Just returned from 5 days in the Keys. Thought I would share a little about my trip in case anyone was planning something similar.
Plan your trip through the Miami area during non peak hours. There are lots of crazy lane changes required and no one cares your towing a trailer. For some reason people want to tailgate you more with a trailer. So avoid 7-9 am and 5-6 pm during the week. Anything less than 80 mph is considered slow it seems.
Even if you are not launching your boat at your hotel make sure they can accommodate it on the trailer. Believe it or not many hotels don't offer boat parking, and when you have a 30 foot mast and can't really occupy a single space it makes things more complicated.
Not a lot of options for on the beach mast up storage, most of the beaches have lots of boulders and only steps to the water. Dockage and mooring buoys are common and usually free at most waterfront resorts. I know that's not ideal but the buoys are not a bad option. Rigging in knee deep water was no hardship. I stayed at the Islander which did allow me on the beach storage on the ocean side, and the Indian Key Fill boat ramp was near by for bay side launching. Ask your resort lots of questions and know who you talk to. 3 phone calls about keeping the boat there may generate three different responses.
Bayside Key Largo, Rock reef Inn was accommodating for beach cats and cheap, but no pool
Weather wise I had east winds between 10 and 20 almost everyday. Few thunderstorms and when they came they left quickly, usually taking the wind with it
There are several reefs worth snorkeling. I sailed 2 miles out to Alligator reef. It was blowing almost 20 and was pretty rough. I was the only under 20 foot boat out there. Mostly 40-50 foot motor and sail yachts. A few tour boats and a few center consoles. As crowded as it was there was still a free mooring buoy. Picking it up in rough seas with so many other craft around was a challenge but not impossible, actually never done it on a beachcat before. Watching the bows rise in the waves only to get yanked down by the mooring line was tough to watch but I still felt comfortable enough snorkeling for a half hour. Ran a line from each corner of the front cross bar and through the mooring eye, in case you were wondering. I came prepared with some good ground tackle, but there are mooring buoys Everywhere
Lots of islands bay side to check out. Lignumvitae state park is an easy sail from south Islamorada. Need to notify the state park your going as they only allow 50 people on the island at a time. Has the highest point in the keys at a massive 19 feet.
Indian key off the Atlantic side is small but full of history. Near shore off the south end of Islamorada. Has an observation tower that shows a great view of the Alligator reef light house. The lighthouse is about 5 miles out and is a blast to sail around and ride swells that form when the waves from the Atlantic gmeet the 10 foot water. Indian Key to Alligator light to snorkel alligator reef was a perfect day trip.
I am never one to rely on someone else for help but there is comfort in having so much boat traffic. If the worst happens someone will more than likely see it, but not an excuse to act stupid
If you don't want to tow your boat Dennis at Islander water sports can rent you a wave, hobie 17 or Getaway. He could also help tell you some other launch places. Nice guy, Tybee 500 veteran and is planing a casual multi leg race from Islamorada to Cocoa Beach next May.
You can still run a ground even if you think your far enough out, and the locals don't like damaging the sea beds. Stay far out and watch the tides.
I'm not an expert, but that's my 2 cents from the trip, I considered it a great one and I considered my Gcat 5.7 the perfect boat for the job.
Stay safe, see you out there