his life. He got his first boat when he was 10 years old in order to cruise around that lake. However, previous boating experience is not a prerequisite to enjoy the lifestyle Mark does today.

“When I first took off, I wrote a book titled ‘Off the Grid.’ Since then, I’ve had a lot of people contact me because they want to live the lifestyle I do even though they haven’t spent much time on the water,” he explained. “I always tell them to buy a 14-foot sailboat and learn how to sail, then buy the biggest boat they can afford.

“The rest comes from learning. You can take all the courses you want, but most sailing knowledge is gained through experience by making mistakes, learning from them and moving on,” he added. “Anyone who has a passion for sailing can learn to adapt.”

Harrowing experiences

Mark admitted to having his share of ups and downs while sailing, and he endured some rather challenging situations. For example, he was dismasted one time and the large sail came completely down.

“That was a pretty traumatic experience and an overwhelming situation. Although I didn’t panic, I think my brain actually froze,” said Mark. “I remember passing a boat when I was underway and, the next thing I knew, he was on the back of my boat asking if I needed help. I’ve also been thrown off a boat by a big wave.”

Because Mark sails by himself quite often, he adopted several rules to ensure he doesn’t get into a really dangerous situation.

“For example, I never leave the cockpit at night and I don’t put myself in those kind of situations,” he explained. “The time I got thrown off the bow, there were other people onboard helping me to line up the sail. I had to be out front and a wave catapulted me over the lifeline. I never even touched the side of the boat. The other people were able to pull around and get me back onboard.”

Sailing on a big lake, like Lake Michigan, really isn’t that much different from sailing on the open ocean, said Mark.

“Sailing is sailing. That’s why I encourage people to learn on a 14-foot boat,” he added. “It’s all about the direction of the wind and adjusting sails.

“Sailing in waves has a tendency to knock you around a little bit,” said Mark. “But, the sail is a big stabilizer in the air that holds your boat on a pretty steady course. So, even in big waves, you’re not really getting thrown around. The sail stabilizes a boat in the wind.”

Battling isolation

Solo sailing can be an exhilarating experience, but it can also be rather lonely.

“I’m just a solid guy who usually doesn’t wish I had someone else around, but it’s hard for life to play out that way,” said Mark. “Most women aren’t willing to just drop everything, jump on a boat and take off.

“As far as loneliness is concerned, I have a huge Facebook following,” he explained. “I once backpacked from Orlando to Key West, and even rode out a hurricane on a sailboat. A bunch of people said, ‘Let’s follow this crazy dude.’

“So, my Facebook friends keep me occupied, thanks to my new Starlink device, which gives me internet now,” he added. “Writing also keeps me occupied, so I don’t think loneliness is a major factor for me.”

“Off the Grid”

Mark’s first book, “Off the Grid: How I Quit the Rat Race to Live for Free Aboard a Sailboat,” chronicles his first solo sailing adventure at age 30, and his life following that ill-fated attempted to sail around the world.

“I only made it to St. Thomas in the Virgin Islands and lived down there for four years on a sailboat,” he explained. “When I left St. Thomas, the motor on the boat went out, so we actually sailed back to America with no motor at all.

“If the wind wasn’t blowing, then we weren’t going. If it wasn’t blowing in the right direction, we were tacking back and forth,” he added. “So we had some pretty challenging situations.”

Mark doesn’t consider himself to be a writer, but rather a storyteller. Over the years, as he recalled stories of his adventures, many people encouraged him to write a book.

“So, I finally decided to do it nearly 30 years after completing that trip. The book is about all I learned on that trip, getting knocked down and picking myself back up again,” said Mark. “When I was writing the manuscript, it didn’t even occur to me that it was going to be an inspirational-type book. I thought I was just telling sea stories. But, when you get knocked down and get back up, people tend to gravitate to those kind of stories.”

Although titled “Off the Grid,” the book is not really about living without electricity or an internet connection. It is more about how Mark mentally lived off the grid while maintaining a positive attitude.

Passion and purpose fueled by hope

Mark considers himself lucky in that he has been able to chase whatever motivated him at the time.

“I’ve never been the guy who wondered what would happen if I failed,” he explained. “I’ve heard most entrepreneurs fail five or six times before they make it. I’m still waiting on the ‘make it’ part.

“I had to pick myself up so many times,” he added. “There is always a little lull after a failure. But, not too soon after that, I’m back up and running again.”

Mark developed a formula for succeeding after turning 50 that involves three major components: passion, purpose and hope.

“I’m not an expert in it, but I think many people over 50 are just floundering,” said Mark. “They have had a purpose all their life; they raised a family and been part of some type of business. But, when it comes to retirement, people need passion and purpose, and they are all fueled by hope.

Mark Reinhardt

“You don’t need purpose or passion to be successful, but you do need hope that it will materialize,” he explained. “You need to figure out what you want to do. Do you want to chase something that gives you passion or do you want to chase something that gives you purpose? Once you narrow that down, then you start building in that direction.”

School of hard knocks

Although his life has been marked by a series of disappointments, Mark always held on to hope it would turnaround soon. For example, although he had never been in the restaurant business, he opened a restaurant/bar combination in 2007.

“It turned almost a million dollars that first year. Then 2008 and the Great Recession took everything away from me during the four years I was trying to hold on to it,” Mark explained. “Before that, I had been flipping properties. When the restaurant was failing, I decided to convert one of my properties into a blueberry farm.

