How to Plan Your First Trip to Maui

Plan your trip to Maui with our tips

There are many things to consider before you visit the island for the first time.

You’re in for a wonderful vacation if you’re planning to visit Maui!  After my first trip to Maui, I learned so much about the green paradise of black, golden, red sand beaches.

Follow these travel tips, and you will have a great experience!

Select your dates

It is important to choose the best time of the year and month for you, your family, and your work schedule. Aside from this, it is important to pick a time that suits your budget and weather needs. The off-season is generally between March-May and September-November. You’ll find cheaper tickets and rooms, and there will be fewer tourists on the island during this period (barring holidays or Spring Break). For those who live in snowy, colder climates, it is more appealing to travel in winter, while summer is for those who live in extreme humidity. 

Where to Stay

Maui has a variety of Outrigger Hotels and Resorts. It is important to select by region and by town. You will likely need to fly into Kahului, even if you are staying on the west side of the airport. It is often cheaper to drive for an hour along the coast than to spend more to fly into Kapalua. Listed below are the top vacation spots in Maui:

South Maui – Kihei, Wailea, Makena

These are the spots where you have the best chance to get sun all day. This is the desert side, with great beaches, restaurants and activities. Although Kihei may be more expensive than south Kihei, it may be worth it. South Kihei Road runs across both north and south Kihei, everything south of Kanani Road are fan favorites. Wailea and Makena offer amazing condos and resorts on great golf courses, the quality is high and so are the costs.

West Maui– Lahaina, Kaanapali, Kapalua, Napili

Lahaina Town, also on the dry desert side, is very busy and concentrated with a lot of great shopping and restaurants. Kaanapali, Kapalua, and Kapalua have large resorts and are both golf course towns. Napili, a quieter village with beautiful beaches, is also a great option. If you are looking for a more laid back, less crowded, relaxing on the beach type of vacation then Napili may be exactly what you are looking for. Kahana, nestled between Kaanapali & Kapalua, has nice beaches and great prices.

Upcountry Maui– Makawao, Kula

Although not many tourists choose to stay in the country of Hawaii, we do recommend it for those who want a cooler experience and great views. These quiet villages are located high up on the Haleakala slopes, so there won’t be beaches. But you will likely be able to see them. It feels as if you are in the Scottish moors. It is beautiful with stunning landscapes.

Research Activities

Many visitors spend their entire time on the beach right in front of their resort/hotel. Others like to explore the island. Some people almost never see their rooms, because they go out all day. No matter what type of person you are or what type of vacation you wish to experience, there are activities that you will enjoy. 

  • Head to a surf school – what better place to ride those waves than on a trip to Maui?
  • Go snorkelling or scuba diving – there are tons of places to peek below the waves
  • Haleakala National Park offers incredible hiking. Head to the top of the crater for incredible views.
  • Walks and historic trails – there is lots to explore on a visit to Maui, so get out your walking shoes and your map and enjoy the scenery.
  • Explore the jungle trails and waterfalls. A trip to Upper Waikani Falls is an excellent day trip.
  • Visit Lahaina – the old capital of the Maui Loa kingdom, and a fascinating cultural hub.
  • Snorkel the old crater of Molokini – if you’re lucky you might get to swim with turtles
  • Swim in the pools of ‘Ohe’o – and enjoy the stunning cascades

This is just a small selection of things to do on a trip to Maui.


Here are some things to keep in mind when packing your suitcase.

  • Reef safe sunscreen, sunglasses, and hats are essential
  • Swimsuit(s)
  • Long pants and a sweatshirt (especially if you visit Haleakala Crater).
  • For hiking and day trips, a backpack is ideal.
  • Camera/camcorder (You should not leave them in the car).
  • Cash (not everyone accepts credit cards).
  • Bug spray
  • Non-perishable snacks 

A bit of planning your travel itinerary can make your visit to Maui much more fun and help you get the most out of this beautiful destination.

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