5 Glorious Days Sightseeing in Maui: Prettiest Areas & a Luxury Beach Resort
Maui, Hawaii is the second most visited Hawaiian island and for good reason—there are so many beautiful areas for sightseeing, Hawaiian activities and attractions, and luxury resorts on the beach.
We tacked on five days in Maui after visiting Big Island and loved both islands, but for very different reasons. Maui was the perfect place to relax and just enjoy the prettiest areas on the island after an adventure-filled road trip around Big Island.
We spent a lot of time at our resort, but we did still see a great deal of the rest of the island, which was a good balance of taking it easy and enjoying the rich culture and sights in Hawaii.
From a helicopter tour to a Luau to a luxury resort, here is how we spent five days sightseeing in Maui, Hawaii.
Overview of Maui Sightseeing Activities
We stayed at Wailea Beach Resort - Marriott, Maui, which is a beachside luxury resort. This post is not sponsored, but I will be talking about Wailea Beach Resort a lot because it was an awesome place to stay and we spent a lot of time there.
The location was great—close to some of the prettiest areas in Maui, including several beaches, Kihei (a town with many amenities), and within not too long of a drive from the airport, mountains, and other Maui tourist attractions.
We easily got around with Uber for most of the activities we did and rented a car for one day to take a longer, more remote drive.
Since we explored Maui after Big Island, we flew in from Hilo to Kahului Airport (OGG), which is the main airport on the island, close to the city of Kahului and with an abundance of rental cars and Ubers/Lyfts.
Our trip was in September, which made flights, accommodations, and activities much cheaper than when we were originally going to go in July. Plus, there were fewer crowds and the weather was absolutely perfect!
Day 1 - Helicopter Tour & Luau
We rented a car on Big Island through Discover Cars, but on Maui we weren’t anticipating much driving, so we planned our first day strategically.
Something that has been one of my interests for a long time is taking a helicopter tour and Maui is an iconic place to do that! Most of the Maui-based companies offering helicopter tours are very close to the airport, so we got a short Uber ride there instead of getting an Uber back and forth from our Wailea resort to Kahului.
The helicopter tour was booked with Air Maui, which was actually one of the cheaper tours available, but still with great ratings. I chose the West Maui & Molokai tour, which was great—from the informative and entertaining pilot to the safety I felt to the gorgeous scenery below.
The tour featured the seashores and rocky cliffs of west Maui, the lush green valleys of Molokai, the eighth tallest waterfall in the world, and a sprawling view of the ocean. When we got to the highlight of the tour—Pu'uka'oku Falls, a 2,756-foot waterfall surrounded by surreal green cliffs—the pilot made sure we all got a great view by expertly maneuvering the helicopter around.
During the flight, the pilot said each of our names and included us in his jokes. After, I realized that he was recording the whole flight and the recording, along with videos and photos, were available to purchase.
After our tour, we took an Uber to Wailea Beach Resort and got ready for the Te Au Moana Luau!
Arriving to Wailea Beach Resort after a scenic Uber ride was immediately relaxing. We were greeted with POG (passion-orange-guava juice) and a lei and then able to walk around the gorgeous grounds. Wailea Beach Resort offers the luau right on their property, which is one of the highest rated luaus in Maui and one of the most quintessential Maui tourist attractions.
The luau starts before it gets dark, which means that we got to experience a breathtaking sunset in one of the prettiest areas in Maui while sipping on mocktails. Several activities were set up around the dining area, including flowers for women to put in their hair, temporary tattoos for men, and games for children.
After it got dark, the fun really began. The roasted pig was showcased and a beautiful performance with Hawaiian singing and dancing commenced. And of course, the most important part—the food!
We were at a table with two other groups and the table was set up family-style, which made it a bit awkward because we were mostly strangers, but there was plenty to go around. Some of the best foods included the ahi poke, the mango basil dressing, the kalbi short ribs, and the pineapple. However, for how expensive the luau was, most of the food was pretty disappointing. The meats were dry, the sides were bland, and the desserts weren’t very good.
If we go back to Maui, I would try a different luau, but I still did enjoy Te Au Moana, mostly for how beautiful the scenery and performances were.
Where to eat:
Doesn’t he look hungry?
We mostly snacked throughout the day, saving our appetite for the luau, but here are some great options around the airport and helicopter pads.
I desperately wanted to try the garlic noodles and pork belly here, so if you go please lie to me and tell me it’s not worth it and I’m not missing out on anything.
Seafood and Japanese food in Hawaii are incredible and this food truck looks fresh and filling. Steak and lobster to go please!
We ate a lot of authentic Hawaiian food in Big Island, and this place looks on par with where we ate, with everything from loco moco to chicken katsu and coconut cake.
