Hm. Going to Carpenteria when I was 5 qualifies. It was my first ever vacation. It was also the only vacation where we took our cat. She howled the whole trip there and back and my father refused to ever drive anywhere with her again.
My latest trip was to Walt Disney World in Florida. It's my first trip there and I've been wanting to go since it opened. It was as good as I had been hoping all these years.