Mar 2, 2016

Young Sailors

The plan has always been to go sailing again. But I can tell it's going to be a lot harder this time around.

We own a house now, and we very quickly filled it with stuff. Very "important" stuff that I have a hard time thinking about parting with. I don't know how this happened, but it did.

It’s stuff like that damn camping gear we never use but we might some day so I hang on to it.

We will need to do something with the house itself. We don't want to sell it, so will end up renting it.

I have my job. When I was younger, it was easy to quit whatever shitty job I had because I could always get a new shitty job. Now I have a really great job. I really like my job.

It feels reckless to throw that away, but in the end I will, because I don't want to look back on my life and say "well I'm dying, but it's okay because I had a really great job."

Taking kids sailing is more complicated than I thought it would be. I always thought it was a given that my kids would love sailing.

Well, Hobie is a really energetic kid. And sailing involves a lot of extended periods of being trapped on a boat. Like when traveling to a far away place. Or when it rains for several days in a row. Fortunately Hobie also really likes reading, and of course TV. So I think it will work out.

None of these challenges are insurmountable. It's just harder than I thought it would be. If I didn't have the previous experience of living on a boat, I can see how we would be too scared to do it. I can see why people wait until they retire, and I understand a lot better now why people said we were "smart for going while you're young".


  1. I kinda just stumbled onto your blog as I was searching the internet today and I had a couple of questions. What advice would you give to a college guy who is currently considering the concept of liveaboard (I guess after school)? I figured that it would be a decent way to get myself started (aka out of my parents' place) and I live in Florida anyway. Just a sophomore now and if stuff doesn't change drastically in the financials it looks like a boat might actually be my best bet. Kinda cool kinda weird concept, but hey, I figured it'd be a little more interesting than renting a flat or getting a condo somewhere. I learned how to sail lasers and optis as a kid so I'm not altogether a newbie to sailing, but I could definitely use some experience on a larger craft. I'm looking online to figure out how much it would cost and if it would actually be doable. But yeah any advice for saving up, getting a boat, renovating, etc? This is a really neat idea.

  2. Dude, go for it!

    What have you got to lose? If things don't work out, the generic "rent an apartment" option is always going to be there for you. But this is definitely the time of your life to try things. Per my post, it only gets harder when you are older.

    I found living on a boat is less expensive. The boat itself is less expensive than a house, and while dock fees can be high ($400-$600) that general includes electricity, wifi, water, and cable. Florida prices might be higher, and live aboard marina's harder to find.

    Florida is a great place to buy a boat. A good strategy I've found for getting a deal on a boat is to use yachtworld to browse for make/models you like, then find an online owners association for that boat. You will hear about people selling their boat before the brokers do, and can often get a better price. Plus you can look at history to see what questions and issues the person has posted regarding their boat.

    My only experience prior to buying a 31 foot sailboat was sailing on a sunfish for a week. The concepts are the same, and bigger boats are actually a lot more stable, respond slower. Of course you can do a lot more damage with a bigger boat (to yourself or others). Just take it slow, use your head. You will be fine. The best insurance is a good anchor.

    For making renovations — look for a tutorial on youtube for whatever you need to do. Your work might not look perfect, but you will be proud of it, and will get better as you go.

    So go for it!

  3. I just stumbled upon your blog while doing some research on sailing. I am looking into buying a blue water cruiser to sail around the Caribbean when I am not working. I currently live in Northern Florida and my work for one month then have an entire month off where I could sail. My only concern is if I don't want to pay to stay at a marina while traveling, how safe is it to anchor out and leave your boat unattended if I wanted to explore the local scene? I was hoping you might have some insight on this from your previous travels that could help. I would either be sailing solo or with a friend but both of us would want to go ashore when possible.

    1. Hi Nathan,

      Some people anchor their boats, board a plane and fly home. That seems really scary to me but people do it.

      Leaving your boat for a few hours is totally fine. As long as the wind/current remains the same as when you set the anchor, there isn't much to worry about.

      If the wind or current does a 180, that is when things can go wrong. A lot of times people will use multiple anchors if they are going to be gone for a while.

      Sounds like you have a great plan! and a great location to be sailing out of! Aim for the Bahamas first. You might find that is the furthest you need to go. We met plenty of people who had been all over the place and said the Bahamas was the best.

  4. Thanks for the reply and the tip about the Bahamas! It is definitely one of the first places I want to sail to and check out. Also, I have been reading your older blogs and they are full of great information. Keep up the good work.

    1. Thanks! Hope to have more posts coming soon! I miss cruising.

      Also, anchoring is a pretty awesome topic full of strong opinions. Which anchor is the best, how to set an anchor, etc.

      One thing to keep in mind with your question, how is anchoring your boat and going ashore really all that different from anchoring your boat and then falling asleep for 8 hours? :)