5 Days In Maui Itinerary: Hawaii Travel Guide

5 days in Maui itinerary
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5 Days In Maui Itinerary: Hawaii Travel Guide

This is a comprehensive guide to the 5 days in Maui itinerary. 

Congratulations if you have decided to go to Maui, Hawaii! 

It’s everything that you could ever imagine and more.

Even if you’re still in the planning stage and haven’t booked your flights yet, I am sure that by the time you finish reading this guide, you will want to book your flight.

I share my complete week-long itinerary details about where to stay, what to eat, what to do, additional ideas, and any tips that I have that will be beneficial for your trip.

I hope this 5 days in Maui itinerary will be helpful for you! 

If you are staying longer, I have day 6th to 7th suggestions as well as other activities to do in the later sections.

Kihei maui hawaii

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My Perspective & Disclaimer

Just to put into perspective, my husband and I went with 4 of our friends, so there were 6 of us in total. We’re in our 20’s and 30’s.

We arrived in Maui on Sunday mid-day and our flight was the weekend after on Saturday afternoon. 

We were there for a total of 6 nights and 7 days.

Our friends left on Friday, so my husband and I had a part of our Friday and all of Saturday to ourselves.

Your needs might be a little bit different if you are bringing family, especially children. 

5 days in maui itinerary

5 Days In Maui Itinerary: Where To Stay?

For this 5 days in Maui itinerary, it makes a difference where you want to stay depending on the activities that you want to do.

I suggest staying in Kihei if you are renting a car and want to be in the middle of everything and are more on the budget.

For perspective, Lahaina is more lively, more people and very touristy, while Wailea is fancier and the most expensive.

Why did we choose Kihei?

  • Closer to the airport (about 15-30 minutes) as opposed to Lahaina or Wailea.
  • Cheaper accommodations
  • Less crowded, more laid back
  • Closer to Road To Hana (more on this in the itinerary section)
  • Not as crowded

For most of the excursions, we actually ended up driving to Lahaina almost everyday and spent a lot of our time there.

Either way, we still chose to stay in Kihei for the majority of our time in Maui because our stay was drastically cheaper.

*My husband and I stayed in Kihei for 5 days and 1 day in Lahaina.

*If you have more than a couple of days, you can always break up your stay between the 3 locations so you can experience each city or you can easily go on day trips.

5 days in maui itinerary

Kahului Airport To Kihei

We personally rode an Uber to pickup our rental car in Kihei.

Depending on where your hotel or Airbnb is located, it will cost around $30-$50 for a 20-30 minute ride.

Other options would be taking a bus or reserving a shuttle.

5 days in maui itinerary

Flights To Maui, Hawaii

From our group, my husband and I flew from Denver, CO through American Airlines while the rest of our friends flew from Raleigh, NC with United Airlines.

Both our flights had a connection from LAX and had no issues.

5 Days In Maui Itinerary: Accommodations

As mentioned earlier, accommodations are very expensive in Hawaii especially in Lahaina and Wailea. 

It averaged about a minimum of $800 per night (for oceanfront rooms).

But don’t let this hinder you from going there. 

 
Kihei hawaii

KIHEI

In Kihei, we found this airbnb with an ocean view for about $400 (including cleaning and service fees). 

This divided by 6 is about $70 per person per night.

We loved this condo because of the view from the living room and the bedroom. 

It had everything we needed from all the kitchen items and dining area. 

There was also an elevator which made it easier for us to carry our things up and down.

It’s super close to multiple grocery store and only 5 minutes away from the Kihei food trucks and restaurants.

 

Lahaina maui

LAHAINA/KAANAPALI

If you are staying in Lahaina, I recommend this airbnb where we stayed. 

I believe this is as close to the ocean as you can get.

I would argue that the view in our Kihei accommodation was much nicer, but this place is much closer to the ocean.

If you feel that you are going to be primarily exploring Lahaina like we did, this would be an ideal choice for your 5 days in Maui itinerary.

Hyatt regency hotel and spa
Hyatt regency maui resort and spa

BOUGIE IN LAHAINA

If you are looking for a more luxurious option, Hyatt Lahaina Maui Resort and Spa is a great choice.

One of my friends who previously traveled to Hawaii stayed here and loved it.

There’s a golf course and you can find one of the most amazing view of the sunset from this location.

