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The Ultimate Maui Itinerary: 5 Days in a Tropical Hawaiian Paradise

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Hawaii is one of those must visit destinations for anybody. It seems like it’s not possible a place could be so beautiful. And the best part? For US citizens, you don’t even need a passport. The entire time I was there it felt so crazy that Hawaii is part of the United States. You have a few islands to choose from for your visit to Hawaii. There are 8 main islands in Hawaii, but the most commonly visited are Oahu, Maui, the Big Island, and Kauai. I consider Maui to be one of the best because it has so much to offer in the form of variety of things to do and places to see. Keep reading for the best Maui itinerary for 5 days in this beautiful paradise!

how to spend your maui itinerary 5 days in hawaii

Where is Maui?

Maui is one of the main 8 islands that make up the islands of Hawaii. Maui is the second largest Hawaiian island, only second to the Big Island. Hawaii is located in the Northern Pacific Ocean, due west of Mexico. Being in the Pacific Ocean, Maui is pretty much in the middle of nowhere. The closest islands are islands like Johnson Atoll, Midway Atoll, and the island country of Kiribati, but even those islands are quite a distance away.

map of hawaii with maui marked with a pin

How to Get to Maui, Hawaii

The airport you’ll want to fly into to get to Maui is the Kahului Airport (airport code: OGG). You can only fly to Maui directly from cities in North America, mostly in the United States, but also a couple in Canada.

The most common flight routes to Maui, excluding other places in Hawaii, are going to be from Los Angeles, San Francisco, Seattle, Portland, and Dallas. You can also fly from other cities in California and the western half of the USA. If you’re coming from Canada, you’ll most likely connect through Vancouver. However, there are seasonal routes to Hawaii from Calgary and Edmonton as well.

If you’re coming from somewhere other than the USA or Canada, you’ll fly through one of those cities I previously mentioned, or fly through Honolulu on the island of Oahu. You can reach Honolulu directly from several destinations in Asia and the South Pacific.

Search for cheap flights to Maui here.

How Long to Spend in Maui

If the title of this blog post doesn’t give it away already, I think 5 days is a sweet spot for length of time to stay in Maui. There’s a lot to see and do in Maui, so 5 days in Maui allows for some relaxing time without sacrificing all the incredible things to do in Maui.

The absolute minimum amount of time I would recommend on Maui is 3 days. If you’re trying to pack in a lot in a short amount of time, like to see all four main islands in one trip, you’ll probably only have 3 days in Maui. Keep in mind, by doing this you’ll sacrifice some relaxing time and maybe 1 or 2 of the longer day trips within Maui.

Likewise, spending any longer than a week in Maui would leave you almost too much relaxing time. If you have 10-14 days in Hawaii, I’d highly recommend splitting it up between islands. Hopefully you now understand a little bit more of why I think a 5 day itinerary for Maui is perfect.

Have more time in Maui? Consider a day trip from Maui to Oahu.

sunset with palm trees and mountains in maui hawaii
view of maui from the ocean
Images provided by the Hawaii Tourism Authority

The Best Time of Year to Visit Maui

Honestly, it’s hard to pick a bad time to visit Maui. The weather is beautiful all year round, ranging from 75-85 degrees. Maui’s summer, April-November, is typically the warmer and drier part of the year. On the flip side, December-March is winter meaning these are the slightly cooler months.

The whale watching season in Maui spans the months of December-May. However, the best time to see whales is January-March. If you’re a big surfer and want to check out the big-wave surfing season, make sure to schedule your visit in winter.

Get ideas for other tropical vacations here.

What to Pack for Your Trip to Maui

Since Hawaii is part of the US, you won’t be too strapped to find most things you could need in Maui itself. That being said, you don’t want to spend your whole vacation running around to stores to pick up things you could easily bring with you. Below is a list of things you should definitely be packing for your trip to Maui, aside from the obvious like shirts and shorts.

