A frustrating situation indeed, one I struggle with as well. I also understand your concern about rough terrain/sidewalks damaging your stiletto heels. I have lost many pairs to rugged city sidewalks/grates as well. What kind of walking surfaces does your park have? Decent paved walkways? If so, the heels should be OK. I guess the issue I'm wondering about is having to wear another pair to the park due to poor walkways near your boat. Where will you store/stash you other boots while walking in your stiletto boots? Perhaps you will stash them in a back pack. I'm hoping you will give it a try, you will realize your capabilities/comfort level quickly, so I wouldn't worry too much about looking silly. Make a few short walking trips near the bench, increasing the distance as you feel more comfortable and competent. I'm betting you will do just fine. The only other method that helps me out is having a bootbud or gal pal along for the walk, is this a possibility? I'm thinking that your neighbors are used to seeing you walking in tall boots with heels, so they probably won't even notice the stiletto heels. I always enjoyed your pictures sitting at a coffee shop in your boots as well. D