Beyond West Maui: Five Nights in Wailea

Trip Reports

After waving goodbye to Hāna, we made the pleasant drive back toward the airport. I dropped off the BMW and then moved on to Ace Rent a Car to pick up a minivan. Ace is not on-airport, but wooo boy was it cheap at under $20 a day. They really were just trying to empty their parking lots and find anyone to rent these things. (You can see some of the cars in the fields waiting for tourists to return in this photo below, but I don’t know which agency.)

I did not love Ace. The van was a little scraped up, so I made sure to take pictures. It also wasnʻt in the best shape. I kept getting an error that the auto-start/stop function which saves gas when you aren’t moving wasnʻt working. On top of that, despite the companyʻs terms and conditions for that location saying that employers and coworkers can be added as additional drivers for free, they absolutely refused to do so. They said theyʻd update the website, but they still havenʻt done that. It wasnʻt a lot of money, but it was enough of a bait-and-switch to make me not be willing to use them again. (We contacted corporate and got refunded after the fact.)

With that sorted, it was time to start picking people up and heading the 30 minutes south where we settled into the Andaz, the northernmost resort in Wailea. I have a deep love for this location. When I was a kid, we used to stay there at the Stouffer, later the Renaissance when the brand was acquired. But that property was knocked down completely and a brand new facility was built as the Andaz Maui ten years ago. Thanks to our relationship with the hotel sales team, we were able to make this our destination for four nights without completely bankrupting the company.

Wailea sits just south of Kīhei. Kīhei is where a lot of locals live, but the beach is also dotted with older condos. It’s crowded, and it feels like people live there. The second you cross into Wailea, it’s like passing into a different world. Kihei feels real and Wailea is like a heavily-manicured Disneyland for adults with lush greenery, golf courses, and swanky resorts.

Back at the Andaz, the main building is shaped like a “T” with the top of the T facing the imposing volcano Haleakalā behind. The bottom of the T sticks out toward the ocean, giving great views all around.

Photo via Andaz

The hotel is built almost as a cascading waterfall. It starts at the open air lobby at the top, and there is a succession of four different pools that work their way down toward the ocean on the southern inside of the T. On the northern side, there is a quiet adult pool.

Around the main building are several scattered villas. We took over ʻIlikai 914 which sits mauka (toward the mountain) at the north part of the property. This three-bedroom unit was perfect. We had four people stay there, and we used the upscale kitchen and sitting area as our base of operations. We cooked breakfast and lunch and kept the liquor stocked so people could come and go as they pleased. Out back was a private lawn with a grill and plunge pool. It was the ideal setup.

Villa Photo via Andaz

There was no fixed agenda for this gathering. The main goal was to get people to celebrate, relax, and take a break from the grind of dealing with airlines and clients all day every day. I really just wanted people to be able to spend time with each other in person, so that the next time they interacted on Slack, it would help them really know each other much better. It seems to have worked as planned, because we saw plenty of people going off in small groups and hanging out.

I was focused on making sure people had options, so I tried to do some kind of excursion each day for those who were interested.

Day 1 – Site Visits

The first day on Friday, we did site visits to other nearby hotels. The Wailea Beach Resort (a Marriott property) has received a lot of work and was a pleasant surprise that I think is worth considering for future travel. It’s almost entirely made up rooms in low-rise buildings, and it has multiple pools including a great kids pool with a waterslide that is isolated from most of the resort.

At the other end of the spectrum was the Four Seasons Maui which generally sits at the top end in terms of price and service. I took this photo from one of the suites we toured.

Day 2 – Volunteering

On the second day, I put together a volunteering opportunity. We had struggled to find any direct, organized opportunities to help fire victims. Everyone was so overwhelmed that we often couldnʻt get a call back. What we did find wasnʻt going to fit with our schedule. So we stuck with our original plan from before the fires to help out at Kipuka Olowalu, and I’m glad we did.

If youʻve ever seen Leodaʻs Pie Shop on the way to West Maui, thatʻs Olowalu. And back in the valley behind, Kipuka Olowalu has secured a 99-year lease on former farmland where it is trying to restore Hawaiian practices and return the land to how it once had been.

We spent the whole morning out there, and we were tasked with helping them clear the loʻi of weeds. A loʻi is a wet kalo (taro) patch, one of the two ways kalo is grown. And after the fires, volunteering had dried up so weeds had begun to overtake some of the patches. We helped restore this one below.

We were only the second group to volunteer after the fires, and they were glad to see us bring a sense of normalcy back. (I think the dog, Joy, was the most glad of all.)

As we were working, they told us about their experiences with the fires, along with a great deal about the land. Once we were done, they took us through their forest to show us different native plants and tell us all about how they’d adapted over time. We finished the day down by the river (more like a stream) where we cooled off in the shade before heading back to South Maui.

