• Jane Liu

5 Days in Sunny Maui Hawaii | A Throw Back Trip Report


(This trip took place prior to the COVID pandemic spread across the world. Please stay safe and reduce travel to protect others)


Maui is the first Hawaii island I went to. And while I've been to many beautiful cities around the world, Maui changed my life and made me fall in love with Hawaii. Since Maui, Kyle and I have very intentionally tried to visit Hawaii every year. No need for me to say anything further, let our 5 day Maui trip speak for itself...


Day 1 - Nakalele Blowhole, The Shops at Wailea, Cafe Olei Kihei

After close to 9 hours of flying, we finally arrived in Maui, Hawaii pretty late in the evening (we'll call this day 0). We got the rental car, drove to the Wailea area of the area, and quickly found our hotel, the Wailea Beach Resort by Marriott. The resort was definitely a highlight (scroll down to day 4 and 5 for more and check out our hotel review coming soon!) of the trip, but it was late and we were exhausted from the journey by the time we got to the hotel so we decided to leave the exploring for another day. We quickly got settled and finalized our plans for our first real day before getting to sleep.


We started Day 1 with breakfast at one of the many restaurants at The Shops at Wailea, a nearby outdoor mall that is walking distance from the hotel. Kyle had a filling breakfast burrito and I enjoyed an egg omelet. We also got to split a delicious guava fruit platter (when in Maui why not enjoy the fresh tropical fruit?). We knew it had to be a quick breakfast stop before starting an activity filled day...


Our major stop of the day was the Nakalele Blowhole on the northern tip of the island. Since Wailea is situated near the southern end of the island, we knew it was going to be a long drive. While not the only scenic drive of the trip, we took in all the sights and sounds of the western shore of Maui, passing through scenic beaches and cute Hawaiian towns on our way up to the blowhole. After almost two hours, we had finally arrived at our destination.


This blowhole is known for its powerful blowhole where the strong ocean waves are forced into a small tunnel and out into the air. On a day where the seas are really rough, the blowhole can spout up to 100 feet in the airs. While we definitely recommend this unique stop for it's beautiful scenery, the area is also known for it's dangerous conditions. Check the weather, wear a good pair of supportive and grippy shoes, and take care when walking from the parking area down to the blowhole. Luckily for us, we had a beautiful day with clear weather and got to visit up close.

On the way back down towards our hotel, we stopped at an overlook along the way and took in the incredible Maui sunset before continuing on to dinner at Cafe Olei. While it was a little hard to find on the second floor of a shopping area, this place was a highly rated restaurant in the city of Kihei and it was only a short drive away from Wailea. This restaurant features such a homey vibe with dim lighting, and delicious seafood. I got myself some sushi while Kyle opted for fresh fried fish. Highly recommend, and would definitely visit again in the future.


Since we arrived late the evening prior, we spent the rest of the evening exploring Kihei and Wailea and stocking up on essentials like water, sunscreen, and of course some fresh fruit to snack on.


Day 2 - Boating, Snorkeling, and Ocean Fun


Day 2 was quite literally an action packed day, and we're so glad we scheduled this in early on our trip because it left us wiped out and sore in muscles we didn't know we had. We started our day very early at 7am heading to our Boat & Snorkeling tour with Pride of Maui. They have brought fun ocean activities to visitors for the last 40 years, and we had a blast! We joined a group for their Molokini and Turtle Town Snorkeling Tour, which was absolutely one of the most fun we had on our trip.


We arrived and checking in for the five hour ride, and the friendly crew provided simple but filling breakfast and fresh juice for their guests and got everyone suited up and ready to go. When the boat docked, we got the opportunity to jump in and snorkel at two different areas of the island known for their thriving wildlife ecosystems. While this is not my first time snorkeling, I was still in awe of how beautiful the ocean around Maui was. There were plenty of colorful fish to look at and if you look closely, you can spot sea turtles as well! The entire trip was roughly 5 hours, and lunch is provided as well. This boat tour has absolutely exceeded my expectation. A variety of adult and non-adult beverages are also complimentary on the ride back to the marina, so remember to bring your ID if you plan to have an alcoholic beverage (I personally, enjoyed the Mai Tai!).


A few hours of snorkeling and sunshine on the boat tour really takes it out of you, so we opted for some easy burger dinner from a restaurant at the outdoor mall near our hotel, and ended our day pretty early and spent some time on our oceanfront balcony before an early bedtime. Highly recommend not trying to squeeze too much in on an action packed day like this.


Day 3 - Road to Hana - An Absolute Must Do Activity

I truly believe Road to Hana is what completely changed my view of Maui & Hawaii in general. Maui is the first island in Hawaii I've been to, and it was such a great experience because the island is not big at all. Road to Hana was such an amazing way to live and experience the entire island from one end to the other. You see all the different micro-climates, weathers, plants, and terrains all in one incredible day, and it's absolutely life-changing. There's a ton to talk about on the Road to Hana, so we will have a separate post to take you through the highlights (coming soon!).


