Where the money genuinely changes the experience, and where it buys marble you won't look at.
Buy location first
In Paris, Venice and Kyoto, being ten minutes' walk from where you want to be is worth more than a larger room. You will feel it every single day.
Buy the guide, not the car
A private, properly licensed guide transforms a day at Petra, Angkor or Amber Fort. Upgrading the vehicle from a Camry to an S-Class changes forty minutes of your day.
Buy time
Private early access, skip-the-line entry, and a seaplane instead of a speedboat all buy back hours. Hours are the scarcest thing on a short holiday.
Heritage over chain
In Rajasthan a converted fort at four-star pricing beats a five-star chain hotel on the ring road, every time. The same is true of Italian agriturismos and Portuguese pousadas.
Where to spend without hesitation
Safari lodges and Maldivian resorts. In both cases the property is the destination, and the gap between categories is real.