Day 3 – ʻIāo Valley

On the third day, I took a group to see the ʻIāo Valley which lies in the West Maui mountains. This is often on the regular tourist list of spots to visit, and I really just wanted to give the team the opportunity to see a lush part of Maui if they hadnʻt been before. The clouds sit on top of the mountains making this valley one of the wettest places on the island. Whatʻs funny is that it backs up on the valley where we had volunteered the day prior, but thatʻs the dry side so the terrain couldnʻt have been more different.

Where to Eat

Each night, we had a different plan for dinner. The first night with people coming in and looking like walking zombies, we just ordered pizza in the villa. We also picked up a dobash and chantilly cake to celebrate some birthdays. The next two nights we broke into four groups and did small group dinners. Then the last night we went out and had a big group dinner.

Hereʻs where we went:

On the last day, everyone headed home at different times. I stayed one more night to make sure everyone got off ok, and to absolutely collapse from exhaustion. My wife and I ate at Morimoto in the Andaz that last night, and I couldnʻt keep my eyes open. Never have I left a trip to Hawaʻi feeling more tired than when I arrived, but donʻt take that to mean it wasnʻt a great time. It was.

If youʻre thinking about going to Maui, go. Definitely be respectful and careful about making plans in West Maui since things are slowly reopening But even if you stay elsewhere, try to go to West Maui and support the local businesses now that theyʻre finally opening their doors again.

Youʻll find the same welcoming aloha spirit that you always find — at least we did — but just keep in mind that everyone you meet has been impacted by the fires. They may have lost loved ones or at the very least they know people who did. Theyʻve all been through unimaginable trauma, so be kind, be empathetic, and enjoy your visit.

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9 comments on “Beyond West Maui: Five Nights in Wailea

  1. Thanks for including the picture of the farm dog… Joy is adorable. Being a farm dog / ambassador must be a dream job for a sociable dog like her, so many new friends to make!

    I echo your frustration on rental cars… Renting a car is an experience that has some friction in the best of times, just in terms of getting settled in a car and knowing where all the buttons/switches are. (I can’t be the only one who has engaged in a desperate search for the headlight switch on a dark highway while driving a rental car, or who has had to resort to Google to figure out how to open the fuel door when fueling up a rental car before returning it; I have colleagues who always try to rent the same/similar model of car for just those reasons.)

    A rental car should be ding free and clean & working inside and out (not necessarily detailed to perfection & a fine shine, but cleaned well enough to look clean from a step away, and without any errors/warnings on the dash or anything like screeching brakes/wipers) at a minimum. That’s doubly true when an agency has few of its cars rented out, as it’s not like they have the excuse of having to rush to clean/repair cars that were just returned by other customers.

    1. I agree with you about rental car conditions.

      I very briefly worked at one of the “high end” rental car companies, and your comment seems adorably naive. The number of poorly cleaned, lightly dented cars that I put on the ready to rent line was too many to count and given the fact my employer posted flat out illegal policies in writing, I don’t care nor do I want to know.

      Tbh, from the scuttlebutt I heard, I’d avoid the numerical European brand and go for a National brand or one out of this world, if you want cars in good condition.

  2. Haha Ace Rental Car took down their terms and conditions after you posted this…. it’s a blank page now!

  3. Not going back to Maui (or really Hawaii in general) until the hotels moderate their rates. It’s still much more expensive than pre-pandemic, even though their occupancy is down a lot.

    I live in the Bay Area and would typically go to Hawaii once a year for 5ish nights. But we’re taking a break from Hawaii in general since even the Big Island is much more expensive. For now, Puerto Vallarta is a shorter flight from SFO, way cheaper, and has better food.

    1. Good plan.
      Let Hawaii realize it can not charge 1st class prices for a 3rd world unfrastructurc

  4. Thanks for including information about Kipuka Olowalu. They don’t have January dates posted yet, but I’ve made contact to let them know I’m available for one of their Wednesday or Thursday work days. Sad about Leoda’s and so many other great businesses that burned down.

    Yes, the hotels are rather out out hand—kudos to you for the disclaimer that your business relationships resulted in a lower rate. I found a B&B in Wailuku … it’s not on the beach, but it’s centrally located. It’ll be just fine.

    Anyone who is going to Waikiki, take note: I stayed at the Ilima in January and found it to be clean, friendly, and cheap ($185/night including resort fee). Parking is free (but limited) and there’s a great tiki bar next door at the White Sands. Not beachfront, but the Royal Hawaiian is a two-block walk away.

    1. Al B- To be clear, I don’t know how much of a discount they gave us for being good partners, but I told them what our budget was and they were able to make it work. They certainly did not expect me to write about this, it was entirely as a travel agent putting a group together. They probably don’t even know this blog exists!

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