Is 3 hotels for 8 nights too much?
 

I have booked six nights in Maui. Could not decide between hotels and I wanted to see opposite sides of the island so I booked 3 nights at the Hyatt Regency and 3 nights at the Grand Wailea.

I am thinking about extending the vaction for another 2 nights. The Four Seasons looks like the way to go but is 3 different hotels for 8 nights too much?

All on the same island? YES!
-Bill

On the same island, I would say yes.

We went to Maui in August, stayed at the Hyatt and loved it. Seeing the 2 different sides of the island would be nice too. I would suggest 4 nights at the Grand Wailea and 4 at the Hyatt.

If it were me, I would see both sides of the island, while staying at only one hotel -- The Four Seasons.

And add to the inconvenience of moving your stuff the "middle of the day" lag time when you have checked out of one hotel and can't yet check into another.

It seems like you will waste more time packing, checking out and checking in than just staying in one location and driving around.

I was just in Maui for 9 days (at one Hotel, the Westin). Stay at one place and rent a car. Who wants to pack 4 days into a trip in Paradise?