Sailing Around the World: Think You Could Hack It?

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Sailing around the world might sound glamorous and romantic. You might dream of being the center of attention at your next cocktail party while you go on and on about your adventures while sailing around the world. But, do you even have a clue what's involved in this sort of endeavor? You think you can hack it, no big deal? Well, why don't you chill for a sec and let’s take a peek at what's involved.


Yes, there’s going to be some cha-ching involved. Let’s hope your savings account is pretty stout because an excursion like this can cost upwards of $70,000 and that’s just for the boat—an old boat.

Once you have a boat lined up, you’ll definitely want to make sure it’s sea-worthy. You’ll need to do all the required maintenance, check the equipment, and get all the supplies you’re going to need for your lengthy stay at sea.

Sundowner Sails Again dishes on all the costs involved. These folks spent months preparing for the voyage and, just so you don’t have to reinvent the wheel, they laid it all out for you so you can get a grip on the total you’ll be shelling out for your next sailing adventure.

But, if you don’t have the Benjamins for a boat and all the gear … you could do what Liz did.

Be Like Liz

Who is Liz? Liz is the ultimate “cool girl” and has been sailing around the world for ten years. Yes, you heard that right—ten years!

How did she start out? She was just like some of you, living the beach life and bartending at night to scrape together a living. Then, she met her benefactor, who wanted to fulfill his life-long dream of sailing around the word vicariously through her. He let her use his boat and the rest is history. You can check out her incredible journey here.

Now if you don't have a sugar daddy like Liz, there are some other ways you can still get this done.

Team up. You can join a sailing crew that’s already in place. You might get a job as a nanny, cook or a crew member on a boat that’s already manned and headed around the world. Or, you and your posse can go in on the trip together (better make sure you all get along—it can be a tight space for a long time).


Still onboard, so to speak? If you’ve got the green handled, you’ve got your team in place and you still want to up your creds, then read on. You’ve still got a shot at being that cool guy who just got back from an adventure around the world … if you can hack it.

Do you love lack of sleep and around the clock navigating? Will you get seasick? Are you going to be able to handle an extreme amount of sun, wind and water? Are you bringing enough food along to make it through the trip?

Oh yeah, and man cannot live on bread alone. So, if you like your cocktails, you better stock up on the booze, too. Sailing around the world can take a very long time so you definitely wanted to be prepared.

Get Your Ship Together

Clearly, you can’t just jump on a boat and head out. There’s going to be a lot of other stuff that’ needs to get handled besides prepping the boat and figuring out the grocery list.

First, make sure you plan where you’re going. Know your projected timeline and your destinations. Check into regulations and local laws so you don’t run into problems when it’s time to dock. Make sure you have all your paperwork on point before you embark because trying to get that sort of thing done after the fact could be a nightmare.

Don’t forget to stockpile your meds, get all your immunizations updated based on the countries you’ll be visiting, and plan ahead for contingencies. Make sure you have a way to get home quickly, should there be a family emergency or if you happen to get sick.

And, by the way, better wrap things up tight back home, too. If you have bills and other responsibilities, then man up and lock all that down before you take off.

Lastly, as if you didn’t have enough on your plate…

Pirates Are Real

Yup yup, you read that right. We’re not talking Johnny Depp, either. These guys aren’t playing. They literally roam the seas in unmonitored waters and wait for dream seekers like you to sail into their traps. They’ll board your boat, steal your stuff and, if you’re lucky, leave you floating off into the sunset in your dingy. So, bottom line, be careful, navigate in policed areas and bring a firearm if that’s your thing.

Can You Hack It?

Still want to try your hand at this? You’ve got some homework to do. But, this should give you a good blueprint to follow and help you jumpstart your trip around the world.

So, the next time someone asks you what you've done for fun lately, now you just might have something interesting to throw out there. Turns out, sailing around the world might be exactly what you need to satisfy the thrill-seeker in you. If you can hack it…

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Stephan Aarstol is an American internet entrepreneur and author of the book The Five Hour Workday, which is based on Tower Paddle Boards' invention of the 5-hour workday in 2015 that would eventually spread the idea to over 10 million people worldwide. Since founding Tower in 2010, it has gone on to become one of America's fastest growing companies and Mark Cuban's best investment in the history of Shark Tank. Tower has diversified into a direct to consumer electric bike company called Tower Electric Bikes, a beachfront event venue called Tower Beach Club, and, where consumers can shop all the world's finest direct to consumer brands from one easy place.