There is a wet and a dry side to the Island. The south side of Maui, including the areas of Kihei, Wailea and Makena, is typically warm and dry, receiving less then 10 inches of rain per year. The west side, including Lahaina, Ka'anapali and Kapalua, receives more rain—nearly triple the amount.
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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.
Both South Maui and West Maui are located on the leeward side of the island, where you'll experience more sun, typically calmer water, and you'll have a number of beautiful beaches to visit.
The south side of Maui, including the areas of Kihei, Wailea and Makena, is typically warm and dry, receiving less then 10 inches of rain per year. The west side, including Lahaina, Ka'anapali and Kapalua, receives more rain—nearly triple the amount.
Both areas have their own unique charm and attractions. West Maui is known for its historical landmarks, cultural entertainment and surf, while South Maui offers a more transient casual vibe, both with luxury resorts and pristine beaches. Each area also has its own distinct weather patterns and natural scenery.
The best times to visit Maui are April through May and September through November. The spring and fall shoulder seasons provide the pleasant weather Hawaii vacationers seek without the high rates and heavy crowds that accompany the summer and winter.
Wailea: For high-end lodgings, look no further than Wailea. This area includes several incredible beachfront resorts, condo complexes, a lovely outdoor mall, and several quality restaurants. Our favorite luxury resorts include the Four Seasons Maui, Hotel Wailea, the Wailea Beach Marriott, and the Grand Wailea.
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.
Pineapple Hill and Plantation Estates are the most exclusive locations for those who want the privilege of expansive land. The Plantation Estates surround the famous Plantation Golf Course and offer spectacular views of the course, the ocean, and the islands of Molokai and Lana.
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.
It doesn't matter as in the case of NORMAL winds, you approach from the east (left side) circle over the west coast and then land to the east (usually bumpy!). Airport on the left side. If there is a Kona Wind not common, but it happens, reverse the order.
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.
Second only to the south shore, west Maui has many of the best beaches for swimming, snorkeling, and just about anything else you could want. And the crown jewel among them has to be the three-mile stretch of white shore and shimmering blue water at Ka'anapali Beach.