Maui Itinerary: How to Plan the Ultimate 4 Day Trip

Planning a trip to Hawaii? Lucky you! Maui is one of my favorite islands in the world to visit. I’ve traveled to Maui several times for fun and for work and every travel experience is so unique. Wondering what to do on your trip? Use this Maui Itinerary to help you plan the ultimate 4, or 5-day trip.

Maui Vacation Itinerary: How to Plan the Ultimate Trip

This Travel Guide includes:

  • Things to do in Maui
  • Where to stay on the island
  • Best Places to Eat
  • Maui Itinerary for 4-5 days
Itinerary for Maui

Maui Tips: Know before you go

Any time of year is a good time to visit “The Valley Isle.”  From snorkeling and swimming to exploring Haleakala National Park, there are so many things to do in Maui.   

When in doubt, don’t go out. Talk to the lifeguards before entering the water. Keep your distance from Hawaiian Monk Seals, turtles and sea life. 

Leave your sunscreen at home, unless it’s reef safe. Hawaii is the first state to ban the sale of sunscreens with coral-harming chemicals. 

It’s a good idea to bring a light rain jacket with you. Keep in mind, Hurricane Season in Hawaii usually runs from June through November. Monitor the local forecast. 

How to pack for the Ultimate Maui Trip: 

  • Bathing suits – In my opinion, you can never have too many swimsuits. I love Vitamin A, LSPACE, and dk active. 
  • Flowy Dresses – These are some of my favorite boho brands
  • Shorts and Casual Tees – Opt for comfortable and breathable fabrics. 
  • Comfortable flats– Pack a pair of shoes you can hike in if you plan on going on some adventures. Keep in mind, some of the trails get very muddy. 
  • Hats for sun protection – I love bringing boho style hats and straw hats. 
  • A lightweight rain jacket – Be prepared! I always carry a jacket in my bag when I’m traveling on the islands. 
  • Travel Bag – I usually travel with a carryon, but I always bring a backpack or small bag for hiking and beach days.

Where to stay in Maui 

I use Airbnb and to search for the best places to stay.

Book Your Next Stay on Airbnb – Click here to search for your next dream vacation rental.

My top favorite hotels in Wailea: 

Search where to stay in Kihei or look here for deals on Hana Hotels

Things to do in Maui

how do you see sunrise at haleakala national park

1. Watching the Sunrise at Haleakala National Park

Watching the sunrise at Haleakala National Park in Maui is one of the ultimate experiences in Hawaii. Known as the “house of the sun,” Haleakala’s elevation is over 10,000 feet above sea level. With 360-degree views of the Maui and the Pacific Ocean, this dormant volcano is a must-see on your visit to Maui. 

The dormant volcano’s “crater” is actually a valley carved by erosion, and the experience of watching the sunrise or sunset from Haleakala won’t disappoint. 

Read the full guide: Sunrise at Haleakala National Park – Ultimate Guide

2. Take a drive on the road to Hana 

The Road to Hana is one of the most beautiful scenic drives on the island and a must on my list.  The drive to Hana can take anywhere from two to four hours from Kahului, but plan for an all-day adventure.  (You might be tempted to stop several times to snap a picture of a waterfall or go on a hike.)  Watch out for the narrow one-lane bridges and take time to enjoy the view.  Remember, you are on island time now!

3. Relax at Red Sand Beach

The trail to Red Sand Beach is short and can be hazardous. Once you get to the cove, you will see rugged cliffs towering over this isolated beach.  It’s an undeniable beauty.  The sand color is more of a deep maroon than red, and I couldn’t help but dig my fingers and toes into it.  My friend Kristen and I always travel with our dive masks and fins in Hawaii, and this was a great place to explore underwater.

4. Visit Hookipa

Whether you are heading out for a surf or want to take a dip in the tide pools, Hookipa is such a gem.  You will also see dozens of Honu (turtles) resting on the beach.  The Ocean Safety lifeguards are super nice and always check with them if you aren’t sure about the ocean conditions.

5. Stay in Wailea

For those looking for a little luxury, Wailea is the place to be.  From fancy resorts to fine dining Wailea doesn’t disappoint.  The Andaz Maui is a luxury resort with infinity pools that overlook West Maui and the island of Lanai. 

The Andaz offers free outdoor activities like outrigger canoe paddling and a mixology class. We saw plenty of Honu (Hawaiian sea turtles) swimming in the crystal clear ocean during our paddling experience.

Forgot your favorite sun hat? Need something new to wear on your vacation? Shop + Dine at The Shops at Wailea, a luxury shopping outdoor mall featuring over 70 shops and restaurants.

6. Snorkel at Kaanapali Beach

Located on the West side of the island, Kaanapali beach has three miles of white sand and some of the most transparent water you have ever seen.  Jump from Black Rock, and definitely, don’t leave your snorkel gear at home!  If you aren’t staying at one of the hotels, you can find free parking in the Beach Access lots.

Best Places to Eat

  1. Mama’s Fish House
  2. Tin Roof
  3. Longhi’s
  4. Merriman’s Maui
  5. Da Kitchen
  6. Monkeypod Kitchen
  7. Lineage
  8. Nutcharee’s Authentic Thai Food
Maui Itinerary: The Ultimate 4-day trip

Best Maui Itinerary: Day 1

Arrive in Maui and explore your hotel and hotel pools. Visit the beach and go for a swim.

Day 2 – Haleakala National Park

Wake up early and watch the sunrise at Haleakala National Park. After an early morning, head to Makena Beach to swim in Big Beach and Little Beach.

Day 3 – Adventure on the Road to Hana

If you’re in search of adventure and love road trips, start early on the Road to Hana and swim in Red Sand Beach. Pack a lot of snacks and on your way home stop in Paia to grab a bite to eat. If you have time, visit Hookipa. This beach is magic. You’ll see countless turtles here.

Day 4 – Lahaina

Head west to Lahaina and Kaanapali beach to snorkel and jump off Black Rock. Relax and take it easy before heading to the airport to catch your flight home.

Day 5

Soak in the views at your hotel. If you’re staying at the Andaz, take the mixology class. During my visit, the bartender was so great about explaining the differences between Tequila and Mezcal from different regions in Mexico. We tried a few varieties and 2 different margaritas made with fresh-squeezed lime juice.

Enjoy one last swim in Wailea before sunset and heading to the airport.


Whether you’re planning a honeymoon, girls trip or solo adventure, we hope this Maui itinerary answers some of your questions. Use these tips to help you plan an unforgettable 4, 5-day trip. Learn about local culture, slow down when you’re driving and embrace the “aloha” spirit.

After Maui, what island should you visit next?


Big Island:


Oahu, HI:


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5 thoughts on “Maui Itinerary: How to Plan the Ultimate 4 Day Trip”

    • I love Banana bread! Thanks for the tip. I’ve stopped at some of the fruit stands before, but I’ll look out for it when I return to Hana.

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