🏝 Planning a Trip to Maui in 2024: Flights, Itinerary & More

Planning a trip to Maui blog post cover.  Text overlaying an image of a silhouette of a young woman walking towards the ocean at sunset.

Planning your vacation to Maui is never as fun as the trip itself, but it doesn’t have to be stressful either!

In our years of full-time travel, one thing that Sophie and I have learned is that arranging a holiday is very much a skill. There are several important planning steps that will determine the budget, pace, and overall enjoyment of the trip.

Finding the best possible flight, choosing the right place to stay, and creating a solid itinerary are all paramount to having a successful vacation.

I have created this guide to help you plan your first trip to Maui from start to finish. I will walk you step-by-step through the process to make it as easy as possible.

Along the way, I will also provide tips, travel hacks, and insights I have learned from over a decade of travel, which includes three separate trips to Maui in the past four years.

🏝 Planning a Trip to Maui Overview

There are several secret beaches like VOR Beach shown here to consider when planning a trip to Maui.

β˜€οΈ How to Plan a Trip to Maui: Step by Step

  • Step 1: Review Hawaii travel restrictions
  • Step 2: Book your flights to and from Maui
  • Step 3: Book any inter-island flights or ferries (if applicable)
  • Step 4: Find the best place to stay for your trip and budget
  • Step 5: Craft your idea of the perfect Maui Itinerary
  • Step 6: Book tours and activities ahead
  • Step 7: Reserve your rental car (if applicable)
  • Step 8: Pack your bags!

Maui At a Glance

  • Nickname: The Valley Isle
  • Where to Stay: Kihei or Wailea
  • Recommend Number of Days: 5-7
  • When to Visit: Spring or Fall
  • Airports
    • Kahului (OGG) – Main Airport
    • Hana (HNM)
    • Kapalua (JHM)
  • Maui Best Things to Do
    • Molokini Crater
    • Beach Hopping
    • Road to Hana
    • Whale Watching
    • Haleakala NP
    • Sunset Luau
    • Island Hopping to Lanai & Molokai

Best Hawaiian Island for:
Travelers who want a little bit of everything, such as romance and luxury, but also family-friendly options, as well as fantastic nature, hiking, incredible famous and secret beaches, and so much more.

✈️ Step 1: Review Hawaii Travel Restrictions

Turquoise waters and white sand beach surrounded by black lava rock as sen by airplane when traveling to Hawaii

Domestic Travel to Hawaii

There are no current domestic restrictions for domestic flights to Hawaii. Additionally, the REAL ID enforcement date has been pushed back to May 7, 2025.

International Travel to Hawaii

For those traveling from international destinations with direct flights to Hawaii, you will only need to follow federal requirements for international visitors to the USA. There are no additional State of Hawaiβ€˜i requirements.

You will need to ensure you either have a valid ESTA or visa for entry.

πŸ›« Step 2: Book Flights To / From Maui

Planning a trip to Maui begins with booking flights.  This photo shows an airplane departing from Maui during sunset.

The most important rule of planning a trip to Hawaii is this: always book direct flights, if possible.

All too often, your first flight is delayed, causing you to miss a connecting flight and thus being stuck somewhere between home and Maui. Or worse, the connecting flight is canceled altogether!

Flexibility is the next priority and is the trick to finding the best flights to Maui. The fewer restrictions you have on the date of arrival and departure, the easier it is to find affordable direct flights.

Skyscanner flight search for flights to and from Hawaii
This SkyScanner screenshot shows how to use the flexible search option to find the cheapest possible flights.

Bearing all this in mind, the best tool available for booking airfare is SkyScanner. This allows flexible searches, which makes it easy to find the best, cheapest dates to fly. You can search for the cheapest flights from home to Maui by date, month, or even year!

Once you have your flights to and from Maui booked, you should look to book inter-island travel if you plan on doing any island hopping.

πŸ›¬ Step 3: Arrange Inter-Island Flights

If Maui is the only Hawaiian Island you will be visiting on your vacation, you can skip this section.

However, it is worth noting that the sister islands of Lanai and Molokai can be included as a day trip in most Maui itineraries, even if you do not intend on staying overnight!

Molokai, also known as “The Friendly Isle” and more grimly as “The Leper Colony”, is a beautiful sister island that can be seen in the distance from many places on Maui. The only way to get to Molokai from Maui is with a 20-minute scenic flight serviced by Mokulele Airlines.

