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Drowning in Sailboat Paperwork

Life is chaos right now, honestly. I happened to also have a doctors appointment this week and no kidding, my blood pressure was really high. It might have to do with my recent weeks having a medical surgery, I’m fine nothing to see here, two major international business trips (India for a keynote and then headed to Australia this weekend), some major, major work related things going on, a couple professional things I have going on and OH, we decided to buy a rental property ...I know, plot twist...lots going on.

Anyway, aside from all that...lets talk about sailing. All this suddenly got real a couple weeks ago when we had a call with our broker who confirmed our boat delivery date, which right now is mid-February. Which is like in 5 minutes. We were also given our hull number and my husband and I started to freak out.


So after that, we pretty much quit binging on YouTube videos (which we like to call boat porn) and I immediately ordered one of those dry erase wall calendars so we could get ourselves organized with a better view of a timeline and started capturing to-do items on post-is that are spread all over our little home office and up and down our hallway.


Here’s the most pressing items that clutter or walls right now

Registration and flagging

After months of gyrations about whether or not we wanted a US flag on our boat, for obvious reasons that are outside the scope of this post, we decided to stick to US flagging for now and call it a day. Why would a US citizen consider a different flag? Well, we have no intention of ever bringing the boat back to the US, since the whole idea is to sail foreign waters and discover the world. The other reason we discussed flagging it separately is initially we were exploring a potential plan to offer crewed charters from our boat, something we might want to do later and didn’t want to lock ourselves out of.


There’s a whole galaxy of items to think through on this front, where you get a skippers license, my husband already had gotten an RYA, so that’s a non-US certification. This means your boat would be flagged outside the US (since the boat’s rules follow the flag it’s under). This would also require commercial yacht certification and inspection criteria in principle. Which means it’s not mandatory compliance but if something went wrong or someone got hurt, there may be problems if you didn’t show compliance. Then there were all these guidelines about where you could or couldn’t operate, and who you could or couldn’t pick up where - which we could never fully nail down - honestly the whole thing is super convoluted and the current laws and international treaties were written for boating as it existed back in the dark ages when people were trading spices and rum and doesn’t at all apply to how cruisers actually want to operate their boat legally in practice. Not to mention all the fees that go along with annual inspections, registrations, and things that seem ridiculous like getting a boat initially surveyed….dude, it’s a brand new boat. Commercial classifications, for the boat and the skipper, getting the boat set up for commercial regs, and it goes on and on.


Backing all this out, then you would be running a non-US charter operation but you would need to file taxes as a US business and by some wacky loophole you can’t claim it as a US business if the boat had a non-US flag. Which to this day doesn’t seem right as long as the business was a US business. However, this whole adventure down this rabbit hole involved countless hours of research and calls with attorneys and tax people...which PS is not my favorite way to spend my time. I finally had a heart to heart with my husband and explained that the whole goal was to have more freedom and the more we started digging into this option, the farther away that goal started to feel so I drew the line. If we needed an additional source of income while on the boat, I would just do a couple consulting gigs and call it a day.


Okay so now that we got that whole boat as a business out of our system. There are other interesting options for flagging in different countries with various pros and cons (and stigmas). We explored to have a Cayman Island flag, mostly because the thought of it made me feel much more yachty and glamorous, but all vanity aside, we couldn’t justify the cost involved and the legal complexity that goes along with it...we did hire attorneys to tell us what it meant, which was pretty much the same as we were told from the Cayman boat registration office by a lovely woman named Natasha. We also explored Jersey but at the end of the day, we landed back with a US flag and USCG documentation...exactly where we started in the first place.


By the way, there are two ways to register your boat, attach it to a state or just have it US Coast Guard documented for offshore. If you register with a state, state laws and use taxes are applied. USCG you are documented as a US boat but once in US waters over a certain amount of time in one place, say 90 days, you have to register with that state if you intend to stay there...though it’s not super clear to me who goes around and checks...like with your car, a parking enforcement person comes by and marks your tire if you’ve not moved...what’s the process of monitoring that? Not like we intend to do that, but it just makes you wonder.


