5-Day Maui Itinerary

Aloha from Hawaii! I was getting sick of being in cold climates for my adventures and wanted to have an adventure filled with sun and sand. Don’t get me wrong, I enjoyed my 3-day trip in Yellowstone and 7-days in Ireland, but I wanted to switch it up a bit!

girl hiking in maui hawaii

If you are looking for somewhere to get some quality hiking, road tripping, swimming, and add some snorkeling, beaches, and surfing then Hawaii might be your next stop! Hawaii is a very diverse place with a lot to offer for every type of traveler. 

First of all, you’ll want to choose which island to go to. Hawaii is made up of 137 islands, but only 8 main islands. Going from west to east, these islands are Niihau, Kauai, Oahu, Molokai, Lanai, Kahoolawe, Maui, and the Big Island of Hawaii. 

Each island has its own unique offerings as far as landscape, culture, and lifestyle and are all awesome to visit depending on what you’re looking to do. I chose to explore Maui and have put together a 5-day Maui itinerary so that you can plan an epic trip without missing any of the must-sees! And for those of you who want to look cute while you travel, check out my other post on cute boho outfit ideas!

When to go to Maui

The good news is, there really isn’t a bad time to visit Maui. Maui has 250+ days of sunshine and warm weather. The rainy season is technically November through March, but the rain spurts are short and usually followed by sunny blue skies. 

In the spring or the fall, you might avoid some of the tourist crowds, as it tends to be a little quieter during these months. You might also be able to grab some deals on accommodation and perhaps enjoy some less busy beaches.

If you are interested in seeing humpback whales, the best time for this would be January to March as this is when they make their trek from Alaska to Hawaii to birth their young in the warm waters.

Day 1: Wailea Beach, Hawaii

Wailea Beach hawaii

Wailea Beach

Getting to Hawaii usually takes at least one long travel day and depending on where you are coming from you might experience some jet lag with the time change. For this reason, I recommend day one of your Maui itinerary to be an easy day filled with beaches, lounging, and maybe a few cocktails for sunset. 

Wailea is the perfect beach to visit on your first day. Wailea Beach is in South Maui and is a long stretch of beautiful beach with gorgeous turquoise water. We brought a cooler and made a day of it relaxing and watching the surfers. The water is crystal clear and the surf is mellow, making it a great beach for swimming and snorkeling and possibly seeing some sea turtles!

Wailea is divided into two beaches, Big Beach and Little Beach, for a 1.5 mile stretch of beach in total. After a day lounging in the sun, we headed to Wailea shops and wandered in and out of the stores buying our souvenirs early. There are lots of amazing restaurants to grab dinner. We opted for Humu Humu for some Hawaiian cuisine on our first day.

Day 2: Haleakala National Park, Kipahulu

Haleakala National Park, Kipahulu
Haleakala National Park, Kipahulu

Since day two jet lag is still prevalent, the best thing to do is to use it to your advantage. Sunrise at the top of Haleakala Volcano is a once in a lifetime experience. The summit sits at 10,000 feet and it’s a winding 38 miles on Crater Road to get to the top. If you do plan on making it for sunrise, give yourself plenty of time to get up there. 

On your way out of Haleakala National Park, you can drive through Central Maui and check out Lahaina in West Maui. Lahaina has a long history in Hawaii as it used to be the royal capital of Maui. 

The action in Lahaina is on Front Street which dates back to the 1800s. Be sure to check out the Old Lahaina Luau for some classic Hawaiian cuisine, dancing, and to experience a Hawaiian luau!

Day 3: Road to Hana

In your Maui explorations, driving on the road to Hana highway is a must. The road to Hana is 64 miles filled with amazing views, hairpin turns, and gorgeous stops along the way. It’s one of the most picturesque places I’ve ever been to so make sure you check out my previous post on how to take aesthetic photos so you can get some Instagram-worthy photos! I would highly recommend stopping at the gorgeous bamboo forest as it is incredible and a sight you won’t want to miss! I would allow a full day for this drive as you don’t want to be rushed. 

bamboo forest in maui
Bamboo Forest, Hana

On this drive, you will drive the road along the whole Northeast side of the island and get a great feel for the rugged coast. We stopped for lunch at Ka Haku Smoke Shack for some delicious barbeque and local cuisine. 

Pro-tip #1: fill your gas tank before passing Paia. 

Pro-tip #2: don’t leave any valuables in your car, rental cars are targeted for break-ins.

Day 4: Kaanapali, Kapalua, and Honolua Bay

Next up on the Maui itinerary is a snorkeling day! Kaanapali beach is a beautiful 3-mile stretch of white sand and the most crystal clear blue water that is home to lots of underwater life. The ocean here is usually calm and there is an abundance of fish and coral that can easily be seen from the surface. 

Just 10 minutes north is Kapalua beach, which is one of the most beautiful beaches in Maui. It is pretty touristy, but it’s worth popping out of the car and checking it out. Kapalua resort is located right there so if you’re hungry you can always grab lunch there, but it is a little on the pricey side. 

Honolua Bay is a couple more minutes north and has some great snorkeling from the beach. You can even sign up for a snorkeling tour if you want some guidance on where to go! It is a little further out than Kaanapali, but if you’re a confident swimmer it’s nothing you can’t handle.

Day 5: Molokini

The last day was my favorite day of the trip. We took a boat ride out to see the Molokini crater with Auntie Snorkel to check out this crescent-shaped volcanic crater. Molokini is about 3 miles southwest of Maui and the entire trip was about 5-hours round trip. 

This is some of the best snorkeling in Maui; the walls of the crater are just teeming with life. Despite being 3 miles from shore it’s a very safe place to snorkel as the shape of the crater protects the snorkeling side. I highly recommend fitting this into your itinerary. 

Five days in Maui honestly isn’t long enough, but you’ve got to work with what you’re given! This Maui itinerary will give you a good jump start to see the highlights, but it’s a great place to explore and go with the flow. Aloha and enjoy!

Also, as always, don’t forget your sunscreen!

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