Thinking of just cruising around the Philippine Islands in a sail boat.
Buying my Hobie Cat would be a good start.
Seriously, it depends on how you want to do it, you can charter and have the captain teach you by OJT (ETA: you still have to have certifications to rent, etc.). Or you can attend a sailing school:
https://www.bwss.com/?gclid=EAIaIQobChMI1LCjhL_b7QIVRPHACh3ZMwexEAAYASAAEgKh-_D_BwE
https://www.offshoresailing.com/sail-and-power-courses/fast-track-sailing-courses/
http://www.mdschool.com/ocean.htm (Maryland)
https://www.greatlakessailingco.com/sailing-school/ (Michigan)
https://asa.com/schools/oklahoma/island-fever-sailing-school/ (Oklahoma)
Google ‘live aboard sailing schools.’
My wife did not share my dream of sailing around the gulf for a while and then sailing the South Pacific…
Well, I cannot top 26 INF’s post but I took the US Sailing basic course. The course was for kids, but my local chapter held an adult specific course for a number of us oldsters over a few weekends. Lots of fun, met interesting people and got a certificate for future rentals.
Thank You !!
Not saying I am jealous, but, bro…I met a few Filipinas while in the Navy…Enjoy your time. 
I learned some good stuff from this little gem https://www.amazon.com/Learning-Sail-Annapolis-Sailing-School/dp/0070240140 (although I don’t recognize the cover in the link I provided.)
Other than reading books or watching Youtube videos, just get out and do it. Find a local club. I first sailed a small Laser at day camp when I was 12. You can learn plenty while on a lake with high winds. If you are close to the ocean, plenty of people out there with sail boats looking for a reason to get away from home. You can maybe chat some people up for some free lessons. Maybe get friendly at the saloon near a marina. You can meet a full cast of characters any where boats are involved.
And, if you do make this dream come true, share some pics and journal entries.
Not exactly on topic, but I knew a guy who wanted to retire and sail the Pacific. But he knew he didn’t really have the means.
I don’t know where he learned, or exactly how the connection got made. But he “retired” early 40s and sails other people’s boats to places in the Pacific. Like they want their boat in the PI for X window they fly in for a bit. He then takes it somewhere else and …
So I knew this guy…
…who started his own business sailing other (rich AF) people’s boats from Boston/Long Island region to the Florida Keys/Caribbean region every fall, and back north every spring. He was so industrious that he started a spinoff where he winterized other (less wealthy) people’s boats every fall and prepped them for duty every spring.
This same guy made more than enough to get by in the off seasons cruising the country on his motorcycle, doing what ever he felt like doing, plus he sailed some amazing boats up and down the coast non stop.
Not a terrible way to live.
Getting practical experience in small sailing dinghies or daysailers is a great way to start. Could be anything from an Optimist Pram or Sunfish to a Catalina 22. You’ll learn how to apply the book knowledge of points of sail, how to handle a tiller, how to read the wind, and so on. And have great fun. Enjoy!
have about 30+ years on boats
sailing and power
sailing mostly cats in the 60+ foot range 6 days a week kinda sailing in the islands
used to live on a 32 footer
also worked stink boats 75 foot mostly one was 125 foot
so a lot of experience on the water 
just start doing it as said get into a club (as mentioned) a hobie or other small craft learn some basics then move up courses can get you on the fast track to basic handling
but IMHO you just have to do it and warm weather tropical is awesome fun !
its not hard but to be really good just takes time and experience you can practice rough weather but till you are in a storm hold fast hahahahahah
nothing like blue water over the bow
BUT to sail around ? live aboard ? small boat based on land ? thats a HUGE opening to sail around
your own boat
what size
what type etc…
can find some crew to help ?
could you crew to learn ?
how long for ?
short term just do a charter
long term crew on a few boats so you can learn and experience I am a cat person and prefer them for many reasons and this is personal mono have pros to
its when you get into weather where experience helps I can say sailing 6 days a week in the islands gets you good really quick since you have to deal with winds and docking mooring 2x a day so on
working crewing on a boat is a lot of fun actually not much money but huge experience and if you could gets you into weather every day and fun of sailing
did 15+ years on dive boats including sailing cats etc…
its doable you just learn as you go BUT its the little things again bad weather having to dock or mooring out
running in weather etc…
navigation and radio
get into some of the sail forums etc…
learning boat mechanics and rigging and such are all things you need in your pocket if you are solo
I did work down in Micronesia kinda close to where you want to go very nice place watch out for pirates though I was on a larger 125 foot vessel in a protected area BUT google sulu sea pirates also the philippine area in general has a lot of piracy going on got some friends down in that area (locals and expats) so check into that and the areas so you know wanted to go so you know where to avoid
Find a local harbor, find their dry dock. Walk up on a saturday or sunday and ask who is looking for crew.
Follow up. They’ll have a fleet or three they can loop you into. I’ve walked onto Sr. Tech Execs boats on both coasts this way. Not too dissimilar to showing up on a construction site in a suit, hard hat and safety vest claiming to be with the insurance company like my mom did in the 80’s and 90’s.
Al
Buy a Sunfish for between $500 and $1500 and learn on it. If you can sail a Sunfish, you’ll do fine on bigger boats. Find out you don’t like it like you thought, then sell it and you won’t lose anything. They get more complicated when they get bigger but as far as sailing, if you can do the small you can do the bigger. I self taught myself on a Sunfish clone…
Thanks
To what end?
I had no idea of what the used sail boat market was like, all I can say is it is crazy if you are willing to buy an older boat or restore a bit of a 30 footer.
Literally, being given away.
You get let in, and can usually wander around. “Where do you keep your hot work logs?” usually gives you access to all cutting and welding records on site. If you’re in a major metro, you chat up the forman for 20 min, ask to see a few areas, take a photo or two from the top safe to be on floor and go get lunch. Gives you a few good pictures for your retirement party once the statute of limitations is up.
Averageman,
My dad just sold his S2 for about what he paid ~10 years ago. 70’s hull in good shape. Good old makes keep their values, but they’re not high.
Al
Make sure you know the area. Piracy is still a going concern in certain waters in that part of the world.
I intend to get some experience crewing for someone when I get there and learning as I go.
I’m actually looking for an “M4 Carbine like” Sailing web site to educate myself.