4 Days in Maui: Beautiful time, with bonus trip to the ER!!

Quick trip: 4 days in Maui

Although we have done some road trips in our area, our 4 day trip to Maui in 2021 was the first real “fly-in-a-plane, whisked away just the 2 of us with no other agenda besides relaxing” vacation in years and years. Maybe ever. I want to stretch out our vacations as much as we can, and I love the idea of shorter vacations more often. So many guides will advise that you need at least a week-10 days in Hawaii.

But what if you don’t have that kind of time? Should you just not go? I am here to show you how we spent our 4 days in Maui.

I hope you are able to read this in an exploratory mood, because that is how we approached the trip. Prioritizing travel is a new phase of our lives, and we approached this as our first big trip-with a curiosity about how we like to travel, what works, what doesn’t, and who we are as travelers.

Day 1-Off to find sunshine

We flew Southwest from Portland to Oakland to Kahului. The flight there was long but uneventful with beautiful views. We got our car and headed south, stopping first for coffee and reef-friendly sunscreen. It was there in the Target parking lot that we spied our first Maui chicken(s). 

I didn’t get a good picture of the parking lot chicks, so this friend at the restaurant will act as a stand-in.


Coffee and sunscreen secured, we headed towards Lahaina. The thing that surprised me was how brown the hills were. It reminded me a lot of eastern Washington, and there were even cows. 

We stopped at Beach Bums for a nice late lunch. We enjoyed the views, and more chickens. Meal was good, service was excellent. 

Next up was check in. Obviously there are a lot of different lodging choices on Maui. We didn’t want a resort, definitely wanted views, and really wanted something with a relaxed vibe. 

View from our balcony


Makai Sunset Inn fit the bill exactly.

Another view from our balcony

The room and the grounds were perfect. It had been built as an apartment complex in the 1960s and had a nice tropical, mid-century vibe.

Our living room

We booked 4 nights at about 17,000 Chase Ultimate Rewards points per night, using the Chase travel portal. 

The welcome flowers. We were traveling to celebrate the 30th anniversary of when we first met. We were greeted by this beautiful bouquet and a lovely note.

After we booked it, we received an email from the property, letting us know that is NOT a resort, there is no pool, kids under 18 are not allowed, there aren’t amenities and some rooms don’t have air conditioning.

We didn’t miss the pool

With receipt of this letter, we are allowed to cancel without penalty. They want to make sure that people know what they are getting into, because apparently people arrive and realize there is no pool and are upset. 

Some people come back here every year. They stay a month or two and have been doing it for years. It is very comfortable for longer stays.

The place was perfect for our needs. We had a living room, bedroom, small but fully equipped kitchen, and bathroom. Oh, and a very long balcony with a view of the ocean, the sunset, and the islands of Moloka’i and Lanai. 



It was at the outskirts of town with houses across the street and it was about a mile walk to the main shopping district on Front Street. 

View of the parking lot

Our first order of business was to go out, get some groceries, and buy some lighter clothes. I had packed summer clothes, but was not truly prepared for the humidity. It wasn’t even super hot while we were there, but my PNW blood is not used to it. 

This dress saw a lot of action during the trip. Very lightweight and it washed and dried quickly.

ABC Stores to the rescue! I was able to get some very lightweight dresses for under $20 each, and a hat. We also went to Ross to get The Dude some shirts because he didn’t quite find what he was looking for at ABC.

We went to Foodland and picked up some very cute shopping bags, some local foods including Spam Musubi for $1.99 each. We also went to Safeway. We definitely over-bought food. In our defense, we are not used to buying for only 2 people or only 2 days. 

The view from the balcony was pretty good at night too. We saw the Southern Cross for the first time.

We fell asleep to the sounds of the Pacific Ocean lapping against the barrier wall. 

Day 2-Welcome to Paradise


After a relaxing wake up, we enjoyed some coffee and views on the balcony. Hawaii is very good at reminding us that we are on vacation. 

Same view, now a little pinker


Our first full day on Maui was a pretty quiet one. We went down on Front Street, walked around, visited the museum

and the Banyan tree.

Our lunch was an oceanfront picnic

and we enjoyed some shave ice at Ululani’s, which uses natural ingredients and is Dude-friendly! Keeping him safely fed on vacation is quite a challenge. 


Our big event for the evening was attending the Myths of Maui luau. The luau seems to be something every visitor should do at least once.

The Old Lahaina Luau is considered the best on Maui, but it was sold out. Myths of Maui was a good mix of storytelling, music, and dance and helped place the Hawaiian islands in their historical cultural context. The food was fine, the drinks were great, and the setting was beautiful. 


Day 3-Not a Great Day

The next day was messy. I was searching for the perfect and I forgot to breathe in the good. 


We had rented snorkel equipment for the week. I think it was $100 for two people’s worth, including flippers and belts. And we got a boogie board thrown in. 


Our hotel has a beach shed where guests can borrow equipment on the honor system. The shed was packed with coolers, pool noodles, flippers, and boards. We grabbed a second board from the shed, got our rental gear, and were off to the beach. 

Board from the shed. That little building behind him is full of beach goodies to borrow.

Here is where it got hectic. I think that part of it was that I was nervous about swimming in the water at all, let alone snorkeling. My brother drowned when I was 4 (he was 18) and all my life, I have had a love-hate relationship with the water. At this point, it has been a long time since I had ocean water warm enough to swim in, and I didn’t give myself time to get used to it.


