Maui Trip Planning For Happy Travelers (2023): Step-by-Step Guide

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Congratulations on picking which Hawaiian Island to visit. With whale watching, the Road to Hana, phenomenal beaches, and so much more, Maui trip planning can be stressful. Here are the essential details on how to plan a trip to Maui.

We called Maui home for numerous years and now our family returns every few months. Here are the steps we take, plus extra details, to plan your trip to Maui. Whether this is your first trip or your 50th, we have you covered.

Planning a Quick Trip?
We have you covered. Jump into Maui trip planning with quick links to all of our best Maui information:
Our full Maui Travel Guide
Maui Done-for-You Itineraries
A curated list of our favorite tours & activities
Your guide to Maui Whale Watching

Maui Trip Planning: What You Need to Know Before You Book

With this step-by-step guide, we will have you confidently finish your Maui trip planning. With ways to save, videos, and insider tips, we have your back for the best trip ever to the Valley Isle.

If you’re a visual learner, see our Maui Travel Guide video below. At a minimum, the video will get you excited about planning your trip to Maui.

1. Best Month to Visit Maui

The best month to visit Maui is September for the best prices on hotels, rental cars, and flights. You will also find the fewest visitors on the island and excellent weather in September.

The best times to visit Maui are the shoulder seasons of September and October and May and April. With schools in session and decent weather on the mainland, demand goes down for a Maui vacation so hotels and rental car companies drop their rates. If you don’t have the ability to visit during the shoulder season, here are ways to have a Maui vacation for less.

We go back and forth on the worst time to visit Maui. You be the judge if a holiday vacation is worth it for your family: How to Plan a Hawaii Christmas Vacation. 

Many Maui trip planners want to visit Maui for whale season. Officially, whale season on Maui is from mid-December till the end of March. See our Maui Whale Guide for details.

For more details on the best month to visit Maui, see our Is There a Best Time to Visit Maui? Yes, and Here’s Why.

2. Cheapest Time of Year to Visit Maui

Maui is by no means a cheap vacation. But there are times when costs are high and other times when your dollar can stretch a bit further. 

The cheapest time to visit Maui is May, September, October, and November. Those months offer the lowest rates on accommodations. 

September has historically been the cheapest time of year to visit Maui due to low hotel rates.

Maui is the most expensive Hawaiian Island to visit (here is the cheapest Hawaiian Island). Maui is ranked third in the world as the most expensive sun and sea destination. 

You can save money when planning a trip to Maui by finding a good deal on a hotel. Here are ways to save on hotels in Hawaii!

When are the cheapest flights to Maui? Based on the data, this is the cheapest time to fly to Maui.

3. How Many Days Do You Need on Maui

We recommend staying for a minimum of 5 days on Maui. The average trip to Maui is 8.1 days per the Hawaii Tourism Authority.

Do you want to go-go-go each day and do every activity on Maui? Do you need some days to sit on the beach and do nothing? Or are you purely coming to relax with your feet in the sand and sip a tropical drink?

Once you know the pace you’re going for, you can start building your list of activities to decide how many days you’ll want to stay on Maui.

Our Maui Wayfinder Itinerary includes 8 excursion days that take you all over the island, from Lahaina Town in West Maui to Upcountry Maui. To be honest, it would be exhausting to do all eight days on your trip (pick your favorites!). Hence, figure out what you want to do in the Things to Do Section to better gauge how much time you need on Maui.

4. How Far in Advance to Book a Trip to Maui

We recommend booking six months in advance for a trip to Maui. When traveling during Maui’s busy seasons of Christmas and summer, book nine months in advance. 

A caveat, if you’re reading this two months before your trip then don’t sweat it. Our advice here will help you with your Maui trip planning.

We recommend booking six months in advance to secure the best prices for rental cars and hotels. Plus, you will be able to pick your preferred hotel room for the dates you want. 

Things do sell out on Maui so book ahead for peace of mind. As we share in our newsletter often, Book Early is our motto at The Hawaii Vacation Guide. As visitor demand increases to Maui, you will find prices will skyrocket. 

For a nice restaurant, like Mama’s Fish House, then book six months in advance for a table and your preferred date. 

Want something that doesn’t require a booking far in advance? Book a Hawaii lei greeting at the airport. A lei greeting is a fun way to start your vacation!

Our favorite Maui snorkel tours and guided tours don’t sell out until weeks in advance (depending on the time of the year), but you want to ensure your whole family can go on the date you prefer.

Final booking tip: By booking early in your Maui trip planning, you can check to see if prices have changed. Lock in a price and then check to see if the price of the discount rental car or hotel has dropped. Then you can cancel and rebook.

5. Where Should You Stay on Maui?

While there are five main areas on Maui, most visitors stay on either West Maui or South Maui to maximize their odds of sunshine, warm weather, and lack of rain. 

