Planning a Trip to Maui: Travel Tips, Itineraries, Hotels & 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.

There are several important considerations when planning a trip to Maui for the first time that will determine the budget, pace, and success of your visit.

Most notably, finding the best possible flights, choosing the right place to stay, and creating an itinerary that is right for you will be paramount.

This guide will walk you step by step through the planning phases for your first visit to Maui.

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Planning a Trip to Maui Overview

Below is a quick summary overview detailing the most important consideration when and things to know when planning a trip to Maui.

Maui Overview

  • 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)

Best Hawaiian Island for people 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.

Hawaiian Words, Customs & Culture to Observe

There are a few customs that are helpful to understand. All too many tourists forget that while this is a vacation destination to 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.

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

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

  • 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.

Top 10 Maui Travel Tips

  1. First book flights, then accommodation, then tours, in that order. These will be your biggest costs and each item determines the date range 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!

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-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.

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
  • Step 4: Find the best place to stay for your trip and budget
  • Step 5: Create your perfect Maui Itinerary
  • Step 6: Book tours and activities early
  • Step 7: Establish how to get around (car rental, tours, etc)
  • Step 8: Pack your bags!

Traveling to Hawaii in 2022

Turquoise waters and white sand beach surrounded by black lava rock as sen by airplane when traveling to Hawaii
The Big Island adventure begins before you even land!

Hawai‘i is welcoming most travelers again. However, there are some pre-travel requirements for international travelers visiting Hawai‘i.

Domestic Travel to Hawaii

As of March 26, 2022, there are no COVID-related requirements for domestic passengers arriving in Hawai‘i.

You can find current information, advice, and guidelines related to COVID and travel in Hawaii on the Hawaii Covid-19 website here.

International Travel to Hawaii

For those traveling from international destinations with direct flights to Hawaii, you will need to follow federal international requirements. There are no additional State of Hawai‘i requirements.

As of June 12, 2022, international visitors are no longer required to show a negative COVID-19 viral test or documentation of recovery from COVID-19 before they board their flight.  However, the CDC is still requiring proof of vaccination for international visitors to travel to the United States. Requirements are constantly changing so ensure you check the CDC website or within your airline for current guidelines.

Planning a Trip to Maui: Booking Flights

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

The most important rule of planning a trip to Hawaii is this: always book non-stop flights for arrival, if possible.

Obviously, not every airport provides direct flights to Maui. That said, finding one is important if available as it substantially reduces the risk of having your Hawaiian vacation derailed. 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!

Return flights are typically less catastrophic when something goes wrong as it will not derail an entire week’s worth of reservations and bookings. Of course, it is still worth weighing the risk of being delayed on your return to determine whether or not to prioritize a non-stop flight home as well.

The next priority and the trick to finding the best flights to Maui is flexibility. The less 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 by 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.

Planning a Trip to Maui: Island Hopping

If Maui is the only Hawaiian Island you will be visiting, you can skip this section. However, it is worth noting that the small and lesser-visited 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 from much of Maui. The only way to get to and from Molokai from Maui is with a 20-minute scenic flight serviced by Mokulele Airlines.

Lanai is the other sister island visible off the west coast of Maui from pretty much anywhere on the island. This is the only island you can get to by ferry as of 2022. Like Molokai, you can also visit Lanai via a small plane flight from the airport through Mokulele.

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.

READ THE COMPLETE GUIDE TO
HAWAII ISLAND HOPPING

Planning a Trip to Maui: Where to Stay

Map of Maui showing the 6 districts in different colors

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 prior to booking.

Learn everything you need to know in the complete guide on
WHERE TO STAY ON MAUI: BEST AREAS, HOTELS, AND RESORTS

For those readers that just want the short version, here are a few useful things to know that will help you decide which is the best area for you.

  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. Lahaina and Kaanapali in West Maui are the next most popular areas and two of the best towns in Maui. They also boast amazing beaches and resorts, but see a few more cloudy days each year.
  4. East Maui is the rainy side of the island and the North Shore is the windy side.
  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.

Planning a trip to Maui for your honeymoon? Consult our
COMPLETE GUIDE TO THE BEST MAUI HONEYMOON HOTELS

The majority of the hotels in Maui can be found 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.

Planning 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.

Only you know your ideal pace and the types of tours and activities that appeal to you. Eight hours by a pool would be boring for some, but relaxing for others.

Crafting your itinerary involves more research and thoughtfulness than we can pack into this guide. For help with the most critical details of planning a trip to Maui such as finding out the best places to stay and the best things to do, consult the complete guide below:

THE COMPLETE GUIDE TO CREATING
THE PERFECT MAUI ITINERARY

Planning a Trip to Maui: Tours & Activities

Once you have your flights booked and have created your ideal itinerary, you will want to begin booking the tours and activities that require them.

Be forewarned that the most popular activities tend to sell out weeks or even months in advance! This means that if there are certain tours or activities you are intent on including, such as Maui’s best luau or a Molokini Crater snorkel adventure, you will want to book it immediately.

Additionally, some popular beaches and areas require permits! The most important to get a jump on if you wish to visit are Haleakala sunrise visits and Waianapanapa State Park, home to the famous Maui Black Sand Beach.

While you are once again encouraged to consult our 5-7 Day Maui Itinerary for specific recommendations, the tours, destinations, and activities below are the most popular things to do in Maui and should be booked as soon as possible to avoid disappointment.

Planning a Trip to Maui: How to Get Around

Maui is easily drivable, making rental cars the best option for getting around when planning a trip to 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 guarantees you the ultimate freedom to explore and is surprisingly affordable. Also, Maui is perhaps the easiest Hawaiian island to explore by car as there are nearly no roads that require 4WD. You can compare car rentals here.

As you will need transport and accommodation anyway, the more adventurous readers may want to consider renting a campervan. While we typically recommend this option to anyone who is planning a trip to Maui for exploration over relaxation, this may not be the island to attempt it as laws and enforcement have become very strict regarding overnight camping.

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 the public transportation option is available but will require careful scheduling; this is not recommended with such precious little time for your vacation!

Packing for a Trip to Maui

Printable Hawaii Packing List for planning a trip to Maui.

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.

For a PRINTABLE CHECKLIST and COMPLETE guide to packing for Maui, consult our
ULTIMATE HAWAII PACKING LIST

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