Anyway...all said and done, USCG documentation runs you about $500 for 5 years, if you want it under an LLC, costs vary but roughly $200 a year unless you need an agent in whatever state you are doing it in, then that’s another few hundred dollars, and if you opt to need an EIN tax ID number, they you have to pay the franchise taxes if they apply to the LLC another couple hundred...and...you can opt to hire an attorney to do all this for you every year and it’s roughly $2,000 a year give or take.


Update: We changed our minds and went with BVI registration, which you can read about here.


Sailboat insurance

Insurance is another topic taking up our time, I’m going to save this for a future post because we are just starting down this path. Suffice it to say, there’s the direct contact with the insurance companies or you can go through a broker, but if you are sailing, say in the med you may have a broker in the UK who doesn’t want to be your broker when you move over to the Caribbean. Then when you switch maybe the terms change so we are just trying to get our arms around all this.


Move estimates

Our initial plan was to just pack as many suitcases as we could and take them with us on an airplane but I’m trying to think this through practically speaking. Here’s how France works. You get off the plane in Charles de Gaulle and you have to either figure out how to rent a car or take the high speed train to La Rochelle. As an American it sounds simple, you just rent a Ford Explorer and shove your bags in the back and return your car to the nearest National rent-a-car in La Rochelle right. Ya, that’s not really how it works. First, in France the cars are tiny by US standards and even if you rent a big one, you run the risk of it not being actually what you ordered and not being able to do a one way trip. France just operates differently and there is a pretty high chance someone in the logistics department one day decides as two people they don’t think you really need a big car. It’s just how they roll.


On the other hand, at the train station, how do two people get 8 suitcases anywhere in time and settled on the train? For anyone who has used the French rail system, it’s super awesome and convenient, and cheap if you are traveling with one suitcase and a backpack. France is also not as generous with their escalators as in the US, because people are used to taking the stairs more and the elevators you can barely fit three people into.


So I reached out to a bunch of shipping and moving companies to get quotes. You can get a container which is like $5K and overkill for what we want to move, you can move boxes or you can ship a crate. For a dozen or so boxes the range is around $2K USD which is expensive but goes door to port in our case. However, when we started breaking down what we were actually moving, the cost is a wash from buying things new on the other side. For example, you decide you want to take some clothes and you go to Target or whatever and buy plastic cups and bedding, you check out and you spend $2K, you could have done the same thing in France at Super Carrefour and Ikea for the same amount on the other side and not have broken your back to carry it or spend the money to ship it. We have friends who swear by getting a container, buying everything you need and shipping it over (one you will hear from next week in a special interview episode), but the jury is out for us still on this one.


Life Insurance

Here's a question for you. If the boat sinks and we both die who takes care of the kids? Well our kids are adults now so there’s that...or one of us dies or vanishes for whatever reason the other person (aside from being totally bummed) is left with a boat and new life to start...and grief to deal with. Not a topic that inspires joy so moving on.


Finalizing commissioning options

We have the orders in of course for the manufacturer and the commissioning agent but there’s a bunch of things still left to figure out. For example, liferaft, line, extra rigging, blocks and tackle, life vests for guests, radar deflector, barometer, hand tools, hoses, flagpost, mooring lines, rescue sling, buoys, wooden plugs, anchor ball, foghorn, boathook, jacklines, shackles, sail repair stuff...like vulcanizing tape, buckets, splicing kits, winch grease, sikaflex...which I think I have a feeling I will be chummy with in my future, funnels, jerry cans and OH you can’t imagine the different fender options there are, and fender covers if that’s your thing. And finally, the tender and outboard motor...probably one of the most hotly discussed topics in our household.


