Hey there, I'm a windsurfer come yacht owner

I have a Northshore 33 that I need to sail home but am worried about getting it to the coast under the rip bridge etc. just wondering if anyone who has done this trip would like to do it again ? Or am I worried about nothing, I spoke to an old guy who sails down there and he just laughed when I told him it was my first trip. Anyway just putting it out there ??