“I went from being bummed out and depressed about losing the restaurant to having a full life again. I was doing the math behind how many blueberries I could sell,” he said. “Once again, I had a new purpose. But, I had to sell that property before the blueberry business got off the ground. However, just having hope I was going to be successful in the blueberry business turned my life around.”

Overcome with joy and happiness

After the restaurant failed, along with the blueberry farm, that’s when Mark opted to hike from Orlando to Key West.

“I couldn’t buy a job because the economy was in such bad shape. I couldn’t even work as a handyman,” he explained. “So I got a backpack and starting hiking to Key West along the coast. I’d pitch a tent at night, and hit the road the next morning.

“One night, I remember being overwhelmed by a feeling of awesomeness. The breeze was perfect as the sun was going down. I realized I could not feel any better than I felt right then,” he added.

“There was a big 12,000-square-foot mansion behind me. There weren’t any lights on in it other than one in the kitchen where this guy was sitting at his table,” said Mark. “I thought even with all his money in that big old house, there was no way he could feel any better than I did at that moment. I was just full of joy and happiness.

“That’s the moment I realized the success I had been chasing my whole life was no longer what I wanted,” he added. “I had almost nothing at that time, but there was nothing which required me to be successful in order to experience happiness.”

Mark Reinhardt

From that point forward, Mark researched ways for him to keep traveling without walking, and his desire to go full-time sailing again was born.

Strong desire to travel

Mark has not given up on his dream to circumnavigate all the way around the globe in his sailboat.

“My goal is not to get stuck in one place thinking it is paradise and I need to stay there,” he explained. “Once I sail all the way around the world, then I’ll consider what my favorite place was and return to it.

“The San Blas islands were a beautiful environment. But, who is to say Fiji, Galapagos and Cook islands – or any of those other tropical island paradises – are better?” he asked. “I have to accomplish my sail around the world. After that, I’ll definitely be looking for something else to do, or decide to make one place my end game and just chill out there for a while.”

Low-cost lifestyle

After making an initial investment in a sailboat, a life at sea is relatively affordable, Mark said.

“It all depends on how well you equip your boat and its overall condition,” he explained. “If you have new sails, a good motor and all the components work, like your water maker, then the monthly cost is really up to your unique tastes.

“The beauty of living on a boat is that you cannot spend money unless you go to land,” he added.

The key to a successful on-sea lifestyle rests in preparing the vessel. The better equipped it is to stay at sea, the less time people need to spend in port.

Mark got a captain’s license 35 years ago, even though it wasn’t required. Nor does the Coast Guard have any special requirements for people to navigate the seas. Insurance companies may require people to attain specific certifications, but that depends upon the company.

“We call some people ‘credit card captains’ because if you have a credit card and can buy a boat, then you can pilot it,” said Mark. “Other than that, there are no real requirements other than learning things which would be beneficial for you to learn.”

By being self-employed for most of his life and not having money to pay for mechanics, Mark learned how to fix many things by himself. That put him in a better position to take care of his sailboat.

“When you buy a boat, there are always things which need to be done. But, when you learn to fix them by yourself, then you know how the equipment operates,” he explained. “There is a lot of maintenance that goes into taking care of a sailboat, but it’s usually preventative maintenance.”

Starting over

If Mark could have a re-do in his life, he would eliminate a huge business failure that created a big financial setback for him. Other than that, there really isn’t anything he’d do differently.

“If I took away everything bad that happened to me, then I wouldn’t be who I am today,” he explained. “I know it’s cliché, but the hardships you go through really shape your life.

“If you look at people who never had to endure any real hardships because they were born with a silver spoon or live a silver spoon life, they are going to have a hard time surviving if that all got taken away,” he added.

Mark has to contend with a bad hip that gives him some problems from time-to-time. Yet, he maintains a rather active lifestyle by spending a lot of time snorkeling.

“I get my exercise through swimming,” he explained. “There are a lot of places on land that I want to explore when I get to them. But, I am only good for a half a mile or, maybe, a one-mile walk before I am in pain.”

Advice for people over 50

Regardless of what people want to do after turning 50, they need to embrace it fully and with passion, Mark explained.

“Some people are passionate about their church and helping the homeless. If that’s what drives you, then that’s what drive you,” he said. “But, once you decide to follow your passion, you should not tell anyone what it is.

“There are so many naysayers who would never have passion for what you want to do. So, they will tell you all the reasons why you can’t do it,” said Mark. “But, you just have to keep those people out of your life.

“When I was talking about sailing around the world at 30 years old, I realized doing something like that would scare the heck out of other people. So, they try to impose those fears on you by saying you shouldn’t try to do it yourself,” he explained.

“I’m not saying don’t take advice once you figure out what you want to go after, but be careful with whom you ask for that advice,” he added. “The richest place on earth is the graveyard because so many people die with their music still in them. I won’t die with my music still in me.”

To connect with him, look for Mark J. Reinhart on Facebook. Although he is at the maximum for the number of friends Facebook allows him to have, people can still message him if they have questions or are interested in the sailing lifestyle.

His book “Off the Grid: How I Quit the Rat Race and Live for Free Aboard a Sailboat,” is available on Amazon and other bookstores.