Some ideas you might like to use/recycle/reject:
1) Make sure taking a year off NOW is a good idea. This depends on the kind of uni you are graduating from. Business first. Work harder, play hard.
2) Stick to your well organized approach (in everything) as seen in your post. It will take you further, sooner - both in professional life and in traveling.
3) You seem into racing
. Stick with it. Start with your racing
mates - ask around, they may direct you to their racing friends elsewhere that can take you racing, or otherwise sailing, into the deeper, bluer waters.
4) Consider sticking with your professional career while setting up a racing/cruising team. When not racing, team members could use the boat for cruising. There are some racing/cruising boats around that can be picked up, fixed up, and used for many years to come.
5) Should you decide to crew on other people's boats, you can be actually paid for this - if you bring in valuable skills and work. Otherwise expect to pay as you go - at times you just pay for your share of food
but when you are desperate while the boat owner is not, then you may be expected to pay for the ride. Last year I saw vagabundos hitching a cross-Atlantic ride for EUR500+. I'd rather fly ;-)
6) Stay focused on what actually gives you a kick but be open to new experiences. If something does not work for you, get out of it and go for the next best thing. Life is short. When you are young, life is a jeans shop - try things out before you buy them.
7) Should you get stuck in an uncomfortable position (e.g. mid-ocean with a crew that hates you) take it as an opportunity to grow - one can only grow when faced with challenges. Easy tricks dope your senses with pleasure - a poor substitute of happiness.
8) Build skills. Ask yourself what is missing then go for it. Get papers along the way - if you need a license
, get it. Do NOT get licenses just because they are there. Build contacts. Build friendships.
9) Avoid lists longer than 9 items. If a list is 10 items long, you may be reading the wrong list.