Maui Trip Planning: Kaanapali or Wailea?

Deciding between these two resort destinations comes down to your budget and whether you want to spot humpback whales.
Josh Garber
By Josh Garber 
Edited by Jeanette Margle
Trip Planning: Maui – Kaanapali or Wailea?

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Maui is the second-largest Hawaiian Island and a dream destination for travelers around the world. Two main tourist areas, Kaanapali and Wailea, are home to most of the hotels on the island, along with lots of vacation rental properties. If you’re planning a trip to Maui and are trying to choose where to stay, here’s how to decide which resort area is best for you.

Sunset views and islands on the horizon

Both Kaanapali and Wailea are located on Maui’s west coast, which means you get beautiful sunsets in either location. Kaanapali, which is on the northwest side of the island, is roughly a 40-minute drive from Kahului Airport, Maui’s main airport. Wailea is located on the southwest side of the island and about a 25-minute drive from Kahului Airport.

Both Wailea and Kaanapali offer stunning views of nearby islands. From Wailea, you can see the islands of Lanai and Kahoolawe in the distance, whereas Kaanapali boasts views of Lanai and Molokai. Lanai is closer to Kaanapali than it is to Wailea. The island of Kahoolawe is visible from Wailea, but it is the smallest of the eight major Hawaiian Islands, meaning it doesn’t wow from a distance the way Molokai — the fifth largest Hawaiian Island — does from the shore at Kaanapali. Given its proximity to Lanai and views of neighboring Molokai, Kaanapali wins on views.

5-star luxury vs. beachfront values

Most of the luxury hotels on Maui are located in Wailea, including the Four Seasons Resort Maui at Wailea, the Fairmont Kea Lani, the Andaz Maui at Wailea Resort, and the Grand Wailea, a Waldorf Astoria Resort. So if you want luxurious accommodations and 5-star service, Wailea has the edge.

If you’re looking to spend your vacation by the pool, consider Grand Wailea, with its 25,700-square-foot, 770,000-gallon pool area made up of nine individual pools on six different levels and connected by a river with whitewater rapids and even gentle currents. The icing on the cake is the Grand Wailea’s three-story Lava Tube water slide, where you can reach speeds of up to 22 miles per hour.

Although Wailea has a near monopoly on luxury hotels, there are some great properties in Kaanapali as well, including the Westin Maui Resort & Spa, the Sheraton Maui Resort & Spa, and the Aston Kaanapali Shores. Hotel rooms are generally cheaper in Kaanapali than Wailea. For instance, looking at dates in November, a room at the Andaz Maui at Wailea Resort would cost as much as $725 per night, whereas a room at the Westin Maui Resort & Spa would cost around $500 per night.

If you’re prepared to spend a lot of cash or points for an indulgent experience on Maui, Wailea’s selection of luxury properties gives this resort area a clear advantage. If you’re not traveling on a 5-star budget, Kaanapali is the better choice.

See humpbacks breach without leaving your resort

Humpback whales visit Hawaii from November through May, with peak season between January and March. Of all the Hawaiian Islands, Maui is known for having the densest concentration of humpback whales, which leads to some great opportunities for whale watching.

During whale season you can often see breaching humpbacks from the beach in front of your hotel. You'll generally have better luck seeing whales breach from Kaanapali than from Wailea, partly because the channel between Kaanapali, Lanai and Molokai has some of the best waters in the world for whale watching.

If you’re going during whale season and hope to see humpbacks breach, Kaanapali is your best bet.

Strolling, shopping and drinking

Kaanapali and Wailea are both right on the ocean, and both destinations have walking paths, where you can take long strolls right across from the beach with beautiful Pacific Ocean views.

The beach path in Wailea is a bit quieter because the hotels in Wailea are more spread out. The beach walking path in Kaanapali is a bit busier but makes up for the bustle by offering more shops and restaurants, including Whalers Village — a lively shopping and dining center within walking distance of many hotels in Kaanapali. Leilani's on the Beach and the Hula Grill, both in Whalers Village, offer a perfect perch to watch the sun set over the ocean while enjoying dinner and drinks.

If you’re looking for a more relaxed atmosphere, Wailea wins. But Kaanapali has the edge if you’re looking for more shopping and dining opportunities.

The bottom line

There is no wrong choice when deciding between Kaanapali and Wailea. If you’re visiting Maui during whale season and want to watch the humpbacks breach, Kaanapali wins. Otherwise, the choice largely depends on your budget and whether you’d like more choices for shopping and dining.

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