Whether you should stay in West Maui (Ka’anapali, Lahaina, Napili, Kapalua) or South Maui (Kihei, Wailea, Makena) is often a heated debate. We try to help you make the right decision for you with these two articles:

• Where to Stay on Maui: your accommodation guide
• Ka’anapali vs. Wailea: pick your perfect spot

Watch our Where to Stay on Maui video (or our 6 Best Maui Luxury Resorts video) for an overview of the places to stay on Maui for your Maui trip planning.

6. Should you stay in a hotel or vacation rental on Maui?

Go for a hotel if you’re looking for the traditional resort experience with big pools, nearby beaches, and restaurants within walking distance. Opt for a vacation rental if you want access to a kitchen, are looking for space, or are looking to save money. 

We routinely stay in both. When doing our Maui trip planning, we’ll book a vacation rental for the majority of our stay so we have access to a kitchen and a little more space for the kids. Then we’ll treat ourselves to a great resort for a few days to enjoy the pool and other amenities. This has been a winning combo for us recently. 

If you’re still not sure what you want to do, we break down the difference between choosing a hotel and a vacation rental in Hawaii. 

7. Do You Need a Rental Car on Maui?

We get this question asked a lot. Oahu is the best Hawaiian Island for not having a rental car. We believe you need a rental car in Maui to do the best things to do, especially things to do with kids on Maui. 

A rental car will be more cost-efficient than using Uber, Lyft, or taxis to navigate Maui. We recommend using Discount Hawaii Car Rental as they have the lowest prices and no pre-payment (tip: book early and watch prices) or a local Maui rental car company.

You can get by without a rental car on Maui by staying in the resort areas of Wailea and Kaanapali. Enjoy a more casual beach vacation with Uber or taxi rides to restaurants or beaches in the area. Here are 11 Tips for Getting Around Maui Without a Rental Car.

8. What to Pack for Maui Vacation

We are all about packing light for a Maui vacation. Erica loves to bring packing cubes to keep us organized and I like to bring sandals (slippers in Hawaii) and t-shirts. 

We witness visitors packing sweatshirts and jeans for their tropical vacation to Maui. The temperature in the resort areas gets down to the low 70s during the night. Maui is a warm place. Unless you’re easily cold, save room in your suitcase with only the essentials.

Here is your essential list of what to pack for Maui:

• Shorts and T-shirts
• One Gorgeous Island Style Outfit
• Comfortable Footwear: sandals and hiking or walking shoes
• Swimsuit (of course)
• Sun-Protective Clothing
• Mineral-Based Sunscreen
• UV-Protective Sunglasses
• Backpack
• Water Bottle
• Beach Bag

See our What to Pack for Your Hawaii Vacation for our full list. Browse our Travel Gear for recommendations on sunscreen, sun protective clothing, and snorkel gear.

Trip Planning When You’re on Maui

The main elements of your Maui trip planning are now complete (airlines, flights, and rental car), here is what to consider once you’re on Maui. 

9. Understand the Geography

Geography on Maui is important because it will affect the weather you experience and what you do while on vacation. One big thing to understand about geography is that each island has a windward (wet side) and a leeward side (dry side)

On Maui, the leeward side of the island includes some great beaches, like Wailea Beach and Ka’anapali Beach. Hence, the resorts are located here to soak up the sunny days as rain is less frequent. 

The windward side of the island is home to the Road to Hana and a lot of beautiful waterfalls. The Road to Hana is a jungle drive thanks to all the rain on the windward side of the island. While mentioning the Road to Hana, decide here if it is worth driving during your Maui trip.

10. Eat Local on Maui

No Maui trip planning is complete without where to eat. Maui has some of the best food in the Hawaiian Islands. Here are some tips on where to eat on Maui.

• Fresh, locally caught fish: If you’re a seafood fan, don’t miss out on the fresh fish. You can enjoy it at either a restaurant or at a fish market. You’ll see options like Mahi Mahi, Ono, Opah, Ahi, and more.
• Maui food trucks are the best in the Hawaiian Islands. Enjoy fresh ingredients, experimental chefs, and food truck parks for the whole family. See our Ultimate Maui Food Truck Guide on where to eat.
• Locally grown produce: Enjoy dragon fruit, coconut, lilikoi, pineapples, locally produced honey, and more. We love doing Maui farm tours, but if that’s not part of your vacation itinerary, try a farm-to-table restaurant like Pacific’O in Lahaina or Ula’Ula Cafe. You’ll get to sample some island flavors while supporting the agriculture industry here. There is a large farmers market in Kula on Saturdays and another in Napili.
• Traditional Hawaiian food: You don’t need to go to one of Maui’s best luaus to sample some traditional Hawaiian dishes. Look for dishes like poi (taro that has been pounded into a paste), laulau (meat wrapped and cooked in taro leaves), kalua pig (slow-roasted pork cooked in an underground oven), and poke (diced, raw fish that is wonderfully flavored).
• Shave ice: Not shaved ice. You may think that this is like a snowcone, but it couldn’t be further from it. Soft fluffy ice shavings that are flavored with different syrups and creative flavor combinations. You might also have the add-on of fruit and ice cream. It’s so, so good. Ululani’s Hawaiian Shave Ice is our favorite on Maui and is located all over the island.

