Working that distance on 2m is going to be very difficult - unless you use an internet backbone such as EchoLink.
If you HT has CTCSS and DTMF on it, you'll be able to access an internet linked repeater with a modest antenna.
Provided your brother is either connected to the internet, or within range of such a repeater (with similar gear), you'll be able to make contact.
The wire antenna you describe is for H.F. (I suspect your boat is about 60' long) Such a wire would work well on a particular band, given a particular height above the metal of the boat. Do a search for dipole antennas, they are very easy to build. Build one to fit your space and try the frequency it resonates at (probably 20m).
OK - there are alternatives, vertical H.F. antennas have their place, being a bit more discreet and in some cases, more efficient.
Maybe a 40m "vertical" would fit (laying horizontally of course).




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