While I'm not going into too much detail on this post, here are a few tips if you are thinking about doing the Road to Hana, I highly recommend doing these 3 things:

  1. Start Early - Road to Hana truly is a FULL DAY TRIP. So please rest up the night prior and start bright and early to ensure you're not driving narrow roads / bridges at night on the way back to your hotel. We were so exhausted from the snorkeling day, and decided to sleep in a little, which ended up being a bad idea as a good chunk of our drive back was in the evening with heavy rain.

  2. Invest in Shaka Guide - an Apple & Android friendly app that works offline to give you the most extensive audio tour as you drive the route! This app made our drive so easy! It utilizes GPS in your phone to inform you of merged lanes, major mile markers, hidden stops for further exploration, and most importantly, where to park for these hidden gem spots! To add icing on the cake, the guide also tells local Hawaiian stories as you drive to keep the trip entertaining.

  3. Bring weather proof jackets, umbrellas, and extra supplies - Maui is not a huge island, but it has ever-changing weather conditions. While we started the day sunny, we experienced drizzles, pouring rain, fog, broken branches, and even a minor mudslide in a 12 hour period. The temperature can also vary drastically depending on where you are on the island. So please be extra prepared as you prepare for the road.


Now with the top tips out of the way, I just have to call out one (and there are many) must stop location on your drive - Aunty Sandy's Banana Bread (210 Keanae Rd, Haiku, HI 96708). It's just before the half way point on the Road to Hana. The stand is not big, not fancy, just a yellow shack with 2 sets of benches and tables. But their banana bread is baked fresh daily and it is sold while it's still warm. Trust me, this banana bread will change your life!



Day 4 - Relaxing Beach Day and Resort Exploration


As much as we enjoy a jam packed vacation, it's hard to come to Hawaii and not just lay on the beach one day. That's what we did on Day 4.

Maui is not a cheap place to stay and the Wailea Beach Resort by Marriott no different. Rather than pay the nightly rate that can exceed $700/night for a standard room, we cashed in our points to make the entire stay free! It is a Category 7 property but points still provide a great value to redeem the entire stay. If you're interested in using your Marriott points for your next trip, please refer to this redemption chart and don't forget to use Marriott's fifth night free perk to make the most of your stay! (if you don't know what I'm talking about, don't worry! A post on maximizing points is coming soon!).


When we first arrived at the hotel, the friendly front desk staff greeted us with leis (flower for women and shells for men) and our Marriott status earned us a free ocean view upgrade, free parking at the resort, and coupons for two free Mai Tai's coupons to be redeemed at the pool bar. The property itself is situated right on the Pacific and our ocean view room was stunning especially around sunset. The property has multiple wings of guest rooms, and each area may experience different vibes. Some are closer to kid friendly pools / slides, some are right next to the adult pool and cabanas.


We spent the first half of the day exploring the resort ground, enjoying the waterslides and the different pools where we redeemed our Mai Tai coupons. For lunch, we found an on-resort food truck with delicious fish tacos and fresh poke. We spent the rest of the day lounging on the beach. Lounge chairs, towels, and umbrellas are complimentary so it's a great excuse to be outside all day, and a good time to get caught up on your podcasts, books, or tanning!


My favorite part of the hotel is actually the infinity pool. For some reason, I've always seen others enjoy one, but never been in one myself. So this was the perfect opportunity to get that cliché photo looking out at the ocean. What makes this pool so unique is, during sunset, the pool water blends in with the ocean background, actually achieving the "infinity" look. Since there are multiple pools, this one wasn't crowded so you can truly enjoy the space.


The hotel is also family friendly. There is a game room with shuffle board, arcade games, video games, and so much more - it's a great place for kids to spend a couple hours (check out the walkthrough in our video). On certain nights, the hotel also hosts a luau. For a fee, you and your family can experience not only a delicious Hawaiian barbecue, but also traditional dancing and performances. Luckily for us, we could watch the luau from the balcony of the room and save on the price of admission!


Day 5 - Saying Goodbye

Last days of any vacation is tough... especially this one. I had no idea how much this trip has changed me and my view of Hawaii.


To be honest, our "goodbye" wasn't as sad as other trips. After check out, we actually had a couple of hours left on the property before we needed to head to the airport. Kyle and I checked suitcases in at the front desk (a tip for travelers who are not in a rush - you can always check your bags in the front and enjoy your day without lugging your stuff around) and spent an hour or so enjoying the game room. But what really let our competitive side out was their hotel escape room! Who woulda thought the hotel had an on-property hosted escape room?! We accidentally saw their set up while walking through the hotel on our last day, and they just so happen to have a slot open. I'm a big fan of a good escape room, and It was an absolutely amazing way to end our trip. And of course we managed to finish!



We had an incredible time in Maui, and we can't wait to get back to explore more of the island as soon as we can.


We've got a lot more to talk about on Maui, so check out our Wailea Beach Resort hotel review and Road to Hana deep dive (coming soon). Have you been to Maui?

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