The Long & Exhausting Journey of Buying A Cruising Sailboat (Insurance, Registration & More)

The Long & Exhausting Journey of Buying A Cruising Sailboat (Insurance, Registration & More)

We’ve received a ton of questions and we’ve had a thousand of our own about the cruising and sailboat buying process.  In short, buying a boat is an exhausting mental roller-coaster that we weren’t fully prepared for.

The ups and downs started with finding the perfect boat and continued on through dealing with a shady broker, negotiating, documenting, getting insurance and finally closing the deal.

Now, in no way, shape or form are we experts in the boat buying process.  We’re coming at all of this as newbies and simply sharing our experience. We did however luck out with a solid team of experts that helped prepare us for the long, loopy ride. I am happy to report that at the end of the ride, no one threw up…not even Jason.

The bad news is, we’re officially broke.  The good news is we are the proud owners of not just any boat but our dream cruising catamaran!  She’s a sturdy ‘05 Leopard 43 owner’s version.  We’ll document our moving-in day, share a proper tour once she’s all tidy and we’ll for sure have a Neptune approved renaming ceremony…all coming soon.

In the meantime, we’ve gone into a lot more detail on the buying process, the hiccups and successes down below for anyone interested. It is a long and exhausting process but it all comes in phases, so don’t panic or let any of this scare you off.  Like any great adventure, if it was easy, everyone would do it.

Finding the Perfect Boat

I don’t know if there really is such a thing as The Perfect Boat but finding one that fits your needs and budget is pretty darn close.  We searched, scoured and inquired about boats worldwide.  Once we saw the Leopard 43 we knew it was the best candidate for us…even though they are out of our original budget. Everyone’s idea of the perfect boat is going to be different.  Variety is the spice of life after all and what works for us, may not be ideal for you.  See our boat shopping wants, needs and experiences here:

Finding An Honest Broker

We decided to go with a broker because we wanted someone with experience on our side. Plus as buyers, a broker doesn’t cost us a penny because it’s the seller that pays the broker fees.

Kent from Just Catamarans came highly recommended as a nice honest person, someone who has done a lot of blue water sailing, specializes in Cats and is also a service guy.  So, we felt like he was our man.  He was very patient and happy to educate us along the ways.  He taught us how to spot signs of trouble in hulls and rigging, pointed out how important access was for troubleshooting and maintenance, and most importantly helped us keep realistic expectations.  He wanted to see us in a good solid sailboat as much as we did.  When negotiations got sticky, he even threw in some of his commission dollars to help with service items…and according to our other sailing friends that’s pretty rare.

Dealing With a Shady, Shady Broker

We were not the only ones who put in an offer on our Leopard 43.  There were 2 other people who also submitted offers and that created a bidding war between the three parties.  It sucked for us, but was grand for the seller.  The hard part was, one of the interested buyers was also the selling brokers client.  That means the selling broker could be the selling and buying broker, making double the commission on the sale.  So he wasn’t exactly jumping to submit our offers to the boat owner.  That was bad for us and bad for the seller.

The selling brokers job is to get his client, the seller, the highest dollar for his boat. Not submitting offers in the order they are received and in a timely manner should have been his top priority, and not his personal pocket book.

After the survey and sea trial we almost lost the boat because the sellers broker was playing games again.  The deal only went through because the owner, John, reached out to us directly after not hearing back from his broker and hearing some chatter from friends at the docks.  The chatter was about a couple who was waiting on a deal to fall through on a Leopard Catamaran so they could buy a boat and a condo at the resort in Vero Beach, a coincidence…I think not!

John’s broker was not sending over our revised offer, silently hoping the deal would fall through when our offer wasn’t accepted by the 5-day deadline.  At that time he’d be able to sell the boat to the other couple and take the full 10% commission.  What a shady punk!  Needless to say the seller wasn’t happy and I wanted to bake cookies with x-lax and drop them off as a thanks for being shi**y gift.

I won’t mention the selling brokers name because I don’t believe in publicly shaming people plus, there is no hard proof other than hearsay from people who overheard discussions on the docks. But I will say watch out…there are some shady characters out there calling themselves Brokers.  Make sure you choose a broker with a good reputation and get a recommendation from other sailors who own similar boats if possible.

This experience really gave us an insight into the sleazy part of the brokerage world that we haven’t had to experience with Kent (our broker).