  • Sunglasses. The sun is really strong in Maui, so make sure you protect your eyes with a good pair of sunglasses. You might even want to bring 2 pairs just in case you lose one. I highly recommend Ray Bans and Quay Australia sunglasses (I’m obsessed with these heart sunglasses I got from Quay, linked here).
  • Reef safe sunscreen. Not only is purchasing reef safe sunscreen important in order to protect the environment, but Hawaii has actually banned sunscreens with oxybenzone and octinoxate because they’re believed to contribute to coral bleaching. The law doesn’t go into effect until 2021, but get ahead of the curve and bring a reef safe sunscreen, like this one here.
  • Bathing Suits. I would say bring 2-3 bathing suits on a trip for 5-7 days. This way you have a spare when one could be drying off. Plus, you have options! I love shopping for bathing suits on Amazon, but make sure they’re able to be returned if they don’t fit.
  • Light Jacket. Sometimes the evenings in Maui can get chilly, so I’d recommend bringing a light jacket or sweater. I would say bring something you’d be able to wear on the cold plane too so you’re not packing too many things.
  • Appropriate footwear. It should be obvious that you’ll want to bring sandals. Bring hiking shoes too just in case you end up on any hikes during your trip.
  • A hat. The sun gets really hot in Hawaii. You should definitely bring a hat to protect your face from the sun when it’s really hot out. I usually bring a baseball hat and a sun hat like this one here.
  • Reusable water bottle. I always travel with a reusable water bottle. You can fill it in the airport or have a flight attendant fill it for you on the plane. Plus, it’ll cut down on your consumption of single-use while in Maui. I personally love Yeti water bottles, like this one here.
  • GoPro Camera. GoPros are super fun for underwater photography. They’re relatively affordable and travel really well considering how small they are. I always bring my GoPro with me when I know there’s going to be water involved! Buy yours here.
  • Portable Charger. This is just a travel tip in general – always travel with a portable charger. If you’re taking photos on your phone or just using it more, it’s going to die faster. Portable chargers come in handy big time. Make sure to get one that has a lot of power, like this one here which will charge an iPhone 4-5 times with one charge.
  • A backpack. Make sure to get a good, handy backpack for when you’re hiking or just want to bring something around with you. I find backpacks to often be better for beach destinations because you can fully zip them up to keep sand out. Get a backpack that can be packed within itself so it doesn’t take up extra room in your luggage, like this one here.

Where to Stay in Maui

The are two general areas that are the best spots to stay in Maui. In West Maui, the best areas to stay span from Kapalua south to Lahaina. The other good area to stay in Maui spans from Kihei south to the Wailea-Makena area. Both areas are about equidistant to the airport at 45 minutes.

Wailea tends to have the more luxury hotels, whereas Lahaina and Kaanapali has some more reasonably priced options. Keep in mind Hawaii is expensive so even the lower priced options are higher than average. Every hotel will offer garden/tropical view options and ocean view or ocean front options. Around the world, the charge to upgrade a tropical view to an ocean view isn’t usually that much. However, that’s not the case in Hawaii. You’ll definitely pay a premium for the views in Maui, so if you’re on a budget, opt for the tropical view option and hope for an upgrade.

Another thing to remember in Maui is that most hotels have a resort fee. These resort fees usually average between an additional $30-50/night plus taxes. Sometimes the resort fee includes the cost of self-parking, but some resorts will charge you again for parking.

Below is a list of some of my favorite hotels in Maui.

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The areas of Kapalua, Kaanapali, and Lahaina are on the left, with Kihei and Wailea in the center.
four seasons maui aerial shot of resort grounds
four seasons maui pool
Images provided by Four Seasons
fairmont kea lani maui resort view
fairmont maui resort pool area
Images provided by Fairmont

How to Get Around Maui

The absolute best way to get around Maui is by renting a car. My favorite rental car company is Hertz. I find them to be super reliable with great customer service which is always helpful when renting a car. That being said, I know a lot of people will want to buy the most economical option. In that case, I recommend searching through somewhere like Rentalcars.com to compare prices across rental car companies.

When renting a car, make sure you’re taking into account the parking cost at your hotel. A lot of hotels will allow self parking for free by building it into the mandatory resort fee. However, a lot of resorts will still require you pay for parking. This could add a lot of money onto your trip, so research this! Valet parking will be offered at most hotels, especially the high end ones, and this will always have an additional cost associated with it.

