Maui 5 Day Itinerary
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The Ultimate Maui 5 Day Itinerary: Sun, Fun & Scenic Sights

Swaying palm trees, golden beaches, shimmering ocean waters: this is the island paradise of Maui. Its charms attract vacationers the world over. The natural playground is a veritable oasis of activity. There’s so much to take in, it can be hard to decide what to see, where to go and how to squeeze in that all important relaxation time. Follow my guide to spending one week in Maui. With this Maui 5 day itinerary, you’ll be able to make the most of your island getaway.

Maui 5 Day Itinerary
Enjoy Kaanapali Beach, one of the best beaches in the world

Day 1: Arrive & Drive to Kaanapali

There are four main places to stay in Maui: Kaanapali, Kapalua, Lahaina, and Wailea. Each has its own lures, but for endless beaches on a budget, you can’t beat Kaanapali. Choose a hotel in that area, and you can easily access the other island hotspots as well as attractions.

On your first day, you’ll be excited but also probably tired. Dive in, but be sure to get some rest so you’re ready for a fun-filled vacation. That said, on your first day go straight to your resort. Royal Lahaina Resort and The Westin Maui are excellent options. After checking in, go to your room, change into swimwear and hit the beach. I always feel like I’ve actually arrived after my toes are in that golden sand.

If there’s time, head to Lahaina that night. This quaint historic village has shops, art galleries and lots of restaurants. Have dinner at Lahaina Pizza Company. They have the best deep dish pizza and Kona Brew Co. beers to wash it all down with. If you have room afterward, stop by one of the two Ululani locations for a Hawaiian shave ice treat.

Maui 5 Day Itinerary
Swimming with sea turtles on the snorkel cruise

Day 2: Snorkel Cruise to Molokini

You can’t spend a week in Maui without visiting Molokini, a small underwater volcano that is a haven for marine life. Pacific Whale Foundation offers a Molokini & Turtle Arches Cruise I highly recommend. You’ll need to wake up early, as the cruise departs at 7 AM, but it’s worth it.

You’ll sail to Molokini while enjoying a complimentary breakfast, all while taking in the ocean sights and snapping plenty of pictures. You’ll snorkel at Molokini Marine Preserve first, where coral formations and bright tropical fish are easily seen. Bring an underwater camera to capture it all. You can rent one from Pacific Whale Foundation if you don’t own one. The double the fun excursion doesn’t end there, though. The best is yet to come.

The aptly named Turtle Arches has beautiful underwater lava arches and a large population of green sea turtles. If you’ve seen the movie “Finding Nemo,” you’ll no doubt be calling everyone you see ‘Crush.’ This underwater experience is honestly one of my most treasured Maui memories. On the cruise back, a light lunch is served to rev your energy back up.

Maui 5 Day Itinerary
Views along the Road to Hana

Day 3: The Road to Hana

To truly see some of Maui’s most remarkable sights, you have to drive the Road to Hana. In fact, any Maui 5 day itinerary that doesn’t include the Road to Hana isn’t one you should follow!

Start out early in the morning and be sure to pack a lunch. As you drive through Paia, you can stop by Charley’s for a hearty start to your day. It will keep you fueled as you drive the 60+ miles to Hana.

Along the way, there are too many sights for you to see them all. Plan ahead and pick out some must-see’s and must-do’s or else you’re sure to run out of time. I recommend Twin Falls, Painted Trees, Wailua Falls and Overlook, Wakani Falls, Waianapanapa State Park, and Hamoa Beach.

Oheo Gulch Falls, at Haleakala National Park, is one of the most stunning sights on the Road to Hana. At this park, there are also sea cliffs and hikes to waterfalls like the Waimoku Falls via the Pipiwai Trail. Keep in mind, driving the Hana road at night makes for a slow-go so try to head back before dark.

Maui 5 Day Itinerary
Taking in the scenery at Haleakala

Day 4: Visit the Haleakala Volcano

Another site that should be included on any Maui 5 day itinerary is Haleakala. Luckily, there are several ways to see Haleakala. Plan to hike within the national park, bike down the mountain, or ride horseback through the terrain. The most popular activity is a sunrise bike tour, which features sunrise views from the summit, then a 23 mile downhill bike tour from the base of the National Park.

Zig-zagging down the mountain at this time of day provides an ever-changing landscape. The sky and the earth meet in a wash of colors and clouds. Of course, Haleakala is worth seeing any time of day no matter which way you do it.

Maui 5 Day Itinerary
Big Beach, Maui

Day 5: Hit the Beach

On the last day of our Maui 5 day itinerary, we suggest you take it easy. After all, a vacation isn’t a vacation without some rest and relaxation. Head north for Kapalua Beach and DT Fleming Beach Park, both of which have been recognized as America’s best beaches.

Southwards are the beaches of Maalea Beach and Makena Beach. Each stretch of sand has its own appeal. See as many Maui beaches as you want, or simply soak up the sun and surf at Kaanapali Beach, which is right outside your chosen resort. For dinner, I like Duke’s Beach House, which has oceanfront views and a tropical vibe, and Roy’s, a fusion Hawaiian restaurant that’s fine dining at its best.

Five Days of Fun Await You

With this Maui 5 day itinerary, you can experience the highlights of Maui while still squeezing in some chill time. And that’s just how a vacation should be.


Ashley is Reserve Direct’s travel expert, visiting Hawaii to find the best travel tips, money-saving deals and insider information. With over 10 years of experience in first-hand-travel adventures, she shares her stories, advice, and current events to help you stay in the know.
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