(I have an office there; and yes, it’s “rough” 😉)

Anyways, if it’s just you and your wife I’d do Wailea. All the hotels are good. Also check out VRBO to get access to condos in Wailea. Some are right on the water (and expensive). You can save a ton of money by getting a good condo in kihei (right next to Wailea ), which also has good beaches. All beaches in Hawaii are public and you can drive to all the Wailea beaches (most have public parking and restrooms).

Things to do:

Beach time! This is the best, including snorkeling

Drive to Hana (go past Hana to Homoa Beach; best on the island). The best experience i had going to Hana included staying the night. VRBO again. Otherwise it’s a lot of slow winding driving for one day. Don’t try to just go around; turn back and come the same way. Make dinner reservations at Mama’s. You’ll thank me later. Don’t expect to just show up. Make a reservation.

Haleakala in the morning never did much for me. Some people love it. It’s Hawai’i, but it is very cold up there. Bring warm clothes.

Snorkeling at Molokini.

Walk front street in Lahaina

The most tourist thing I’ve done is paragliding with my son. That was fun. You’ll be near the lavender farm (up country) which was ok, but the best was relaxing with some lavender herbal tea and maui cookies after

Have fun!