Perfect 5 Day Itinerary for Maui, Hawaii

Perfect 5 Day Itinerary for Maui, Hawaii

March 2021

Perfect 5 Day Itinerary for Maui, Hawaii

We still dream about how perfect this trip to Maui really was! I created a rough draft itinerary during quarantine and was able to put it to use a year later. Want to spend the entire trip relaxing on the beach? What about hiking or and being active instead? Or exploring wildlife? Maybe a little bit of everything – Maui has you covered. We went with a little bit of everything so that is what you are going to find in this itinerary. Feel free to adjust based on your perfect Maui vacation.

Know before you go

  • You will most likely want a car for some or all of your time on Maui. While it is not a huge island, everything is paced on and primarily along the perimeter of the island so you will want a flexible way to get around. Unless you plan on hanging at a resort the entire trip, look into renting a car. Do this early in your trip planning process as island resources are limited – this includes rental cars.
  • Credit cards are accepted everywhere as well and tours can be booked in advance online so your need for cash is limited but always have some for tipping.
  • Plan ahead as excursions, dining reservations, and accommodations fill up quickly.
  • Island hopping is easy and very common! If you have more time off, add another island like Oahu to the trip.

Where to stay?

There are many different parts of the island you can stay in. We wanted to be central to be able to explore the entire island so we settled with Kihei which ended up working perfectly! Located right by the highway, you really can get anywhere on the island with a relatively short drive. This Airbnb was located in a small condo complex that had parking included, beach essentials, in room washer and dryer, and a pool. These amenities were so helpful to make sure when you are looking for a place to stay to look for similar offerings.

Get the Free DESKRIB Guide “How to Find the Perfect Airbnb” – sign up here

What is there to do?

  • Beaches – Probably the most obvious thing to do on a Hawaiian vacation! And there are a ton of beaches. Depending on where you are located on the island, you will have a variety of beaches to choose from.
    • Since we were staying in Kihei and also had a car, we visited Maluaka Beach and Kalepolepo Beach during our trip.
    • Many of the beaches on the west side of the island look beautiful – Napalil Bay, Black Rock Beach, Kahekili Beach Park, to name a few.
  • Haleakala National Park – A very popular stop for Maui vacations known for spectacular views of sunrise and sunset. There is also a bit of hiking that can be done at the summit. For more information, check out this blog post on visiting Haleakala National Park.
  • Hiking – Hiking on the island is amazing! I wish we had more time to conquer some of the trails. Word of advice – check the weather carefully before you embark on a long trail – it is quite different than that of the coastline!
  • Water activities – You must get in the water while in Maui! There are a ton of options from renting equipment to do it yourself to going with a tour group.
    • Rent paddle boards or kayaks
    • Snorkel with a tour group – including the famous Molokini crater
  • Whale watching – If you are lucky enough to be visiting during whale watching season, this is a must! We went at the end of February and had some incredible whale encounters.
  • Road to Hana – the number one reason to rent a car is so you have the ability to experience the Road to Hana. There is so much to say about it so I will leave additional posts below to explain it all.

What to eat?

I have to say I was so surprised by how good Maui food was and it remains some of the best food we have had in awhile. While there are many reason to return to Maui, the food certainly is one of them.

  • Tin Roof – So good we visited twice!
  • Piko Cafe – So good I wish we had more time to visit twice!
  • Leoda’s Kitchen – The most incredible selection of pies and sandwiches.
  • Ululani Shave Ice – Your daily serving of shave ice is essential and this is the best place to get it. In the Kihei location, you can also grab spam musubis.
  • Tamura Fine Liquors – For your poke bowl cravings. Yes, it is in a liquor store and yes, it is delicious.
  • Mama’s Fish House – The ultimate treat-yo-self meal (and spoiler, it was worth it!).
  • Paia Bay Coffee – We would be here all the time if we lived here! Just had the best vibes.
  • Paia Bowls – For your acai bowl pleasures. You must have an acai bowl while in Hawaii!


Putting it all together, here is an example itinerary of how to structure a five day trip to Maui. As always, feel free to use this as a guide and insert your preferences along the way.

Day 0Arrival to Maui
Day 1Haleakala National Park sunrise
Beach time
Day 2Hiking trail
Lahaina Pali Trail
Waihee Ridge Trail
Beach time or explore new part of island
Day 3Excursion on the water
Molokini crater
Whale Watching
Beach time or explore new part of island
Day 4The Road to Hana
Day 5The Road to Hana

To see our complete itinerary – here!

See all blog posts from Hawaii – here!

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