Skydive KW is NOT up-jumper friendly. They are a Tandem operation only! Even at that, they only fly a couple times a week. Probably best anyway since I understand that the owner is a real winner. Odd sincee most Aussies I know are pretty cool. There are a few boogies a year held in Marathon which is 50 miles north east of KW. Awsome jumping with outstanding views. One comeing in Nov. put on by Skydive Sebastian. Great time. Went last year. As far as Key west. Don't take your rig. Spend your time in the water diving and party at night. They have some kick-ass bars down there.
the airspace over Key west is restricted because of all the commercial and military planes flying. That is why Skydive KW is actually in Sugarloaf Key 17 miles NE. Enjoy you visit. The place is awsome.