The Trip of a Lifetime

Why did we want to travel?

There were a few key reasons for traveling and for taking a vacation. First, my wife completed her Master’s program and this was a way to celebrate her amazing work and dedication. Second, unlimited vacation often leads to less vacation than if the number of paid time off was explicit and if I don’t take occasional breaks, I will burn out. It is also good to step away and consider all that you have accomplished and assess whether your path is aligning with your goals. Finally, to experience a place with a different culture than home.

Why did we choose Hawaii?

If I remember correctly, I suggested that we visit Seattle. My wife, being a fan of warm and sunny beaches had other places in mind. A friend spoke very highly of Hawaii, saying that it literally changed his life. He even signed a phone contract while there to get an 808 area code for his phone. Also, my mom visited Hawaii when she was young and mentioned it a few times. We never talked about it in detail or saw pictures. I talked to my aunt to see if she had any pictures. She couldn’t remember much about my mom’s trip either (she didn’t go). All that she could remember was that she visited the King Kamehameha Statue. Which after a little research doesn’t help much because there are four of these statues, two on the island of Hawaii, one in Oahu and one in Washington, DC. The final reason was to go somewhere that we could enjoy the beauty of nature. Somewhere that had beaches as well as mountains, as I wanted to do some hiking. Hawaii is also known for its Kona coffee. Being a coffee fan, I would be lying if I didn’t at least mention that this influenced my decision a bit.

The Trip

After booking the trip, I started watching videos on YouTube and one channel in particular that had great videos and that were super informative with a good description was Preston and Krista. We got a lot of inspiration from these videos, but didn’t do everything that they did and did a few things that they didn’t do. I would strongly encourage their videos as a starting point and do the things that interest you, but also leave time to adventure and find parts of Hawaii that are beautiful to you.

The highlight of the trip was on our third day on Maui, when we decided to take a trip to Haleakalā National Park. We didn’t have plans to go on any long hikes or stay for the sunset. On our way to Haleakalā, we stopped to pick up a few snacks (chocolate and peanut butter covered pretzels, gold fish and wheat thins) and drinks (32oz water and vitamin water) because there are no places to eat in the national park and we expected to be there through lunch.


Our route is highlighted here, but this map also includes the various routes on Haleakalā. I found this map on, who kindly shared the original source. Winterbear’s post Backpacking Haleakalā Crater contains beautiful images (significantly better than I am capable of taking) of Haleakalā, you should definitely check out the site and some of their other posts!

We made it to the Halemau’u Trailhead, which was one of the first visible parking lots and there was a guy — we later found out that his name was Jose — who looked like a tour guide, standing near the sign. We rolled our window down and he asked us where we were going. We responded that we really didn’t have any plans, nor did we really know what to do. Then, Jose started describing the possible trails/hikes that you could do, but that there was one in particular that many people did, the 11.2 mile hike from the Sliding Sands Trailhead, near the Pu’u’ula’ula summit, to where we currently were, the Halemau’u Trailhead. We were pretty certain that we would not be able to do an 11 mile hike. We are active, but have never hiked before, didn’t come fully prepared and 11 miles seemed fairly long for a first hike. Either way, Jose was wondering if we could give him and his wife a ride to the Sliding Sands Trailhead, where they would be starting their hike.

On the roughly 3-5 mile drive to the Sliding Sands Trailhead, we introduced ourselves and Jose and his wife, Paulina introduced theirselves. We asked where they were from and they said Columbia and they asked we were from, we said “Pennsylvania”, they said, “Where is Pennsylvania?!” and we replied, “Near Pittsburgh.” and they said, “No way!” and that they were originally from Columbia, but that they had moved to the United States for college and then later got jobs in Pittsburgh.

I knew that I wanted to do the hike, even though I wasn’t entirely convinced that we were prepared, but I knew that I would have to convince Meghan, my wife, to do it. Surprisingly, she was pretty easy to convince.

Then, I started asking Jose more about the hike and he started asking us questions like, “Are you active? Did you come prepared? Do you have at least 2L of water per person?“, to which we responded, “Yes, we work out and can easily run 5 miles and that yes, we stopped on the way and picked up liquids.“, but then, I pointed to my shorts and Luna sandals (which by the way are made for running and hiking. Luckily, I wasn’t wearing my Birkenstocks). They were both wearing wind-breakers (we were also wearing sweatshirts and windbreakers because we knew it would be breezy at the summit), long pants and hiking boots. He seemed pretty concerned that I wanted to do the hike in my sandals.

I would be lying if I told you that I wasn’t concerned that wearing sandals would be the wrong decision, I did have some comfort knowing that I had completed a 7 mile run in them and had been wearing them for about a month at that point so I had them properly adjusted and molded to my feet. While on the hike there were two incidents that did involve me wearing shorts and sandals. First, there is no shade on the Sliding Sands trail, you are walking in terrain that looks like Mars, so the sun was beating down and I was worried that I would have some pretty bad burns. Fortunately, we brought lots of sunscreen (see, we weren’t that unprepared). Second, about 2 miles into the hike, my right heel slipped out from above the sole of my sandals while walking down Sliding Sands and I stepped on a sharp, coral-looking rock and it cut my foot a little. It was bleeding and my heel later did feel bruised, so I was walking exclusively on the ball of my foot for the rest of the hike.

The hike was beautiful, our favorite part of the trip and something that I would highly recommend to anyone who is interested in beginner-level hiking. The sunset at the end of the day is also quite remarkable to experience, but very, very cold temperature-wise. This is something that was outside of our comfort-zone.

We met up with Jose and Paulina a few other times for food and to check out beaches while we were on Maui and then later, Kauai.

A Few Opinion Tips

  • Don’t rent a Jeep (unless you really want it)
    • There was only one point where I wish we had a jeep (off-road beach)
    • A Jeep would have made the Highway to Hana more difficult
    • Honestly, I would suggest renting the smallest, cheapest car
    • most locals on maui and kauai drove older cars with sun-damaged paint
    • it was actually super easy to pick out locals from tourists, who all drove clean, new mid-tier cars e.g., Chevy Malibu, Ford Fusion, etc)
  • Expeditions felt over-priced and tourist-y
    • I understand that people make a living from these businesses and people are willing to pay the price
    • But if you are on the edge about paying it, skip them
    • You can do most of things yourself anyway (e.g., Highway to Hana, Haleakalā National Park)
  • A lot of the experiences worth doing (in terms of time) were free or very cheap
    • All beaches in Hawaii are open to the public
    • Haleakalā hike ($25 national park fee, good for 3 days)
    • Helps cover field trip costs for kids
    • Restoring park trails
    • Visitor center improvements (restrooms, parking lots, etc)
    • Controlling invasive species
    • I would be willing to pay much, much more (e.g., the price of an excursion)
  • Focus on experience it because pictures and videos don’t do it justice
    • I’m not saying don’t take pictures, etc., just that unless you are a professional, they aren’t going to do a great job of displaying the beauty