Medical loose ends

Next item up is tying off on medical matters and medical plan, so I still need to get my antibody test, that basically tests your blood and you get a record of what you’ve already been immunized for, who has a record of that lying around? Apparently it’s good to have that with you in case countries ask for it or require you to get a shot somewhere that you’ve already had, like Yellow Fever for example. Unless you are French like my husband, they keep a record of it for you which is actually a really cool and convenient thing, seems like an efficient use of tax money. I covered Medial Matters in a previous episode but there are some loose ends, like did you know you could get a series of shots to prevent shingles? Honestly, anyone I know who has had them say it’s the worst thing ever so that’s on my list.


Emergency & medical training courses

And finally, scheduling some final courses we have been putting off. No lie, the exercise of scheduling these classes alone are hours I’ll never get back. I sound like I’m complaining, I am complaining, it took forever. Do you take the 3-day Offshore Medical course that’s a thousand bucks and requires you to fly across the country, which really makes it 5-6 by the time you are done, and more money to fly and do hotels etc. It seems pretty basic but for it being more specific to sailing. Or, do you take the 10-day Wilderness First Responder course that’s the same cost but looks way more useful, is in the state, but takes more time.


After much hemming and hawing, we chose the latter. We opted for doing one in Mammoth Lakes which is a 5-6 hour drive for us, but the dates are better for our work schedules and life events...AND, honestly even a course in Marin County from where we are in the Bay Area would require us driving back and forth through San Francisco everyday which is a crapshoot, could be an hour, could be five one way...or we stay in a hotel in SF and go broke doing it. San Diego would have been an option, but it’s a flight and it requires you to camp so 1) we would need to rent a car from the airport and drive another 3 hours into the woods and 2) we just downsized and I sold all the camping gear in our garage sale.


To figure all this out we had to cross reference about 20 different websites to find the right information so it did take quite a bit of time to get the details and debate all the logistics. Then we turned to fitting in the sea survival course, with is another two day adventure. We booked and paid, checked it off this list and put it on the whiteboard calendar.


Other distractions

Cutting back to something I said in the beginning, we are also in the inspection process on a house we made an offer on. This has been on my radar and part of the financial plan for a while, but with the state of the economy right now we were back and forth whether we wanted to pull the trigger now, or when the economy melts down which should be any day now. Turns out, we found a place we loved as a vacation rental and a home base and all the math works so we just decided to get it done. Like any big decision such as this, I’ve been tossing and turning over it, doing the math over and over this way and that way, but in the end, I just have to trust myself - and the good news is my intuition on this also feels really good. I’m also really excited to set up a little rental experience, it’s something new and I’m learning a bunch about occupancy permits and fire inspections...but I had to mandate a new post-it note ordering system on my wall. All rental property things in blue, all the boat things are orange, yellow and pink. Just a lot to juggle.


To top it off, we had the bright idea to book a vacation in Hawaii over the Thanksgiving break which sounds good in theory...like three months ago, but now just stresses me out. The wisdom of my years reminds me that it’s the right thing to do, the goal is to make some memories with my husband’s daughter before she hits graduation, so I am looking forward to that. I’ll be great once we get there in a week or so but as things turned out I will be meeting them there since I need to squeeze in a quick trip to Australia for a board meeting.


After we get back, I roll into a week long summit for work then 2-3 weeks of crazy nestled in there somewhere my husband decided to book a 2 day course called Inner Engineering. It’s taught by a yogi dude who teaches you how to meditate and find joy from within...which could not be more ironic given my headspace right now.


So what have I learned? First, these are definitely great problems to have. World class problems and I embrace them all. I’m so grateful. I don’t tend to get angry or depressed or resentful in life in general, my negative feelings tend to show up as anxiety. When I get anxiety typically I get into lock down mode, where I try to control little things around me to make myself feel better so these are points in time where I decide to reorganize closets or do a fit of gardening or pressure wash the outside of my house. What I’m trying to focus on is just how grateful I am to be overwhelmed with life and it’s abundance of gifts right now. And I’m sure when we are bobbing around in the ocean somewhere I will laugh hysterically at the person I am at this moment.


I'm also reminded to live in the present, which is also why I do these postings, even when I feel like I really don’t have time. It forces me to memorialize the experience as it’s happening so I will not only appreciate it, but so I’ll also remember it.


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