We will will be on Maui for five days for the first time this winter, arriving and departing from Kahului.

We would like to stay in two locations to experience the scenery and Hawaiian culture.

We are thinking we would spend the first two or three nights in the SE part of the island and the last two or three nights in the NW part to be close to the airport for our departure.

We are looking for suggestions about where would be best to stay and which part of the island most deserves three nights.

I would recommend staying in Kapalua or Napili. Very beautiful scenery and water and yet close enough to activities, yet peaceful.
Make sure to splurge and go to a luau.
You won't be disappointed.
We love Old Lahaina Luau.

I would suggest you pick one or the other and stay there. the island is not that big that you can't drive to the other side for day trips, and five days is not long enough to warrant loosing a day making a move from one resort area to another. If you want to stay in another place that is different and to experience some Hawaiian culture, try stay Hana for a night or two.

We love the SOUTH end (Kihei-Wailea)
Kamaole Sands owner rentals are reasonable..Mana Kai if money not a factor.
Lahina is touristy..If you don't Have time for Hana...drive as far as Keane
pennisula, making sure to stop at Hookipa, Baldwin Beaches and Mama's Fish House...We love haleakala, but not worh
getting up for their sunrise..

As far as scenery, there isn't much difference between the NW ( Napili, Kapalua, Kaanapali) and the SE(Kihei,Wailea)resort areas. To experience two different areas as far as scenery and culture, Hana would fit that bill. Since this is your first time on Maui and only 5 days, I would strongly suggest staying at one location and making day trips rather than loose a day moving.

SE Maui to me is Hana. Wailea is SW to me. I think you could do 3 days in Hana and 2 days in NW Maui, but you will be crying for Hana on those last 2 days.

Wow! Thanks for this great information. HTTY

With five days in the wintertime, I'd sleep in Wailea the whole time with just a day trip to Hana. As others have said, the island is not so large that you need to lose a day to moving. Happy planning!