i've towed my V to the keys 4 or 5 times, 1500 miles ,round trip. i have also met friends down there who rented boats. i think i'd rather have my own boat. i like my boat and i like boating in my boat, so if i'm more comfortable in my boat, that's what i want to be in. just do your prep work and it shouldn't be a problem.
as far as tandem vs single, i have a tandem and love it. i tow with a tahoe w 5.3 and get bout 10 mpg and i know it's back there.
i take spare hubs, 2 of them, already packed with grease. just take off the castle nut, slide the old one off and new one on. take 2 spare tires, because if you need one, then you feel naked without one for the rest of the trip.
if you have a good gps, running aground can be avoided, blue is good, white go slow, brown, turn around.
is it worth it, up to you. i'd rather spend the money on my boat and rig. plus it's kinda cool to take the old girl to some new places every now and then
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