It wasn’t pretty, or graceful I might add, but we made it safely out AND back in to our slip at the Naples City Dock!

After a few weeks safely secured at the Dock, we decided it was time to bite the bullet and get this girl (ahem, s/v LAHO) sailing. We can’t just let her sit here forever now can we?

The apprehension of having to dock her by ourselves is what’s been stalling us for a few weeks. As newbie sailors, we continue to be very concerned about the docking part of this new adventure. You never want to be “that guy” playing bumper boats in the marina as you try unsuccessfully to dock your boat, while ultimately damaging your or another expensive yacht.

Plus, it doesn’t help that our slip is center stage to the Dock’s observation deck, which is almost always chock full of voyeurs just waiting to see you screw up. 🙁

After weighing all our options, strategizing a plan, second guessing ourselves a bunch, photographing, videoing, and marking our dock lines with a sharpie, we finally scrounged up the courage to just do it!

We bought this boat for a reason didn’t we?

“Life is short, break the rules, forgive quickly, kiss slowly, love truly, laugh uncontrollably, and never regret anything that made you smile. Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”  ~Mark Twain

Sunday afternoon May 26, 2013 (and my birthday!!!), we threw off our lines and set sail! With Oliver in tow, of course!

We headed out of Gordon’s Pass in Naples into the Gulf of Mexico and day-sailed about 3 miles off the coast. It turned out to be not much of a sail since the winds were pretty weak. We only used our jib sail, but practiced tacking a few times while we were out.

After a few hours, we had to motor back in since the wind was rather nonexistent.

Neither Jereme nor myself were all too thrilled to head back in since that meant we would have to finally attempt..DUN DUN DUUUUNNNN… DOCKING!  And by ourselves. Ugh.

So, with a plan in place — Jereme would drive us in, and I would throw off the lines and stop this baby from hitting the dock! — we gave it a GO!  (Not sure who technically had the more difficult job, but there was no chance in hell I was going to be responsible for driving, at least not this early on.)

We very slowly and very cautiously drove into the marina. Jereme gracefully arched the boat out to the right to make the left turn into slip #64. Meanwhile, I was standing on the bow anxiously holding my line (and breath) waiting for just the right moment to do my part to stop the boat.  As luck would have it, out comes a neighboring boat owner to lend us a helping hand. That sure was nice of Gary, but BOY did he throw me off kilter.

Now, what the heck do I do? 

Throw him my line or stick with the plan we strategized over and over again?  Decisions, decisions.

I followed my gut and just threw him my line. And missed. Awesome. I pulled the line back as quick as my hands and fingers could manage and threw it once more. He caught it!  Thank god. Gary quickly placed it over the piling, while I simultaneously pulled the line to stop the boat.

My efforts weren’t quite quick enough. The boat may or may not have kinda sorta hit the dock. Oopsie!

The good news is, it just hit a little bit. If there’s such a thing? No scratches, no damage (other than our ego), and most importantly no damage to anyone else’s property. Yay!!!  🙂

That’s success in my book.