Making the leap from being a dirt dweller to seafarer

What is it about the sea that calls to so many? There is the beauty and power of the sea, the sense of adventure from traveling the oceans, and the freedom of wide open spaces. There are many romantic notions which make up the allure of the sea. So why do so few make their life on the sea? As every old salt knows, while seafaring life can be minimalistic and extremely gratifying, it’s anything but simple. Unlike the images you see on YouTube and Instagram, the barriers to this lifestyle are numerous and high. It’s definitely not for everyone but it can be done by just about anyone who is committed to making the dream a reality.

The journey to the full time liveaboard life has taken our family nearly 10 years. And while we both committed to making the transition from life on land to life at sea, the old adage, “easier said than done” has certainly proven true in our experience. The initial hurdles to casting off are the hardest of all. Once you manage to free yourself from the typical trappings of a mortgage, car payments, the daily commute to get to work, and hordes of “stuff”, life gets a lot easier.

In this post, we’re going to get real about the steps you need to consider if you’re serious about making the transition from life as a dirt dweller to full time seafarer. It’s not an easy road but it’s well worth it.

Start by doing your homework

Living on a boat full time is clearly a bit unconventional but the change from landlubber to able seaman is much bigger than I can adequately explain. It’s an amazing life and well worth the trade offs. But for the unprepared, it could prove to be an epic misadventure. It’s important to take the time to educate yourself about what you’re getting into. I don’t just mean binge watching YouTube videos. You need to get a hands on education and as much experience as possible.

We hear a lot of tales of couples or families with little to no prior sailing experience getting the sailing bug and buying a boat. While this has been done, we can’t personally recommend this approach. Modern technology has helped lower some barriers to entry: you can shop for boats on Yacht World, auto-plot a course from A to B with Navionics, and much more — but there is a lot more to it. Any fool with enough money can purchase a boat, but buying the right kind of boat for your intended purposes, knowing how to sail and maintain it, and keeping yourself and your crew safe are a whole other matter. We recommend a combination of informal, formal, and immersive learning experiences to build competence and confidence.

The good news is: you can start at home. Crack open a book (or eReader) use the web to start learning basic sailing terms and the points of sail. This will help tremendously the first time you step foot on a sailboat to crew with more experienced sailors. Next, learn basic sailing knots like the bowline, figure eight, square/reef knot, clove hitch, and rolling hitch and their applications. We strongly advise taking an online course on boating safety and the rules of navigation. Most states in the US already require this form of training in order to legally operate a vessel on navigable waterways. We also recommend taking a first aid and CPR course. As you begin to transition to hands on experience, continue reading as much as you can about piloting, weather routing, safety at sea, storm tactics, and provisioning. It doesn’t have to be all study and no fun. Pace yourself. Read books by voyaging couples and families like the Pardey’s and Copelands or watch videos about the life for inspiration. Just remember: these are subjective accounts; there is no substitute for personal experience on boats.

While you’ll always have more to learn, and may never feel completely “ready,” you can reduce the steepness of the learning curve and avoid costly (and potentially deadly) mistakes by investing in your education — starting right now.

Get hands on training and experience

After some personal due diligence, it’s time to get as much time in boats of all shapes and sizes as possible. Connect with the nearest yacht club or sailing group near your area. Social media is a great resource to connect with other sailors. Volunteer to crew or offer a helping hand with boat work. You’ll be doing a lot of the latter, so you might as well get started.

Once you confirm you enjoy sailing, not just the romantic idea of sailing, it’s time to invest in more formal training courses like those offered by the American Sailing Association (ASA 101 - 104) or US Sailing. As you gain experience, consider renting and chartering. This is a far more practical way to learn and experience different types of boats from monohulls to cats than buying a boat right off. It’s also a good idea to consider at least a few tours of club level racing at your nearest yacht club on smaller boats. This will greatly accelerate your sailing skills and help you learn to develop “feel” for the effects of wind, current, and waves on the boat and helm. Alternatively, you may start out as “rail meat” on a larger boat with an experienced crew. As you learn, and the crew gains confidence in you during practice, rotate through as many roles as they‘ll let you from trimmer, to bowman, to helmsman.

At this point, you’ll be ready to consider your own boat. Proceeding in the sequence described above isn’t required, but you’ll be much better educated on what you like and considerations that will help narrow your search. Don’t be afraid to seek help from a buyers broker or other experienced sailors.

Keep in mind: sailing the boat is the easiest part of sailing life. Docking, anchoring, and working on the boat are the biggest challenges. A course on diesel engine maintenance and repair is also highly advisable.