Did I mention that there are penguins, swans, and flamingos on site?

This location also offers its own Luau.

5 days in maui itinerary

When Is The Best Time To Visit Maui Hawaii

Is there really a bad time to go to Hawaii? 

Rainy season in Maui is from November to March, but it doesn’t rain continuously enough to spoil an entire day.

The rest of the year is considered dry season where it’s sunny and beautiful.

It might be tempting to think that it will be less crowded during the typical off-season which is wintertime in the mainland US, but it’s the opposite in Hawaii.

Maui is most popular during the wintertime in the mainland because everyone is trying to get away from the cold.

I am typically a very flexible and book everything last minute kind of person, but that doesn’t work very well in Hawaii.

If you know that you are coming during high season or anytime really, book everything months in advanced.

I personally recommend going during the summer specifically from May to September because the weather is incredible.

5 Days In Maui Itinerary: How Much To Budget?

I’m going to be honest and say that Maui, Hawaii is one of the most expensive places I have ever been to.

This is a splurge trip. 

There are ways to travel there on the cheap side, but unless you travel with a big group to easily split the cost and are super committed to cooking every meal, then you are going to end up spending a lot.

PER DAY PER PERSON BUDGETARY COST

Meals: $100 (Breakfast, lunch, dinner, snacks, and drinks)

Excursions: $100

Parking/gas: $20

Miscellaneous: $50 

Without considering the cost of stay and rental car/transport, I will conservatively say to budget $270 per day. 

Meals were on average $25 + tip.

For a 5 days in Maui itinerary, the expenses can definitely add up. 

Your pocket will definitely be lighter when you get home, but I promise you that it’s all worth it.

Of course you wouldn’t be going on excursions everyday. 

There are so many things to do, but realistically I recommend over budgeting than under budgeting.

How To Get Around In Maui

Although you’re in an island, Maui is quite spread apart. I highly recommend renting a car.

 

If you’re only staying in your resort or exploring the city, then you can get away with riding an Uber.

 

However, with how this 5 Days In Maui Itinerary is set up (it’s set up for lots of fun and adventure), you would want to rent a car.

 

Not just any car, I highly recommend renting a jeep, so you can take the top off and have the full Maui experience.

2021 jeep gladiator rubicon

We rented the 2021 Jeep Rubicon in particular, and it’s probably the most fun car I’ve ever been on.

I used to never care for rental cars or transportation (I’d rather walk most of the time), but for this 5 days in Maui itinerary, it definitely adds to the fun.

I rented from Turo which is a car rental version of Airbnb. 

Rent your transportation early when we were booking ours 2 months prior to departure, there was a car rental shortage because so many people were traveling to Hawaii.

Gas cost: about $55 for a full tank

To give you a rough idea, a full tank lasted about 2-3 days.

How Is Parking Like In Maui, Hawaii?

KIHEI

There is a lot of parking in Kihei, so that was never a problem.

LAHAINA

Free 3 hour Public Parking Lot near front street. They really do monitor the 3 hours, so make sure that you don’t overstay.

Address: 116 Prison St, Lahaina, HI 96761

Go to Republic Parking for public parking. I believe it was $3 per hour which was cheaper than the other neighboring public parking lots.

Address: 153-155 Dickenson St, Lahaina, HI 96761

ROAD TO HANA

I’ll discuss Road To Hana in more detail in the itinerary section, but parking in some of the sites here can be a bit difficult.

You might have to turn back around and wait because some spots are more popular than others or have a smaller parking area.

Most of the time, the parking spots are off to the side of the road.

Always keep on a lookout and be careful.

2021 jeep rubicon gladiator

5 Days In Maui Itinerary Day 1

GET SETTLED/ FREE BEACH DAY

Chances are, you had a 5+ hour plane ride from where you were to Hawaii.

My husband and I personally had a total of 7 hour plane time, while friends from NC had to travel for 10 hours.

Since you are probably tired and exhausted from travelling, I recommend having a chill flexible day to get acquainted with the time difference, check your Airbnb or hotel, and visit the beach.

  • If you’re traveling with a significant other, I have some recommendations here on how not to want to fight each other during this trip: SEE POST

Check out Kihei’s public beaches. The most popular ones Kamaole I, II, and III. While you are driving, you will see that the ocean is literally by the road, so you can easily bring a towel, park off to the side of the road and hang out by the water.