Day 2 - Kihei & Beachfront Resort
After roadtripping in Big Island and then having an early flight to Maui, followed by a day of activities, we decided to finally slow down and take it easy at Wailea Beach Resort. I highly recommend at least a day or two of relaxing in Hawaii—just soak up the prettiest sights from a beach chair or poolside cabana, instead of stressing about getting somewhere and doing something. (I’m really telling myself this—most people I travel with, including my husband, prefer to relax much more than I do on vacation!)
Luckily, our resort offered so many ways to relax and was within a very short walking distance to two incredibly scenic beaches. We decided to visit Wailea Beach, with its soft golden sand, gentle waves, and views of other Hawaiian islands in the distance. Our resort offered free beach chairs to sprawl out on, which we took full advantage of.
We also visited Kihei this day, mostly to eat and go to church. It is a relaxing town, right off the beach, and a launch point for many tours, including the famous Molokini Crater snorkeling and scuba diving site.
We returned to our resort though, swimming in the adult-only pool, going down the water slides in the family-friendly swim area, playing life-size chess, swaying on the swinging chairs, and walking the beautifully-manicured grounds.
Where to eat:
Kihei has some really great food worth checking out!
We had brunch here, which I really enjoyed. I got the hamburger loco moco and my husband ordered the banana macadamia nut french toast, which were both really good. All the food looked good, honestly. Just don’t feed the chickens roaming around!
This place was kinda hard to find, but it is so worth it! There are tons of food trucks set up in the beautiful South Maui Gardens, offering everything from Hawaiian shave ice to tacos and Thai food.
Day 3 - Snorkel & Bike to Makena Beach
Day three was supposed to be another easy beach day, but I got a bit ambitious with our plan and it ended up being our most exhausting day—but a very memorable one!
I started my day with a free yoga class on the lawn overlooking the ocean. It was so relaxing and lovely—except when I saw a sea turtle in the water. I got so distracted when it turned over in the waves and seemed to struggle getting back upright. No one else noticed the turtle, so I was rooting it on in my head while also trying to follow the yoga steps. Luckily, the turtle righted itself and all was well and I was able to focus again and finish the session peacefully.
Wailea Beach Resort offers free bike rentals for two hours, but hardly anyone seemed to use them, so we had them for twice that amount of time and they didn’t seem to care.
We set out on our bikes in the mid morning and headed for our first stop: Makena Landing, a great snorkeling spot near Turtle Town. Yes, I wanted to go there because it is the closest thing to my name than any other location I’ve seen, but it was one of the prettiest areas in Maui so I’m glad we went!
The parking was very crowded, mostly with locals who had the day off for Labor Day, so we were glad we brought bikes. However, that meant we had to stash our stuff somewhere where it hopefully wouldn’t get stolen. A friendly local woman who was having a family gathering noticed us and promised to keep an eye out for our stuff while we snorkeled!
The water was very clear and gentle, so snorkeling was easy to handle (much easier than our snorkeling at Two Step in Big Island), including the entry point which was a small beach. We saw a sea turtle and lots of beautiful fish and coral.
After snorkeling, we hopped back on our bikes and headed further south to Makena Beach. Years ago, someone heard my name and told me the most beautiful beach in the world shared the name. When we arrived, I was very pleased to see that the beach was not crowded at all and was, in fact, very beautiful—definitely one of the prettiest areas in Maui!
Makena Beach is fairly remote, so no buildings or signs of civilization could be spotted from the gorgeous golden sands, and it was enclosed with a cliff on the north side. Honestly it was the perfect place to relax before our ride back.
Overall, the bike ride was around 10 miles, with many hills, so we were pretty tired when we returned. Next time, we’d probably opt for an Uber, but the experience was definitely memorable and the road from Wailea Beach Resort all the way to Makena Beach was stunning!
Where to eat:
Wailea Beach Resort has several restaurants and all but one were really good. The bad one? Andiamo Pizza. It did not hit the spot in the way we were hoping after a long day, while we cuddled up watching Lilo and Stitch in our hotel room. Here are better places to try.
Between yoga and the bike adventure, we ate açaí at this bar by the ocean. The açaí was fresh and beautiful and energizing for the long day ahead! Other breakfast options there include smoothies and banana bread.
Wailea Beach Resort has one of the best restaurants we have tried together. We started sharing a sushi roll and then I got the rich and creamy truffle ravioli which blew me away. My husband got the herb-crusted ono fish. We both loved our meals, but did not share entrees—I don’t like most fish and he doesn’t like mushrooms, so it was a win where we both got to savor every bite!
Day 4 - Surf Lesson & Haleakala
I did ride a few waves, but the lesson mostly looked like this—my husband as a pro and me to the side admiring his skill.
