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Check Out These 3 Must-Try Day Trips From Kaanapali

West Maui welcomes you to discover its hidden gems

The Vacationeer
Incredible aerial image, mother and calf humpback whales swimming, crystal blue water, Maui, Hawaii.

Maui, the second largest of the Hawaiian Islands, is ideal for open-road adventures. There's always something new to discover, from stunning sun-kissed beaches to lush mountains.

And this guide offers three scenic road trips from Kaanapali to add to your Maui vacation itinerary. 

Why Now Is the Perfect Time For A Maui Road Trip

Gorgeous coastline, aerial image, empty open road, lush greenery, crashing waves, clear skies, Maui, Hawaii.    

There's never been a better time to explore Maui by car. Thanks to an abundance of rental cars in Maui, it's more affordable than ever to hit the road and discover the island's hidden gems. Plus, with fewer visitors on the roads (due to 2023’s wildfires), you can enjoy a more relaxed and personal experience as you explore the beauty of Kapalua, Wailuku and Wailea. 

While West Maui welcomes visitors back, many locals are still rebuilding their communities — please travel respectfully.

Road Trip 1: Kaanapali To Kapalua

The drive from Kaanapali to Kapalua is short, covering approximately nine miles. While Kapalua is known as one of Maui's premier resort areas, the short drive there offers opportunities to explore some of West Maui's sleepier spots. Once you arrive, it's a haven for outdoor enthusiasts.

Child frolicking along stunning shoreline, golden sands, crystal clear water, sunny blue skies, Kapalua, Maui, Hawaii.      

Things To Do In Kapalua

  1. Stop off around the five-mile mark at Napili-Honokowai, between Kahana and Kapalua. Here, you can soak up this serene coastal town's low-key energy and enjoy breakfast at Gazebo Restaurant, peruse the farmers’ market or check out the Honolua Bay Marine Preserve
  2. Arrive in Kapalua ready to appreciate the area's natural beauty. D.T. Fleming Beach is ideal for digging your toes in the sand, whereas a hike along  Kapalua Coastal  Trail or Lahaina Pali Trail affords active travelers unforgettable island views. 
  3. Wind down, refuel and enjoy live music at one of Kapalua's special daily events.  

Road Trip 2: Kaanapali To Wailuku

The journey from Kaanapali to Wailuku is a bit longer, but the 26-mile scenic views make it well worth the trip. With quaint wooden storefronts housing mom-and-pop businesses around Market Street, Wailuku offers natural beauty and cultural charm. 

A couple admiring verdant mountain tops, blue skies, flowing creek, Iao Valley, Maui, Hawaii.       

Things To Do In Wailuku

  1. Find out more about this town by taking the "Rediscover Wailuku" walking tour. The tour features over 20 of the town's historical and cultural attractions.
  2. Known as the gateway to the Iao Valley, it's a can't-miss for nature and history lovers alike. 
  3. The Maui Ocean Center is home to one of the world's largest displays of live Pacific corals, and the aquarium exhibits only Hawaii-native marine life. This educational excursion is great for all ages, rain or shine. 

Road Trip 3: Kaanapali To Wailea

The longest of the three-day trips, the drive from Kaanapali to Wailea, is about 31 miles. Wailea is known for its luxury resorts and beautiful beaches, but the route is also peppered with worthwhile stops, offers stunning coastal views and opportunities to discover Maui's diverse landscapes. 

Picturesque aerial image, cliff-side golf course, stunning coastline, blue skies, Wailea, Maui, Hawaii.      

Things To Do In Wailea

  1. Fuel up and make a difference in Lahaina, the historic area damaged by wildfires in 2023. Supporting local businesses is one of the most helpful things you can do. Kihei CaffeLeoda's Kitchen and Pie Shop and Mala OCEAN Tavern are all open and serving the iconic cuisine they're known for. So stop in and show your support. 
  2. Embark on an excursion of a lifetime in Maalaea Harbour. The fully-narrated two-hour whale-watching tour gets you up close with the region's famous humpback whales for an unforgettable experience. 
  3. Once in Wailea, you'll have a long list of activities to choose from, from playing a round at a championship golf course set against a picturesque backdrop to attending an authentic luau for dinner. 

Where To Stay: Hilton Vacation Club, Ka'anapali Beach

Located on Maui's western shore, Ka’anapali offers stunning ocean views, luxurious accommodations and easy access to local attractions. It's a perfect launchpad for your Maui vacation adventures.

Read "Here's How I Got 3 Hawaii Vacations in 1 Trip by Island Hopping" for ways you can maximize your Maui vacation. 


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The Vacationeer

The Vacationeer is a collective of Hilton Grand Vacations storytellers whose goal is to inspire travelers to go further. We're always on the lookout for new destinations to explore, useful travel tips, and unique ideas to help you plan the most memorable vacations possible.

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