Fun 4 Days in Maui Itinerary: Native Hawaiian Businesses

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My first trip to Hawai’i, specifically to the island of O’ahu, was simply transformative. However, for a lot of reasons, I didn’t think I would be returning to the islands for quite some time. Partially because of the price, yes, it’s very expensive and the only way I swung my first trip was by crashing on a friend’s couch and borrowing their car. Another big part was an ethical reason, which I’ll get into later. So, to my surprise, my last trip of 2024 was spending 4 days in Maui.

*note, if you don’t care about me and just want a 4 days in Maui itinerary, pls feel free to skip ahead

So what happened?

The Maui Tourism board reached out to me.

NO NO NO NO, it’s not what you’re thinking. As you may remember, Maui suffered a devastating fire season in 2023, with one of the biggest fires decimating the historic town of Lahaina and surrounding areas. The Lahaina fire resulted in 102 confirmed deaths with a handful of individuals still missing. Over 2,200 buildings were destroyed, the vast majority of which were residential. The “experts” value the total damage of the fire to be in the 5-6-7 billion dollar range but…in my humble opinion, there is not dollar equivalent.

The lives, the history, the land and environment.

Again, there is no dollar amount.

While we could have a WHOLE discussion on they hows and whys of fires becoming more prevalent and destructive over the years, I don’t wanna get too sidetracked. In light of the fire, I was involved in a few various relief fundraisers for the Maui/Lahaina fire in 2023, mostly here in Oregon (there is a large Hawaiian and Polynesian community) with various organizations but also supporting a friend’s fundraiser who lives in Hawai’i.

Fast forward to 2024, 6 months after the fire, a PR consultant for the Hawai‘i Tourism United States and Maui Visitors and Convention Bureau reached out to invite me to a virtual conference for updates on Maui’s ongoing recovery. It was unfortunately on a workday for me, so I couldn’t confirm attendance, but we kept in touch and exchanged information and resources via email. They also introduced me to folks from other organizations such as Maui Cultural Lands and Hawaii Farm Project.

Fast forward again to December 2024 and after months of learning more about Maui and Hawai’i tourism, and a REALLY good flight deal, I decided to spend 4 days in Maui with the intention of experiencing and highlighting into Native Hawaiian owned businesses in the tourism sector.

When I relayed my plans back to my connections with the tourism boards, they were very excited and even offered to sponsor my trip. However, I decided to PAY for my 4 days in Maui with my own money. No part of this trip ended up being sponsored, but I do appreciate their offer and continued collaboration with me as I explore what Hawaiian means…and what it could mean in the future.

When to Visit Maui

Okay whoops, I droned on a bit longer than I intended to. Now, your reason for visiting Maui will…most likely not be the same as mine, haha, but eventually we end up at the same point. Visiting Maui.

In terms of WHEN to visit Maui in the calendar year, I’m of course not the expert but word on the street is that the “best” months of April-May, September-November have the most comfortable weather (upper 70sF/24-27C) with less rain. I mean, it’s really splitting hairs at this point because it’s pretty solid year round, but if I had to pick I’d go with September or October for the highest chance of clear skies and slightly warmer temperatures as a personal preference.

I visited in December, which is the beginning of the winter season (December-March) and higher crowds due to winter holidays, but the temperatures were still comfortable but with some sporadic showers. While winter is generally the rainiest season on Maui, it is also the best time for surfers because it makes for better waves. In contrast, the waves are typically calmer in the summer, with slightly higher temperatures (80sF/27-32C), but crowds pick up in summer as well.

Of the Hawaiian islands, Maui typically has the most expensive hotel rates on average, but restaurants and grocery items were cheaper than O’ahu (for example). So definitely have that price range in mind as you budget for your 4 days in Maui!

Where to Stay on Maui

Maui is a pretty compact island, so if you plan on renting a car then the location doesn’t really matter as much as the hotel – and I’ll recommend a few Native Hawaiian owned hotels in a minute. However, if you won’t have a car, then the area might have more of an importance.

Throughout your eventual 4 days in Maui, if you want to check the weather I recommend putting the city or town you plan on visiting. If you just put in Maui, you’ll get the average for the island, but different sides of the island can experience drastically different weather so you’ll want to be more specific. And that goes for all of the Hawaiian islands! In general, the leeward side of the Hawaiian islands will be warmer and drier, and the windward sides will have a higher chance of rain and cooler temperatures.

