When first cultivating the dream, one will encounter a barrage of myths and distractions. While none are fatal on their own, the sum total are usually sufficient to undermine the most ardent enthusiast, relegating him or her to the "someday" throng.
Myth #1: I can't afford to do anything like this
Reality: If you drive an SUV, make a house payment or hold down any kind of gainful employment, it's a no-brainer. If you don't, then you'll have to get creative, but it's still very possible.
One of the things that surprised me most was the number of cruisers who are doing it for a fraction of what I originally thought it required. Make no mistake, you can spend a lot of money very quickly if you want to. But that's a choice, not a requirement.
It's a guess, but I believe 20-30% of cruisers we met were doing it on average or sub-par incomes. Two teachers from Quebec. A waitress from Norway who met and married a construction worker from Australia. They and their two sons are out 8-9 months per year in a boat that cost less than a used Camry. The air, water and stunning environment was the same for them as the next guy. Oh, and two fresh-from-college kids who saved for a couple of years are doing an 18-month cruise before starting a family.
No, you can't live forever on no income, but you can escape for a year or two with a little planning and research. One of the most popular Cruising World authors lives and cruises on a boat he bought for $3,000. His annual expenses are less than $20k per year and he and his wife don't live like paupers. They live like kings, actually, at their own pace in remote anchorages shared mostly with starlit nights and occasional boating brethren.
Myth #2: Sailing is hard, even dangerous
Sailing is as hard or dangerous as you make it. Sure, the tangle of lines (ropes) and strange terminology are intimidating at first, but basic sailing technique is accessible to anyone capable of following a recipe or changing a car's engine oil. Twelve year olds race comparably complex small boats in earnest.
Reality: It's not the sailing know-how, or sailing techniques, that are likely to hurt you or your family. It's possible to make a serious mistake and break something that might snap back or fall on someone but, if you're paying attention, that's a rare scenario, like running head-on into a garbage truck with the forks down.
What hurts people and sinks boats is something you can't learn in school or from a book. It's called Good Judgment, the ability to make wise choices under pressure in the face of ambiguous information.
Since good judgment is part nature and part experience, the easy substitute is to err on the safe side, always. The primary factor influencing your decision-making for the worse is a timetable. The three times we have sailed in really uncomfortable, though not dangerous, conditions was because we had a plane to meet or catch.
The word "deadline" contains its own definition.
Myth #3: The ocean is really dangerous
It can be. However, with research and planning many cruisers report circumnavigating without encountering a single serious weather situation. However, going around the world is not what we are talking about. Stay close to land if you want, go offshore if you want. The point is to live, for a while, in tune with nature and unhurried by the crush of commercialism.
Reality: The most dangerous part of sailing is riding in the dinghy. You are often out too late, in currents that are headed the wrong direction, and/or alone. It's common to forget to bring a VHF radio and outboards and their fuel systems are high maintenance items that are easy to take for granted. I have heard of and experienced more near misses buzzing around in the 'dink' than out in the big water. Getting swept out to sea with a defunct outboard is not nearly as glamorous as being caught in the Perfect Storm, but it's far more likely.
Myth #4: You need years of boating experience
No one is going to argue that experience is bad. The more the better, absolutely. If your experience is limited, then start with simple short trips, do the Intra-Coastal Waterway where help is close by and the waters calm.
But the most experienced racing sailor in your state may not have the all important cruising skill, which has nothing to do with sailing.
Reality: The most important skill a cruiser can have is anchorage selection and anchoring, in that order.
You spend the vast majority of your time anchored in a wide variety of conditions. It's imperative to understand how anchors interact with the sea floor and be imaginative enough to play out a wide variety of 'what if' scenarios in your mind ahead of time. Then, you need to make decisions based on those contingencies.
We routinely see presumably excellent sailors in all ranges of craft making poor anchoring choices. I have made some really stupid ones myself and, thankfully, catastrophes are very rare. The most common casualty is your night's sleep, your pride and your gelcoat; but without those, the cruise isn't nearly as much fun.