As I said moments ago, I get a ton of questions about my sailboat. And I’m going to hash them all out right now! Not that I think this will come anywhere close to ending the questions and that’s okay. I’m excited too.

Where is the boat now?

Currently, she is dry docked, which means on land specifically on stilts, outside of St. Augustine.


Well, y’all all saw the video of Island Girl being brought on land, when they take her out she goes up in a swing on a movable tractor thing, same deal with being put back in the water. If she goes on a trailer to be shipped somewhere, the mast has to be stepped (taken down) and lifted up by a big ol’ crane. Both of these options take a lot of prep and planning, neither are cheap. It is part of what I signed on for, but it is a good chunk of change. So, she’s currently staying where she is for the following reasons: storage is super cheap at her current dock and it isn’t really worth paying all that extra money to move her around when I haven’t fully decided where I want her to end up.

Why don’t you sail her to Charleston?

Well, obviously the first snag there, I can’t sail…yet.

Why don’t you hire someone to sail her here then?

Coming up from St. Augustine where she is to Charleston, what is a 4 hour drive by car is about a week trip by sea even for an experienced sailor who buckles down and hustles. To take her by sea to Pensacola would be, at a minimum, 3 weeks and going all the way down the around the tip of Florida. That kind of time doesn’t come cheap. Plus, she doesn’t have a motor.

She doesn’t have a motor?! Also, sailboats have motors?!

Nope, no motor. Which made Island Girl’s price tag much more appealing. Here’s the deal, if I’m patient and keep a lookout, I can snag a used outboard motor for $200. If I just go grab one, it will be closer to $800. Learning from my past experiences, I know enough to not sink a ton of money into Island Girl until I know for sure this is the route I want to take. She doesn’t need a motor for me to dock her in a slip and live on. She definitely doesn’t need a motor if I go with my fallback plan (see below).

How will she get somewhere?

If she goes back into the water, it will be the same as when we took her out. The big sling on wheels scoops her up and lowers. If I move her, she’ll have to be put onto a custom trailer. She’s got a 4 foot draft so she has to be pretty high up. That involves a big crane to lift her and a big crane to step the mast (taking it down). Same thing coming off the trailer.

So she’s just sitting there?

Island Girl is a sound sailboat, solid hull and not a single soft spot on her decks. Even still, she’s got some sprucing up to be done. Her beautiful teak wood is getting varnished, custom cushions are being made for the cabin, berth, cockpit, and for sunning on the bow. Lighting in the cabin, upgrades to the head, etc. More than esthetics, some minor work on the hull while she is out of water. Up top she is being painted, maybe down low too. We’ve got 5 tiny bubbles that I’m thinking I’ll wait until after the season to address and there’s not really any point in painting her now if I’m doing that next year. She is going to be beautiful.

Are you going to get pink sails?

Even I know my limits on the extra. No pink sails. Same on the motor, I’m not putting a ton of extra money in to anything that expands more than making her live-aboard ready. And if I were, it wouldn’t be new sails. Island Girl has a full set of sails and rigging in fab condition, no need to replace them especially when having new sails done is thousands and thousands of dollars. But, do expect to see pink Sunbrella all throughout the rest of her.

What is this backup plan?

If anything from this crazy life of mine and the last year or so on the road, I’ve learned to ALWAYS have a back up plan. Did I blow my whole boat budget on Island Girl? Hell no. We’re using fake money amounts here because even though I share tons with y’all, the exacts of my financials isn’t everybody’s business. So let’s says I paid $50 for Island Girl. Everyone kept saying if I just spent $1,000 I could just get a boat that was all ready to go! What if I don’t love boat life? (Gasp, I know?! Who will I even be if not a boat person?!) I’d rather make a $50 mistake than a $1,000 mistake. Hello, RV lessons learned. So I’m going to put maybe $20 into my $50 boat, see how I like it and go from there.

Really, I just want to be able to unpack all my stuff in one place.

Now, if the worst turns out to be true and I’m not a boat person (just the idea of that makes me clutch my chest with anxiety, this absolutely cannot be true), I’ve got a couple of options. First, turn around and sell her for double what I paid and put into her (yes, it really was that good of a deal). Second, sell her sails and rigging to cover a year or two’s slip rental and set her up solely as an AirBnB.

So you’re bringing her to Charleston?

I still don’t know. Charleston isn’t cheap y’all! We’ll see how things go. I’ve got a hard deadline of April 1st for my work and she’s having her own work done so no need to rush any decisions. I’ll figure it out when the time rolls around.

Are you going to rename her? Isn’t that bad luck?

Yes and sometimes. There is a whole renaming ceremony that takes place to make sure you stay on Poseidon’s and all the other gods’ good side. Don’t ask me what, I haven’t even begun to decide that. You’ll all be invited to the ceremony where part of the appeasement to the gods is lots of good food and booze.

Big Takeaway:

Boats are expensive, but the one thing I’ve found cheap is the storage rates where she is currently. Remember the big crane and stepping the mast? Yeah, that’s expensive. Huge ordeal. And I don’t feel like doing it multiple times. She’s already on land, let’s get everything done we need to while we can instead of the whole process just to move her to a different dock to work on her then the whole process again to put her in water.

On top of all that, the owner of the dock and the guys working on her are really good, genuine, honest people. I trust them and their work. Especially since they come at an affordable rate. The estimates I got in Pensacola, which is a pretty low budget water town, were about four times as high as the quotes where she is docked. In short, moving her only once, paying low dock rates, getting skilled labor at a beyond fair price is the course I’ve charted (ba-da-dum!). Everything else can be figured out in due time.

So yeah, the boat is good! Plan is going well! And yes, you’ll all be welcome to come aboard….well, almost all of you. Like I said the other day, sailboats are for tacos and houseboats are for haters.