The Best Mind-Expanding Maui Experiences
A trip (and life) is nothing more than a series of experiences. I feel this most keenly during vacation — because, in the end, that’s the final currency of a vacation — the experiences you had. Especially, Step 3 “mind-expanding” experiences ala Wait But Why’s Truthism. At least that’s how I like to travel.
In any case, we just got back from an weeklong trip to Maui where I had many Step 3 experiences. I wanted to document them here. It’s mainly for myself, but I thought some others might find this useful. None of the experiences I talk about is a big secret. Most are in some guidebook somewhere. But most guidebooks are a laundry list — they don’t organize by profoundness. That’s what I’m trying to do here.
1. Swimming with the Turtles at Po’olenalena Beach
I had been looking for turtles for the whole week. I finally found them on the last day we were in Maui. They were all apparently hanging out at Po’olanena Beach. Seriously though, we got here around 7:45 am and I snorkeled out about 25 feet from the shore and almost ran into a 5 foot turtle. I snorkeled for an hour in the water and saw a posse of 5 turtles doing their thing here. Floating around, picking stuff off the ocean floor, curiously swimming around me. My mind was blown.
I probably took 30 minutes of footage with my GoPro, but then I made the mistake of taking out my microSD card out of the GoPro and trying to put it in an external reader on my MacBook. The pressure of putting it in the slot cracked the card and I’m pretty sure I lost all the footage — it’s gonna require a hardware level intervention to get the data off that now :(.
Nevertheless, I’ll remember my experience of swimming with the turtles forever (even without my footage). Hands down the most mind-blowing experience in Maui for me.
Key Tip: Go early before 8am to see turtles.
2. Hiking into Haleakala on the Sliding Sands Trail
Everyone goes to see the sunrise on Haleakala. We didn’t do it. Mainly because none of us wanted to wake up at 3am to drive there to see it. It’s not necessary — the place it epic even in full sunlight.
Instead, we got up at a normal time and got to the crater by 10am and hiked the popular Sliding Sands Trail into the crater. I thought it’d be super crowded, but like all National Parks, only 1% of visitors actually get over 1 mile away from the parking lot. So if you get that far, it’s only you and the volcano.
We hiked in for about 3 miles until the parents (and the three year old) were tired. We ate our packed lunch over-looking the crater floor. Down at the bottom there some additional trails where you can hike around the lip of the cinder cone — but it was too much to get everyone down there. Despite turning back before the bottom, I still had an amazing time.
The crater has an other worldly atmosphere to it. It literally looks like the surface of Mars. Though it looks super inhospitable, there is so much life adapted to the environment. For example, near where we turned back, we saw a huge grove of silversword plants. I remember reading about these plants in an old Reader’s Digest National Parks book I had while growing up. They flower once every like 50 years and then die. It was awesome to see it in real life 30 years after reading about it.
Life, uh, finds a way. — Ian Malcolm (Jurassic Park)
We left the crater soon after finishing our hike. I regret that we did. We were originally supposed to stay up there and watch the sunset and stargaze. We ended up driving out cause everyone was tired and didn’t want to wait two hours. In retrospect, we should have just hung out in the car until sunset and then seen the stars. I’m sure the show would have been ridiculous. Next time.
Key Tip: Forget the Sunrise. Hike into the Crater instead. Stay for the Sunset and the stargazing.
3. Stargazing at La Perouse Bay
Because I felt like I missed out on the Haleakala stargazing, I drove out to La Perouse Bay at night to see the stars. Turns out that the stargazing is SPECTACULAR there.
La Perouse Bay is on a huge lava field only 10 minutes from Wailea, where we were staying. Because it’s a black lava field spilling into the Pacific, the sky is super dark there. Before the moonrise, we could see the Milky Way arcing over the ocean. I’ve never seen this starry a sky over the ocean.
Key Tip: Make time one night to drive out to La Perouse Bay, especially if you’re staying in Wailea. You’ll see this below.
4. Driving the Pi’ilani Highway back from Hana
The Road to Hana is a classic tourist pilgrimage on Maui. Most people drive to Hana and then just turn back and drive back the way they came. We didn’t. Instead we drove all the way around the island, coming back along the southern flank of Haleakala along the Pi’ilani Highway. If you like adventure, this is the road for you.
