I think that this thread has been a good one in terms of turning away from the initial, "should I buy this boat" to a discussion of how someone gets into sailing and distance voyaging. I apologize that some of this is taken from an article that I had written quite a few years ago.
The dream of voyaging under sail can be a powerful one. From the advice that you may have already received and are likely to receive you can tell that there will not be a consensus of opinion on how to go distance cruising. There was a period when several times a month I would receive an email from someone who is considering doing just what you are proposing; learning to sail and eventually going distance voyaging. I have watched literally dozens of folks go through this. Some are successful in getting 'out there', some discover that they simply enjoying sailing and find that they really have no need to 'go out there’; some have discovered that the sailing life is just not for them, and others have not even gotten past the dreaming stage.
From what I have seen, the most successful have been the ones who have been somewhat systematic about going. There is a lot to learn before one can safely venture offshore. No one would assume that they could buy a jet airliner take a few lessons and be able to fly around the world. I think most rational people would expect to start with a small plane and work their way up. But for some reason people assume that they can just go out and buy a big boat, take a couple lessons, read a few books, and then go safely cruising.
While there are people who literally taken a few lessons, read a few books and successfully gone cruising, those who were successful following that route are far more rare than those who have done some kind of apprenticeship. Learning to sail and learning to cruise, and gathering a reasonable level of knowledge before they went. No matter how much you know, there will always be more to learn, but I suggest that you at least take the time to learn the basics. As a basic fact, having taught literally hundreds of people to sail on all kinds of boats, in my experience the bigger the boat the steeper the learning curve, and therefore the more frustrating the process will be if you buy ‘a big sailboat’ and try to learn.
I find myself saying this a lot lately, but here I go again. We all come to sailing with our own specific needs, our own specific goals and our own specific capabilities. The neat thing about sailing is that we all don’t have to agree that there is only one right way to go sailing. There is no more truth in expecting that there is one universally right answer about many aspects of sailing than there is in trying to prove that vanilla ice cream is universally better than strawberry ice cream. One area of sailing for which there is no one universally right answer involves the amount of knowledge one requires to go sailing. The other is what is the right boat to own.
For some, all they need or want to know about sailing is just enough knowledge to safely leave the slip sail where they want and get back safely. There is nothing inherently wrong with that approach. Lack of knowledge will impact the level of risk, cost, comfort, and performance, but if you want to get out there with minimal knowledge it can be done. But for others, like myself, there is much more to sailing than simply developing a rudimentary knowledge of sailing basics. If you fall into that camp, it is next to impossible to learn to sail really well on a boat as large as the one in question.
While I am in no way suggesting that this makes sense for everyone, for those who really want to learn to sail well, I strongly suggest that they start out owning a used 23 to 30foot, responsive, light-weight, tiller steered, fin keel/spade rudder (ideally fractionally rigged) production fiberglass sloop (or if they are athletically inclined then a dinghy.) Boats like these provide the kind of feedback that is so necessary to teach a newcomer how to really sail well. Boats like these have small enough loads on lines and the helm that everyone involved can participate and learn together. If there are other people involved, especially if there are children, having everyone involved and being able to learn and participate will typically result in each person becoming more engaged and less likely to be bored and feel kidnapped. But most importantly, boats under 30 feet provide quick responses to changes in course, or windspeed or sail trim. Those tactile responses provide information to the new sailor that helps them quickly sense and better understand the interactions between wind, water, and the boat.
By sailing well, I mean understanding the nuances of boat handling and sail trim in a way that is extremely difficult to learn on a larger boat. Used small boats generally hold their values quite well so that after a year or even few years or so of learning, you should be able to get most of your money out of the small boat and move on to a bigger boat actually knowing much more about which specific desirable characteristics of a boat appeal to you as an experienced sailor rather than the preferences of some stranger on some Internet discussion group.
Starting out accidents will happen, with a small boat the forces are small and so injuries are generally minor, and the cost or repairs quite small. But the huge forces on a bigger boat increase the likelihood of someone being badly injured, maimed or worse, and having repairs that are far in excess of the purchase price of a smaller boat.
The argument that newbies often throw out is the nuisance and expense of buying a small boat and reselling it. That argument is largely based on fallacy. You can often find a 30 or less footer for under $10,000US that is in good condition. Even if you sold the small boat for half of what you paid for it, you would still come out ahead of the difference in cost between a one year slip for a 30 vs 40 plus foot boat, or the insurance for a couple years, or even basic maintenance.
Any work the small boat needs will help you better understand boat maintenance at minimal financial risk. So for example, i work at West Marine one night a week. A few weeks ago a family came needing all new running rigging for a 28 footer they had just bought for roughly $6K. I suggested VPC for halyards and jib sheets, and Stayset for the traveler, topping lift and mainsheet. In total that was around $350.00 in line. He bought a fid kit and planned to learn to splice on the internet. This week a family came in with amid-40 foot cruiser, that needed all of its running rigging replaced. My estimate of the cost of that line was closer to $4-5,000.
In any event, I strongly agree with the idea that at the very least you try to get some sailing lessons. I think that sailing with others is also a great way to get a toe in the water. But nothing beats the experience of having a lot of time on the water, experiencing a broad range of conditions while in command of your own small boat. Beyond that if I were in your shoes, I would sit down and put together a list of all of the things that I would want to know before I set off voyaging such as:
• Boat handling
• Sail trim
• Rules of the road
• Boat husbandry, repair and maintenance
• Diesel/ gas engine maintenance and repair
• First aid
• Heavy weather tactics
• Legal restrictions on leaving and entering foreign countries
• Navigation, (Piloting, dead reckoning, electronic, and maybe the basics of Celestial)
• Radio operators license exam requirements
• Safe and dangerous fish to eat
• Survival skills
• Yacht design basics including desirable and undesirable features
Once you have what you think is a complete list, it might be helpful set up a schedule to try to develop any of those areas of skill that you currently feel you are lacking. As much as possible I would try to involve all those involved to learn as many of those aspects as each is capable of understanding. This process could take as little as a year, but more often takes two to three years. The process itself can be very rewarding and can build the kind of bonds that are required to be cast away on that oh so small island that a boat underway represents.
After sailing for a few years you should be able to further define your goals and develop your own sense of what is the right size and type of boat to do what ever you choose as your course.
Whilst I appreciate Jeff's thoughts very much, and I had a very long sailing experience before I own'ed my first boat.. Indeed I sailed since I was 12. However I feel that many sailors put too much emphasis on the difficulty of sailing.
If a person retires now at 50 or 60 from a profession of intellect, with cash to buy a boat big enough to cruise the world, then I say buy it and go now. I say that because if the person has been in a career where they've had to use their brain, an engineer, the sciences, a lawyer, doctor, academic, etc etc then the art or science of sailing is really quite simple and a few months with lessons and Cruising For Dummies on their knee, then they're probable set to make their own voyages of increasing lengths.
Those of a Trade background, plumbers, electricians, farmers, police, military, are probably even better suited for a quick take off because their hands dirty
experience means an engine room is not a shocking new world.
Modern cruising boats are not made for racing.. They are kitted out for lazy people willing to forsake that extra half knot by installing aysemteric spinnakers that don't need spinakker poles, furling mains without reefing lines, jibs that don't need tacking etc etc.
I was shocked the other day to see a cruising boat with running back stays. The couple are new to sailing and didn't know how to clip them forward to shrouds to get them out of the way when not in use... No modern cruising boat has them!
My thoughts are if a person has a brain they can go get a modern boat and head off into dream world in a very short time. Responsibly. Safely. Enjoyably.