Interesting thread. It depends on the person. More than 10 years ago I had a fun date where we started off running on the beach, exploring a place that was rumored to be a FEMA camp (the guy kind of dwelled on conspiracies) and we got run off by a guy in a big pickup truck with a cowboy boots and hat, went to another Beach and I wrote his name in the sand with my dress leather heeled boots (he took a picture and it's like I'm floating in heaven. He called it an angel) and then for dinner. It was kind of adventurous and he was bragging to his dad about that date when he got back home.
Another date that was a lot of fun was in Chicago, it was our second date. We explored the magnificent Mile. My first time there. I loved seeing the architecture and was surprised by the friendliness of people helping when I needed maybe some advice or direction to where to go.
Another date, some years ago, was in New Orleans. I had met him in Biloxi and we were going to be in New Orleans at the same time. Unfortunately it wasn't that great of a date. But I have good memories about my stay in New Orleans -doing a 2-hour run, visiting and Rice's house and looking at architecture, and staying at a bed and breakfast for under $40 for the night with a claw tub bathtub and breakfast by a pool. The best part of all of that was the stories that I shared with some of the locals.
Lastly, there was a guy that I went on a date with, 18 years old and in the Japanese Army. He had a Peugeot and driving gloves. He took me up to chichibu, Japan where there were these Waters with ionic properties. You could feel the freshness and the change of oxygen once you got there. It was a really interesting experience to be in a car like that and how he wore gloves for that. There was a 12-year age difference too.
I can think of other dates in the past, it wasn't always about the place but having something with adventure in it or an experience or stories to tell after. That would be my ideal date.