You can absolutely do it for 2,000/month or less.  Lots of people are.  

Drink local beer/rum/crystal lite
Avoid marinas/land activity in any tourist area except as a splurge (BVI, Etc)
Red beans, rice, pork, chicken, local produce and whatever fish you catch
Keep the boat simple, small and low tech
Boat and all debt is paid
Basic insurance
Minimal trips back home
Some kind of health insurance paid - the real challenge for most of us
Skype, email or ssb - no cell or sat phone
For the most part, the further south the cheaper (think VZ)
Good dinghy so you can minimize marinas and anchor

If the above doesn't hinder your dream - go. Take lots of pictures and make 
everyone jealous. (And don't mess with your 401k)

John


Sent from my iPad

> On Feb 11, 2014, at 4:32 PM, Curtis <cpt.b...@gmail.com> wrote:
> 
> We are talking Freedom? or service-vs-servitude.
> The whole reason I want to go is for freedom., I want to see and
> experiance the places I have read about and meet other like minded
> folk like us. I want to live simple. I want my stress to be a hung
> anchor with the prospect of suiting up the tank and regulator mask and
> fins. I want to smell the rain. I want to have to reef. The wind is so
> Light here in Beaufort I never get to reef. I want to have fun finding
> light houses and old citys and history exploring. I want to learn
> about nirds. i want to see the wild life . I Dont want to see a car
> for months. I dont want to see a baggy pants high rimed chevy driving
> gettow thug for 2 years. I want to open a can of redbeans and boil -a-
> bag of rice. I want make crazy love to my wife on deck under the stars
> why she is still in d mood.
> I want to make coffee in watch the sunrise every day and take a map in
> the afternoon.
> 
> 
> I think I can have this for 20 to $25,000 a year. I hope.
> 
> 
> 
> 
> 
> 
> 
> 
> 
>> On 2/11/14, Dennis Cheuvront <capt...@gmail.com> wrote:
>> Here's a site for some great cruising early in life:
>> <http://www.navy.com/>
>> 
>> Worked for me!  Got to see lots of tropical lands.  Some were even
>> friendly.  :)
>> 
>> Dennis C.
>> Touche' 35-1 #83
>> Mandeville, LA
> 
> 
> -- 
> "All men dream: but not equally. Those who dream by night in the dusty
> recesses of their minds wake up in the day to find it was vanity, but
> the dreamers of the day are dangerous men,for they may act their
> dreams with open eyes, to make it possible."
> 
> T. E. Lawrence
> 
> .
> 
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