Good luck in your pursuit!
First, I wouldn't be too concerned about finding that mythical "fully-kitted" or "turn-key"
boat that's ready to sail around the world. Many so-called turn-key boats have aged
electronics, or
rigging, or... My
advice...buy a solid boat and user your
money to fit it out yourself. (That way you also explicitly know that
equipment.)
As many have suggested Cornell's World Cruising Routes and World Voyage Planner
books are fantastic
references to get you started. But, they are not they holy grail of the routes to take or follow. As Boatman61 pointed out...1 problem is that many other cruisers follow the routes in his
books, and miss a whole lot of interesting places. Another problem is that
weather patterns are changing. For example, traditional
route from
Seattle to
Hawaii is to sail south along the US coast to about 38-32 degrees north latitude then
head westerly to
Hawaii with the trades. However, in the several races and in my own crossings from
Seattle to Hawaii and SF to Hawaii the tracks were almost a Rhumbline due to the location of the "Pacific High."
That being said, my best
advice is to get some pilot
charts for the specific area you want to begin your adventure (Also check out
https://prevailing-winds.de/) and study them. Also, get online and study the weather patterns every day. A sailors life revolves around weather. You can view real-time weather for free using a site like
https://forecast.predictwind.com/atlas/#Wind after you register, or even Windy. I wake up with a cup of coffee and PredictWind, and I check PredictWind before I sleep. (Other than weather...a day consists of "light time" and "dark time," and seasons are simply "typhoon season" and "not typhoon season.") The importance of understanding weather in the area you are travelling cannot be over-emphasized IMHO.
When voyage planning, I also like to use paper
charts. Yes, I have electronic charts...but IMHO...a paper chart laid out on a table gives me a bigger picture for planning purposes.
Next, learn how to maintain and
repair all your systems onboard. (Bonus points for knowing how and when to apply Gorilla Tape!) Seriously, ocean travelling puts a lot of wear and tear on
gear, and often times you'll end up somewhere that doesn't have
parts or
service and you will be on your own to fix problems that will arise. It's not a matter of if problems occur...it's when will they occur...and they usually occur at the worse possible times.
Get some
offshore experience. I know many "paper" master mariners (aka. 6-pak captains) who couldn't navigate their way out of a well marked channel. While you state you have 40 years of
boating experience, sailing
offshore is completely different than inland or coastal cruising.
There are many "rendezvous" that organize "armadas" of cruisers. On the
west coast there is the Co Ho Ho, the Ba Ha Ha, the
Pacific Puddle Jump, etc. I'm not a rendezvous guy, so I can't speak to that. Finding "buddy boats" to island hop with is pretty easy in most
marinas or pubs where cruisers hang out. A lot of times it's simply word of mouth advertising.
The
equipment list could go on for days, and there are many threads (and debates) on that subject. Some equipment is for
safety, some for comfort, and some equipment is for risk aversion/tolerance. For example, some people will insist on extra
sails. I don't carry extra
sails because I can
repair minor tears and such, and they take up a lot of space, and in more than 25k ocean miles I've never needed a spare sail while cruising (although sail changes are common when ocean racing). I do carry a life raft. Some may say its overkill and an
inflatable dinghy is just as good. On the
east coast of US the USCG response time is about 4 hours avg. In the Pacific response time is often > 4 days and it's often not by USCG.
Finally, don't rush it. Some people want to circumnavigate to tick a box on their bucket list. I think they miss a lot of rewarding experiences and places. I personally find it more enjoyable to sail to off the beaten path islands, spend some time in local communities and engage with the locals. I've plowed fields with a
single blade plow pulled by a
water buffalo, mended fishing nets, planted casava and harvested kava, helped build houses, learned to play pani with the
kids, volunteered to
ferry food and
med supplies during the pandemic, and a BIG PLUS is taking some locals sailing for a day. (I'm surprised that in many popular cruising places how many of the locals have never been invited to go for a day sail, or even invited onto a boat.) IMHO, that's what cruising is all about.