Develop a plan and commit

After you’ve gained some experience on your own boat and commit to transitioning to full time liveaboard life, it’s time to develop a plan with milestones and target dates to achieve your goal. This is exactly the same as developing a project plan. A lot of people tend to focus most of their attention on finding a boat and getting it ready, but there is a lot more you need to consider. Selling or renting your home, updating passports, setting up a mail forwarding service, outfitting your crew, updating immunizations, arranging a year’s supply of prescription medications, etc. Also, if you have pets, you’ll have to decide whether they will come with you or go to family/ friends. This is a hard decision. But taking pets, especially dogs, can make life more complicated.

Buying the boat

We hear a lot of tales of folk who jump from never having set foot on a sailboat to sailing around the world. Stories like “Chasing Bubbles” come to mind. But rest assured, this is neither common nor wise. It’s become a bit of a cliche, actually with the seeming explosion of interest in “cruising” thanks to YouTube sailing vlogs. Sadly, very few of these dreamers will ever leave their local waters, much less complete a multi-year circumnavigation. They certainly don’t need to. There is nothing wrong with cruising the Great Lakes, the Chesapeake Bay, or the Caribbean. The point is, often times, the first time green sailors (aka land lubbers) encounter an unexpected hardship or get into a bit of a blow they aren’t prepared for, they get scared and either never venture out in anything but the mildest conditions or sell their boat and abandon their dream. It doesn’t have to be that way and we don’t want that to be your story!

When looking for a boat, consider: Where do you plan to sail most? Primarily coastal sailing with some island hopping? Do you plan to sail with the seasons or winter in colder climates? Will you make multi-day offshore ocean passages or do you plan to stick to inland waters and the ICW? Will you spend most of your time in the deep waters of the West coast or the relatively shallow waters of the East Coast, Chesapeake Bay, and Bahamas? How many people will be aboard full time? What about pets? How many years do you plan to live aboard? The answers to these questions are key to choosing the right type of boat for your needs.

What is your budget? Don’t just buy the biggest beast of a boat you can afford. Consider the real cost of ownership to buy, refit, and maintain your new home. I don’t care how new or well cared for the boat appears, expect to invest 20-30% more than the initial purchase price (best case) to outfit for full time cruising and budget accordingly.

The big purge

Getting rid of 95% of your “stuff” is a necessary step and it may prove challenging. It’s not just that all your things won’t fit on your tiny floating home, most of it will prove useless.

Even if you’ve moved many times and purged over the years, you are going to be shocked at how much “stuff” you manage to accumulate. This is especially true if you have children.

We recommend organizing all of your things into the following categories:

1. Essential things to take on the boat

2. Things to keep in storage (in our case, this was just family heirlooms and things with sentimental value we could keep with family)

3. Things to sell

4. Things to donate

5. Things to throw away

Category #1 has to be kept to a minimum. Don’t be surprised when multiple purge cycles are necessary.

Staying connected while working remotely and homeschooling from a boat

If you plan to continue to make a living while traveling afloat vs running down savings or living on passive income, you’re going to need a plan to stay reliably connected. Being connected at all times is certainly not required for homeschooling but it is a big help. While this is achievable, it is a little tricky. Marina WiFi is notoriously unreliable. And while WiFi signal boosters do work, unprotected connections are increasingly uncommon, not to mention they present a higher security and privacy risk.

We recommend relying on mobile network data with multiple layers of redundancy. To stay connected in remote situations, we also have a satellite connection which does not support streaming video but is capable of low speed browsing, two-way phone calls and SMS so we can stay in touch with family and friends anywhere in the world.

Making the transition

At this point, you are probably as well positioned as anyone can be to make “the leap,” as we like to call it. Much like parenting, no one is ever totally ready. You’ll spend an increasing amount of time on your boat now, as you should. Move onto the boat progressively, if at all possible. Try working and cooking on the boat. Don’t wait to figure this stuff out later.

Take the boat out away from the marina as often as possible too. Don’t just go day sailing — practice anchoring out, heaving to, reefing, and jibing. Do overnight passages and establish a watch rotation. Learn your boat well and how it behaves in increasingly challenging conditions. Make increasingly longer and more challenging trips.

In conclusion

If this seems like a lot to consider, that’s because it is. It’s also just the tip of the iceberg but one can only say so much in a single blog post on such a vast subject. We aren’t trying to dissuade anyone. Far from it. The journey is well worth it but the unvarnished reality is there aren’t any shortcuts. We hope you find this post helpful in your journey and if you have any additional thoughts, advice, or questions, let us hear from you!

God bless and fair winds,

Ben Ward

S/V Koinonia