I start in January right after the holidays when there's no vacation ahead, just a pile of work to be done: Vision - I should be at the beach chilling right no

I start in January right after the holidays when there's no vacation ahead, just a pile of work to be done: Vision - I should be at the beach chilling right now Strategy - Let me book a trip to the beach for Christmas today to get the best deals, when no one thinks about Christmas since it's January. Design - I like to be free on vacation so I'd usually look for apartment rentals or even houses (airbnb or specific websites depends on the location). I try to avoid hotels so I don't have to leave the room every morning at the same time. I don't want to tip the hell out of my day as well while on vacation. I can make my own bed. I prefer having a kitchen where I can cook whenever I want. My own fridge, etc. Execution - Budget is key, I start to look at how much I can afford. Then I split it into 2 categories - flight cost and room cost. If I fly very far I'd lower my room budget or look for places slightly outside of the tourist places, where I could easily get to whenever... If I fly domestic then I make sure to rent a very nice place. In terms of day to day expenses, I usually save a little bit of cash here and there from January until the trip. So it's not even budgeted and I have a pile of cash to travel with when the day comes.