Hawaii: Tips on How to Truly Experience the Hawaiian Islands

So many people go to Hawaii every year for vacations and many of them miss out on what Hawaii has to offer. There’s a good chance you’ve been to Hawaii and stayed at a fancy resort and drank Mai Tai’s on the beach while soaking in every ounce of sunshine until you looked like a ripe tomato.

Here’s my take. Unless you’re going to a beach with something distinctly different from 99% of other beaches (mountains, crystal clear water, reefs, etc.) then all beaches are about the same. Every beach I visited in Hawaii would have fallen into the 99%, just beaches. That doesn’t mean they weren’t beautiful and relaxing, but they really weren’t that different from anything on the mainland coasts of the US. With this being said, why are we paying all of this money to go to Hawaii and do something that we could do in San Diego or Miami for a fraction of the price? If we are going to spend the money to go to Hawaii, let’s make it worth it and squeeze every ounce out of experiencing all of Hawaii!

This blog is to help encourage you to experience the pure, natural beauty of these islands and help give you memories that you’ll talk about for years to come. People don’t talk about Mai Tai’s in 20 years, but they do talk about hiking to the best view of their life.

*Onlookers at the Haleakala Crater Summit silhouetting a sky on fire!*

Get Out of Your Resort!

Rule #1. Don’t stay in your resort.

If you want to splurge on a fancy beachside resort, be my guest! There are some great ones on the Hawaiian islands. BUT. Don’t stay there all day. There are so many things to do in Hawaii that are relatively cheap (many of which are actually free) that would multiply your experience many times over. I think a lot of times it’s easy to just stay inside the confines of the resort because it’s convenient. You can have drinks brought to you, you don’t have to think, you don’t have to spend energy, etc. Those days can be so good! I actually encourage a day or two like that on a trip! But let me unpack a few things you can do on the rest of the days that will 1) blow your socks off, 2) keep you feeling great and get the endorphins going, 3) give you far more memories than laying on a beach ever could.

Hiking in Hawaii

The best thing Hawaii offers in my opinion is the number of epic hikes you can do! I LOVE hiking and being active when I travel. Not only do I sleep 10x better at night, but it keeps me feeling healthy and less guilty when I stuff my face with fistfuls of seafood afterwards. Below are a few of the best hikes that I’ve done in Hawaii!

*All difficulty levels and distances taken from All Trails app…

Stairway to Heaven (LEGAL SIDE) – Oahu

- Starting Point: There’s a parking lot at the trailhead for the Moanalua Valley Trail. This begins the hike up the LEGAL side to Stairway to Heaven (also known as the Haiku Stairs). The lot closes at dusk, so make sure you start early in the day.

- Difficulty: Hard

- Distance: 10.6 miles (out and back)

- Tips: The biggest thing is to make sure you know the weather for the day. If it is going to rain AT ALL, I need to advise you NOT to go! We made this mistake and it was an incredibly dangerous hike that could have cost us our lives (I’m not being dramatic here). It is still a tough hike in dry conditions so be prepared, bring PLENTY of water. This hike is going to take anywhere from 8-10 hours round trip. Look out for guava trees along the way for a nice refreshing snack and mental pick-me-up! There is a $1000 fine for going up the stairway from the bottom, hence the addition of “legal side”. We didn’t risk it on the way down either, but some people say you only get fined on the way up, not on the way down. Proceed at your own risk.

Olomana Trail – Oahu

*The view of the 3rd peak from the 2nd peak on the Olomana Trail!*

- Starting Point: Park a ways away as there are towing operations in the area. The trailhead is on the road to the Royal Hawaiian Golf Club off of Loop Road. The entrance to the trail will be on the left with small signage.

- Difficulty: Hard

- Distance: 4.4 miles (out and back)

- Tips: This is a very tough and strenuous hike. Be prepared mentally and physically before you go. There will be spots where you are bouldering over rocks using ropes, other parts where you are hiking up rocks that seem more like giant stairsteps, and other parts that are a bit of both. The view from the first peak is spectacular, but the view from the second peak is the moneymaker. Getting to the apex of the second peak is tough, so go slow. We didn’t even consider the third peak due to time and fatigue, but we saw others going up. I’d suggest the third peak only if you have enough sunlight, the right climbing equipment and heavy experience.

