Full Time Sailing – Thoughts, Expectations & Uncertainties

Nikki Wynn

Mar 6, 2016 — 8 min read

We had one last hurrah in Texas where we carved out quality time with family, picked up right where we left off with friends and Jason served his jury duty like a good citizen. Now we’re on a mission to drive the 1324 miles from Ft. Worth, Texas to Ft. Lauderdale, Florida.

It’s time to get serious about sail boat shopping. We can only do so much of it online and we’re at the point where we need to get on board and out on the water. We’re looking for a used Catamaran and there seems to be a lot of them sitting in Florida. Our friend Pat recommended a boat broker out of Ft. Lauderdale that’s supposed to be a really nice guy (aka, not a shady salesman). Our goal is to get to FL, get on some boats and figure out what boat (and size) we think will best suit our needs and wants.

I feel like the past 5 years of being full-time RV’ers gives us a useful perspective as we’re heading into this shopping and living aboard a sail boat thing. We’ve learned a lot over the years that should transition and alleviate some of the shock and learning curve most newbies have…or so we’re hoping.

Living in small spaces, off grid and rolling with the proverbial punches are all things we’re accustomed to. However, it doesn’t mean we’re free from the anxiety of what’s ahead.

We’re not big planners…we’re un-planners and we don’t enjoy much of the planning process. We like the doing part. The learning, the experiencing and the conquering of goals is what gets us springing out of bed like we slept with a caffeine drip.

Sure, we’ve been scouring the watery depths of the internet and watching plenty of YouTube videos but we’ve still got a lot of thoughts, expectations & uncertainties swirling around in our heads.

Our Sailing / Ocean Experience

While we’ve logged hundreds of hours on the water in various motor boats over the years wakeboarding, water skiing and fishing…sailing is an entirely different adventure.

Our first time sailing was January 2013 and you can read about it here: First Time Sailing, with Pirates, in Arizona. Since then we’ve sailed with friends in San Diego, Chicago and Charlevoix, MI. We’ve loved each experience and it only deepened our desire to live on the water full time.

Here is the unofficial brain-dump of things we have on our mind right now. It should be fun to come back in a few years when we’re a little more seasoned and revisit these worries and excitements.

April 2017 UPDATE!!! We’ve been sailing and sailboat owners for one year now. Whoop Whoop! So, we thought it was the perfect time to come back and update our own unknown thoughts, expectations and uncertainties. To see our one year update video, click here: gonewiththewynns.com/dream-first-year-sailors

Sailboat Shopping

Can we get what we want/need within our budget and have enough left over to get the boat ready for living/sailing? Things are no-doubt about to get expensive!
- No, you officially blew the budget out of the water and took out loan! See the damage here: gonewiththewynns.com/exhausting-journey-buying-cruising-sailboat
Size – We think we want around 35-40ft Catamaran, preferably closer to the 35’ size.
- Turns out a 35ft catamaran is great for coastal cruising, but not as well suited to sailing around the world. We landed on a perfect for us 43ft Leopard. You can see the first time we sailed her here: gonewiththewynns.com/sweet-life-sailing-dream-boat
Sales Tax – We’ve heard of some interesting ways of avoiding sales tax…which is worth investigating, but we don’t want to do anything illegal or shady.
- We ended up registering with the Coast Guard. You can read the full scoop here: gonewiththewynns.com/exhausting-journey-buying-cruising-sailboat
Insurance – How much and what type of coverage do we really need. We’ve read about a lot of cruisers that choose not to have any insurance, or print fake cards to get past customs.
- Insurance was a must as we couldn’t take a risk with such a large investment. Insurance info here: : gonewiththewynns.com/exhausting-journey-buying-cruising-sailboat
Gadgets – Which gadgets/tools do we need right away? Epurb VS. Sat Phone / Auto-pilot / Wifi Booster / Cell Phone Booster / Ipad apps VS. installed GPS plotters (or both).
- Oh baby did we need way more gadgets than we ever anticipated. One year later we’re still working on getting all the gadgets. You can see everything our boat is equipped with here: gonewiththewynns.com/curiosity-sailboat

Stuff To Learn

Knot Tying / Vocabulary
Safety Lessons / Sailing lessons
Weather / Hurricane Seasons
Boat Maintenance, engine maintenance
Man (or cat) overboard routine
Rope Splicing
Emergency Sail Repairs & Stitching

Sailing school taught us most of what we needed to know and then Kent and the team at Just Catamarans filled in a lot of the gaps. Looking back, there isn’t anything that has happened over the past year that we felt unprepared for. All the investments in education have proved to be more than worthy. All of our sailing schooled and maintenance episodes can be found using the tabs on the sailing page: gonewiththewynns.com/sailing