Kihei Food Truck Park. If you can’t decide what food to eat, the best way is to go to a food truck park. Food trucks in Hawaii are a part of the island life.

Address: 1 Piikea Ave, Kihei, HI 96753

Coconut Fish Cafe. For dinner, have some of the best fish tacos in the island of Maui.

coconut fish cafe
Kihei maui

5 Days In Maui Itinerary Day 2

LET THE FUN BEGIN

Take surf lessons. The majority of us have never gone surfing before, and I highly recommend Lahaina Surf Shack.

Cost per person for group lessons:

Our guide was so patient, relaxed, informative, and attentive.

If only our stay was longer, I would’ve continued on with more lessons.

The lesson itself took about 2 hours, and they provide everything from the rash guard, surfboard, as well as detailed instructions on what to do once we get in the water.

There were 6 of us, and we all were able to ride a wave at least 2 times.

Have lunch at Cool Cat Cafe. This restaurant was a really good lunch spot located in Front Street, walking distance from Lahaina Surf Shack.They had delicious fish sandwiches, Aloha burgers, Frosé (Frozen Rosé), and root beer floats.

Lahaina surf shack
5 days in Maui itinerary
5 days in Maui itinerary

Spend the afternoon walking around Front Street:

  • Banyan Tree– This was truly fascinating because each branch of this 150 year old tree’s branches would grow their own trunks. 
  • Old Lahaina Courthouse– If you want to learn more about Maui and Hawaii’s history. It’s free to go inside
  • Badass Coffee– For a little afternoon pick me up iced coffee, the owners were super nice!

There are plenty of stores in this area to buy souvenirs and get snacks.

After you’re done shopping and eating, time for some more adventure for this 5 Days In Maui Itinerary!

Head to Black Rock Beach to go cliff jumping or just lay on the sand and tan.

Getting to the actual cliff is a bit confusing, so make sure you ask for directions and there are lots of public parking in the area. The ones we found were about $3 per 30 minutes which seems to be a standard in Maui, Hawaii.

Honoapiilani Food Truck Park. Another day, another food truck. There are so many choices here from poke, pho, and from prime ribs to pasta. Eating from food trucks is the island way.

Address: 130 Kai Malina Pkwy, Lahaina, HI 96761

5 days in maui itinerary

5 Days In Maui Itinerary Day 3

ROAD TO HANA DAY!

Embark on the Road To Hana Journey.

This is an intense day of driving, so make sure you are well rested the day before! Lots of narrow windy roads and one way bridges.

You really have to commit an entire day to it because the drive itself is a journey on its own.

Imagine a 6 hour drive (to and back) up to the mountain and along the way, you can stop at different places for all kinds of adventures.

Think seeing waterfalls, hiking, beaches, swimming, and more all in one trip.

We started at 7 am and still was not able to see everything.

We grabbed some coffee and breakfast from Have Coffee in Kihei, but packed a lot of snacks and drinks.

It’s impossible to see everything, so make sure you prioritize the stops.

My biggest tip about this day is to download the Road to Hana Maui GyPSy Guide:

Worth every penny, and it’s only less than $10. 

It is basically an audio guide that provides tips and background about the entire Road To Hana journey.

If we did not have this guide, we would honestly not know where to stop and not have any knowledge of what we were passing while driving. 

The app also provides great recommendations on where to stop and prioritize. I’m not in any way shape or form affiliated with them, but our entire group really enjoyed the narration throughout the entire drive.

road to hana

Here are the stops that I recommend:

  • Ho’okipa Beach Park
  • Twin Falls
  • Keanae Peninsula
  • Keanae Arboretum for the eucalyptus trees
  • Aunty Sandy’s Banana Bread (great lunch stop)
  • Nahiku Market Place (you’re going to want coffee and some more food)
  • Hana Beach Park
  • Koki Beach
  • Wailua Falls (My favorite)
Unfortunately, we did not have a reservation nor the time to go to Black Sand Beach Waiʻānapanapa State Park 
 

Note that you need a reservation the day before, no same day reservation.

Reserve here: Waiʻānapanapa State Park 

If you have time, go to Haleakala National Park to visit The Pools at ‘Ohe’O because we arrived there at 4:45 pm and the park itself closed at 5:00 pm.

