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Planning Your First Trip to Maui

Below we've made a simple checklist of 10 steps to prepare the best trip of your life!

dates#1 Choose your Dates

You need to decide what time of year, month work best for you, your family, and your work schedule. ALSO, and just as important, you need to choose a time that fits your needs as far budget and weather. Our off-season is usually around March-May and September-November. At this time, you'll get cheaper tickets/rooms and there will be less people on the island (barring any holiday or Spring Break). Coming during the winter is attractive to those that live in colder, snowy climates, and in the summer for those that have incredible humidity where they live.


Maui stay#2 Where to Stay

Maui is made up of a diverse range of micro-climates and unique towns. You need to choose by area and by town. Keep in mind you'll likely want to fly into Kahului even if staying near the airport on the west side. Driving for an hour along the beautiful coast is usually better than spending a fortune flying into Kapalua. Here are the best areas to stay.

South Maui - Kihei, Wailea, Makena

This is your best chance of having sun 100% of the time. It's the desert side with some great beaches, restaurants, activities. Kihei is less expensive, but only south Kihei is really nice (in our opinion.) South Kihei Road runs the entire length of both north and south Kihei, so don't be fooled. We like everything south of Kanani Road. Wailea and Makena have amazing resorts and condos on golf courses with great beaches, but you'll pay for it.

West Maui- Lahaina, Kaanapali, Kapalua, Napili

Also on the dry desert side, Lahaina Town is very concentrated and busy with great shopping and lot of restaurants on the water. Kaanapali and Kapalua are golf course towns on the water with big resorts. Napili is a more quiet village area with some pretty beaches too. Kahana is nestled between Kaanapali and Kapalua and has some nice beaches and good prices.

East Maui- Hana Town

Hana is generally what you think of when you imagine Hawaii. Lush rainforests that hug pure coastlines of lava rock, empty beaches, and slow living. This is where all the waterfalls are too. There aren't many choices on where to stay, but you can rent a condo/house or stay at the Travaasa Hotel. Renting a place can be good, but we've had a few bad experiences. Staying at the hotel is one of the best experiences we've had while in Hana. It's in the heart of town with amazing amenities, friendly staff, and a full spa with ocean views.

Upcountry Maui- Makawao, Kula

Not many visitors stay Upcountry, but we recommend it to those that want a cooler experience with great views. These quiet villages are high on the slopes of Haleakala, so you won't have beaches, but you'll likely be able to see them! The weather is much cooler and it feels like you're staying in the moors of Scotland. It's gorgeous with some beautiful landscapes.


Top 25 Best Maui Activities

car rental#3 Rent a Car

Get a good price on a reliable car. Major considerations are getting a vehicle that can hold all of your luggage and yourselves, gas mileage since you may be driving a lot, and your preference of a convertible. If you want to surf and need a rack, make sure it has one or buy a portable one. You'll most likely be flying into Kahului Airport, so rent your car from here online beforehand. Here you can find some good Maui car rental rates.


to do#4 Research Activities

Some visitors spend all their time at the beach in front of their hotel/resort. Some like to do some exploring of the island. Others rarely see their rooms and are out and about all day long every day. What ever type of person you are, you're going to want to do some activities (outlined below by visitor-type.) Book them ahead of time for discounted prices by calling (808) 670-1061 or look through their curated Maui activities.


Resort Goers

If you came to relax and that's it, then stay at a beach front accommodation and consider the following activities: Luaus, Shows, Golfing, Snorkeling, Stand Up Paddle, Restaurants, Massage, Beach Portraits.

Sight-Seeing Explorer

If you came to relax at the beach, but you still want to get out and see some of Maui, these are some fun ways to see our island: Road to Hana, Hiking, Molokini Snorkeling, Whale Watching, Sailing, Submarine.

Hard-Core Adventurers

If you're itching for excitement and adventure, you should consider: Helicopter Tours, Scuba Diving, Ziplines, Volcano Biking, Hiking, Sport Fishing, Parasailing, Kayaking.


beaches#5 Research Dining & Food

For many of you, you'll be renting a condo or some kind of accommodations with a kitchen.

Maui has some award-winning restaurants and some pretty crappy ones too. So, it's good to get an idea of where you'll be going when visiting Maui. Read through this site, and consider buying one of the many Maui Guidebooks, and learn about the amazing restaurants, snack shops and food trucks.


packing#6 Pack

Some things you will want to consider bringing when busting out your suitcase:


  • Sunblock, sun glasses and hats (the sun will get you!)
  • swim suit
  • Sweatshirt and long pants (if you go to Haleakala Crater, you'll need even more than this.)
  • A backpack (for hiking and day trips.)
  • Camera/camcorder (you'll want plenty of pics/video. Just don't leave them in your car!)
  • Some cash (not everybody takes credit cards here.)
  • Music (CD's and/or Ipod for use in your car rental and hotel rooms)
  • Bug Spray (Depending on where you'll be staying, and whether you taste good, you'll be bitten)
  • Snacks (airlines are getting cheaper and cheaper these days.)

NEW: Maui Photography Flights

Historic Iao#7 Learn about Maui

Hawaii is a magical place to visit. In the least, it leaves everyone with a sense of inspiration and serenity. If you want to get the most out of our islands, learn something about our unique culture, powerful history, Hawaiian legends and geographic landscapes. You'll appreciate it much more if you do. Also, learn about some of the dangers and things to watch out for. Paradise can turn sour if you don't know what you're doing. Cliffs are unstable, reefs are razor sharp, roads are twisty and wet, bugs bite, waves crash, and the sun burns.


Show#8 Stay Updated

Ever watch Willy Nelson play in a small bar? Enjoy a 5 course meal by star chefs at a pop up restaurant on a farm? Watch bon Jovi live from the beach followed by a firework show? have cocktails and great food while mingling with celebrities? We have! These are some of the amazing events and shows that most visitors don't know about. Follow us on our social networks with Twitter, Facebook, Instagram, and keep an eye on our growing Maui Event Calendar.


Hammock#9 Review/Share your Experience

The best way to plan a trip is to get helpful tips and information from other people that have recently been to Maui, so help others by sharing your experience (good and bad.) Our blog is open to anyone that really wants to share their experience with photos, video, reviews, and more. Feel free to contact us and let us know if you're interested.


bamboo Forest#10 Plan your Next Trip!

There's no better time to begin planning your trip to Maui than right after having been. Everything is fresh in your mind, and you'll be able to correct any mistakes you made in planning the first time. Write down the restaurants you really liked, the activities you'd do again, the resorts/hotels you'd like to try next time, and start picking dates. Refer to #1 on this list and get ready for an even better trip than you're about to have! ALOHA!


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