I wanted to share my experience with you guys that are thinking of going bigger. I typically fish in the lower keys and have gone up & down in boat size many times. My current ride is probably the best boat i have ever owned but it's actually over sized for the keys. Perfect for the Bahamas & key west if you can find a ramp and trailer storage. I have itemized the challenges below.
My boat is a 32' (cc 32'-10" x 9'-10") & 3x axle trailer.
1. Dedicated tow vehicle. Min 2500 -3500
2. Total weight with tow vehicle 20,300# with 200 gallons of gas
3. Total tow length is about 65'
4. Height is an issue on some secondary roadways (Power lines)
5. Turning radius is an issue
6. Gas station access is an issue
7. Trailer parking is a major issue.
8. Ramp access is a major issue.
9. Plenty of ramps in the lower keys for smaller boat/trailer combos but not for the larger boats.
10. Very hard to turn in/out a retail shopping center, food etc. Must plan everything ahead.
I think the best sized boat for the keys is probably a 25' cc.
“Everyone behaves badly--given the chance.”
― Ernest Hemingway
My second choice and this is because i've got a family is a Grady White Freedom 27. It's a dual console, and it's heavy so I would need a F250 to tow it but it's dry, stable, runs on 150s. I like the dual console setup because you have more room in the boat without the CC hogging it all up. it's got a head, the wife loves that idea.
Those are the two boats I am going to be targeting when I decide to step up.
EDIT: i would also add that if I had your boat, i'd probably just drive it down on the water. That boat is so big you probably need the placards and flags and all that mess and i don't want to have to fiddle with all that crap. I would launch at Flamingo north of Marathon and just run it on down wherever I was staying.
The hotels and motels in the keys are some of the most expensive in the entire USA. The only way around them is to have a boat with a cabin. That is what we did in my younger days. We would spend two weeks living on our 24 ft boat. We cooked on a Coleman stove and lived off lobster and canned vegetables. Sometimes we would pull the boat up to US1 in Key West and my wife would jump onto the riprap and buy lunch at the BK. Things were more relaxed back then so we were able to get ice and water from near shore places. (Homeless had not invaded Key West yet).