Plus we had to think about which beach would be best, and learn how to use the equipment. So we spent much of the day driving up and down the west coast of the island, in search of the perfect beach. It was beautiful, but it was also tiring and disappointing. 


I grew kind of resentful towards this equipment. We had rented it, so I needed to make sure that we maximized our enjoyment of it, by finding the perfect beach. But I also have this background fear of ocean swimming. It was a lot to carry around with me on this beautiful tropical vacation. My plan is that next time, I will go a lot slower with myself, plan a day, map out the beach beforehand. I try to acknowledge my limitations and where they come from. In the moment, I couldn’t figure it out but hopefully now that I have had a little space, I can move forward. 

We finally found a beach and had a little bit of fun. The Dude had more success at snorkeling, but he really needed more time to figure it out. By the time we found “the right beach,” the sun was setting and when the setting sun was blaring off the ocean, it was not a good time to figure out snorkel gear. 

We decided it was time for a reset. Food truck delivery and a sunset dinner on the balcony sounded divine. But our vacation had other plans for us. 

The night got rough. But first, the sunset did not disappoint.


Our food arrived and we served ourselves out on the patio. Two bites in and the Dude started feeling awful. Tightness in his chest and neck, burping, trouble breathing. It was terrifying. He didn’t want to be bothered and couldn’t really answer questions. I had trouble figuring out what to do next. Like, does this escalate to 911? Is there someone I can reach out to here? I felt very scared and trapped and alone. I was also thinking, what if he has to stay here in a hospital for a while? What will that look like?


When I was a teenager, we went to Disneyland and my dad ended up having to stay in the hospital for a week after they did a surgery on his intestines. My mom was suddenly in charge of the RV and of course, she did okay, but it has left a fear of possibilities embedded in my brain. 

I got the Dude some Gas-X because I was pretty sure it was heartburn or reflux related since it came on when he started eating. He got some very good burps out and was feeling better. I told him to call the nurse line connected with our HMO. The nurse thought everything was probably fine, but that it would be a good idea to go to the hospital to just have it checked out. 

Since he couldn’t drive in case it was something serious, I had to drive us to the hospital, which was about 45 minutes away, in the dark, on roads I don’t know at all. I was in full-blown anxiety mode. By this point, the Dude is feeling fine and making jokes in the passenger seat, while I am gripping the steering wheel and hoping for the best. 


We approached the hospital through a residential neighborhood and the whole thing was feeling odd. We arrive at the hospital and are pushing ahead towards the emergency room when a nurse in a witch’s costume comes out to take the Dude’s vitals. She told me to go park and I said, “You know this is all a little strange already, with the COVID tent waiting rooms and closed off ER, but now we are being greeted by a witch.” She assured me she was a good witch and I went to park and went to wait in the portable carport/tent that was the waiting room. 

The hospital waiting room.

While waiting for the Dude, I watched a young woman who was sitting next to me get her discharge paperwork and crutches, and have the bandage checked out before she left. All while sitting on a folding chair under a tent in a parking lot at night. It was surreal. And then chickens started walking past in the parking lot.

The Dude was okay and I decided to start really taking the scene in. I got a pic of the nurses n costume for my scrapbook, and they took one of me in the same pose. 

The Dude was fine, it was indeed just some heartburn. I was not fine. My anxiety was really high and would remain that way through a good part of the next day. 

Day 4-A day of anxiety and redemption


Our last full day! I wanted to lie in bed and feel miserable, but this is Hawaii. Couldn’t do that. We got up and drove to Iao Needle, hoping to take a hike. But the parking lot was full and crowded, so we left.

Now for the decision, should we go to Haleakala or not? Reading all the reviews online, I wasn’t sure if it would be okay to go mid-day because every review focuses on sunrise or sunset. But we had a lovely chat with the manager at the inn and she highly recommended we go. So we went and it was so worth it.

Although I am sure the sunrise and sunsets are glorious, midday is fantastic. The colors were so amazing and the clouds were all below us.

The island of Manhattan could fit inside the crater

It was really and truly incredible. I am only sad that we didn’t stay longer and explore more of the lower elevation trails.

My happy but anxious face.

After Halekala and a little bit of time being lost, we headed back to the beach for one last sunset. We had returned our snorkel gear by this time, but had a boogie board from the shed. The sunset was gorgeous, the mood at the beach was upbeat, and my anxiety finally started to notch down. 

After that, we headed back to the room to wind down, pack up, and try to get a little sleep before leaving early for the flight back to the mainland. 

We forgot the leis in the fridge. The bouquet made it to the mainland but I left it in San Jose.

Day 5-Time to go home, almost

Well, the adventure wasn’t quite done! A delay from Maui put us in a position to miss our connecting flight back home. How we tried to make the most of our unexpected layover will be a post for another time!

Read the cost breakdown for this trip here.

Where we ate:

Number of trips to Foodland: 3

Number of trips to Safeway: 3

Favorite beach: Honolua Bay

Favorite activity: watching sea turtles from the balcony

Favorite spot on the island: Top of Haleakala



If you haven’t been on vacation in a while, or if it is a different type of vacation than you usually take, it is okay to view it as an experimental trip, one that gives you the opportunity to figure out what you like and don’t like to do.

Plan less and leave a lot of downtime

You take yourself and your mental stuff with you. 

You can learn a lot about yourself while you are traveling if you are open to listening

Get advice from people who have been there or live there, but don’t be afraid to do your own thing your own way. This is your vacation, make it your own.