Chasing Hawaiian Sunsets

There’s something magical about Hawaiian sunsets.  Every night, thousands of people congregate on beaches, balconies, hiking trails and anywhere else with a view of the setting sun to watch the dazzling show in the sky.  Having been to Hawaii many times, I’ve witnessed a lot of spectacular sunsets, but I hadn’t had the fortune of making it through an entire trip seeing the sunset every single evening, invariably something would occasionally keep me from being outside to watch day turn to night.

I just returned from a month long trip to Hawaii, and above all else, my #1 priority was to be outside to watch the sunset every night – even if that meant standing in a hurricane to watch a dark and stormy sky fade from grey to black (yup, that happened!).  34 incredible days on the islands meant 34 opportunities to chase the setting sun, and I am happy to report that I didn’t miss a single one.

Every night, as the sun approached the horizon, I would stop what I was doing, go outside if I wasn’t already there, turn towards the sun and count my blessings for another beautiful day in paradise.  I would also feverishly snap upwards of 100 pictures each night as the colors danced across the sky, hoping to capture the moment in all of its glory.  No sunset picture will ever come close to conveying the feeling of being physically present as the warm glow of the suns rays illuminate natures most breathtaking landscapes around you, but I hope the tale of my sunset chasing adventure throughout Hawaii and the pictures that accompany it come close to briefly transporting you into that space of incredible beauty.



#1 – “Kahana Ocean Front”

Kahana Reef Condo #122

After a long day of travel, I finally made it to Maui!  As I was getting settled in to the Airbnb that I would spend my first three nights at, I was treated to this view of the sun disappearing into the ocean from my ground floor patio.  Being just feet from crashing waves and beautiful sunsets, I couldn’t have asked for a better way to start to the trip, everything about this condo was perfect! I watched in total peace, thankful to be back in paradise, as the clouds rolling off of Molokai in the distance slowly changed colors for what seemed like an eternity.


#2 -“Hibiscus Glow”

Makaluapuna Point

I spent my first full day on Maui snorkeling, swimming in the Ritz Carlton pool and catching up and with friends who just happened to be on the island at the same time.  While they coordinated dinner, I took a short walk down to the nearby “Bay Course” at Kapalua, where I found these Red Hibiscus glowing in the dwindling day light just past the green for hole #4.  Little did I know at this time, I would end up seeking shelter with them at the Ritz later in the week as Hurricane Lane pummeled Hawaii.


#3 – “Highway Above The Bay”

Honolua Bay Overlook

On the way back to my condo from exploring the “Chutes and Ladders” tide pools, I pulled over at this lookout along the Honoapiilani highway overlooking Honolua Bay to watch the sun cast its final rays of the day.  Earlier that afternoon, I was sampling Valley Isle Kombucha at the Alchemy Tasting Room in Lahaina when I learned about the pools which could only be accessed by a “dangerous” climb down a 100 foot vertical sea cliff wall.  I had to check them out, and they didn’t disappoint!  Neither did this sunset.


#4 – “100 Surfers”

Ho’okipa Beach Park

Before settling into the Paia Aloha Surf Hostel for the night, I stopped by Ho’okipa Beach Park, a popular surfing spot.  I counted nearly 100 surfers waiting to catch the perfect wave back to shore as the sky faded from orange to black.  Some of the outermost bands of the now Category 5 Hurricane Lane were beginning to push through gusty winds and scattered showers.  By this point, I had received notification that my camping permits for the following four nights had been revoked.  I was crushed…I came all this way to backpack through Haleakala Crater, and I had to accept the reality that I wasn’t checking that off my bucket list this trip.


#5 – “Dinner at Dukes”

Dukes Beach House, Maui

Before hiking into Haleakala, I was supposed to spend one night camping in Wai’anapanapa State Park near Hana on the east side of Maui.  With torrential rains expected to pound that side of the island over night, I was forced to find other accommodations – fortunately I still had friends at the Ritz who welcomed me in to ride out the storm with them.  We took advantage of the “calm before the storm” by visiting the Maui Ocean Center Aquarium and then had a nice beach front dinner at Dukes while being treated to a sunset that lit the entire sky ablaze. Moments after the sun went below the horizon, the skies opened up and it started pouring rain!  It would be several days before we saw the sun again…


#6 – “In the Slow Lane”

The Ritz-Carlton, Kapalua

Not all sunsets mean colorful skies.  Hurricane Lane was making its awfully slow crawl past the islands, and the clouds were just too thick to catch any glimpse of the sun – the sky was grey as far as the eye could see.  In anticipation of the storm, the hotel completely cleared the pool deck of anything that could turn into projectiles, but that didn’t stop a crazy few (us included) from going for a swim during the storm.  We could only tolerate sitting in the room and watching the weather channel for so long!


