As the recent thread on the affordability of sailing devolved into a political discussion and got bumped into Off Topic I got to thinking about how things have changed since I first had the dream. The question of financing, how much you will need and how to get it is something each of us has to answer for themselves.
For the absolute minimalist Annie Hill's "Voyaging on a Small Income"
still has some good information, albeit a little dated - she recommends to investing in government bonds that yield 10% interest to provide said small income.
Still, Annie has a lot of useful information for someone wanting to cruise on the cheap.
But building your own plywood boat equipped with oil lamps and sewing your own sails is not for everyone; perhaps not for anyone in the 21st century. Nor is living on "Pulses" beans and rice. Still, we have run into people who live remarkably cheaply - completely, or nearly, off the grid, getting by on subsistence fishing and hunting supplemented by dumpster diving and foraging.
We have met people cruising in $500 plastic classics rescued from boat yard abandonment propelled by much repaired sails with auxiliary propulsion via homemade oars or salvaged outboard motors. A skilled scrounger with an inventive mind might fully equip a cruising boat for next to nothing.
There is a lot of fun and personal satisfaction in cruising safely and comfortably without resorting to West Marine to equip your boat or Safeway to fill your larder. Lin and Larry Pardey present more reasonable means of economical cruising in "The Cost Conscious Cruiser"
There are two questions, really: First is where do you draw the line?
For example, I buy new rope for dock lines, anchor rodes and running rigging but have many times bought or traded for used cleats, blocks etc.
The second question is: Just how badly do I really want to go cruising? It is all too easy to say "I won't go without XXX"
This can just be a handy excuse but I have my own list. For instance, I won't go cruising without good ground tackle and a working VHF but I do not require a freezer full of steaks or ice for my whiskey.
I expect most of us will find a niche somewhere between an open sixteen foot dory with a rock for an anchor and a bag of chips and a six pack for provisions, and a fully equipped sixty footer with a well stocked wine cellar as depicted on the cover of the latest issue of "Cruising World"
(Although given the choice...)