Kate, you've never been to either Miami or Key West? Go to Miami. Way more to do, IMHO. Key West is a fun experience (esp. during Fantasy Fest) but Miami wins overall.

I love Key West for the reason NeoPatrick mentions: the complete lack of pretense. It took me several visits before I finally convinced myself that I didn't need to take a "nice" outfit to wear; it's just not necessary, even for the best restaurants.

We don't spend much time on Duval, either, and that's inevitably where most tourists are. And Fantasy Fest? Egad! We arrive in Key West the night of the final parade, and even though we watched it for years, we just stick to the calmer areas of town now, and are happy when things clear out the next day. I can't think of anything much worse than being stuck in Key West for that entire week.

Thanks for all the great responses! Gives me something to think about. I still haven't decided what to do.

I hope it's worth it as we chose it for our 10th wedding anniversary in July. We liked the sound of it being an open air party atmosphere. We did enjoy Bourbon Street in New Orleans and like the Riverwalk in San Antonio. So, hoping it will be a little like those places.

We've done lots of research and found so many resturants we would like to try, but obviously won't have enough time. We've also planned a sunset cruise and a snorkle trip. Looking forward to just realxing and going with the flow.

FWIW Towards the end of July there is Hemingway Days which is a lot of fun with the look-a-like contest where a lot of older guys try to look like Hemingway when he lived in Cuba, 20 years after he lived in Key West. A fishing tournament, a Meet The Papas reception, street fair. I,ve been going down every year for it for the last few years.

Pjk