#7 – “Lane, Lane, Go Away!”

The Ritz-Carlton, Kapalua

We spent the entire day cooped up indoors again, watching the weather news and waiting for Hurricane Lane to pass.  Not willing to miss any sunsets, I stepped away from the dinner table at the time the sun would be setting to run outside, into the wind and rain, just long enough to snap a picture of the dark stormy clouds that dominated the sky all day.  With most flights to and from the islands cancelled, my friends were forced to extend their stay an extra night.  Fortunately for me, that meant one more night with a roof over my head…


#8 – “Kihei Showers”

Lipoa St, Kihei

Hurricane Lane began to deteriorate and Hawaii airports were resuming operations.  My saviors were able to catch a flight home, meaning it was time for me to find somewhere new to stay. Camping was still definitely out of the question, so I booked an Airbnb in Kihei where I would spend my last few nights on Maui.  Heavy clouds and occasional showers persisted all day, but a tiny sliver of sun light was able to break through the clouds in the distance right at sunset.  It wasn’t much, but dang it was nice to finally see a few rays of sunshine again!


#9 – “Hippy Drum Circle”

Little Beach, Makena State Park

With the worst of the storm over, I was ready to get back outside and do some hiking.  The first trail I went to was closed, and so was the second, so I gave up and opted for a wonderful massage at Aloha Massages in Paia instead.  After that I headed down to Little Beach, which is typically known for its nude sun bathers… but on Sunday nights, drummers, dancers and fire spinners put on a show for hundreds of (mostly clothed) spectators as the sun sets.  As the beat of the drums pulsed through the crowd, the dark clouds that blanketed the sky all day gave way just enough to allow a little bit of the setting suns glow to shine through.  Several yelp reviews caution against partaking in the special brownies and cookies being sold on the beach, but in my opinion that advice is unwarranted…


#10 – “A Hui Hou, Maui”

Sugar Beach Resort

My time on Maui was coming to a close and in the morning I’d be boarding a flight to Molokai.  After a jam packed day of exploring the Ali’i Kula Lavendar Farm and Kula Botanical Gardens, I drove to the summit of Haleakala to carry on my tradition of watching the sun set from 10,000′ on my final night on the island.  Pouring rain and thunder greeted me when I reached the visitor center, so I headed back to sea level to watch the setting sun from the comfort of my condo balcony.  With a backpacking trip through Haleakala still sitting at the top of my bucket list, I knew it would only be a matter of time until I returned…  until we meet again, Maui!


Hurricane Lane completely altered the course of my stay on Maui, and although I left disappointed that I didn’t make it into the crater, I made the most of the situation and was able to experience a bunch of things that I wouldn’t have otherwise had the opportunity to do.  My grand Hawaii adventure was still young and I had plenty of exciting adventures waiting for me on other islands!



After years of visiting Maui’s west shores and looking across the Pailolo channel to Molokai, it was finally time to stop wondering what it was like over there and go experience it for myself.  I was drawn by the stories of natives still living according to the traditional Hawaiian culture and the radically slower pace of life on the island.  There are no mega resorts or street lights to be found on Molokai, and the locals intend on keeping it that way.  Despite their efforts to shoo off the tourism industry, I found many locals that were friendly and eager to share stories of their land and ancestors that had been passed down through the generations with me.


#11 – “Peaceful Pier”

Kaunakakai Harbor

I spent my first day on Molokai getting the lay of the land and checking out a few highly recommended stops like Purdy’s Macadamia Nut Farm and Kumu Farms road side produce stand.  As the sun began to fade, I took a stroll along the Kaunakakai Harbor where I found this empty pier inviting me to take a seat and watch the colors radiate in the sky.  This was another one of those sunsets that seems to go on forever, constantly evolving as the clouds rolled across the sky, illuminated by an ever changing array of colors.


#12 – “Up, Up, and Away!”