For Maui specifically, the leeward side will include areas such as West Maui (Lahaina and Kapalua) and South Maui (Kihei and Wailea). It’s is also where you’ll find the bulk of resorts on Maui, so there’s also higher prices and a bit more crowds, especially since Lahaina is still in recovery. Kahului, where the airport is, would be on Maui’s windward side so a slightly higher chance of rain but there are a lot of shops and restaurants and attractions in this bigger “city” environment (and slightly cheaper prices).

Best Hotels in Maui

Okay so now that you have a metaphorical lay of the land – where should you stay in Maui? I found two Native Hawaiian owned hotels on Maui that you should base your 4 days in Maui around.

Book on: expedia | booking

The first, on the leeward (dry) side of Maui is The Mauian. While its technical address is in Lahaina, the hotel is closer to Kapalua. On my trip, I didn’t visit that side of Maui but this is a great hotel if you would like to station yourself there. Aside from being Native Hawaiian owned, the hotel also has NO RESORT FEE and FREE PARKING, which is major for Maui.

The guest rooms are “distraction free” and do not have televisions, stereos, or phones so visitors can more easily unplug and enjoy each other and the beautiful scenery. That said, they do have a shared space that offers television with vcr/dvd player and a library of books, games, and movies.

Book on: expedia | booking

The second is Maui Seaside Hotel in Kahului over by the airport. Super convenient, one of the more affordable hotels on Maui, AND it’s beachfront. They are currently under renovation (I highly recommend booking a renovated room – they’re so nice!) but even their older rooms are clean and comfortable. While there is a resort fee ($20 USD/day) and a parking fee ($15 USD/day), it is much cheaper than the average hotel on Maui. Plus, they’re currently running a discount on their renovated rooms that includes free parking and free amenities if you book directly from their site.

The hotel is right in the action of Kahului, so if you don’t have a car you can easily walk or catch a rideshare to all of the yummy restaurants and fun attractions in the area. The real highlight of this hotel is the incredible staff – they truly embody the essence of Aloha and have the best recommendations for whatever you’re looking for.

Both hotels also offer various discounts for AAA members, veterans and active military, and local Kama’aina/Hawai’i residents. Book one of these two hotels for your 4 days in Maui!

Flights

Imma be honest, I can’t help ya too much with the flights. Unless you’re coming from the West Coast USA…the flight is probably going to be expensive too. However if you ARE coming from the West Coast, you can get some really great deals.

My go-to airline is Alaska Airlines, and if you live on the West Coast, you should get into them if you haven’t already. I was able to score plane tickets for my 4 days in Maui for under $200 (~$178 I think) USD ROUND-TRIP because Alaska had a surprise sale. But even freak sale aside, you can find flights from major West Coast airports (LAX, PDX, SEA, SFO, etc) to Maui for $300-$350 roundtrip pretty frequently if you’re keeping an eye on it.

On that note, if you’re a frequent flier of Alaska, I highly recommend getting their airline credit card (visa). They have one of the best mileage programs for West Coasters and you also get an annual companion pass where you and a +1 can fly anywhere Alaska flies BOGO. My first trip to Hawai’i, I used a companion pass which came out to about $250 each round trip!

I’ve also flown to the Maldives, Qatar, China, the UAE, Jordan, Japan, (and South Africa and Fiji upcoming!) COMPLETELY USING ALASKA POINTS. So well worth the investment in my humble opinion.

Daily Itinerary

Alright, enough with the prep talk. You’ve booked your flights, reserved your hotel, packed your bags, and you’re ready to jump straight into your 4 days in Maui. Now…what do you do? Don’t worry, I’ve gotcha! I’m gonna give you a day-by-day itinerary for what to do for 4 days in Maui while supporting Native Hawaiian businesses.

Have fun, of course, but your tourists dollars mean so much more that way.

One more note before we get into it: renting a car is my personal preference, you just get a little more physical freedom that way, but it isn’t completely necessary if you’ll only have 4 days in Maui. Either way, I’ve structured this itinerary so that each day places you on one area so you’re not driving/uber’ing all over the place!

Day 1: Arrival/Kahului

Your first day will definitely differ depending on what day and time you arrive, but the MO is the same: ease into Maui. You have 4 days in Maui, take the first day easy.

You’ll be flying into Kahului (I’m…assuming), so let’s start there. Super convenient if you’re staying at Maui Seaside Hotel, you can head over and check-in/drop off your bags if it’s too early.

Lunch/Dinner (depending on arrival)

I wasn’t able to verify many restaurants in Kahului that are Native Hawaiian owned, so the following suggestions are restaurants that are locally owned and super tasty!

