Am I dreaming too big?

[donkey_jaw]

One item on my bucket list is to sail around the caribbean for a few months. Let me state this first, I have never sailed a boat but love the allure of it.

How does this sound.
-I take sailing lessons and when i feel ready I purchase a small sail boat. Probably in the $10,000-$15,000 range. Something I will probably have to handle by myself (I don't need a list of recommended boats. There are pages and pages of those). I sail south from North Carolina through the intercostal waterway. When the weather is right I take the plunge from southern Florida to my next destination. I've been a planner my whole life and taken great care to make the best preparations for each endeavor I undertake. This way I am prepared for an inspection by coast guard, weather, engine failure, etc.... I do this for a few months. Get my fix. Then sell the boat. Even if I have to take a 20%-50% loss when i sell the boat it will be worth it for the 3-6 months of experience I have. I don't care to sail for the next several years. Just long enough to get it out of my system.

You guys are the pros here. What are you opinions?

Thanks