It seems as though planning for fun is a fool's errand. I mean, sure. Coming up with options is never a bad idea.
If you want to explore a city you don't know, for instance, you don't want to go in completely unprepared. You want to know what kinds of museums are available, you want to have a general idea of what the culture and the cuisine is like, or what is special to the area. You might even want to plan a few days soup-to-nuts, from your morning coffee at the corner cafe to the gondola ride at dusk.
We'd planned almost every day of our Italian honeymoon, chock-a-block with art we wanted to admire, and ruins we wanted to explore, and pasta we wanted to eat, and monuments we wanted to photograph. So much we wanted to do, to experience together.
But if you want to have fun -- if you want to have a RIDICULOUS amount of fun -- you have to leave room for spontaneity. And truly, the most meaningful, memorable, and ridiculously fun moments on that trip happened on the night we left unplanned. We wouldn't have stumbled into the unreviewed restaurant with the exquisite panzanella, or fallen in love with that weird spitting fountain face, or stopped to revel in the unexpected harmonies of a trio of buskers -- who carries around a hammer-dulcimer? -- or heard the teenager cry out his request that they "play Freebird!" We wouldn't have lingered in the crisp Tuscan breeze, nothing to do but hold on to each other, and to hold on to a day that we knew would become a memory even as we lived it.