You’ll Never Be Ready. Go Anyway!

By Carolyn Shearlock © 2015 • all rights reserved

Thinking of going on an extended cruise? Most of us don't feel "ready" and can think of ten things we need to do before going. If the boat is seaworthy without them, go anyway!

It’s so easy to get trapped in the mindset of doing “just a couple more things” before heading out on an extended cruise. I hate to say it, but the fact of the matter is that the boat will never be 100% perfect and ready. At least ours never has been.

A couple of days ago, Brittany of Windtraveler posted a fun piece on her blog — The Best Cruising Advice in Six Words. I love the quotes there from a wide range of cruisers — some with thousands of miles under the keel and some just starting. And that got me thinking about what my six words would be (we’d been out of internet range so I missed Brittany’s call for quotes).

My six are something my mom told me numerous times: You’ll never be ready. Go anyway!

In other words, saying you’re going to do something is easy. You can prepare without fully commiting to the plan. The tough part is that transition from preparing to doing. It’s a lot easier to keep “preparing” — doing what’s familiar — on the grounds that things aren’t perfect yet.

Taking that next step is scary. If you’re not super-adventurous, how do you do it?

Taking baby steps helps. You don’t have to cross an ocean the day you launch. There’s time to figure things out. Start simply. Go for a single night. Travel just 5 miles. Go a little further next time. But above all, start.

Another big help for us was having a bail out plan. When we bought our first cruising boat, we kept our apartment and everything in it for nine months, until we were comfortable with the transition to our “new life.” This time, we began as snowbirds and at the end of the winter, realized that we wanted to stay on the boat . . . so we sold the house. Both times, knowing that we weren’t making an irreversible commitment made it a lot less intimidating to start. 

But there were still things we wanted to do to the boat. Things we wanted to learn. What about those?

Probably everyone has heard that cruising is “fixing your boat in exotic locations.” There is a certain amount of truth in that, whether it’s a repair or an upgrade. But what it really means is that no, everything doesn’t have to be perfect when you leave one place for another. Work can be done wherever you’re going. You can (or maybe I should say will) learn as you go, as things arise.

We found that we still have to overcome the “not wanting to leave” syndrome every time we settle into a new cruising area. Once we get used to it and it feels comfortable, the tendency is to find reasons to stay in the area.

On one hand, we want to explore new places. Really, we do. But it’s just so much easier to go where we’ve been before. Where we can follow our previous track. But we know we’re most alive when doing something new. So, it comes down to do we want to take it easy or challenge ourselves? It’s easy to say “challenge ourselves,” but harder to do it. Are we really ready for that new experience?

There’s only one way to find out. Go anyway!

NOTE: I’m not saying to head out in a boat that’s not seaworthy or if you don’t have the basic skills necessary for what you’re planning to do. But you have to push the envelope a little, too. If you don’t try new things, you won’t realize exactly what skills you do have. We’re still doing baby steps with our boat and in the new-to-us cruising grounds of the Florida Keys. And hopefully — probably before we feel totally ready — we’ll go further afield, too.

Print Friendly
How to Copy

Do You Find The Boat Galley Useful?

You can support the site when you buy from Amazon by using the links on this site or clicking below. No extra cost to you!



  1. Timely post as I’m finalizing my boat for a cruise. I had to set a hard date to leave or I’d be preparing forever. Even if I have to just leave the slip and anchor in the basin for good weather, I’ll get underway.

  2. Have the basic skills like docking using a radio reading a chart a 24 hour sail… The best USCG post I know is USCG defying natural selection since 1792…

  3. Such a great read! To me, you seem to have an endless supply of tips, ideas, and recipes. I’ve often wished I could have all the information in your head. And, as one still land based in Chicago, I very much appreciate all the information you’ve made so readily available. It’s a different world, so much easier to learn, so much support out there, than when my dad would eagerly await Cruising World, hoping to learn more about his heroes, the Pardeys. Sadly, he never saw blue water but he loved his wooden Seabird yawl.

    • Thanks! Yes, the internet makes it so different. When we started cruising, we got some user manuals and so forth online, but there weren’t blogs and the real-world experiences. I love reading all the different things online — makes you realize that there are all sorts of ways to be on the water. Some have a blue water dream, some want to coastal cruise and others want weekend jaunts near their home. It’s all good!

  4. Just do it.

  5. We are only doing weekends at this point. Maybe after Christmas we might try a week. There is nothing like casting off and being on your own.

  6. do it while you can. health can be a fleeting thing.

  7. Lynn Clough says:

    Very timely post for me! We are currently in Herring Bay on the Chesapeake. I had hoped to be on our way south over a week ago. But life got in the way and my DH is still feeling more systems need to be checked out before we leave the dock. I do feel I cannot push until he is not overly stressed by his worries.

  8. Thats what ports are made for…..

  9. Where in the keys are you? I’m near key largo ocean side mm 92.5

  10. We have done just that ? as we were in Spain and Portugal for quite a few years and probably spent much more time repairing and upgrading than sailing. We decided it was getti g to the point were we really had to do more as all we had done to the boat would have just been in vain really. So we sailed the boat down to Gibraltar to buy and install electronic equipment and gain some much needed experience. After 3 months there we set sail 2 weeks ago, we completed our first ocean passage and after 7 days and 12 hours. We are now in Lanzarote in the Canarie Islands. So I totally agree with your tip it worked for us ?

  11. Todd Hoevel , nuthing wrong with keeping an apartment for 9 mo.

    • I’m thinking a storage unit and my truck/enclosed trailer to start, maybe a condo I can rent as well, ether way the hardiest part is setting a date, I’m close to setting that date, at least to start the boat search…8 to 12 months from now.

Add Your Thoughts