Day four was packed with adventure, including both of our favorite Maui tourist activity: surfing! We rented a car this day from our hotel and hit the road.
I had never been surfing and my husband only has briefly, so we took a surfing class with Maui Wave Riders in Kihei. They were very organized and efficient, teaching us techniques before we got into the water and then helping us master them in the water. The waves were small, so it made the setting for newbies like us very low key.
I learned to stand on the board (“eyes up!!”), turn, and paddle back to the start of the waves. I’ll admit, I was pretty terrible, but I did manage to ride a couple waves and had so much fun learning a new skill! To top off the experience, we saw a sea turtle swimming near us and a photographer on the beach captured photos of us surfing that we were able to purchase.
After our surf lesson, we stopped at Ho’okipa Beach to watch windsurfers and water surfers on much bigger waves than the ones we practiced at. Then, we drove to Haleakala National Park, known for its sunrises and sunsets above the clouds. The road up the mountain was winding, but not too bad. Definitely not as winding as the alternative plan to our day: the road to Hana.
A note about the road to Hana: So many of the reviews I read about the Road to Hana said it is a very windy road, with bumper to bumper cars, so it takes over two hours one way. Add that to the time it would take us to get to the starting point from our hotel and we were looking at over five hours of driving in one day! That would barely leave us time to stop at any of the prettiest areas on Maui’s east coast, so we decided to skip it. However, the next most common reviews say that it was the highlight of their trip and the sightseeing was worth it! So, next time I’m in Maui, I’d choose an overnight stay in Hana to break up the trip and have time to see everything, including the other part of Haleakala National Park.
We arrived to the summit section of Haleakala about two hours before sunset, which gave us enough time to do a short hike to the Leleiwi Overlook, with incredible views of the crater and red hills below, and then reach the summit before the parking filled up. During busier seasons, we would probably need to get there even more in advance due to the popularity of watching the sunset there. It is even more popular during sunrise, so the park requires year-round reservations to enter between 3am and 7am.
Watching the sunset was a bit cold, but a very unique and beautiful experience. The amber sunlight filled up the sky as it reflected off the clouds and cast a pink glow around the cloud edges. We had our cameras ready, but did have to get creative to keep people out of our photos—there were so many people up there!
After the sunset, we drove to the Haleakala Visitor Center parking lot to look into the crater once more before all the light disappeared and then to stargaze on the top of Maui. It was definitely a pretty area to spend our last night on the island.
Where to eat:
This was a great pit stop on our way to Haleakala. We bought a fresh pineapple from their nearby pineapple farm, and ate fresh slices, along with giant macadamia nut cookies and banana bread.
After a long day of surfing and driving and hiking, we were in the mood for a hearty bowl of warm food, so this place in Kahului really hit the spot. I ordered the delicious pad thai and my husband had curry.
Day 5 - Relax & Fly Home
Our last day in Maui was bittersweet—we really enjoyed our first trip to Hawaii together, but we were ready to get home. We had an evening flight, so we spent the day soaking up the amenities at Wailea Beach Resort for the last time.
I walked along the ocean to the other nearby beach, Ulua Beach, we had lunch by the pool, and then we walked to the Shops at Wailea for souvenirs and gifts to bring home. The Shops at Wailea have restaurants, high-end shopping, and souvenirs stores, making it a top Maui tourist attraction in Wailea.
Checking out of Wailea Beach Resort was easy as all of our extra fees for activities we added on were charged to our room. We also were able to store our luggage until our Uber came to take us to the airport.
Where to eat:
There are many chain restaurants at the Shops at Wailea, including Tommy Bahama Restaurant, Wolfgang’s Steakhouse, and Ruth’s Chris Steakhouse. If you’re just there for shopping, indulge in Lappert’s Hawaii Ice Cream, Honolulu Cookie Company, or Island Vintage Shave Ice.
KAPA was our last meal at Wailea Beach Resort and a great way to end our trip. We tried the kalua pork nachos and the seared ahi sandwich as we enjoyed our final ocean views.
That’s a Wrap!
Our time in Maui seeing some of the prettiest areas on the island was something we will remember forever. It really felt like paradise, especially since we splurged on a luxury resort near the beach, which was the perfect base on days we didn’t want to go anywhere. There are so many other Maui activities and tourist attractions we didn’t make it to, and other top-rated resorts with ocean views that we could choose between, which means there will still be plenty to see if we ever return in the future!
What are some of your recommendations for our inevitable return trip?
If you liked this tropical itinerary, check out my New Zealand North Island and New Zealand South Island itineraries. For other romantic getaways, see my La Fortuna, Costa Rica guide or the route I took on my first visit to Italy.
Don’t forget to pin this blog for when you’re ready to plan your Maui itinerary!
