Hello David, Frank Pappy's is a must.My first trip to the Keys was towing my 20' O'Day to Bahia Honda from NJ with a buddy.We spent ten days there,when the Ocean was too rough,I lowered the mast and went under the 20' high bridge to the Bay side. www.bootkeyharbor.com is a great site with a lot of info.Several years later,my wife and I towed our Catalina 270 down and spent two months in the Keys using Burdines in Marathon as our base.There was a charge for leaving our pickup and trailer there,when we were not at the marina.We have sailed to the Keys and Bahamas twice from NJ since in our Beneteau 331.We do love the Keys.The past few years,we have been down there with our pickup camper,towing a 17' powerboat.There are a lot of pics of the Keys on my wifes blog, www.bumsrest331.blogspot.com camping and farther back in the blog,sailing.Good Luck, the Bum