I’d like to tag onto what Bob has pointed out below because to a large degree I 
am in the same place.

Like Bob, I actually enjoy spending the time and money on the refit of our 
boat. As I and others have said it makes little sense financially but there are 
rewards for me.

I’ve always dreamed of cruising. That got started reading about Robin Graham 
and “Dove” sailing alone (somewhat…) around the world in the 60’s. Of course I 
was 17 so any adventure was something I wanted to do, never mind the logistics. 
Of course it didn’t help that my mother thought is a great idea and encouraged 
me to do something like that in life. I chalk that up to a teenage boy driving 
his mother bat-sh*t crazy…

Anyway, fast forward forty-some years and the desire is still there but it is 
much, much different. I’ve been fortunate enough to have traveled and lived all 
over the world. I’ve spent weeks crossing the Pacific and the Atlantic (ships, 
not sailboats…). I’ve raced sailboats, inshore and offshore every free moment 
I've had since I was 25. I’ve sailed boats to and from the Caribbean and up 
down the East Coast. Sailed down the Baja Peninsula, in the Med, Japan and 
Australia. Even the Great Lakes! Like many others on this list, I have 
vacationed on sailboats in the BVI’s and done a short cruise over to the 
Bahamas.

I guess that I’ve done enough of that type of cruising to know that for me, the 
fun is in the planning, preparation and the "small-bore" traveling. My wife and 
I are in our early sixties, retired and financially secure enough to do any 
type of cruising that may interest us. But I no longer have any desire to sail 
across oceans. I don’t even really care to spend any time in the Caribbean. I 
have found that sitting at anchor for days on end, reading a book and relaxing 
is a bad fit for me. And I am well aware of the fact that much of the time is 
taken up fixing things so it ain’t all cool drinks and soft breezes...

So my plan is, like Bob, finish the refit of our boat, fuel her up and head 
South. Minimal setup and gear. If that step works out then I’ll take the next 
jump over to the Bahamas. If I’m having fun doing that then maybe I’ll stay 
there for a while. If not, back I'll come and figure something else out. And I 
will be as happy as can be. All just part of the voyage. I think that I’ve come 
to understand that I’m caught up in the small things about a trip rather than 
the larger endeavor. I no longer think of a cruise as having to accomplish item 
A in X amount of time. But who knows, I may find that I recover that young 
desire to sail the world. Gonna need a bigger boat! 

So, back to the OP, my feeling is go whenever you can and want to. The voyage 
will fit your desires and circumstances.

Okay, enough rambling. Disclaimer: just my $0.02.

Cheers,
Dave Godwin
1982 C&C 37 - Ronin
Reedville - Chesapeake Bay
new: Ronin’s Overdue Refit

On Feb 11, 2014, at 5:09 PM, Robert Boyer <dainyr...@icloud.com> wrote:

> This subject is very close to me but in a different way and I probably have a 
> different perspective because of my age.  I am now 66 and in good physical 
> condition.  Last year, I began a 30-year retrofit of my Landfall 38 for 
> cruising to the Bahamas in the fall of 2016--I'll be 69 years old at the time 
> I leave.  I can't predict what my health situation will be like in 2016 or 
> anytime for that matter and I can't worry about it.  I have taken off for 6 
> months 20 years ago and cruised to the Bahamas and back (from Annapolis).  
> So, I have done the short term cruising that some here have talked about--I 
> do strongly recommend this for anyone at any stage in their life.
> 
> As far as pouring a lot of money into your boat and never getting the chance 
> to go anywhere (like someone brought up here), for me, "messing about in 
> boats" is as enjoyable as cruising somewhere--its all part of the journey, 
> viewed from a wider perspective.  If I die from a heart attack just a few 
> months before we are supposed to leave for the Bahamas, I still had lots of 
> fun retrofitting my boat and would find peace with that.  Whether by cancer, 
> a car accident, or whatever, we can all die at any time.  We have to do what 
> we love to do and hope that we can live long enough to do much more of it.  
> Others may not find the pleasure that I do by simply messing around my boat 
> and I can understand their need to cruise somewhere to get this pleasure.  We 
> are all different.
> 
> From the 6-month cruise I did a long time ago, I can assure you that it is 
> not all palm trees and hammocks and beaches.  A lot of cruising is doing 
> simply tasks (like doing laundry) in exotic locations.  Even though the 
> Bahamas are beautiful, I never found a place that I considered "paradise" and 
> wanted to stay the rest of my life.  There are all kinds of compromises to 
> places like there are for boats.  For this reason, I think the wider journey 
> (retrofitting your boat, traveling up and down the ICW, etc. are all as 
> valuable as any cruising destination could be.
> 
> Most of my life I have owned a business.  When I took off for 6 months, I 
> thought I would just resume when I returned but the business was in shambles 
> and I had to rebuild it.  So, leaving in the middle of your life and 
> returning has its consequences.  As Wally says, we are all "revenue 
> generators" here at home.  The time to take off cruising permanently, in my 
> opinion, is when you are young (in your 20's) or when you retire in your 
> 60's.  
> 
> I don't know if what I have added to this discussion is of value or not--I am 
> just one person with my own opinions.
> 
> 
> Bob Boyer
> S/V Rainy Days (1983 C&C Landfall 38 - Hull #230)
> email: dainyr...@icloud.com
> blog: dainyrays.blogspot.com
> 
> "There is nothing--absolutely nothing--half so much worth doing as simply 
> messing about in boats." --Kenneth Grahame
> 
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