The most important thing to remember when you’re renting a car is always buy the insurance. If you’re booking the car through Rentalcars.com, they’ll likely offer you insurance through them as well. To save yourself a hassle, I would just buy the insurance when you’re picking up the car. Usually the insurance policies directly through the car rental company will have a $0 deductible if anything happens to the car so you just get to walk away. If you book third-party insurance, you may have to go through an insurance claim process which is a huge headache. Always. Buy. The. Insurance!!!!

jeep driving down the road to hana in maui 5 days in maui
Image provided by the Hawaii Tourism Authority

Maui Itinerary: 5 Days in Paradise

Now that we’ve gotten all the nitty gritty details out of the way, it’s time to start planning out your 5 days in Maui!! This itinerary is built out with some free time available. I’m the first person to tell you I don’t want to sit around my entire vacation and do nothing, but you’re in Hawaii! Take some R&R time for yourself to just relax at the beach or at the pool. There will be plenty of time for activities.

Day 1: Arriving in Maui

Most flights from the US arrive sometime in the early afternoon. By the time you drive over from your hotel, it’ll be mid afternoon. Take it easy this day. If you want to get right in and get things going, I would recommend something easy like a sunset dinner cruise or an afternoon whale watching cruise if it’s the right season. It’ll be the perfect way to start your trip to Maui off with a bang!

If you don’t like the idea of a cruise and want to get out of your hotel room to keep yourself awake (fight that jetlag!), head down to Makena Beach State Park in Kihei. Makena Beach is considered to be one of the best beaches in Maui, so it’s absolutely something you’ll want to visit.

There are two beaches here: Big Beach and Little Beach. I’m sure you can figure out the difference by the name. There are two big parking areas by Big Beach, so you’ll be okay to take your car here. Make sure to bring snorkel gear here too as there are some awesome snorkeling spots. You can probably rent snorkel gear at your hotel, but if you plan on doing a lot of snorkeling, it’s easier (and probably cheaper) to just buy a mask and snorkel yourself and bring it with you.

maui itinerary 5 days - makena beach at sunset

Day 2: The Road to Hana

The Road to Hana is one of the most talked about things to do in Maui and an absolute must do on this Maui itinerary in 5 days. It’s a full day adventure and you’ll want to start early to beat the crowds and to make sure you can see everything you want to see. Let’s first talk about whether or not doing the Road to Hana with a tour is right for you.

Even if you’ve rented a car, you might want to consider a tour to see the Road to Hana under a couple of circumstances. The drive isn’t scary, but it’s definitely an adventure to say the least. The Road to Hana drive is only 52 miles long, but has 620 hairpin turns and crosses over 59 bridges, some of which are one-lane wide. There are parts of the drive that are more inland, but there’s also lots of driving that is right on the edge as well. A lot of people would rather be on a tour to be able to take in the scenery and not have to worry about driving and I completely think that’s a valid point on this drive in particular.

That all being said, the Road to Hana can definitely be done without a tour. I personally used and highly recommend the Gypsy Guide Road to Hana app. It links up to your GPS and guides you along the drive while telling you all about the history of Hawaii. The app keeps you at a good pace while still allowing you time to stop and soak up the famous spots along the Road to Hana. The app choose the 5 “not to be missed” stops, along with several other waterfalls, beaches, and viewpoints along the way. Make sure to pack a lunch and bring it with you since you’ll be out all day. Below is a great list of things to make sure you bring on your Road to Hana adventure to be fully prepared.

Road to Hana Mini Packing List

  • Bathing suit
  • Hiking shoes or sneakers
  • A towel or two
  • Sunscreen
  • The Gypsy Guide Road to Hana App
  • An extra set of clothes in case your first set gets wet
  • A lunch, water, and snacks

If your desire during the Road to Hana adventure is to really get off the beaten path and see the best the Road to Hana has to offer, I cannot emphasize the need to start early enough. Time will fly by shockingly fast and before you know it the day will be over. Some of the more off the beaten path things to see on the Road to Hana involve a bit of hiking which is great, but takes extra time. Some of the stops are also places you’d want to spend some time at, but you can only do that if you allow yourself as long as physically possible.

5 days in maui itinerary road to hana

My best recommendation is to check the sunrise and the sunset for that day. Make sure you’re at the starting point by the airport before the sun has risen so you’re ready to start right as the sun begins rising. On the way back, I would suggest starting to head back maybe an hour before the sun is supposed to set. The light will linger a little while after the sun actually sets. It’s not that you can’t do the drive in the dark, but it was definitely a more stressful drive in the dark.

