Depends on the height of the receiving aerial, basically line of sight. 5 miles at full power is not unreasonable but reckon on just a couple to be safe.
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My wife has not given me permission to express any opinion here
As has been said - if you can physically see the other radio aerial (line of sight), you should be able to talk to it.
However, the word 'should' is important to understand. From the many potential probelms that limit range, probably the greatest is that when you use the hand-held, you will more than likely not have the aerial in a vertical position. Best range comes from transmission at right angles to the aerial - hence, range will be restricted if the aerial is not perpendicular to the ground.
Operationally, you will probably find you have a greater range from the 1 watt transmission from your fixed set using your boat's external aerial mounted high up, even if this power is less than that from your handheld. In other words, higher up = greater chance of "seeing" the other party; fixed aerial should be vertical = max range; external fixed aerial is usually the correct tuned length for the frequency being transmitted = greatest range.
In essence, hand-helds should only be used for short range communication - is this where I say IMHO?
I wouldn't disagree with anything that anyone else has said because "line of sight" is the theoretical max range. However anecdotally, some years ago I decided to try for myself and mounted a "base antenna" on my garage roof, about 10 feet up, and went of with the handheld in the car - I got about 5 miles up the road with a small hill and lots of houses and trees in between. Maybe I was lucky and there were some special condtitions that helped propagation, I don't know. Why don't you take it out to sea and call the Coastguard for a radio check - everyone else does, then ask him where his antenna is. Coastguards tend to have big antennae on the top of cliffs so that would give you an idea of your max range in an emergency. I suspect you might be surprised at just how far you can get.