Pipiwai Trail – Maui

- Starting Point: After entering Haleakala National Park, you’ll see signs for the trail. It is a relatively flat trail, with moderate and gradual elevation. If I were to rate this, it would be an easy trail. I saw tons of families going up and back.

- Difficulty: Moderate

- Distance: 3.4 miles (out and back)

- Tips: Bring insect repellent! You’ll pass through a beautiful bamboo forest, but this also means the presence of mosquitos. Trust me, you’ll thank me. The trail is pretty straight forward with a beautiful waterfall at the end. I highly encourage waterproof shoes or Chacos as you will need to get wet to get to the base of the waterfall!

Queen’s Bath – Kauai

*The most epic FAILED backflip ever caught on camera.*

- Starting Point: If you follow the GPS to the area, you’ll drive through a neighborhood and come to an area with about 10 parking spots. You may need to be patient and wait for a spot to open. Please don’t park in front of people’s houses. The trailhead is to the right of the parking.

- Difficulty: Moderate

- Distance: 0.8 miles (out and back)

- Tips: The only reason this is moderate instead of easy is due to the mud on the way down. If it dry, it is easy to navigate to the baths. The baths themselves are dangerous for the most part, except for one, the Queen’s Bath. When you get to the rocks, make a left and go down a few baths and you’ll find a beautiful one with clear water! Enjoy a relaxing swim, jump from the rocks, or even attempt your first ever backflip like I did!

Makaua Falls – Oahu

- Starting Point: Park by Swanzy Beach and walk a half mile to the end of Huamalani Road. There’s signage at the end of the road signaling the beginning of the trail.

- Difficulty: Hard

- Distance: 1.3 miles (out and back)

- Tips: There is a fork fairly early on in the hike, one goes up a ridge and the other follows the dry river bed. Stay on the trail to the right to follow the river bed. There are pink ribbons marking parts of the trail. For the most part though, you can just follow the river bed all the way to the falls. There are several areas where you will need to scale a wall with a small rope. To do this, you’ll need to be prepared to get wet. I personally took my shoes off and did it barefoot, but I don’t recommend this for safety reasons. I highly recommend doing this hike with a partner! The waterfall is super skinny and oftentimes will run dry depending on recent rainfall, so for the best views you’ll want to go right after a rainfall! While it says it is only 1.3 miles out and back, it takes much longer due to the bouldering and crisscrossing of the path. Take it slow, be safe.

Sunrise and Sunset Missions

Being made up of such small islands, Hawaii offers SO many beautiful locations for both sunrise and sunset. With both coasts on each island within an easy driving distance, you might even be able to catch both on the same day! Below are a few of my favorite spots that you MUST try if you’re in Hawaii.

Haleakala Crater – Maui

*Arguably my favorite candid I’ve ever shot, from the top of Haleakala Crater at sunset.*

It’ll take you about an hour and a half to drive up the 10,000 foot mountain from the nearest town. But the elevation gain and hairpin turns will send your adrenaline through the roof once you summit. From the Crater Summit you can see not only all the way to the opposite end of Maui, but also to Lanai and Molokai! I suggest trying to arrive about an hour before sunset so you can wander around, see the crater, then grab a spot to view a spectacular show of fire in the heavens! Most people leave when the sun goes down, but the night I was there, this is when the colors really started! I encourage you to stay until it’s pitch black and take in a view of the stars as well! One thing to note is that even when temps are in the 80s and 90s on the beach, the Crater Summit will get into the 40s for sunset so DRESS WARM! If you think I’m joking, you’ll regret it. Sunrise is an option here as well, but with the amount of time it takes to go up the mountain, you’ll have to leave incredibly early to catch first light.

