7 Things We’d Do Differently

We’ve been liveaboards for 100 days now. Wow, I can’t believe it’s been that long. Time is flying by and it seems like only yesterday we spent our first night on board. Over the last 100 days, we’ve learned a lot about Kairos, about the countries we’ve visited, and about each other. We are so grateful for this opportunity and despite the ups and downs, it’s been amazing. Looking back, however, there are a few things that we could have done better. For those of you considering setting out on a similar adventure, here are the 7 things we’d do differently if we could do it all over again.

1. Buy a Well Maintained Boat. We previously read that it would be difficult to get boat insurance if we purchased a boat over 30 years old. That became the cut off for us. Now we are convinced that the age of the boat doesn’t matter as much. What DOES matter is how well the boat has been maintained. New and old alike, boats have problems. There’s always going to be something to fix or improve. The marine environment is very harsh on equipment. But a well maintained boat will have a lot less headaches.

Kairos (formerly known as “Kansas Out of Oz” and formerly, formerly known as “Clever Skiff”) was in her prime about 15-20 years ago. She was all decked out in the latest systems and electronics. We aren’t taking her anywhere she hasn’t already been. She cruised these islands for many years while we were managing our awkward teenage years. It’s nice to think that our boat is the one taking us to new places and not the other way around. But now many of her systems are outdated and she was not well maintained the two years prior to our purchase. We’ve spent a lot of time repairing/replacing pumps, electrical systems, wiring, hoses, and teak brightwork. All boats require maintenance, but we started off this adventure fixing several years of deferred maintenance on top of the normal stuff. It turned out to be more than we expected.

2. Consider Buying a Boat in the Caribbean.  It never crossed our minds to look for boats in Grenada or the BVIs. The boat hunting logistics seemed too difficult. However, we now think fellow cruisers Monday Never got it right when they purchased their boat in the BVIs.

The route from Florida to the BVIs is known as the Thorny Path to Windward. The trade winds blow from the East/Southeast, so we are constantly trying to sail into the wind and waves. It can be brutally uncomfortable and means we have to wait for good weather windows. It’s the most frustrating leg of our journey and here we are trying to tackle it with minimal experience. By purchasing a boat in the Caribbean, we could have skipped the Thorny Path all together and sailed comfortable up the island chains with the wind on our beam.

2. More Space. We looked at boats in the 37 to 42 foot range. These are common lengths for cruising boats, but we find that many cruisers have opted for a 40-44 foot center cockpit boat. And for good reason. These boats (Endeavors, Whitbys, Brewers) are spacious. They have full size mattresses, walk in engine rooms, and two bathrooms. While we love Kairos’s sleek lines and traditional aft cockpit look, with two large dogs on board, we often wish we had more space. We scoffed at the idea of two bathrooms on board when we were first looking at boats. Now we think it would be nice.

We were intimidated by these 42 footers that we viewed as monsters during our boat hunting trip in Florida. We were concerned that with our lack of experience, they would be too big for us to handle. We now know how quickly we learned to maneuver Kairos and that a larger boat would not have been an issue.


3. Bigger Dinghy. I really wish we would have practiced dinghy rides with the pups while we were still at the marina. We have it down now, but we could have saved ourselves a lot of headache if we would have figured it out at the marina instead of in rough seas at anchorage. We are also in the market for a larger dinghy. Our current set up works, but a larger dinghy with a rigid bottom would make life easier (and drier).

5. Timing. Everything takes longer than you think it will. We wanted to spend time with our families throughout the holidays, so we planned for our adventure to start afterwards. Getting the boat ready for cruising and waiting for good weather took longer than we expected. Therefore, we didn’t get to the Bahamas until the very beginning of March. Avoiding hurricane season means that our cruising season starts in November and ends in July. We wish we would have bought a boat in August so we could have fixed it up in the fall and then started cruising at the beginning of the season instead of midway through.

6. Understand and Monitor Weather. We knew weather would be a big part of our adventure, but I don’t think we fully grasped how much it would control our lives. Weather determines if we are going to stay in an anchorage for 4 days or 4 weeks. It determines if our dinghy ride to shore will be wet or dry. It determines if we need to seek shelter in a marina. It determines if we are going to sail or motor. It determines our routes and anchorages. It determines if you are going to have a nice smooth passage or an uncomfortable one full of cursing. Knowing the forecast and understanding how it applies to your route is very important. We wish we would have studied it more before we left the marina.