Want to know the best Maui restaurants? Here are our Kihei and Wailea restaurants and Lahaina restaurants to eat at.

For a local experience, watch our 5 Favorite Maui Food Experiences for ideas to wow your partner.

11. Things to Do on Maui

Perhaps you jumped straight to this one for your Maui trip planning. Understanding what you want to do on your Maui vacation helps decide where you want to spend your time and money, and even where you want to stay. 

Here are the most popular things to do in Maui.

• Humpback whale season is from mid-December till the end of March. We found Maui to be the best Hawaiian island for whale watching. Our Maui Whale Guide will tell you how to do it right or enjoy one of our seven favorite Maui whale tours.
• Haleakala National Park is a stunning destination. See the endangered Nene bird and Silversword (‘ahinahina in Hawaiian) that only grows at the summit. Go hiking for the day and decide if the Haleakala sunrise or sunset is right for you.
• Napili Bay is a beautiful bay on Maui’s northwest shore. Come for the day to swim and snorkel with Hawaiian Green Sea Turtles (stay 10 feet away in the water). As a bonus, The Gazebo is great for breakfast and the Sea House is excellent for happy hour and dinner to end your day. Both are located on Napili Bay.

See the articles below for so many more things to do on Maui!

• 33 Things to Do on Maui: Leave the Crowds Behind
• 68 Things to Do on Maui with Kids
• 14 Things to Do on Maui on a Budget
• 16 Things to Do in Lahaina, West Maui

12. Can’t-Miss Activities and Tours

A tour is not required for your Maui vacation. Maui is full of things to do that are free or low cost. But, Maui has some amazing tours and excellent tour companies to take you out on the water or explore the island. 

See all our researched and vetted Maui tour companies here. We also have Hawaii Vacation Guide Coupons for many Maui tour operators. 

Here are the most popular Maui tours:

• Road to Hana is best done with a local guide. The dangerous road is now more challenging with traffic and no parking tickets (see our Road to Hana Etiquette), so let an expert take you to all the best stops. Save 10% with promo code HVG10 at checkout.
• Molokini Crater is a unique Hawaii snorkel destination. The crystal clear water and vibrant reef are worth a morning snorkel trip. Let our favorite catamaran crew take you out from South Maui for a sunrise tour or mid-morning tour.
• Whale Watching is a must when you visit Maui from December through March. See our seven favorite whale-watching tours to pick the tour right for you.

13. Use the Right Sunscreen on Maui

Starting in 2021, Hawaii required only reef-safe sunscreens to be sold in the state. We share Hawaii reef-safe sunscreen brands here.

Maui has taken further action to protect the reefs around the island. Maui requires only mineral-based sunscreens (zinc oxide and titanium dioxide) to be sold on the island. We share our two favorite mineral-based sunscreens in our Travel Gear, one is a local Maui brand.

14. Learn About Maui Culture

The people of Maui are what makes the island such a special place to visit. From the Hawaiians to the plantation migrants who came in the nineteenth and twentieth centuries, the culture is uniquely Hawaii. 

Check out the museums and cultural activities below during your vacation as the icing on the cake for your Maui trip planning.

• Hale Ho’ike’ike at the Bailey House in Wailuku to learn Hawaiian history, local history, and see original artifacts.
• Hawaii Wildlife Discovery Center to learn about the ocean and Maui’s reefs at this interactive exhibit in Kaanapali’s Whalers Village.
• Hawaiian Outrigger Canoe Ride – learn how the Polynesians travel the Pacific and between the island while you paddle as a team on an outrigger canoe. See Ali’i Outrigger Canoe in West Maui or Hawaiian Outrigger Experience in South Maui.

15. The Ultimate Maui Trip Planner

Maui trip planning is not easy. We hope this step-by-step guide has helped you feel confident in planning the best honeymoon, anniversary, or family vacation to Maui. 

If you’re looking for an easier way to plan your days on Maui, our Maui itineraries will do 80% of the work for you. We don’t book your rental car, flights, or hotel for you but our guides will tell you how to have the best Maui vacation ever with what to do and how to do it!

Even experienced Maui trip planners get our itinerary!

I just wanted you to know that my family and I purchased the Maui itinerary and we are wrapping up 12 days on the island. We did so much of what you recommended and it was awesome for everyone. We have three college-age kids and everybody enjoyed the things you suggested, including the restaurants. Thanks for all of the work that you put into this. Mahalo.

Gunnar A.