..............for example, buy boat on east coast USA. Sail coastal to Florida (or South if already in florida) towards Carib.(where you indicated you planned on going).
As you proceed south you will work out all/most basic boat issues and determine what you need for your own personal cruising style. Also, as you go you will meet others doing likewise and exchange experiences and ideas .
you'll find out quickly what your preferences are and if cruising is for you.......
We moved aboard in our twenties with this "josthecobbler" plan. It made for an easy adaptation and is working for us.