I'm buying a sailboat with my wife and daughter and sailing the world in 18 months (waiting for the last of my options to vest). Think about it! It's ~$60-100k to get the boat, and you can live on ~$24-30k/year doing it. There's a huge community out there of cruisers who do it full time.
From the other families I've talked to who have traveled the world with their children by boat, or countries by caravan/RV/Airstream, boredom doesn't seem to be an issue (compared to a lackluster childhood in Suburbia).
Lots of people out there breathing who aren't living.
I met two different couples who literally sold everything, drove to Florida, bought a boat, had an instructor on board for a week, and sailed away with no previous experience. Neither has gone past the Caribbean but they both did fine. One of them now runs a day charter on a catamaran.
I spent several years learning and improving sailing skills before heading off. 2-3 years of weekends and a few vacation weeks would probably do it if you started with that as your focus. It takes a lot of people that long to find a boat and get it set up the way you want anyway.
Originally, we were looking at a Lagoon catamaran, 38-42 feet. Due to personal circumstances around an elderly parent (can't sell our house, they'll need to live in it while we're out sailing), we're now looking at a Beneteau 381 (and a few others, needs to be blue water capable but would also like to have a lot of guests on during passages).
I'd love a Lagoon, but unless my options are worth >$100K at a liquidity event, its not in the cards.
