How do I do this?
Where do I work?
I work remote for a tech startup in NYC with unlimited paid time off. Yes, I abuse it but I also work my ass off to be able to.
How do you pay for this?
I have the Chase Sapphire Reserve card which I use for everything to get points to pay for most of my flights.
$300 Travel Credit (airbnbs, cabs, metrocards, etc)
Priority Pass Lounge access (free food and booze while you wait)
I use Skyscanner as well as Google Flights to do my preliminary search. I also use Skiplagged (the app) to check for flight deals and set up alerts there. Kayak is great for exploring options with no firm destination in mind.
I love Skiplagged because I'm a light packer and the idea is to skip the last leg of your flight. For some reason, flights with a layover as your destination could be cheaper than a direct flight. Skipping the last leg of your flight means you'll be taking a direct flight so only pack a carry on!
How do I know where I'm going next?
This is a tough one and obviously a number of factors affect my next trip. What it all comes down to is weather at the time I'll be there. I'm a solar powered adventure seeker so I like to be away from the cities but off-peak season as well.
Currently I'm on a SE Asia binge so the last major country I need to visit is Vietnam. I plan on doing stints in South American countries as well and probably city hopping in Europe.
How do I plan the rest?
I don't! I'll book domestic flights within the country (buses take too long and I only have so much PTO) but as for what I plan on doing, I rely on the people I meet to plan my next day!