First off, the first 9 miles after Kipahulu District of the National Park is unpaved, full of potholes, super narrow, and skirts along the edge of a cliff overlooking the ocean. Couple that with the sun being directly in our eyes the whole time makes for a comically stressful driving experience. My dad and I would laugh out loud on some turns because we literally couldn’t see anything but the glare off the windshield. We just drove forward hoping that the car wouldn’t fall into the ocean (and that other cars weren’t coming from the other way). So many things could have gone wrong. But they didn’t. We persevered and now have a great story to tell. This is what adventure is about :)
But seriously, the road was beautiful. Since this is the leeward side of Maui, there isn’t a dense jungle — instead there was open grassland. Also, no one lives on this side of Maui, so it’s totally undeveloped. We had unobstructed views across the island to the ocean. We stopped at a bunch of places — the best was this spot where you could see Haleakala peeking above the clouds and the sun was setting over the grasslands. It looked like something out of Middle Earth.
Key Tip: Don’t drive back on the Road to Hana, drive back on the Pi’ilani Highway and circumnavigate Haleakala.
5. Hiking a Bamboo Forest on the Pipiwai Trail
The bamboo forest on the Pipiwai Trail to Waimoku Falls in the Kipahulu District of Haleakala National Park just south of Hana. The forest is better than the waterfall at the end. There’s a magic to a bamboo forest that is hard to describe. A light wind rustles the leaves, but anything stronger you get all the bamboo stalks hitting against one another making this hollow noise. Coupled that with me thinking that some Kung Fu warriors were fighting high above me Crouching Tiger, Hidden Dragon style — it made for a transcendent experience.
Key Tip: If you take the Road to Hana, hit up the Pipiwai Trail. Hit the trail before 3:30 so you have enough light to hike back down.
6. Spending the Day at Big Beach
Hawaii is about going to the beach. And my favorite beach on Maui is Makena Beach (also known as Big Beach) just south of Wailea. It is super long, super wide, with beautiful soft sand, and a shore break that great for boogie-boarding. Furthermore, you can see Kahoolawe and Lanai off the horizon and it’s easy from the road. We spent a solid 4 hours here — swimming, boogie boarding, making sand castles, and just relaxing. It was a beach day at it’s finest.
The best part was following it up with fresh coconut water from the side of the road. These really big “Samoan” coconuts were $15 each! So expensive. But worth it. That guy selling them was saavy businessman. He has a stranglehold on the market and he knows.
Key Tip: Spend a day on Makena Beach. This is Hawaii beach at it’s finest.
7. Dinner at Mama’s Fish House
This restaurant is a Maui classic. It’s expensive, but worth it. We got a reservation three weeks in advance (before we went) and go there an hour early for the reservation. This was fine because we ended up taking a bunch of pictures by the beach and in a canoe there. They made us wait almost 30 minutes past our reservation (which pissed me off), but the meal and the service was so amazing that it was ok in the end.
I had one of the fish they had caught that day. Best. Fish. Ever. Our waither was awesome too — he had worked at Mama’s for 17 years. He had moved to Maui after graduating high school and had lived here ever since. I love these Hawaii stories. Makes me want to just move to the Islands sometime as well. The pace of life is so … tranquil there.
Also, randomly we saw Justin Timberlake and Jessica Biel (with other family members) there. First, and only, celebrity sighting on Maui!
Oh, and get this Lilikoi Black Pearl at the end. So good.
Key Tip: Make Mama’s your splurge meal on Maui. Make a reservation at least 3 weeks in advance. Get one of their fresh fish caught that day.
8. Drinks and Sunset at Four Seasons Wailea Beach
Wailea Beach is fronted by three swanky resorts where the average room price is near $1000/night. But, you don’t have to front that kind of money to have the ultimate Wailea Beach experience. Instead, park your car in the public lot, walk into the Four Seasons lobby, sit at the bar and have a drink there. They have live slack key guitar music and hula there every evening. After the drinks in their open air lobby, walk down to the beach and see the spectacle that is the sun sinking into the Pacific.
Key Tip: Don’t stay in the Four Seasons (unless you’re a total baller). Get drinks there instead. Then go watch the sunset on the beach.
9. Eating Lots of Coconut Shrimp
I guess you can eat coconut shrimp anywhere, but eating it on Maui when you’re tired from swimming and covered in salt water crust is a Step 3 experience. Two best spots we found:
- Island Chef’s coconut shrimp in the Nahiku Market on the way to Hana
- The Kinaole Grill food truck in Kihei
Key Tip: Eat lots of coconut shrimp whenever you get a chance.
10. Eating Ululani’s Shave Ice on Kenolio Beach
Not all Hawaiian shave is is created equal. Ululani’s is the BEST. They shave their ice down into a perfect powdery snow and they use real fruits to make all their flavorings. We went to the one in Kihei twice. Both times there was a huge line — that’s always a good sign.
My favorite shave ice was the 3 way combo of mango, lilikoi (passion fruit) and coconut. Pro tip — don’t eat it on the Ululani patio — instead walk it across the street and eat it sitting on the beach.
Key Tip: Eat Ululani’s shave ice as many times as you can without getting diabetes.
