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My advice, buy a cheap beater boat right now. Soething in the 25' to 30' range (big enough to support overnighters and multi-day trips) that can be sailed as is, but could use some maintenance, upgrades and repairs. Then for the next few years be fixing it up while you sail it. Take longer and longer trips, learn navigation, heavy weather sailing, repairs underway etc. Then in a few years when you're ready to really dive in to the cruising world, you sell that boat (hopefully at a decent price considering the years of elbow grease you've invested in it), buy the real cruising boat of your dreams, and live happily ever after.

Keep in mind that actually sailing a boat is only a small part of the cruising lifestyle. There's the old addage: "Cruising is fixing your boat in exotic locations".
 
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