I can only tell you what I did, which was during a recessionary period. I don't know how old you are, how much education, or what kind of job skills you have.
I saved every scrap of money for 2.5 years (literally had holes in my shoes for my suit job), bought a boat BEFORE I quit somewhere in that time, purchased
equipment for it (but no work done), then quit in very early spring. That gave me early spring to outfit the boat, and go sailing at the end of spring shaking down the boat and heading south. I had enough for a cruising kitty. However, in the following
winter I worked a
contract to up it a bit again.
It's not easy coming back to shore to work but it can be done. It's also to have skills that are relatively liberal in that people are accepting of it and that you took a "sabbatical". It would also help if you have many different skills so you can have multiple jobstreams. Take courses at local community college etc in mechanics etc. It will also help you with your boat and can be a blast
learning new skills.
During the saving and
buying period I educated myself by helping other people on their
boats, taking an advanced
celestial navigation course, helping in a woodworking boat shop, and researching as much as I can about sailing and the
route that I would be taking. So, there are things to do when you don't have a boat, have a boat but are not ready to go or work on it.
The world is unfortunately I think much worse this time around. Not only the economy but also much more crowded and
commercial in sailing locations.
As for retirement, I am starting to believe that is a myth. To sustain a lifestyle and
health I would probably need 2-5 million dollars in cash to get the interest. That of course is impossible, and I will have to work anyway just to stay interesting.
My next boat is primarily a
live-aboard with "stop and go" cruising. Not sure what I will do about the work situation, and it makes me nervous thinking about signing over a check, but I know I will do it. For one, I will save on rent. For another, the social situation of living with other boat owners is enriching and I miss it. You have to live. I know I can work where I am and up to the point when I decide to leave. I could always take a
vacation, move the boat, work some more, move the boat again.
If I were you:
- Continue to save money and
research boat models and prices on the listings. You want to get a good boat that will last you a while and won't be sucking you dry. Go out and look at
boats you narrow down as being worthy. Look at as many models as possible from your
research. After a while the emotional element will go away so you wont feel angst about going. You will learn about your needs from the experience.
- Create a cashflow -
income + expenses and relative savings.
- Create an outfitting worksheet with ALL the
equipment you will need and their relative costs. Figure out how much money you will need for equipment over time. Also figure out relative costs for major upgrades when you
purchase the boat (new
engine etc). They may not apply to every boat you look at but will help you decide your choices and offers. This sheet will also tell you how much longer you will need to save and give you dates.
- Get education on shore - volunteer in boat places, help others, read, courses, skills etc. Plan your
route and
cruise. How long will it be? Where will you go? What season is best to leave? NOTE: all of this I consider just as important as outfitting the boat. It's outfitting yourself!
- When you are ready, and find the boat, buy it with the intention of living on it while working, or just keeping her on
mooring. Don't quit your job but fix her up and learn her quirks. This is really important time period. You need to get acclimated to the lifestyle and to learn from people in it. Just as if you were climbing a mountain, you need to get acclimated to the lifestyle change, else you may just be overwhelmed and quit the dream.
- When the season is right for shakedown, when you have outfitted the boat to a reasonable point, when you have a solidified plan, when you have a cruising kitty that will not only get you to where you want to go but also have a small
budget to return at the end of it, when you have acclimated your lifestyle, then either take a long
vacation, a "sabbatical", or quit. That sounds like a lot ($ etc) but believe me it is not and it's surprising how fast that time period goes.
NOTE: I blew a lot of money on a boat and a reasonable journey. I never regretted it.