This may seem like a silly question...
I've read alot from this site and others that many people have received upgrades upon check in (ie. reserve a cheaper Mountain view and get upgraded to ocean view).

Do the check in people offer this, should you ask for it, or any other tricks to get the upgrade. Is it possible at places like the 4S, Fairmont, or Grand Wailea? Thanks a bunch!

We normally stay in a hotel for a few days at the end of our condo stay at both the Fairmont and Grand Wailea and have received an upgrade every time. At the GW we were not charged any additional money, but got a much better location both times (once with an ocean view and once with a partial ocean view). The GW has rooms that are a fair distance from the pool area, so at the very least, ask for another location if the hike to the room is too much (I think I clocked it as a 10 minute walk one stay before we switched rooms). Last summer at the Fairmont, we asked for an upgrade and got a full ocean view room for $100 more per night plus he threw in 2 full breakfasts each morning (they have an awesome spread there). I believe that room's upgrade would have cost $300 per night, so the $100 was totally worth it. It doesn't hurt to ask and most of time they will accomodate you. I firmly believe that if you get to your room and are not happy with the location, call the front desk and ask for something else. We are always happy that we did.

the week between Christmas and New Years we stayed at the Outrigger Wailea. when we checked in i asked if we could be upgraded from a Garden View. for an additional $90 per night (well worth it IMO) we were given a great 6th floor oceanview. it never hurts to ask!

thank you for the advise. that was our plan is to stay at a more reasonable place and then splurge the last couple of days

I stayed at the Outrigger Wailea in the Summer of 02. I reserved the cheapest room they had from Travelocity at about $189 per night then they upgraded me to an oversized oceanview room at no additional charge! I didnt even have to ask, I think it just depends how booked they are.

You will LOVE Maui. I have been three times and loved it every time. Stayed at Kapalua Villas one year, very nice but way windy on the beach and far removed from town. Stayed at Aston Kaanapali Shores another year. Great value and a great ocean view room with kitchen on the top floor $99.00 per night...another internet find.