I've done the tests for a UK magazine using my Icom HH VHF with 5 Watts transmitter power.
HH cockpit to cockpit about 2 miles, better if you hold the set above your head! (Okay for receiving not too good for TX!)
HH in cockpit to yacht main VHF set with masthead antenna - about 5 miles.
HH in cockpit to Coastguard antenna height 1000 feet on hill. Communications were still loud and clear both ways at 35 nMiles.
Range from liferaft expected to be about same as above for small wave heights only.
The calculations navigator97 did sound right, in a theoretical environment.
This fits my real world experience with my icom handheld quite well. traveling with another boat out to Block Island last year, once I got more than about 5nm ahead of them, we were unable to communicate handheld to handheld. What we did whenever we wanted to raise one another was the calling party went below and got on the ships radio with the mast mounted antenna and hailed the other party. With one party using the ships radio, and the other on the handheld, we were able to communicate clearly until about 8nm separation. Past 8nm (my boat was quite a bit faster) communication with the handheld was receive only, and had to use the ships radio for all outbound communications. This fits the theoretical numbers pretty well also.
As far as talking to someone 100-250nm away on your VHF, that is entirely possible in the right atmospheric conditions (most often happens when it's calm and foggy). In the wireless internet industry (I used to own a wireless internet company) it is known as (atmospheric) thermocline ducting.
There was one particular instance on a serene foggy morning, the kind where you can see the different layers of fog stretch out over the corn fields for miles, we had lots of loss f signal warnings on our equipment, and when diagnosing the situation, I picked up a strong signal from a microwave transmitter belonging to another company that was nearly 100 miles away in the next state. I called their Sr Engineer up and confirmed he was able to very clearly pick up my signal as well.
These transmitters are tower mounted with the antennas normally angled down towards the ground to focus the output power to the ground for an area about 6-7 miles out from the tower, and in normal conditions the signal becomes indecipherable from background noise beyond about 11 or 12 miles.
So the question is how did a signal that normally never travels more than 12 miles pick it up nearly 100 miles away at a signal strength that would lead me to believe his transmitter is only 4-5 miles away? Thermocline Ducting is the answer. The weather that morning was dead calm air, the ground was warm, but the fall sky was cold, and it caused the air to settle in different thermal layers with heavy fog in some, and clear sky in others. Since there was zero wind to stir these layers up, they sat there until the sun came up and warmed everything up. My transmitter happened to be sitting in a clear, more or less fog free layer, in between 2 dense fog layers. Those fog layers went uninterrupted for at least 100 miles and just happened to also be the same layers the other guys transmitter was in. Our signals literally bounced inside that layer with very little signal loss for 100 miles...
These layers, if spaced correctly, will act as a super efficient long range antenna cable, and can transport signals for extremely long distances with amazing efficiency. They don't often last for very long as any wind will normally break them up.
The proper meteorological term is an Inversion layer, in case anyone was wondering.
http://en.wikipedia.org/wiki/Inversion_(meteorology)