
One of the (many) hurdles we faced as new boat owners was obtaining boat insurance as liveaboards. Many insurance companies simply will not insure boats whose owners live full time on the boat… for obvious reasons, they would much prefer the boat be used as little as possible and tied to a secure dock for the occasional “weekend warrior” use, instead of having two newbies like ourselves on the vessel 24/7 in the open, blue water. Just finding an insurance company who was willing to entertain insuring liveaboards was a struggle… we would eventually find out that the insurance company would also require additional training with a fully-licensed captain, and that captain would have to train you to the point where they could sign off on an insurance waiver that you were “worthy” to operate the hopefully “to be insured” vessel. At the time, it was early March 2020… the pandemic was begging to force much of the world into total lockdown. We were forced to find a captain crazy enough to help some strangers learn how to sail during a pandemic. Who the hell would sign up for something like this? Turns out it would be a crazy, South-African LEGEND by the name of Mr. David Hibbard. But ultimately finding him wouldn’t be easy…

Before we even knew who David Hibbard was, our broker, Jim, had provided us with a few other captains/ sailing schools to help satisfy the insurance requirement. After looking into them a bit more and speaking to several of the captains directly, we were not too happy with the willingness of the captains to actually train us. We wanted more than just a sign-off… we really wanted to use this time as a learning tool to get some serious sailing education. Prior to this, we had one week of sailing in the Sea of Cortez and that was it. We were complete newbies so we wanted a bit more “hands-on” experience. We reached out to Bluewater Sailing School to see if they could offer the specific training we were looking for. The blog, Gone with the Wynns, is the reason we chose to go with this school as they too had no experience with sailing and were able to be trained up to skipper their own sailing catamaran.

A few emails back and forth with Blue Water Sailing School and we had a clear line of sight on what they could provide as instructors, and they followed the correct curriculum to get us ready to captain our own boat. The plan was, once we closed on the boat, take off from the Fort Lauderdale area, sail across the Gulf stream and cruise the Bahamas for a week. While in the Bahamas we would work through the insurance-provided checklist and tick all the boxes to get sign off as competent operators. This was extremely attractive to us as we knew the Gulf stream could be particularly tricky to cross and to be able to accomplish that twice with trained professionals seemed like a worthwhile endeavor. And plus, we would be in the Bahamas, baby!
The only problem with this plan was that after we had sailed to the Bahamas and back, we would still have the boat stuck in Fort Lauderdale and would need to have it up to the Chesapeake Bay by summer, once again for insurance purposes (the insurance companies do not let you stay in certain “hurricane” zones, like Florida, at certain times of year during the hurricane season. In fact, our insurance company would require us to be north of Cape Hatteras, NC by July 1st). Despite this, we still decided this would be the best route in order to get our insurance sign-off quickly while also getting in some much-needed sailing education. We would figure out getting the boat up north afterward. Within several days, we were officially booked with Blue Water Sailing School for our trip and we would just have to wait a couple more weeks before we were Bahama-bound.

With the insurance and a plan for a captain sorted out, we anxiously awaited the final steps for closing on our new boat back at Kelleys family’s lake house in Virginia. After signing some papers, having them notarized and sent back to the yacht closers’ office, we simply waited for the funds to clear and we would be all set. March 17, 2020 was not a typical Saint Patrick’s day for most people given what COVID-19 was doing to the world, but it was an exciting day for us as it was the day we officially closed on our boat. This was the same day the US government finally recognized the severity of the coronavirus and many states and counties began to require residents to shelter in place. At the same time, the stock market was plummeting and all the news agencies were predicting a recession as a result of the stay-at-home orders and movement restrictions. Needless to say, the excitement of owning our first boat was quickly diminished by the thought of purchasing a luxury item like a catamaran during a recession that surely would devalue as rapidly as any other investment one could have made. Gulp! What had we just done?!

The next month and a half was as long for us as I am sure it was for most people who were stuck at home, not sure what the hell was actually going on and just wondering daily what was going to come next. While some worked out and others baked bread, playing cards over some Yuengling beers seemed to be our savior for keeping our sanity throughout all the craziness. As all this was going down, we were trying to have JustCatamarans repair some items on the boat that we had agreed upon with the insurance company to fix as part of “vessel compliance”. Unfortunately, all of that eventually came to a halt as everyone was told to stay home. So until we could get these items fixed on the boat, we weren’t going anywhere. On top of this we had heard from the Blue Water Sailing School that they were not able to facilitate our training because they were unable to find any captains who felt comfortable enough to work. So again, we were back to figuring out how we were going to get the proper training in order to be able to operate our vessel and have it to the Chesapeake before July 1st.
Back where it all began at the Annapolis sailboat show in October 2019, we had met a very interesting South African gentleman at the Lagoon boat display. He introduced himself to us as David Hibbard and explained that he had spent the last three years sailing around the world with his wife and two kids on his own Lagoon 400 sailing catamaran. After a cordial chat with him he also explained that he was a captain and a personal cruising coach, which we found intriguing and thought may come in handy later on when we bought our boat, so we took his card and carried on with the day. It turned out that keeping David’s card handy was one of the best things we could have done. Nearly six months later, we would end up reaching out to David and it turned out he was the only one to even entertain the idea of moving a boat during the early stages of the pandemic; he had no fear of the Coronavirus, at a time when no one had any idea what this thing was… just one of many moves that earned him his “legendary” status. Every other captain we reached out to either didn’t call us back or was too afraid to be with two strangers. From the moment we reached out to David he was extremely responsive and had our best interest at hand.

Morgan, our insurance broker, recommended that we hire a captain to take us up the east coast so we could learn the “ins and outs” of the Intercoastal Waterway, as well as navigating inlets and other navigational challenges that are unique to the East Coast of the US. This made sense as this was going to be our primary cruising grounds. With this in mind we presented this idea to David and he was all for it. We would be able to learn everything we needed to fulfill the requirements by the insurance company while at the same time get some solid sailing experience overall. What was even better was that he had sailed around the world on a boat similar to our Leopard 38. Getting hooked up with David was truly awesome and he would continue to be a major asset in our travels as we learned the boat in the years to come.