Enjoy some live music and dinner at Ohana Seafood Bar and GrillThis was such a fun way to end the night.

sail maui

5 Days In Maui Itinerary Day 4

BOAT DAY

Enjoy unlimited Mai Tai’s and Mimosas with Sail Maui. Who doesn’t love a day on a catamaran? We had originally booked the Lana’i Picnic Snorkel, but due to some limitations, we did Lana’i Coast Snorkel Tour instead.

Tour cost: $160 per person, about a 5-6 hour sail

This includes snorkel gear and reef safe sunscreen, breakfast, lunch, snacks, and beverages including mai tais, champagne, and beer.

The crew was incredible, and I would highly recommend it to everyone (unless you have terrible sea sickness then this might not be the right activity for you).

The views of Lana’i were amazing, and I also just love being on the catamaran.

It gives you the true vacation mode feeling. We also saw a couple of dolphins.

The snorkeling views was not as impressive since the waves were so big and strong that we could not in the main spots.

alihilani sau maui
ululates hawaiian shaved ice

Have lunch number 2 at Paia Fish Market. Bomb fish and chips and shrimp.

Enjoy the best shaved ice of your life at Ululani’s Hawaii Shave Ice. One of the things you cannot miss on this 5 Days In Maui Itinerary is trying the Shaved Ice from

They have several different locations throughout Maui, so you have no excuse.

When I tell you this is the best smoothest most memorable shaved ice I’ve ever had, you just have to trust me.

Enjoy a relaxing afternoon at the beach. We went to Po’Olenalena Beach since it wasn’t very crowded. Another choice would be Wailea Beach.

Check out Island Gourmet Market for dinner. You’re probably wondering why would you go to the grocery store for dinner, but grocery stores literally has best poke while we were there. Also, do not forget to try spam musubi.

poke maui hawaii

5 Days In Maui Itinerary Day 5

This 5 Days in Maui Itinerary is honestly so jam packed, I highly recommend treating this as a chill day to either enjoy your resort, but I will offer my suggestions.

Go Parasailing. Two of my friends did this and I almost regret not going because their GoPro footage looked incredible.

Cost per person: $110

Get a tattoo from Pacific Rootz Tattoo in Kihei. They are the oldest standing tattoo shop in Maui.

They accept walk-ins and make sure you ask for Francine Walraven.

Try Jollibee. If you have never heard of Jolibee, this is basically the Filipino version of McDonalds. Our entire group were Filipinos, and we really just had to.

5 days in maui itinerary
Keanae peninsula

6 Days In Maui Itinerary- Optional Day 6

This is an extended version of the 5 Days In Maui Itinerary, Optional Day 6.

Watch the sea turtles and go snorkeling at Ho’okipa Beach Park. This was our first stop in Road To Hana. Ho’okipa Beach is worth the stop if you don’t want to do the entire journey.

Have lunch at Tin Roof. They have Hawaiian food with a lot of Filipino influence. The line was super long, but for great reasons. Everything we had was super fresh and memorable.

Walk around Whaler’s Village. There are plenty of stores and restaurants here. Perfect for people watching. This shopping area is right by the water, so numerous people come here for the sunset.

Have a sunset dinner at Monkeypod. This is  only restaurant in Whaler’s Village the accepts walk-ins. The rest of the restaurants only have availabilities if you book 2+ months in advanced.

What’s with the crazy bookings?

It’s because most of the restaurants here are by the water which provides the most amazing view of the sunset.

I suggest getting seated by 6:30 pm to catch the view of the sunset. We only waited for about 20 minutes while some of the reviews mentioned that sometimes the wait could be up to 2 hours.

5 days in maui itinerary
5 days in maui itinerary

7 Days In Maui Itinerary- Optional Day 7

SAD DEPARTURE DAY

Since we only had a few hours late, I spent the entire morning walking on the beach (it was only about 20 steps from the location of our Airbnb that I mentioned above).

Grab some caffeine and breakfast at Hawaiian Village Coffee.

Check out Leoda’s for some local pies and brunch. While I was planning this trip, all the tips suggested to not leave the island without going to Leoda’s to get pies. Truthfully, the pie that we got was not the best (maybe we should’ve gotten a different kind), but I recommend also trying the Ahi tuna sandwich because that was an incredible last meal in Maui.