If you have time and aren’t completely exhausted, walk around the downtown area of Paia. You would’ve passed this little town to start your Road to Hana drive. There’s a bunch of cute little cafes in this are that are worth checking out. If you want a more sit down dinner experience, check out Mama’s Fish House. It’ll be harder to plan since the Road to Hana day can be a bit unpredictable, but consider making a reservation as it can get really busy.

maui itinerary 5 days road to hana views
Images provided by the Hawaii Tourism Authority

Day 3: Snorkeling at Molokini & Turtle Town + Luau Dinner

One of the most famous snorkel spots in Maui is at the Molokini Crater. This crescent moon shaped island sits about 3 miles off the coast of Maui. This area was actually used by the US during WWII for bombing practice, but has since been named a Marine Life Conservation District and Bird Sanctuary. The reef has recovered from the damage as is now the home to a beautiful reef with lots of tropical fish and birds.

The inside of the crescent shape is shallow, where the reef is located. On the backside of the crescent is very deep water. However, if the water is calm enough, the captain may take the group around the backside and let you jump off for a couple minutes. If you’re a strong swimmer, I highly recommend doing this! I was only in the water a short amount of time, but seeing what seemed like infinite blue ocean beneath you was one of those experiences that sticks with you. I’ve never seen such a deep, beautiful blue color, and I highly recommend people try this out!

Book a tour to snorkel at Molokini & Turtle Town here.

maui itinerary 5 days molokini crater
5 days in maui itinerary molokini crater
Images provided by the Hawaii Tourism Authority

Another popular snorkeling area in Maui is Turtle Town. If the name doesn’t make it obvious enough, this area is home to tons of sea turtles. The area is pretty close to the shore. It’s crazy to think all the people on the beach probably had no idea how many turtles are only about 100 yards off shore.

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While snorkeling with sea turtles is a huge bucket list item, please remember to be respectful of the turtles. They’re wild animals and need to be treated with respect. Don’t try to touch them or feed them. When you’re swimming with them, they may come up to you which is okay, but make sure to give them their space. If they come up close to you, it’ll be because they want to, not because you’re forcing them.

Your time snorkeling at Molokini Crater and with the sea turtles in Turtle Town is only a half day tour, so you should be back to your hotel in the early afternoon. Take the rest of the afternoon to relax and enjoy your hotel’s pool and the beautiful beach right outside your hotel.

Tonight is the perfect night to participate in one of the classic touristy things to do in Maui – a luau! I’ll be the first to admit that luaus are kind of expensive, but it’s a huge part of Hawaiian culture and something you just kind of have to do when you’re in Hawaii. If you’re lucky, your hotel will have a luau there. If not, chances are one of the hotels nearby has one. And remember, your dinner is included in the price, so it’s not all that much money when you remember that. Make sure to get a good sleep tonight, because tomorrow is going to be an early start!

Book your Hawaiian luau here.

Day 4: Haleakala Sunrise + Lahaina

The first activity of the day is going to take some dedication and commitment because of how early of a morning it’ll be. A Maui itinerary for 5 days wouldn’t be complete without a sunrise visit to Haleakala. The Haleakala National Park is one of the best spots for sunrise on the whole island of Maui. Make sure to wear a coat and long pants as it will be cold, at least in comparison to what you’re been used to the last few days.

Depending on where on the island you are, it can take up to 2 hours to drive up the mountain to see sunrise. Plus, you’ll want to arrive early in order to get a good spot. I would say give yourself an extra hour in addition to how far you are from Haleakala. This will allow you enough time to get there early to get a good spot, and to allow for extra time.

If you’re doing sunrise by yourself with your rental car, you have to reserve a ticket for your specific day. You can get that ticket through this link here. Remember, the ticket is per vehicle not per person, so you only need 1 ticket. The tickets are only $1.50 and open up 60 days in advance. Try to do this as close to 60 days in advance if possible because the tickets will sell out, especially over holidays and on the weekend.

Reserve your ticket for the Haleakala sunrise here.

If you’re planning your trip to Maui more last minute and there are no tickets for your date left, don’t worry. You can always do a tour to see the Haleakala sunrise. The tour takes care of that ticket reservation, so as long as there’s a spot for you on the tour, you’re good to go.

