Ahh, the quest for the perfect island boat.
I looked for 10 years and went through 20+ boats. My favorites were always 24' tritoons with big power and full enclosures. You could hang out on them, transport materials and make quick trips back and forth. Every change I made had its advantages and disadvantages.
One season I had a 25' tracker pontoon with a hard top as my work boat. The roof was great, but it was a twin tube and didn't have full enclosure. The motor was a 115 but it was a dog. There is something to be said about a boat you don't care about. I could throw whatever on it, not cover it, and never worried. Didn't even care when my leonberger ate one of the seats!
Another favorite was a whaler dauntless 200 with a 200 verado.
It ran 50+, had decent deck space and didn't have to be covered. A simple 3 sides enclosure could have been added had I needed it.
Awesome boat.
My suggestion is pick out the place first, we can help you find the right setup to match.
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