We have since learned that 15-20kt winds behind our beam is a nice comfortable sail. But it feels almost suicidal if the same wind is on our nose. Knowing what wind and sea conditions you are comfortable with at each point of sail is something that would be nice to know before setting off on your adventure. We learned very quickly, but we could have avoided some hellish days if we knew beforehand. I suggest reading the Island Strategies section in Bruce Van Sant’s The Thornless Path To Windward.

Having a good weather source is also important. Our favorites are Chris Parker, Windy, Passage Weather, and Buoy Weather. But we quickly learned that knowing the forecast alone isn’t good enough. We now follow forecast trends. If we are targeting a departure during a weather window that starts on Saturday, we will watch that window and review the forecast every day the week leading up to it. If the forecast remains the same or gets better, then we know it’s okay to go. If the forecast starts trending for the worse, then we reconsider. We’ve received a lot of on the job training, but we wish we would have practiced monitoring weather before we set sail.

7. Know Our Electrical System. As chemical engineers that have worked in operating facilities, we have a good handle on most of the mechanical systems on the boat. Even if it’s our first time looking at the system, we are familiar enough with the components that we quickly figure it out. The same is not true for electrical systems. We know a lot more now than we did when we first purchased the boat. However, we wish we would have learned about common boat electrical systems prior to purchasing our boat. Knowing how to use a multimeter and understanding your boat’s electrical system is a MUST. If we would have done a little more homework prior to the boat survey, then we could have inspected the electrical systems and uncovered the deficiencies prior to purchasing Kairos. This would have given us more bargaining power or at the very least we would have given upgrading the systems a higher priority. Instead we were adding solar panels and replacing/rewiring our batteries just days before our departure. We felt that the survey alone did not provide a thorough enough inspection and we’d encourage new boat owners to self-inspect the electrical systems during the survey, prior to purchase.

We’ve learned from our engineering days that even the most successful projects have lessons learned. While we could have done these 7 things better, we have also done many many more things right. Learning is a part of this adventure. If it was easy and headache free, then we wouldn’t enjoy the sunsets, the lazy beach days, or the peaceful sails as much. There are a few things that we would do differently, if we could do it all over again. But one thing we absolutely wouldn’t change is saying “YES” to an adventure of a life time.

9 thoughts on “7 Things We’d Do Differently”

  1. Happy 100 Days!! With two dogs aboard our first boat (34′ aft cockpit seafarer) I can totally understand you’re desire for more space! We now have a 42 ft center cockpit with a queen(!) size aft cabin and it is heavenly! But, you know what? You’re still out there sailing! And that is something many people will never be able to say. Fair winds guys, love following along until we get out there again 🙂

    1. 2 pups on a 34′ must have been a little tight. There’s a lot I love about our boat…but I am super jealous of your queen size bed! I hope our paths cross at some point. We love following you too. Can’t wait to hear about wedding plans. Congrats again.

  2. Congratulations on your 100 days. I grew up with salt water to my backyard in Maine. Was trained in electronics in the military and since my retirement from the military working full on yacht construction, repair and systems installation and repair. Along the way I have come up with things that work for me but, as you have found, a boat new to you can have a steep learning curve along with the continuing maintenance. You have heard Break Out Another Thousand for boat. I was sort of musing one day and came up with Brilliantly Organized Attitude Tester. It just seems to fit. Enjoy the next 100.

    1. Sounds like you have a lot of experience. I like your acronym better! We’re trying to hang on to our thousands :).

  3. Love this post! And your detailed descriptions of why you would do things differently. And your pics are gorgeous. Thanks for sharing! We are not too far behind in the grand scheme. Maybe we’ll run into you out there!

    1. Hey there Luna Sea! Thanks for following. The first 100 days have been a real adventure. We’re fortunate that we get continue this crazy lifestyle. I hope to see you out there!

  4. Love this. There are a lot of things that I wish we had done differently. I particularly love the idea of buying a boat in the Caribbean. Hmm, maybe next time?? Thanks for sharing!

    1. It’s good to reflect sometimes. For everything I wish we did differently, there are 10 things that I’m so happy we did the way we did. Most of all, I’m just happy to be out there sailing!

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