Transitioning from RV to Boat

Selling/donating un-needed items.
- Check!
Sell our little Smart Car.
- Check!
Cancel our memberships (Costco, Massage Envy, AAA, etc)
- Canceled all of those and signed up for all the boating varieties. Tow Boat US, Dan Diver Network, ASA…
Slowly Introduce the Cats – life vests, tethers, carpet hanging off the boat, toss them into the water.
- They are great swimmers but even better at being cautious. They love lounging on the boat and like fishing as much as we do.
We really need to get a tan and get into shape before we start running around in bathing suits!
- Ha, more like buy stock in zinc based sunscreen and as for the getting in shape…we’re still working on that.
Buy a second Stand Up Paddle Board
- Check!
Buy water tight bins to store foods and sensitive gear.
- Yes, lots and lots of sealed bins: gonewiththewynns.com/product/storage-boxes
How much of our clothing will we get rid of?
- Still need a variety of clothing (can’t wear bathing suits everywhere) but only a couple pairs of shoes.
What Kitchen Gadgets can we fit in the tiny Sailboat kitchen vs our RV kitchen?
- Surprisingly all of my gadgets came with along with a couple of new ones. All my kitchen gadgets can be found here: gonewiththewynns.com/store
Sailboat refrigerators are tiny and it’s gonna hurt leaving our residential RV fridge.
- Yes, still miss the fridge space.

Lifestyle Thoughts

Finding Wi-Fi is going to be a pain in the a** and upload speeds are going to STINK.
- Yep, stinks all the way around…get used to it! Some places it works great, others not so much.
Anchoring out will be like wild camping.
- Dead on! Nothing beats the freedom of living life on the hook. With our beefy anchor sleep like babies!
Free diving, snorkeling, surfing and fishing trips, no more hiring an expensive charter.
- Check, check and check! Living on top of the worlds largest swimming pool and aquarium is beyond stimulating. Still working on my comfort level with sharks, but I’ll get there.
Should our Dinghy be powerful enough to wakeboard behind?
- We did go with a powerful motor for the dinghy and it was the right choice. Now we just need a wakeboarding sponsor to send us some gear…because we’re now broke but happy sailors.
Medical care might actually be easier and less expensive abroad.
- We’re still sorting this one out…we should know better than to put easy and healthcare in the same sentence.
We’re going to make a lot of mistakes…probably ones that will cost us money.
- Not too many costly mistakes…yet.
Will we have to bribe border agents often with booze and such? We’ve read lots of stories online.
- So far so good and all legit. People are mostly good, especially if we go in with the right attitude.
Will we find organic foods, Non-GMO, craft beer, good coffee, etc, or do we need to stock it?
- Stock up!!! Remote islands are not good places to shop.
How long before we’ll be spearing fish, grabbing lobster and cookin’ fresh crabs from the back of the boat?
- In the first month!
Is there a way to test fish for Mercury and other toxins?
- Still not sure about this one but we haven’t searched hard.
Understanding weather both visually and radio reports.
- Sailing school covered that!
How long will it take to get our sea legs and get comfortable sleeping on the boat?
- No problem at all…not even on day one.
Exercise on the boat and getting in enough land time. Will it be a challenge?
- Yes, depending on where we are, there may not be trails or long stretches of beach. We’ve gotten used to exercising on the boat doing yoga and using our suspension bands: http://amzn.to/2qcjDqU
Saltwater and humidity are going to destroy our gear 2x faster. How long will our cameras/computers last?
- It does take a toll on everything. Computers are holding up okay but the cameras are taking a beating.
Will we have any time to play between scrubbing the deck, doing boat chores, filming, editing video and writing?
- I won’t sugar coat it…it is a ton of work and yes a lot more work than RV’ing but the rewards are worth it.
Can we afford this lifestyle for more than a couple of years? The boat alone is going to make a huge dent.
- The boat was a much bigger hit than anticipated. So far we’re managing and Patreon is helping a lot. Only time will tell.
Is Jason going to get sea sick often? He better suck it up and get accustomed!
- Great success! So far he hasn’t gotten seasick on our boat!

As you can tell we have a lot to tackle in the coming months and things should start to get pretty exciting. We’re taking things one step at a time and we’re in no rush. We want to make sure we set ourselves up for success, and not failure.

If you’ve got tips, tricks or recommendations…we’re all ears! Leave us your thoughts in the comment box below.

However, please refrain from the doom and gloom comments, it’s not constructive or helpful. We are well aware of the risks, we will take sailing safety courses, we will be as prepared as possible. We know you only warn us because you care (we love you too) so please try to share any warnings in the most positive and constructive way possible.