South Maui has two main thoroughfares: South Kihei Road, and the Pi’ilani Highway (Hwy 31.) South Kihei Road runs right along the scenic shoreline, and at its southern termination connects to the main north-south thoroughfare through Wailea and Makena. The Pi’ilani Highway parallels the coastline about a half-mile up the mountain and is a much faster (though less scenic) route that bypasses most of the beach-town destinations. The Pi’ilani Highway is your best bet if you know where you are going. If you’re just taking your good old time, sightseeing, or generally checking out the lay of the land, South Kihei Road is a better choice.
Ignore maps that connect South Maui with Upcountry Maui. No public roads exist to connect these areas. Many private, gated, nonexistent and/or 4WD roads show on GPS and online maps of Maui (including Google Maps.)
The largest shopping center is called “Pi’ilani Village Shopping Center” and is the only shopping center on the Pi’ilani Highway. Anchored by Safeway and Hilo Hattie’s. Pi’ilani Center also has a gas station, Ruby Tuesday, Starbucks, Outback, two banks and a dry cleaner – among many other shops you’ll find useful if staying in South Maui for any period of time.
There are many smaller strip-malls, restaurants and places to shop scattered along the length of South Kihei Road – Pretty much anything you’d expect to find at a typical smaller US beach town is available somewhere along this road.