The first thing you need to check out of the rate race is your health. Without it, you're not going to have any quality of life regardless of your plans. Daily non-impact exercise is a must, swim, row, orbital machine... anything that won't impact your joints and raise your heart rate for 20 min/day goes along way to keeping your health care costs in check. I swim 6K/week.
Eat a high fiber, low fat diet with omega 3 oil supplements. You can't change your genetics, but you can hedge the cards you were dealt.
By keeping yourself healthy you will be more likely to be ahead of the game when purchasing health insurance with a high deductible saving significantly on the monthly premium. Bank roll the difference for the unexpected and collect the interest instead. 5K-7.5K of a high deductible keeps the premium low and allows you to have control over your money, not an insurance company, but it all starts with your health. The only way to beat the system is not to get sick!!!!
The other important key is, you need to be a jack of all trades, good sailors tend to be out of this mold anyway, but learn to do all of your repairs whether your home, car or boat, computer... If you have to pay for services it's with money you could have spent on other things. Think of it this way (and I recognize it is a bit of a stretch), for every dollar you spend on services you had to earn that dollar, and pay taxes on that dollar, so it's not just the dollar you save, but also the taxes you would have had to pay on that earned dollar you save.
I will be pulling the plug on my business in 18 months and rolling the dice with my investments as well. SS is not going to happen for anyone with any net worth, beware you will be tested right out of it, other government entitlements whether sate or federal are in serious peril, the US is running on fumes.
Good luck with your retirement decision.