• Sparky’s: Native Hawaiian owned AND DELICIOUS AT THAT!! Serving both classic and creative Hawaiian food, swinging by Sparky’s is the perfect welcome to your 4 days in Maui! I flew in on a Sunday and they were closed, but they’re not far from the airport and on the way to Maui Seaside Hotel!
• Kalei’s Lunchbox: Talk about a classic Hawaiian plate!! You can get all of the staple Hawaiian flavors in one place, and they give you a LOT of food. It’s great for when you’re just hopping off the plane starving (that’s where I went).
• Tin Roof: heads up, there’s no indoor dining with just a few small tables on the patio, but it was one of my favorite meals on the island. Highly recommend their poke of the day and their mochiko chicken was equally delicious. I recommend ordering in advance though because the line can get long! (though I recommend going on day 2)
• Tiffany’s: Owned by the same dynamic duo behind Tin Roof, Tiffany’s is a sit down spot with a good amount of tables so very large group friendly. We got a good spread (2 apps, 2 entrees, 1 rice) and everything we ordered was an 8.5/10 or above, but the butterfish truly stole the show!
• Balai Pata: I didn’t get to this restaurant, but a lot of my friends highly recommend it. The menu showcases Filipino cuisine in the context of Hawai’i and everything sounds absolutely delicious.
• Costco Food Trucks: Last but not least, if you need a quick but delicious bite, there’s a number of food trucks in/near/around the Costco parking lot and is conveniently close to the airport!

Turn in Early for the Night

After you eat, settle into your hotel, wash all the airport germs off of you, and just relax. Breathe. Unpack and go sit by the pool or a walk along the beach. I’d recommend taking the rest of the day (or night) to unwind. Your 4 days in Maui are going to go quick, and the itinerary only gets busier from here.

We so often forget to actually take a BREAK on our breaks, and then we’re confused as to why we’re tired when we go back home and to work. So chill out and go to bed early. You’ve got a busy day ahead – and a busy 4 days in Maui!

Day 2: Kahului (or Lahaina)

If you’re staying at the the Mauian, day 2 will be a good one to hang out in Lahaina and Kapalua. However, since I didn’t visit those towns and Lahaina is still recovering, I can’t give great updated suggestions. In the meantime, staff at the Mauian can give you the best insight on what to do and where to eat!

However if you’re staying in Kahului or want more time to check out the town, let me walk you through it. I recommend waking up early on your second day so you can do one of the most unique and special activities during your 4 days in Maui!

Breakfast

SixtyTwo MarcKet has great seasonal breakfast, and open early which is exactly what you need today! Their menu changes and tweaks itself through the season, but they are known for their crepes and eggs benedicts. It’s a great introduction to your first full day of your 4 days in Maui.

Morning Activities

• Traditional Lei Making: This activity is the highlight of day 2. The hosts Pihanalani and Hoku are Native Hawaiian women who started their experience to give tourists a more grounded knowledge of leis and what they really mean. I did a full write-up of this traditional lei making tour, but the gist is that it is amazing and the hosts are incredibly sweet!
• Native Intelligence: After your tour, head over to the store Native Intelligence, a store that carries all Native Hawaiian owned brands and souvenirs! I picked up teas, a hair clip, and a few gifts for friends. I also highly recommend their jewelry items, they were the most unique and beautiful I saw while in Maui. Depending on when you finish breakfast, you could also go here before the lei making tour because it is close to SixtyTwo!
• Maui Nui Botanical Gardens: If you still have stamina before lunch, you can head over to the nearby botanical gardens before leaving the area. The gardens are a nonprofit dedicated to the protection of Maui Nui’s rich native plants and cultural heritage. The gardens also hire local cultural practitioners to demonstrate and teach their crafts (like xeriscaping) to visitors and your ticket prices directly goes towards the preservation of Native Hawaiian Plants and supporting Garden partners with the local schools, hula halau, and other civic and not-for-profit groups.
  

Lunch

You’ve probably worked up quite the appetite. For lunch, chose any of the spots you didn’t get to yesterday, but personally I’d recommend Tin Roof if you didn’t go on Day 1. Geste Shrimp Truck (or any of the Costco parking lot food trucks honestly) are another great option! Order in advance and take your food to a nearby beach to eat delicious food with a great view!

Afternoon Activities

Whether you grabbed your lunch to go or not, the beach that I went to was Ho’aloha Park. One, because I saw they had picnic tables, but also because it’s a great location and really close to Maui Seaside Hotel if you want to pop back into your hotel room to freshen up (or take a quick nap).

While the water is nice and you’ll see lots of folks canoeing and wind-surfing, it’s not my personal preference to swim at this beach just because it is right off the harbor. There are sand volleyball pits and the beach isn’t very busy so you can have a peaceful stroll. Occasionally, there are sea turtles, but please keep a respectful distance and don’t disturb them!