Because Catamarans seem to be selling like hotcakes these days we didn’t have a ton of bargaining power.  Seriously, by the time we were inquiring about a boat it was already sold, or sale pending.  Not to mention there were other buyers lined up waiting for deals to fall through on most every quality cat out there.  Sadly, John, the owner wouldn’t meet us in the middle like we hoped, but did meet us ¼ of the way.  Sometimes, you just can’t escape circumstance.

We could have walked away and lost the survey, sea trial and haul-out investment, gave back the RV, found a rental apartment, and kept looking for who knows how long…but we felt it was a fair price and this boat was in great shape for us to move into and begin living (and learning to sail) immediately and there is value in that alone.

The original list price was $359,000 and didn’t include the dinghy.  Our final paid price was $316,000 and included the dinghy which is worth somewhere shy of $10,000.

Way Over Budget & Getting a Loan

We initially saved up two separate accounts for our ocean adventures: The boat purchase fund and the cruising kitty (that’s what live aboard boaters call the travel fund).  Our boat purchase fund was $200,000 and our cruising kitty was $100,000. In the end we pulled the cruising funds to pay for the boat.  Probably not the smartest idea but we’ll attempt to live as cheaply as possible over the next year to get some cash back in our cruising kitty.   Plus, we need to stick around a comfortable cruising ground the first year to get to know our boat and learn the art of sailing.

To make up the remaining amount, we attempted to get a loan to help but owning our own business and not having a stable address/income doesn’t exactly look good to a typical bank.  We were able to pull a loan from our variable life insurance policy at a low rate of 2% while keeping our policy intact.  We didn’t pull from our IRA’s or other locked investments so we still have some padding should we end up in a worst case scenario situation.


Along with the purchase of a boat comes a giant heap of paperwork.  Paperwork that if done incorrectly could be very costly.  This is why we decided to hire a Documentation Agent.  We went with Kimberly Clark at ASAP Marine Documentation and Registration Inc. as we were told she was a paperwork stickler…just the kind of person you want for this job that’s all about the details!

She wouldn’t allow us to close until she had all necessary paperwork in her hands.  She and Just Catamarans warned us how many boat sales are held up because the seller doesn’t have the dinghy paperwork or the importation documentation.  If you close without this paperwork it can be an extremely costly mistake.  Kimberly confirmed there were no liens or withstanding unpaid bills on the vessel that might come back to bite us later on down the road.

Having a documentation specialist on our side made the paperwork process seem like a breeze, but I know we’d have been pulling our hair out, stressed to the max, had we attempted to do it all on our own.


Another reason we hired Kimberly was because we had a lot of questions about where to register and what type of taxes we’d have to pay.  We also wanted to put the vessel in our company name and not our personal names.  She asked us a series of questions and then advised that registering with the United States Coast Guard for our needs would be better than Delaware (where a lot of people register boats for tax shelter purposes). Since we are travelers and will not be in one state for an extended period of time we can register with the Coast Guard and avoid paying sales tax to any specific state. When all the paperwork comes back from the Coast Guard we’ll get a nice neat binder of everything so when it comes time to sell, it should be a breeze!

Should our travels change and we decide to stay in one state for an extended period of time we will have to look into registering with the state where the vessel will be used most often.

Naming the Vessel

Sadly, we were required to name our new boat almost immediately, which is something we didn’t expect.  We’d been tossing around names for months now but not very seriously.  I had read some blogs and talked with fellow cruisers about the unspoken rules of naming a boat and they did have some advice.  Keep it short, make it easy to spell, make it unique to your story and make sure its something you want to be called over and over.  In the boat world we will be known by our peers as the name of our boat more than our actual names.  So, we tried to think quickly and the one name we agreed suited us best is Curiosity.  S/V Curiosity, I think it has a nice ring to it.  Plus, the Wikipedia description pretty much nailed it for us.


We (and fellow boaters we talked with) felt including the word “cat” in our name might be a little cliché, so that was out. Our website name Gone With The Wynns didn’t seem like a boat name and its too long because we’ll be required to spell it out phonetically.  So, we went with what made the most sense to us.  I hope you like it as much as we do.  You guys gave some fantastic name suggestions in our last post and we loved the creativity and excitement of it all!  In our re-naming ceremony video/post I will list out some of our faves…many are just too good not to share.

Total Documentation Cost $895 including the dinghy paperwork, USCG registration and Canadian Registration check.


