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Current plan is to sail off this fall.  Still formulating ideas for the long-term.  I know that I have no desire to cross the Panama Canal, so the Straights or the Horn may be in my future.  
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The Cruising Plan
Current plan is to retire this year and then take the SaltyDawg rally down to the Caribbean. We will see where we go from there.
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Hope you like the pictures (scenes from Nevis, BVI & Grenada).

The Long Term Plan
The long term plan is to untie the dock lines and sail away.  I am not planning for a 2 or 3 year cruise.  I’m planning to spend as many years as I can sailing.
    At this time my goal is to slowly equip the sailboat and get to know her inside and out. I’m currently learning how everything works and how it is put together.   I am learning how to repair everything and I’m getting to know all the signs and signal that things are or are not right and need attention.  I’m improving my sail trim abilities and learning how to optimize the performance of the sailboat.  I want more experience on her in different weather conditions.  So far, I’m quite pleased at her performance in light air as well as her ability to handle 30 to 35 kts of wind.   I have yet to experience winds above 35 kts while sailing Music. (Update: make that 48kts thanks to a squall on the A2B race)
    I’m also building the cruise kitty.  Since I plan on staying out indefinitely, the kitty needs to be sufficient to supply funds for the long haul.  Timing this with retirement and other factors is my current consideration.  Two added considerations are the puppies.  I should be fine cruising with them while I’m in the US and Western Hemisphere, but when I move further out, they will present more problems with foreign rules and regulation.  I would hate to have them put into a quarantine center for 30 or 90 days just to visit a country on the cruising path.  They are 12 years old at this time. 
    Expected costs for cruising is a black art - just like budgeting for the future!  My basic needs are minimal.
    I need some clothing (but no more custom tailored suits).  A couple pairs of jean, shirts, sandals, hats, foul weather gear and some warm clothes should do me.
    I eat local when I travel so food costs are usually low and their is only one mouth to feed.  The cost will depend upon the cruising area I’m in at any given time.  The first-world will be much more expensive than third-world countries.
    The boat needs money (Jupiter can attest to that).  Assuming that all the upgrades are completed and the critical items are in excellent working order when I depart, maintenance and insurance will be the primary costs.   I expect that maintenance will be more than insurance cost.  This would include periodic haul outs to maintain the bottom.  It also includes wear and tear on the sails and running rigging as well as maintenance of all the boat systems, such as, replacement filters, spare parts for pumps, engines and replacement tools.  I typically don’t use much fuel, so I don’t expect a large fuel cost. I will also need budget for upgrades as technology progresses.
    Next would be rules and regulation costs and navigation costs and communication costs (if needed by then).
    My current guess is 15 to 30K per year will work for a baseline budget.