You could honestly spend the rest of the day at the beach, but if you want a change of scenery or just need to cool off, here are some suggestions! You have a whole 4 days in Maui, trust me there will be a lot more beach!

• Queen Ka’ahumanu Center: I love a good mall stroll. At this one in particular, make sure to swing into Na Koa Brand, a Native Hawaiian owned store, that sells clothing and accessories. Their snapback are SUPER cute. You’ll also find Cat Cafe Maui, a cat cafe where you can enjoy both drinks and…well, cats. All of the cats are adoptable and the cafe hosts fun events that involve painting, yoga, movies, crochet, or even bingo!
• Maui Specialty Chocolates: I personally don’t like chocolate, but my friend who moved from Maui said she always picks up chocolates from this family owned shop when she goes back to visit.

Dinner

Refer to the list from Day 1, though I’d lean towards Tiffany’s or Balai Pata for dinner. You can, and if it’s busy when you’re visiting SHOULD, make reservations to both of these restaurants. However, the week I visited was slower than normal (according to some local residents) so I was able to walk into Tiffany’s and get a table for two without waiting.

But again, that all depends on crowds, when in doubt, make a reservation or call for availability a few hours ahead! You can also go back to restaurants you enjoyed the day prior – feel free to “repeat restaurants” throughout your 4 days in Maui! I’m just here to give you options 🙂

Night Activities

In contrast to O’ahu, Maui is pretty quiet when it comes to nightlife. I’m not much of a drinker, so I wasn’t seeking out the bar scene anyway, but I think it’s still good to mention in case you might be expecting a livelier night out in Maui.

In Kahului, and most of the towns in Maui, I found that the vibe after dinner is more of a relaxed atmosphere. If you want to stroll around a bit before heading to bed, you can walk the dedicated (and well-lit!) path at Kaanapali Beach, and there’s also a shopping center with desserts and whatnot. Very cute.

You should also check the calendar for the Maui Arts & Cultural Center (MACC) for any shows or performances they may have during your 4 days in Maui. I’d also recommend stopping into a convenience store or grocery store, because Day 3 begins earlier than breakfast.

Day 3: The Road to Hana

RISE AND SHINE travelers, today you’re going to Hana!

Hana is a small town on the eastern end of Maui, and is one of the most isolated communities in all of Hawai’i. Why? BECAUSE ITS WORK TO GET TO IT. The town is nestled in the rainforest lining the island’s rugged coastline cliffs, with only a one-lane narrow road to get you there. The “Road to Hana” has become THE biggest tourist attraction in Maui because it is absolutely beautiful, if not harrowing – though that might actually add to the attraction.

Technically, you can drive the Road to Hana on your own, but here me out. The best way to experience the Road to Hana during your 4 days in Maui is by taking the guided Hana and Beyond Tour. They are a Native Hawaiian owned tour company on Maui with a vision for regenerative tourism on the island. I cannot give enough praise for my experience with them (check the linked review of my tour to get more in-depth), and by taking a guided tour you are decreasing the amount of traffic congestion on the road and freeing it up for residents, road and utility workers, and emergency vehicles.

Plus, again, the Road to Hana CAN BE harrowing. Even though we did have a rental car during our 4 days in Maui, it was still wayyy worth it to take a tour. I saw a car hit another one on the road while on our tour. You do not want that rental company fine, okay? You also get the added benefit of getting a local and decolonized perspective of Maui (and Hawaiian) history and cultural context. It’s really dope.

They’ll pick you up sometime around 6am and you’ll be on the tour until about 4pm – so pretty much all day. Lunch and water/soft drinks are included, though I recommend bringing snacks if you get peckish.

Once you’re back at the hotel, take the rest of the day to relax, maybe grab a quick bite or go for a chill stroll, and call it a day.

Day 4: Kihei/Wailea

Day 4 is fun. If you’re only staying 4 days in Maui, then this is your last day to really take in the island, and taking in the island is exactly what we’ll be doing. Again, I’ll note restaurants that are specifically Native Hawaiian owned!

Breakfast

You could get breakfast at your hotel, but I’d recommend heading down to Kihei for a bite to eat at the famous Nalu’s South Shore Grill. I’d also recommend getting there as close to opening as you can. There are no reservations and they may close down online ordering if they get too busy. If you arrive and there’s a long line, don’t panic. You have to order before you are seated.

The food is absolutely delicious, and if you haven’t tried the Hawaiian loco moco dish yet, this is the spot to do it. Their omelets and acai/fruit bowls are also super tasty!

