Certain decades in one’s life just seem to make it simpler to get to that point of untying the dock lines of your own cruising boat and sailing for distant shores. My wife, Windy, and I first did it in our 20s—before the house, the kids, and the careers. We had few ties to cut before sailing away for seven months to visit eight countries on a small, coastal, classic-plastic cruiser that I bought for $8,500. For many others, the cruising lifestyle is a goal only realized once they reach their golden years, when they no longer have to report to the office each morning and the kids are off on their own. These folks usually plan extensively for their escapes, and they possess the time and means to make it accessible.