Big Beach/Little Beach – Maui

Big Beach and Little Beach are right next to each other on a westward facing beach making it perfect for viewing sunset. Big Beach has a reputation for being a bit of a wild scene at times, so if you’re looking for a quiet relaxing evening, go as far south as you can on Little Beach. There are plenty of areas to grab a seat, open up a beer, and experience every ounce of the tropical sunset that you’ve dreamed of.

Sandy Beach – Oahu

Sandy Beach is just off of the main highway on the east coast of Oahu (facing east obvi). While it’s facing east, one of the most spectacular views I had was actually of sunset here! I have to imagine that sunrise can be equally as breathtaking but consider it a strong candidate for both times of day! If you are staying in Honolulu or Waikiki (as most tourists do…), Sandy Beach is an easy 15-30 minute drive from wherever you are. This makes a PERFECT spot for a sunrise mission without costing you hours of sleep.

Sunset Beach – Oahu

I mean, how can I NOT include a beach called Sunset Beach?! Located on the north shore just north of some of the biggest surf waves you’ll find in the Pacific, Sunset Beach definitely lives up to its name. Full of soft sand, beautiful waves, and enough space for most of the island to watch from, this beach will act as more of a theater for a jaw-dropping sunset to the west. There are plenty of food stalls around the area so you can easily combine dinner with sunset any night you’re in the area! I took so many pics of other sunrises and sunsets that I decided to leave my camera in the car and simply enjoy this view without any distractions, hence no photo included.

Extra Adventures

I can’t recommend hiking and sunrise/sunset missions enough! They are free, easy, exhilarating, and evidence of God’s handiwork. But maybe you’re looking to do something a bit different than those. Below are my top three non-hiking activities that I did in Hawaii!

One Ocean Diving – Oahu

As I was preparing to go to Hawaii, a friend of mine who lives on Oahu told me about this company that takes you to swim with sharks in open water. Obviously, I was immediately interested. After looking into it and realizing it really wasn’t that expensive, we booked it and our adrenaline began pumping immediately! We literally volunteered ourselves… no, we PAID to be real life shark bait for Jaws 4. Located off of the north shore, One Ocean Diving takes you about 3 miles off shore to an area where Galapagos, Hammerhead, and Tiger sharks frequently hang out. Even before we got out of the boat, we were surrounded! The sharks were roughly 10-15 feet long, but seemed relatively disinterested in us as they lazily swam below us. It was an experience I will NEVER forget! This is not as death-defying as it sounds or as I made it seem, I promise. Galapagos sharks are known for being relatively passive and these were the only ones we really saw. Be sure to bring a DSLR camera with underwater housing or even just a GoPro to document this once in a lifetime swim!

Pearl Harbor Memorial - Oahu

I’m a big time history buff and I love seeing places in real life where big moments in history took place. Pearl Harbor is definitely one of them. I encourage you to go and take a tour of the area and be reminded of what it takes for us to live in freedom in our country. There are a limited amount of free tickets given away every morning so I suggest going before 9am both for decent parking and free tickets. Tickets are available for purchase after the free ones are gone. The Memorial fills up quite a bit after 9am so go early for a great experience. Please respect the area and those who lost their lives here.

Road to Hana – Maui

Ok. So I gotta admit I didn’t actually make the drive on the Road to Hana. I know. I’m mad at me too. It’s on the northeast side of Maui. I went on the southeast side because I could knock off more things on my list if I went that route. But everything I’ve heard from people is that it is one of the most magnificent drives you can make in Hawaii. With that being said, I must say there are a number of these types of drives along the coasts that will leave you in awe. So while I encourage you to make the drive on the Road to Hana, I DEFINITELY encourage you to find a mountainous coast and try to drive for 2-3 hours and soak in the views of monstrous ridges exploding from the ocean, covered in rainforests, hiding a countless number of waterfalls.

Final Thought

My ultimate hope for you and your future trip to Hawaii is that you would simply do something. Do something that takes your breath away. Do something that allows you to see into the creativity of God. Do something that involves truly LIVING. Not just sitting on a beach. And then when you’ve lived enough to the point of exhaustion, THEN go to the beach and work on that tan.