Kapalua will not be windy in July. That time of year would be when they get their best weather. Kapalua does not have any of the nightlife you mention. Wailea actually has more walkable restaurants than anything in Kapalua.

Kaanapali has more nightlife in the form of the Whaler's Village.

Other than that, you would have to drive into Lahaina. Either Kapalua or Kaanapali would put you in fairly close driving range of Lahaina. Wailea would be 45 minutes away.

Really, no where on Maui is like Waikiki (thankfully).

Kaanapali is only 3 miles from Lahaina - and I think there's a regular shuttle.

As for wind, last time we were in Kaanapali in July (2007), surf lessons were cancelled because there wasn't enough wind!

We have stayed twice in Kaanapali, both times in July. I don't remember any problems with the weather/wind. It was absolutely gorgeous! Kaanapali has a long boardwalk along the beach which connects the hotels to each other and an upscale mall.There are a few decent restaurants at the mall, and it's an easy ride into Lahaina, where you'll find more restaurants and plenty of shops. Lahaina, of course, is considerably smaller than Waikiki, but it's a good place to explore for an afternoon or after-diner stroll.

Some of the hotels like the Sheraton and The Westin, used to provide shuttle service into Lahaina on a regular schedule.

For our first visit, we stayed at The Sheraton Maui, in a building overlooking Black Rock. The rooms were very nice, but the property is really spread out. It used to take us about ten-15 minutes just to walk to the main lobby! We stayed at Kannapali Ali'i in a beautiful oceanfront
condo for our second visit a few years ago. It was heaven on earth. Outstanding comfort, wonderful ocean views from the living room, and only steps from a quieter part of the beach.

Don't know where you heard about it being windy up by Kaanapali/Kapalua in July, - as the word used to be (way back in 77 anyway) that the Kiehi area (now defined as Wailea I guess) was the windy place.

Both ends of the West side have their pluses and minuses - but I also love Napili - between Kaanapali and Kapalua.

If you have a car - you can drive into Lahaina - for strolling and shopping - as well as down Kiehei way.

BTW - good snorkeling going out along the rocky area/Black Rock by the old Sheraton in Kaanapali.

We've stayed all over the island and prefer Wailea. Just depends on what you want. Wailea is a little more ritzy, all the restaurnts are nice but pricey, but there is Kihei to grab a quick bite or just have a more casual night. I would choose between there or Kaanapali. You can easily take day trips up to Kapalua and snorkeling at Honolua (one of my favorite spots on the island).

If you do stay on the north side, the Feast at Le Le luau is amazing!!

As stated by others, Kaanapali is not known for being windy. Kapalua is. For the things you listed, I believe your best place to stay would be Kaanapali including short drives to Lahaina Town for local culture, shopping and restaurants. Also there are many great restaurants in the Kaanapali area. Wailea is limited in local culture and restaurants as it is primarily high end condos and resorts.

<have a nice dinner and be able to stroll along the street at night and walk into some open shops (similar to Waikiki).>

That sounds most like Lahaina to me.

Assuming you did not wed in your seventies you might be about thirty years old,yes?
If so then the Kaanapali area is best for you. Being close to Lahaina with a shuttle would give you lots of possibilities.
As a snorkeler/diver and in my fifties I choose Kihei.
You will have trade winds that blow in the afternoons but you will be happy that it's cooler.

Completely agree with suze and logandog. Sounds like Kaanapali might be a better fit for you.

Wailea is ritzy and a short bit from Kihei but there isn't too much happening there, in comparison to Lahaina. Lahaina is going to have a little of everything: tacky touristy places, upscale restaurants, sidewalks to stroll, a tiny bit of local culture, the movie theater...all in about a 4 block span of space. Kihei has all that too but it's more spread out (4 miles of space.)

Just back from Maui and we stayed in the Kahana area along the "lower road" I really like this area- short drive to Lahaina or Kaanapali if you want night life.