Despite technology, travel discovery sucks.

My wife and I have been together for about 12 years in that time, we have had some amazing vacations based on personal knowledge or hopping into a European airport and picking a last minute destination. My wife is an EU national and had the benefit of lots of vacations, working in tourism, and traveling the world. I'm a California native, traveled, but best at talking to CA destinations.

In the past decade, the best vacation spot we have been to is La Palma (Canary Islands). I can discuss the features that made that trip amazing but there is no way to express that into a modern travel search engine. In reality, it was a cheap, last minute trip, that had air fare, an amazing house, and rental car on La Palma over Christmas / New Years many moons ago. But the rural setting, lack of tourists, nature (hikes) and other intangibles made the vacation.

That trip was 11 years ago. To date, there is no search site capable of taking the assorted variables and producing a comparable output. Last minute travel sites like L'Tur (german) have starting point, destination, and maybe an activity, but ... it misses the soul.

For this trip I am reaching out to friends and colleagues. We are looking at AirBnB, VRBO, and other options. We're planning on contacting a couple of the last minute travel options (in Europe) to engage with a human -- I might reach out to an agent here -- that said, it seems like travel discovery based on prior experiences is lacking.

I've often thought, if I had the money and time, my dream startup would solve the problem of "here are my likes, here is where I am, provide me relevant content". That is very local focused, the next step up from that is, here is the sort of travel I am interested in (for this trip), here is roughly where I want to go, help me narrow down the options.

Can this be solved by data (big or small) or is it still something requiring a human touch?

(updated for formatting)