this is actually what im currently doing. personally i think it's not possible to be not working at all. You still need to watch and work occassionally but it's very possible to spend just 1-2 hours a day for work (or look at new ideas etc.) and spend the rest of the days travellingBrazil.
..need I say more?
I personally want to live and experience many different cultures. The idea is to make money to the point where you no longer have to work behind a desk because the money is just recurring.
I'm looking into Nicaragua right now. They have the caribbean and pacific coast, you can get citizenship for like $3k in total. Climate warm year round, there's paypal and you can buy beachfront property for like 100k. Not that many tourists overall, especially compared to europe, and it's the poorest and safest country in central america. You want surf you go to the pacific side, you want to just chill out on an unpolluted Caribbean island/beach look into corn islands
Spain, France, Portugal are probably your best when it comes to surfing and nightlife.
Speaking from experience, I'm surfing as well.
Did you guys move solo or with a friends?