During the day in Wailea there are not a lot of options besides the beach activities that Maui is famous for. You can visit the Wailea Shops where you can peruse the high end shops and watch for celebrities. They also have a great little deli that always has a line at lunch and some tasty pineapple topped burgers at the restaurant.
The number of high quality golf courses here will astound even the pro golfers.
Some of the best things to do in Wailea is to hang out at the Hotels. Their lobbies are open to the public and they have plenty of great restaurants with great lunch deals if you are local and can show a Hawaiian driver’s license.
At night there are parties at most of the big hotels and everyone is invited. You can be guaranteed that the prices for drinks will be much higher then anywhere else on the island and there will probably be some cover charges.
If you want a great overall experience then stay at a little Bed and Breakfast place called the Pineapple Inn. This little inn is located in a beautiful Wailea neighborhood and has only a 4 guest suites and a cute two bedroom cottage. They will make you feel right at home and give you all the scoops on what to do, when and where to do it. The beauty of this place is that the backyard pool, hot tub, grill, lounges and everything you would dream should be in a backyard in Maui. The views from the hottub, the privacy and incredible setting for the pool beats any other hotel hands down. If you are traveling with a family then the two bedroom cottage is perfect for you to rest and relax.
There are some restaurants, golf courses and a mall to visit during the day but nothing really happening otherwise unless you are staying or doing activities through one of the major hotels. This is a high end area so be prepared for that. The best thing to do is Wailea is to hang out in the mall and spot celebrities. Be prepared to be disappointed, they don’t look like they do on TV, in the movies or on the concert stage.