- Maui Film Festival: Held in June, this one takes place in Wailea and Kahului. The festival has drawn national acclaim for its film premieres and screenings.
- Restaurants Week: With over 20 participating restaurants, the Restaurants Week is a celebration of Wailea's finest cuisine. It is generally held in the month of November.
- Wailea Wine and Food Festival: Held in December, you have to be a part of this if you are a foodie!
And if you are visiting over the New Year’s Eve, do check out the firecrackers’ display at the beach at midnight.