No contest for me: Our planned family cruise of 2005.

We bought the Zombie Princess in New Orleans in June of 2005 for an
intended 6-months-to-a-year cruise in the Caribbean. Worked on her in
July and August and were about ready to go when, after more than 30
years without a major hit, New Orleans got creamed by Katrina. The ZP
survived and we re-prepped her to depart NO as soon as the bridges were
working. However, before that happened we had to ride out Rita at
anchor. Yee-ha! Finally, the major bridges were fixed and we escaped
NO. We crossed the Gulf of Mexico to Naples, FL. I tried to tuck in
behind a weather system which was supposed to be dissapating but we
caught it bigtime for some of the worst weather I've ever sailed in. My
older daughter puked for four days; we had to force her to (minimally)
hydrate. Finally got down to the Dry Tortugas with the hope of actually
starting a lovely, warm, tropical cruise. We were there for one day;
then the rangers told us to evacuate to Key West cuz Wilma was coming.
After Wilma ran over the boat in Key West, the kids were completely
uninterested in continuing "cruising" and we were pretty exhausted
ourselves. So we terminated our "Caribbean cruise" in Key West in
December and returned home for Christmas.

Definitely my worst adventure ever.

Frank