Maui's beach parks are spectacular on any side of the island, but the beaches on the leeward side are generally considered to be the most beautiful. To save you a Google search, “leeward” is a term that refers to the side sheltered from the wind.
Maui's leeward side inarguably presents the best beaches on the island—if by “best” you mean golden sand, perfectly-swimmable waters, outstanding snorkeling opportunities, lulling waves gentle enough for first-time surfers, and sunshine in spades.
For a more authentic feel, skip the mega-resorts of West and South Maui and head to the North Shore, East Maui, or Upcountry, where you're more likely to interact with locals than with tourists. Upcountry is the least touristy area.
If you're looking for the best deals on accommodations, spring and fall are the cheapest months to visit the island because demand is down. This means the island is less crowded as well, which is another benefit of visiting during these months. Our personal preference is April - May.
What is Maui's South Side like? Maui's South Side is known for some of the island's most expensive real estate and its ultra high-end Wailea resorts. Nearby Kihei, just north of Wailea, is known for its relaxed beach town vibe and long stretch of sand. Both tourists and locals intermingle in Kihei.
South Maui is certainly one of the most popular areas for locals and tourists given the abundance of beaches, accommodations, and housing. It's close enough to Kahului to provide easy access to shopping but doesn't have the feel of a city.
Kaihalulu Red Sand Beach located on Maui is known to have rough water and is reported to be one of a handful of red sand beaches around the world. Makena Beach in Maui has the nickname of “breakneck beach” because the surf breaks right on the shore, making it very dangerous to swim in.
Kahekili HighwayOne of the most dangerous roads in Maui is also considered one of the most dangerous roads in the country. This is Kahekili Highway, also known as State Highway 340. Drivers navigate rocks to one side and steep cliffs on the other for about 20 miles between Kapalua and Wailuku.
Like anywhere, the more time you spend on Maui, the more you can see. I recommend at least one week in order to experience all that Maui has to offer. You can still get a flavor of Maui even if you just visit for one day. However, as a minimum, try to plan 3 to 5 days in Maui.
There's plenty of gorgeous water to be found at Maui's beach parks, but the clearest is in Honolua Bay, especially during the summer. Honolua is Hawaiian for “two harbors,” and the bay was originally used to receive ships and unload supplies.