We had really low expectations about getting insurance and had prepared ourselves for the worst.  There were many people commenting with how expensive it was or how we’d have to pay a captain to sail with us the first year, or how we couldn’t get hurricane insurance and if we did it wouldn’t be affordable.

So we did some research and asked around for recommendations on which company to go with and what to look out for.  We again chatted up fellow boaters around at the docks (boat people are extremely friendly, much like RV’ers), talked to the current owner and of course got Kent’s two cents on the whole thing.

In the end we contacted two different brokers and received over 8 quotes from different agencies.

Bill Hodgens WR Hodgens of Marine Insurance Inc. and Susan Everhard at Global Marine Insurance Agency. Both agents were very pleasant to deal with, helpful and quick to respond to all our questions.

One of the Lloyds of London policies from Bill came back at what looked like the best and most affordable policy.  We informed Susan and rather than quickly brushing us off, she offered to review the policy to see if she could beat it.  After reviewing the policy, the craziest thing happened…she advised us to go with Bill’s policy! She said it was a good policy at an affordable rate.  Thank you Susan for being an honest business person looking out for the interest of the customer, even when it doesn’t benefit you!  We’ll end up calling her again when the 1 year renewal comes up.

The Lloyds of London policy we ended up with has a 2% ($6320) deductible, $1,000 of personal effects and covers our Dinghy too (we already have personal articles policy that covers our camera gear and other important personal/business stuff).

It had the least amount of restrictions and the most freedom – While we have to have a captain or a qualified sailor on board at first, we can get that removed as soon as we have a captain sign off saying we are competent sailors.  We’ve signed up for a week long intensive A+ Cat course with Bluewater Sailing School.  Once we have that certification we will then get a captain to sign off and we will be free to roam as we please, sans captain.

Sailing Locations – This policy allows us to be in the Hurricane belt, but with a $16,000 deductible if we are hit.  We can travel anywhere along the east coast of the USA including FL and Bahamas as long as we don’t go more than 200 miles off shore.  As our experience grows over the next year, we will be able to go much much further.

Cost: $3860 per year but it’ll drop quite a bit when we renew (assuming we don’t have any claims)


It’s time to spend some cash!  There really were only a few things involved in the closing at this point, most everything had been taken care of.

It was as simple as signing a small stack of papers and transferring the money by wire to Just Catamarans.  Hitting that send button was hard.

This is more money than we have ever spent on anything…ever…including when we bought a house.  It didn’t feel like a gamble but like the biggest investment we’ve ever made in ourselves and our future.  People said we were crazy when we did this the first time with the purchase of Windy the RV. There’s no question people will doubt our sense of adventure and sanity with this endeavor.  We are confident we’ll succeed in this next phase of our journey and that is all that really matters.

The cash was confirmed in their account with 24hrs. They transfer it to the owner and we officially own the boat and our insurance went into immediate effect.  The only additional closing costs was a $25 wire fee from my bank.

We could stay in Florida without paying Florida sales tax on our boat for 60 days or apply for a 90 extension at no cost.  However, that still isn’t long enough for us to have the service done, take our sailing classes and sail out of the state.  So, we applied for a 180 day FL Extension. Cost $425

The end…we are now boat owners!

Whew!  I don’t know about you but I feel like I need a stiff drink after all of that.  Seriously, it feels like buying a cruising sailboat is even more paperwork and hassle than closing on a house (but then again it’s been well over 10 years since we purchased our house)!

What’s Next

Since the owner took the boat back to Vero Beach after the survey & sea trial, we’ve got a ton of logistics to sort through so we can move out of the RV and into the boat, then sail it back down to Ft. Lauderdale to get scheduled for service.  Then we’ll need to remove our technology upgrades from the RV, sell the ones we don’t need and install the rest onto the boat.  It’s been an exhausting roller-coaster to say the least. However, we’re hangin’ in there, taking a lot of aspirin and looking forward to eventually anchoring out and enjoying a sunset aboard our sweet, new-to-us cruising catamaran!

We’re gonna live on a boat!

P.S.  Just in case you are wondering about my cell phone/bag in the video…it’s called a Ugo.  It’s my nifty new waterproof, floating bag that is perfect for this new lifestyle. Check it out in our gear store here:

Disclaimer: None of this is a paid endorsement. There’s no affiliation, compensation, sponsorship or discounts with Kent our broker, Just Catamarans, or any other marine product, service or sailing brand.