Step 1: Learn what it's like to live on a sailboat (specifically a catamaran)

Good friends of ours, Ray and Lisa, recently made there move to live on a boat after retiring.  I used to work with Ray at Device Solutions, a electronic/software contract engineering design firm.  His retirement plan went through a couple iterations, but he and Lisa ended up finding their perfect Motor Yacht, a trawler name "Scout", which they actually just untied from her slip in New Bern, NC to start travelling down the Eastern Seaboard.

You can learn more about them and there adventures on their blog. 

We went to visit them in New Bern and they turned us onto a couple of Vloggers, Jason and Niki Wynn, and their website and YouTube channel "Gone with the Wynns".  The Wynns started by travelling the US in an RV and then a few years ago, sold that and moved onto a 43' Leopard Catamaran and are currently making their way around the world.
Watching their videos gives viewers a great glimpse into what living aboard a sailboat and travelling really entails.  They don't gloss over the downside, but the upsides look pretty amazing, so the maintenance and waiting out weather and dealing with broken parts seem all worth it.
We've now watched every single one of their episodes, from looking for and buying a catamaran up through sailing in French Polynesia, where they are now.  As we began to watch their adventure and learn more, we became more enamored with the idea.  I guess it's time to learn more and see if this is something we would like in practice, not just fantasizing about.

-Mike