I think my Watkins 27's VHF antenna would scrape the bridge at 39 feet!
Masthead is 38 feet. Mebbe at low tide?? bt then ya have 3'-8" of keel ta mind
Walt Scott designed her for the ICW.
I'm biased; but fer me, it'd be the Watkins. The "Commodore" and I spend nearly four days a week aboard, whenever possible; but nearly every weekend. With any luck, the Keys are in my proposed future, too