Lanai is the other island visible off Maui’s west coast. This is the only Hawaiian island you can get to by ferry, which is the method I recommend. If you prefer a scenic flight, they are available through Mokulele Airlines.

If you plan on doing any island hopping during your visit, booking your flights or ferries should be the first thing you do after arranging transport to and from Maui.


🏨 Step 4: Book Accommodation in Maui

We Dream of Travel custom-made map showing the six regions of Maui.

Deciding where to stay is one of the most important parts of planning a trip to Maui! Accordingly, you may want to spend a little extra time getting to know the regions and best areas to stay in prior to booking.

For those readers who just want the short version, I recommend Kihei. It has the widest range of options, is near 15 beaches, and has reliably sunny weather.

Here are a few useful things to know that will help you decide which is the best area for you, personally:

  1. Maui is very small. The entire drive from the two most distant towns (Kapalua Bay to Hana) is only a 2 hour 45 minute (81 miles) drive.
  2. The least rain and most sunshine is in South Maui. For this reason, and the incredible beaches nearby, Kihei and Wailea are the most popular areas to stay.
  3. Ka’anapali in West Maui is the next most popular area to stay. It has more beachfront hotel rooms and upscale resorts than anywhere else on the island.
  4. East Maui is the rainy side of the island, and the North Shore is the windy side. Accommodation is typically cheaper here, but less desirable.
  5. For 5+ day visits, consider splitting your time between two regions to experience more of Maui and reduce drive times in your Maui itinerary.


Where to Stay on Maui

At no cost to you, we receive a small amount for any bookings made using the links below.

Most of the hotels in Maui are in West Maui and South Maui.

Ka’anapali in West Maui is the best for those who do not want to leave their resorts and have everything they need for a Hawaiian vacation in one place.

For everyone else, especially those looking to explore at least a little bit, Kihei in South Maui should be where you look for accommodation. It is centrally located with beautiful beaches and the bustling town of Kihei offers a wealth of spectacular beach resorts.

For those who want to drive the Road to Hana and/or get off the beaten path, Hana is a lovely town on the rainy side of Maui that most visitors will only ever see as a stopover town.

🌴 Step 5: Plan your Maui Itinerary

The most important thing you can do to ensure an amazing vacation in Maui is to spend a little time creating your ideal itinerary.

Crafting your itinerary involves more research and thoughtfulness than I can pack into this section. Instead, I have written two comprehensive guides on planning the perfect Maui itinerary which you can find here:

Only you know what the perfect Maui vacation looks like for you. If you are active and as into sightseeing as we are, I promise these guides will be helpful.

Of course, some of you just want to lay on a beach and enjoy the sun! In that case, you don’t need an itinerary at all – just a cocktail!

⛡️ Step 6: Arrange Tours & Activities

Once you have booked your flights and crafted your ideal itinerary, you will want to begin booking whichever tours and activities you are interested in.

Be forewarned that the most popular activities on Maui tend to sell out weeks or even months in advance!

We badly wanted to do the Molokini Crater on our first trip to Maui but made the mistake of waiting until we got there and were unable to go as a result.

If there are certain tours or activities you are intent on including, such as the Molokini Crater snorkel adventure, you will want to book it as soon as you can.

Additionally, some popular beaches and activities require permits even if you do not need to visit by tour! The most important to reserve ahead of time are Haleakala sunrise visits and Waianapanapa State Park permits (home to the famous Maui Black Sand Beach).

Some of my favorite Maui tours, destinations, and activities are listed below with links to tours:

πŸš— Step 7: Reserve Your Rental Car

A drone photo by Adam Marland showing Hwy 30 running parallel to the immaculate coral gardens of Olowalu Reef on Maui.
Maui is easily drivable, making rental cars the best option for getting around when planning a trip to Maui.

Renting a car is by far the best way to get around Maui. This provides the ultimate freedom to explore and is surprisingly affordable.

Also, Maui is perhaps the easiest Hawaiian island to drive around, as nearly no roads require 4WD.

You can compare car rentals here.

On one of our visits to Maui, we opted to travel and stay in a campervan. This was a great way to maximize our time and see as much of the island as possible. Of course, this option is not for anyone prioritizing comfort!

If you are not comfortable driving on Maui, your options will be limited to tours, rideshare apps (Uber / Lyft), and public transportation. Be warned that public transportation is available but is extremely limited.

🧳 Step 8: Pack Your Bags

Printable Hawaii Packing List custom made by We Dream of Travel.

You’ve done it! The flights are booked, the schedule is made, and you are ready for a once-in-a-lifetime trip to Maui! All that’s left is to pack your bags!

