It mostly depends on how rich and old you are. And also on how much you like sailing. A small boat on a small budget will soon tire you out. A newer large boat can be a lot of fun. I know a couple that has been living on a 48’ sailboat in the Carib for the last 7 years and loving it!
Some friends of ours sold their house and bought a Dodge dually and a large 5th wheel trailer. Travelled all over the place for about 5 years. Loved every bit of it.
Eventually bought another house but still use the rig to see the sights.