After you finish your sunrise at Haleakala, grab a quick breakfast. After you’ve filled up on good food, head over to Kaanapali or Kihei to hang out at the beach for the day. Since you were up early, hanging out at the beach in the afternoon will give you an excuse for a much needed nap to recover from the early morning. Naps don’t count as wasting time if you’re laying on the beach, right?

It’ll be up to personal preference for which area you decide to go on, but I would base it off of where you’re staying. If you’re staying in the Lahaina or Kaanapali area, you may want to hit up the beach in Kihei to see a different area of Maui and vice versa if you’re staying in Kihei or Wailea.

If you’re wanting to check out a beach in Kihei, I recommend Kamaole Beach Park. This area is split up into 3 stretches of beach. They have full facilities, parking, and lots of great snorkeling for when you wake up from that nap!

If you decide to venture to the Kaanapali area, there are a few options for beaches. There’s a ton of great snorkeling at Black Rock Beach, so I would head there if you want to get some extra snorkeling time. There are also some spots to do some cliff diving here, so if you’re an adrenaline junkie, this might be your speed! If you want to drive a little further, Kapalua Bay Beach is a great option as well. It might be a little less crowded since there aren’t a bunch of resorts right on top of the area. Another beach to check out right next to Black Rock Beach is May’s Beach.

In the late afternoon when your beach day is over, pop over to Lahaina to walk around for a little bit. There are some cute shops and restaurants in this area. If you’re a burger lover, stop at the famous Cheeseburger In Paradise for a delicious burger and drinks. To really top off the night, head over to Ululani’s Hawaiian Shave Ice to try Hawaii’s most famous desert – shave ice! No Maui itinerary is complete until you’ve tried shave ice.

kihei maui 5 days itinerary
kaanapali beaches maui itinerary 5 days
Images provided by the Hawaii Tourism Authority

Day 5: Lazy Beach/Pool Day + Head Home

You’ve sadly made it to the last day of your Maui itinerary. 5 days here is the perfect amount of time, but will never feel long enough!! Don’t worry, you’ll just have to plan a trip back!

Most flights out of Maui back to the continental US will leave at night. You can sometimes find a flight that’ll leave in the early afternoon, but take advantage of the full day if you have the opportunity to get one of those night flights.

Wake up early and have a nice breakfast at your hotel and head right to the beach or the pool. You have to soak up all the hours you can!

Make sure to ask your hotel for a late check out to soak up as much time as you can before having to check out. They won’t usually guarantee it, but you can always ask. Don’t forget that just because you’ve checked out of your hotel doesn’t mean you have to leave. Hotels will let you stay and use the facilities while you wait for your flight. Hotels with a gym or spa will even let you use those facilities to shower before your flight if you’ve spent the day at the beach or pool.

After a lazy day at the pool or the beach, it’s finally time to say goodbye to this beautiful island you’ve called home for the last 5 days!

5 Days in Maui: The Short & Sweet Version

Look, I get it. You’re busy, I’m busy, we’re all busy! If you’re looking for a quick overview of what a Maui itinerary in 5 days will look like, you’ve come to the right spot of this blog post. Keep scrolling for an epic summary of how to spend your 5 days in Maui!

Day 1: Arriving in Maui

Day 2: Road to Hana

  • Decide if you want to do a tour for the Road to Hana or if you want to do it yourself – the drive can be kind of intimidating! However, the DIY version allows you more flexibility with stops and how much time you spend in each place.
  • Walk around the town of Paia on your way back from the Road to Hana.
  • Have a nice fish dinner at Mama’s Fish House before heading back to your hotel.

Day 3: Snorkeling at Molokini & Turtle Town + Luau Dinner

  • Start off your day with a snorkeling trip to Molokini and Turtle Town to see lots of fish and other wildlife.
  • Remember not to touch the sea turtles and other wildlife!
  • Finish off your night with a traditional Luau dinner show! There should be options at your hotel or a nearby hotel.

Day 4: Haleakala Sunrise + Lahaina

Day 5: Lazy Beach/Pool Day + Head Home

  • Wake up early to get a nice breakfast. Spend the day lounging at the pool or at the beach to soak up your last few hours and reflecting on your incredible 5 days in Maui.
  • Request a late check out from your hotel. Even if they don’t grant it, you can hang out at the resort and use the facilities until you have to leave.
  • Fly home and get started on planning your next trip to Hawaii!!

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