I bought my own boat 3 months ago with no experience really with boats or sailing.
On our inaugral 2 week
cruise we bumped into people who tried all of your above options and to be brutally honest if you are preparing for any kind of
extended cruising anything but buying your own boat will be a waste of your time and
money.
Several couples we met were on charters. At 2-4 thousand a week a week each year a week was all they could afford. When something went wrong they called the charter company, i saw headsails flying out of
furler tracks and jammed
mainsail furlers and all sorts of other user error problems. Really nice beautiful boats with tvs and microwaves but since they didnt own the boats and only went out a week a year they didnt know much of anything. While they were nice people they were truly spoiled as sailors, cruising around on quarter million dollar boats which they knew very little about how they worked. I had to strongly advise and help one couple with a partially detached headsail thatnwas flapping like mad in 30 kt
wind to take it down because they were destroying a 3 thousand dollar sail before my very eyes just leaving it like that while they waited for the charter companys
emergency after hours guy for hours to return their call.
Moral of the story on chartering: its a rental, you will treat it like one and you will spoil yourself and possibly never be happy with the boat that you can actually afford after driving a rental. You will pay through the nose, enough that you could buy a small simple boat after two charters and learn very little beyond basic sailing. Its a good plan if you only want a week a year for a couple years until you find a different hobby but in prep for
extended cruising its a waste of time and
money, with exception to seeing if cruising is really something you want to do.
We met some nice couples who did fractional ownership and IMO it sounded like a pain in the neck. They paid a 1500 buy in fee and 120 per month to share a boat with 10 people. Their boat was nowhere near as nice as mine that i got for 4 grand and they were on the hook for 10% of every upgrade or
hardware that anyone bought. The boat was loaded with other peoples crap, they only got to use the boat for one week in the summer (but first come first serve during the winter), the
dinghy they were constantly complaining about because someone bought one that weighed 500 pounds and for the amount of sailing they got in it seemed to me to be a complete waste of money. Often i see ads for fractional ownership and it is basically a way for someone to pay their moorage and keep their boat. I saw an ad for a sweet 26 ft thunderbird for 4 thousand and a week later the same boat popped up where the guy was trying to sell a one third share of the same boat for 4 grand plus 1/3 of the moorage and upkeep. Guess he bought the boat and realized how much a slip and
insurance costed.
Moral of the story on fractional ownership: unless its within the
family or amongst good reliable friends who you can count on to hold their end of the bargain financially its not worth the hassle. Again it never feels like its yours and for the amount of sailing you will get in no real way to prep for extended cruising. If one partner knows a lot about sailing that person will tend to take over and be the go to guy and you will never learn the self reliance that you will need. You will find the boat gets filled with crap that you get the privelidge of paying for that you never wanted in the first place.
Sailing clubs and volunteering on other peoples boats as crew: great if you want an intro to basic sailing but again as you are not the owner you are never the one in charge and you will never get the practice making the judgement calls that you will need to make doing extended cruising. You can have a lot of fun daysailing but you will be crew rather than
captain and beleive me they are remarkably different experiences.
When you buy a boat, especially an older one for a few thousand, you have to learn every little thing about it. The crazy
wiring installed 3 owners ago, the
wiring that leads to nothing because it was disabled 10 years ago, how much
battery capacity you need, how big of
fuel tanks you need based on your cruising style, what your favorite sail arrangement is, the handling characteristics of your boat, how to determine what is not right by asimple
funny noise, etc.
To me it seems an extraordinary waste of time, money, and resources to get into sailing any other way other than just
diving right in and buying a darn boat. At least from the examples ive seen and heard from 2 weeks cruising and meeting people at the docks. Especially chartering - i explained to some of these folks that for the
price they paid for a week that they could own a boat like mine - because they were spoiled with a quarter million dollar boat they they could never afford to own (between maintenance and initial purchase price) they could never see themselves even setting foot on a 30 year old 26 footer. Its really too bad for them. I met a very enthusiastic older british man who owned a half million dollar boat who had been sailing for 40 years and he looked at my boat with awe and wonder at the crazy advanced
rigging on my boat and was very excited to see i had a continuous
furler, something he had just paid ten grand to install on his boat a week before i met him. If my boat was good enough for him, it is a shame that these chartering people paying the value of my boat for a week of cruising would never even know that i actually had some more advanced
hardware than their shiny new charter vessel and that it is actually much easier to sail.
Anyways while i know i got a good deal there are many good deals out there for used boats. Some people just dont use a perfectly good boat anymore and want to see it be loved, some are upgrading, and some just know that maintenance needs to be done and they are too lazy to do it.
If you intend to have a long sailing career just buy your own boat, start small and get to know your boat for all her quirks and maintenance and then a couple years before your big
blue water cruise buy your
offshore boat and sail it and get to know it. No need to start with a 30-40 footer get something small like a 24-28 footer its easier to
dock and sails, maintenance and slip
fees are cheaper.
My two bits.