Should I stay or should I go?

crazystrause · #1 (**permalink**) 10-05-2011

I have only paid my slip lease in Annapolis until mid November leaving me with some serious decisions to make. I could go ahead and pay the second half of my slip fee and leave her in the water all winter like last year. I could pull her and block her up over the winter, giving me the opportunity to remove the seacocks and repaint the bottom. Or….. I could do what Ive been talking about for so many years and just head south for the winter.

I just got my house rented for another year, and staying at home or with Sabrina leaves me without a rent payment and the opportunity to save some serious cash. As of today I will have 4 more solid paychecks which Im thinking combined with the income from the house being rented should afford me a relatively comfortable lifestyle over the winter.

Other than getting an expedited passport renewal for the potential jump to the Bahamas I dont see anything but my own fear of the future holding me back.

Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.– Mark Twain

Anyone want to join me?

jerryRiggin · #2 (**permalink**) 10-05-2011

And what are you sailing on? What's your sail plan? Wherever the winds take you in the Bahamas or sail to one place and stay there ?
Sounds like fun!

crazystrause · #3 (**permalink**) 10-05-2011

1968 Bristol 27. I was thinkin maybe just get a job serving tables in Miami (or similar) and make the jump over to the Bahamas for a few weeks of fun.

I figure Ill head down as fast as the weather will let me mid november and once i reach Jacksonville ill re-access my plan and if anything just enjoy the warm weather.

Undadar · #4 (**permalink**) 10-05-2011

I enjoy pondering questions such as this. However; from my own life, I know that there are a huge number of variables that must be balanced and it is nearly impossible to effectively communicate all of these via email/forum. If it is as simple as what you have said, I would go. Enjoy the journey if you decide to go.

JD
JdFinley.com | Sailing, software development, and life…
You can observe a lot just by watching.

WanderingStar · #5 (**permalink**) 10-05-2011

Two questions for you: 1. Are the boat and skipper adequately prepared? 2. How sorry will you be if you don't go?
I took time and money to bring my boat up from Florida. I don't regret a bit of it, I plan to bring her back maybe as soon as next year.

Tempest · #6 (**permalink**) 10-05-2011

Mid-November seems a tad late to leave Annapolis. Is it doable, sure. Optimum? I'd shoot to leave earlier, if you can get ready.

123456Wannasail654321 · #7 (**permalink**) 10-05-2011

go

jerryRiggin · #8 (**permalink**) 10-05-2011

So the goal is to base in Miami with intermittent trips to the bahamas for a few weeks at a time? What is your trade (I'm thinking about what options may be available to you)? Any reason for Miami in particular?

imagine2frolic · #9 (**permalink**) 10-05-2011

My advice is go as soon as you have things in order. The boat, financially, and your skills all need to be taken care of. One thing you can't buy back is time, and if your health turns sometimes they just can't fix what's broken. Do it as young, and as soon as possible. No one knows what tomorrow may bring.......i2f

jrd22 · #10 (**permalink**) 10-06-2011

Sounds like you're hoping the general consensus here will be to advise you to go. So I vote go!