If you do not get to travel often, or even if you do, having a printable checklist that includes all the essentials can help relieve the stress and nagging feeling of what you may have forgotten.

Beyond that, there are going to be some things beyond the basics that you’ll want to pack that you maybe didn’t even know existed. These are items like reef-safe sunscreen, sand-repellent towels, and reusable grocery bags, as Hawaii has banned plastic bags.


🌺 Top 10 Maui Travel Tips

  1. First, find affordable accommodation, then book flights, then book tours, in that order. These will be your biggest costs, and each item determines the optimal dates for the next.
  2. Bring your own snorkel and mask. Daily rentals often cost more than buying new equipment!
  3. Pack beach shoes! Lava rock, as well as thorns from kiawe trees, are common on Maui beaches and painful.
  4. Get your permit or book a tour way in advance and bring warm layers for the two most popular tours: Haleakala sunrise and Molokini Crater.
  5. Buy an underwater camera. You are guaranteed to swim with a few turtles if you know the right secret beaches on Maui to find them!
  6. Beat the crowds on the famous Road to Hana scenic drive by staying overnight in Hana.
  7. Bring only reef-safe sunscreen. All other sunscreens are illegal in Hawaii.
  8. Take advantage of the close proximity of Maui to the lesser-traveled sister islands of Lanai and Molokai by arranging some day trips. Flights and ferries are very affordable.
  9. Wailea in South Maui has the most reliably sunny weather on the island.
  10. Do not miss the secret Red Sand Beach; one of the few of its kind in the world!

πŸ€™πŸΎ Hawaiian Words, Customs & Culture to Observe

A Maui travel tip is to learn Hawaiian customs such as the Hawaiian shaka greeting seen here.

There are a few customs that are helpful to understand.

Too many tourists forget that while this is a vacation destination for them, it is home to the locals. As such, it is important to treat people on the island as if you are guests in their home.

Beyond typical manners, here are a few Hawaiian customs to know:

  • Tipping: Locals survive on tourism! In the US, 18-20% has become standard, 15% minimum.
  • Aloha: This word means a lot in Hawaiian, including both “hello” and “goodbye”, but also “love” and “peace”.
  • Mahalo: The Hawaiian word for “thank you”.
  • Island Time: The Hawaiian culture is a “lei-d” back culture (pun alert!) Expect a slower pace and less concern with punctuality on Hawaii than on the mainland.
  • Attire: Outside of a few luxury clubs or restaurants, casual attire is the expectation. Flip-flops (known as slippers in Hawaii) can be worn to any restaurant or outing.
  • Shaka: The “shaka” is the hand signal using the thumb and pinky with a side to side motion that is often translated to “hang loose” on the mainland. In actuality, it is closer to “aloha” and/or “mahalo” in Hawaii. It can be hello, goodbye, thank you, or anything really with positive intention. Think of it a bit like a polite wave or a thumbs up.

πŸ“† When to Visit Maui

Sunset is the best time to be out, but any time of year is a good time to plan a trip to Maui.

There is no bad time to visit Maui or any of the Hawaiian islands. However, certain months offer certain advantages or disadvantages, such as a higher likelihood of rain and clouds or less availability due to crowds.

The rainy season in Maui is from November to March. The West Maui Mountains and Haleakala create their own weather systems, so the best place to stay during these months will be in South Maui near Wailea.

However, the winter months also bring migrating humpback whales which are truly incredible to witness off the shores of Maui.

The best months to visit Maui are April, early May, September, and early-October. This is during the dry season but avoids peak tourist season.

🌴 More Maui Travel Guides

The two of us work very hard to create these free travel guides to help you plan your dream vacation. If you think we’ve done a good job and would like to say thanks, please consider clicking the donate button below πŸ™‚

If you found this guide useful in planning your visit to Maui, you will want to browse some of our other guides to the island as well:

πŸŒ„ More Hawaii Travel Guides

The two of us work very hard to create these free travel guides to help you plan your dream vacation. If you think we’ve done a good job and would like to say thanks, please consider clicking the donate button below πŸ™‚

πŸ“ Enjoyed this guide to planning a trip to Maui? Pin it! πŸ™‚

Photo of author
Written by
Adam Marland is a professional travel blogger and landscape photographer from Oregon. After over a decade of experience as a freelance travel photographer, Adam found national acclaim when he became the National Park Foundation's β€œChief Exploration Officer” in 2021.

Leave a Comment