Morning Activities

Why not start the day off with the coolest thing you can do in Hawai’i? SURFING. I mean, you’re spending 4 days in Maui, get your shaka on! Aloha Ocean Adventures is a Native Hawaiian owned surf company that offers small group and private lessons in Kihei. They are a family run businesses and are great with kids and younger people, but are also kind and reassuring to the young at heart with absolutely no experience whatsoever.

It is the best introduction surfing and furthering your surfing skills. They also offer added context to the sport from the lens of Hawaiian history, and even do “surf safari” or surf excursions for folks who are more advanced. For that though, you’d definitely need more than 4 days in Maui to really get into the Indigenous surfing experience. But you can definitely get a taste!!

Lunch

For lunch, I have a few suggestions. You only have 4 days in Maui, so I won’t blame ya if you get a lil somethin’ here and a lil somethin’ there. Hint hint. Nudge nudge.

For vegans or those wanting a break from meat, there’s Earth Aloha Eats just across the street from Kalama Park. If you want to double down on meat (I mean, you just finished surfing all morning!), Da Kitchen is a super tasty spot serving up classic Hawaiian plates. There’s also Kinaole Grill Food Truck which is DELICIOUS, but just a heads up, there can be a bit of a wait so I wouldn’t go if you’re absolutely starving, but it is more than worth it.

Or, for something lighter, and one of my favorites, 808 Sugar HI for an incredibly refreshing acai bowl. Though, if you run into an Ululani’s Hawaiian Shave Ice during the rest of the day, stop whatever you are doing and grab their shave ice!!!

Afternoon Activities

There are beaches up and down Kihei into Wailea, so it’s another great day for chilling at the beach. Like, you could spend the rest of the day basked out at one, or you could beach hop to keep it fresh and flirty. End out your 4 days in Maui the same way you started. RELAXING.

While going up and down the beaches, you’ll come across various markets depending on the day. For example, Kihei Swap Meet (Mon-Sat) and the Maui Gift & Craft Fair (Wednesdays). You can find some great artisan crafts and jewelry. I was able to buy some super cute rings AND support small businesses.

If you’re not much a beach person (I’m not, yes even tho I spent 4 days in Maui haha), so after some time I headed over to the Shops at Wailea to…well, continue strolling around but now swapping the ocean view for random shops and knickknacks. The Shops at Wailea are FANCY, but even if it’s not in your wallet range, it’s a good window shopping experience.

Dinner

Ah and last but not least, let’s close out our 4 days in Maui at one of the coolest spots in the area. The South Maui Gardens. It is a huge “food truck” area, but the space really lives up to its garden name. Everything feels super spacious, it’s kid friendly, and there are a variety of cuisines available to perfect for big groups. They even host hula shows and events (both free and ticketed) so be sure to check the calendar for during your 4 days in Maui, you might have to rearrange when you visit Kihei!

Now as to dinner, remember back in Kahului when I mentioned Sparky’s? Well they have a food truck in the South Maui Gardens!! Since I wasn’t able to visit in Kahului, I was elated to learn they had a location in Kihei, and since their menu is so huge you can try more items and pair it with bites from other trucks.

Conclusion

Okay honestly…is 4 days in Maui enough?? Well…not really. Although the island is small, there is still SO MUCH to do. There’s still Haleakalā National Park, various state parks, and Lahaina (if you didn’t make it over). The Maui Humane Society also has a program where you can volunteer to hang out with a shelter dog for a day and take them out on the town for some fun and exercise. It’s super cute, though I found out about it too late to sign up.

Hopefully this list has given you a lot of direction as you plan your 4 days in Maui, and I hope on your visit you prioritize supporting Native Hawaiian businesses and show that we visitors CARE about the history, culture, and people that make Hawai’i HAWAI’I. Not only do we care, but we put our tourist dollars where our mouth is.

Again, it’s the least we can do if we visit Hawai’i. I’ve seen some multi-day tours that promote Native Hawaiian businesses to their guests, but they lock that information behind a wall unless you sign up for the group tour. They say that you can’t learn about Native Hawaiian history or culture UNLESS you visit the islands with their company (which of the ones I’ve seen are not Native Hawaiian owned btw). I HATE THAT.

I don’t believe in gatekeeping Native Hawaiian businesses from visitors. If you are going to visit Hawai’i at all, you should have the information and resources readily available to support Hawaiian businesses. Point blank simple.

Anyways, don’t get me started because this post will never end hahah. Let me know what you’d like to do during your 4 days in Maui. Anything glaring (aside from the National Park!) that I missed? If you know of any other Native Hawaiian owned businesses that visitors (and residents) can support, let me know in the comments below!

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