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The classic 27's are all pretty heavy boats, and when full of fuel, gear, ice and water, they will all need a 3 axle trailer.

The beam of these boats exceeds the legal limit for trailering without a permit, so I do not trailer mine any more than I have to.

I use a 2013, 6.7L diesel F-350 4X4 SRW equipped with a factory trailering package to pull mine and it is rated at 14000 GVW, correct for the load. I am pretty sure that even a gasoline powered 2WD dually should be rated above 10000 that you would need for a classic Whaler 27, but check the rating on the label inside the door frame to be sure.

Don't purchase one of these monsters without considering your needs carefully. These are BIG, WIDE BEAM boats. Mine measures 34' from the tip of the pulpit to the back of the engines, (it has a Whaler Drive). I keep mine dry stacked at a Marina and only anticipate using a trailer in case of hurricane or maintenance that has to be performed outside of my Marina.
This is DEFINITELY NOT a boat you would want if you intend to keep it at home, transport it to a ramp, and then launch and retrieve it when you use it. It takes 2-3 agile people to launch and retrieve in a ramp situation. If that is what you are looking for, you would be wise to look at 22'-25' Outrages that have the narrower beam, and weigh much less.