There’s a souvenir shop right next to Leoda’s if you needed to do some last minute shopping like we did.

You can never have enough Ululani’s Shaved Ice. We went a second time because it was just that good.

5 days in maui itinerary

Other Activity Suggestions In Maui

If you’ve made it this far in my Maui Itinerary, thank you so much for reading.

Feel free to follow, pick and choose, or completely ignore everything that I mentioned here.

It won’t hurt my feelings. Everyone travels differently. 

Depending on your accessibility, time, schedule, and comfort zone, you will like other things.

Here are my other suggestions of things you can do while in Maui:

Go to a Luau. I received mixed advice when it came to seeing a Luau, which is why we didn’t prioritize it, but one of my friends really loved the Luau at Hyatt Regency Maui Resort and Spa. It includes dinner and drinks in addition to the show itself.

Book a Sunset Cruise in Lahaina. While we were at Whaler’s Village by the ocean, I saw multiple cruises during sunset. It’s such a good idea to book one as an alternative to fighting for a table in the restaurants. At least on a sunset cruise, you are guaranteed a front seat to watch the sunset.

Go snorkeling. Even though snorkeling was a part of our boat tour, you might prefer a cheaper option or to not be on a boat at all. I recommend renting your snorkeling gear instead and check out different beaches. Water rental places should be available all around Maui.

Watch the cloud inversion in Haleakala National Park. This was one of the spots that we missed out on during Road To Hana. Numerous people go during the sunrise (note that you will need a permit). If you can’t get a permit, I heard that the view during the sunset is just as good. The Pools at ‘Ohe’O is also located here, so don’t miss that!

Hike the Iao Valley State Monument. This one is a super short hike that we missed because we already had such a packed itinerary and also wanted to rest.

5 days in maui itinerary

Maui Travel Tips

Here are some planning tips when visiting Maui, Hawaii:

  • I am the biggest advocate for winging everything and booking things last minute, but since Maui is so popular, you really have to book everything in advance especially accommodations, restaurant reservations, and car rental.
  •  Most of the most popular nice dine in restaurants in Lahaina are reservation only, some you have to reserve 2 months in advanced. Monkeypod takes walk-ins.
  •  If you did not have the time to reserve a table at a restaurant, order to go and eat by the water.
  • If you are looking for fresh Lei, you can find them at in grocery store in the fridge section. We found ours at Times Supermarket. The specialty Lei stores usually sell them for $40+ but ours was only about $15.
  • For Road to Hana, download the Road to Hana Maui GyPSy Guide App. Such an entertaining and helpful guide
  • You will find the best poke from grocery stores. We had poke from food trucks and restaurants, but the best and cheapest one came from Island Gourmet Market. This grocery store also had souvenirs, liquor, and more. 
  •  For the ultimate fun experience and have the means to, rent a Jeep. Don’t even question it. You have to.
  • Protect the ocean. If you are getting in the water, make sure you are using reef safe sunscreen.

Other Posts To Check Out

I hope this 5 Days In Maui Travel Guide is helpful for you.

Whatever you decide to do in Maui, it is guaranteed that you will have the time of your life.

It’s an absolute paradise, and I found myself not wanting to leave.

I now understand why some people come back to this place over and over.

Let me know if you have any questions!

Do you have other recommendations when visiting Maui, Hawaii?

Have you been to the other islands?

PIN FOR LATER 

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2 Comments

  1. Great blog Gian! I was wondering if you received any backlash due to the mass influx of visitors to Hawaii and particularly to Maui. A friend of mine has been circulating an IG post about locals not wanting visitors and even the Mayor of Maui begging airlines to stop selling tickets. I know my aunt didn’t want us to go to Hana because there was tourist violence but it was super disheartening seeing the post my friend shared. Just wanted to get your feedback and see what type of reception you’re getting. This was a great blog to follow for Maui pre-COVID. Will you put any COVID restriction notes on the blog?

    1. Thanks for this! Yeah, I made sure to post some precautions on my ig stories specifically some from Aja Dang & have not received backlash. I am not posting precautions on the blog post itself since it’s an evergreen post and the restrictions change all the time and don’t want to mislead anyone. It would also be unfair for us to tell people not to go when we both went.

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