Mauna Loa Highway overlooking Molokai Airport

My alarm clock knocked me out of bed while the sky was still pitch black and I began my drive to the Halawa Valley on the east side of Molokai to watch the sun rise.  As day broke, it began to rain, and my guided hike to the Halawa Falls was cancelled.  I spent the day exploring other parts of the island instead.  I was heading back to my Kaunakakai Airbnb after visiting the Kalaupapa Lookout on the northern side of the island when the sun began to set, so I pulled off along the side of the road adjacent to the airport.  This little plane just happened to be taking off right as the intensity of the colors in the sky reached their peak.


#13 – “Kepuhi Rays”

Kepuhi Beach Resort

After staying a couple nights on the southern shore of Molokai, I relocated to the west end of the island to experience what that side has to offer.  The balcony of my condo would have made for an amazing sunset view, but I wanted to stroll along the beach and plant my feet in the sand instead.  I had visited a few other near by beaches during the afternoon, but the water was murky and sand covered in debris from the storm, so it was nice to have clear water and soft clean sand between my toes as I watched the sunset.


#14 – “Upcountry Sundown”

Mauna Loa Highway

I hadn’t given up hope on seeing Halawa Falls, so I woke up early again and drove all the way across the island in hopes that the weather would cooperate for a hike, and it did!  The hot and humid 4.5 mile round trip hike was broken up by a cold and refreshing swim under the raging waterfall.  On the way back to my condo, I stopped at Maunaloa, a small village that sits at about 900 ft elevation in the hills overlooking the west end, which made for a perfect spot to watch my final Molokai sunset of the trip.


Molokai is a tiny and quiet island, without the major attractions or tourist traps that can be found on the other islands.  It was perfect for relaxing and soaking in nature without mobs of other people around.  In fact, I had entire stretches of beach completely to myself and seeing other people wandering around the condos I stayed at was rare.  The locals were friendly and welcoming, and the landscape breathtaking.  I looked back across the channel towards the beaches and resorts on Maui where I had often contemplated making a trip to Molokai one day…I felt complete having finally made it.  My stay was short, but my family was en route to Ohau, and I had to hop on over there to meet them.



#15 – “Lagoon Light Show”

Ko Olina, Honu Lagoon

After landing on Oahu and meeting up with my mom and sister, we checked into our timeshare and headed straight outside to wander around the property and soak in our first Oahu sunset of the trip.  I found this cluster of palm trees with an unbeatable view of the sunset along Lagoon #2, just to the north of the Marriott we were staying at.


#16 – “Hanging At The Hotel”

Marriott’s Ko Olina Beach Club

By morning, my sister and I took to the skies in powered hang gliders over the north shore of Oahu… by night we were back at the hotel watching another gorgeous display of color radiate off of the water and clouds as the sun dipped below the horizon.  The instructors at Paradise Air Hawaii were amazing and floating over the coastline for nearly an hour was definitely the highlight of our time on Oahu!


#17 – “End Of The Road”

Keawaula Beach

While hang gliding, my instructor planted a seed in my mind about skydiving out of the same air field, which quickly turned into making a reservation for a sunset jump the following evening.  Unfortunately, when I arrived at the dropzone, the plane was grounded due to storms overhead, and my jump was eventually cancelled. We made it back to our hotel before sundown, so I decided to drive out to the end of Farrington Highway, to the western most point of Oahu, to catch the sunset from a different location.  The scattered clouds made for a dramatic display of color throughout the sky and their reflection off of the water was unreal.


#18 – “Paradise Found”

Paradise Cove Beach

My morning started with a 5am drive back up to Haleiwa where a North Shore Shark Adventures boat was waiting to transport me a couple miles off shore.  A blast of adrenaline woke me up the moment I jumped in the cold ocean water surrounded by 10 Galapagos sharks!  I was in a cage… but it was still a rush seeing those huge animals in their natural habitat.  After that, I visited Waimea Valley before heading back to the hotel for some relaxing pool time.  As the daylight began to fade, I walked along the winding path that snakes between the man-made KoOlina lagoons and several beachfront resorts, eventually ending up at  this cove, and the home of the Paradise Cove Luau. 


#19 – “Northern Tip”

Kawela Bay Beach Park

My mom and sister wanted to visit the Polynesian Cultural Center so we spent the afternoon wandering through the villages and exhibits there, followed by a delicious luau dinner.  The evening show wasn’t starting for a little while, and the setting sun was completely obstructed by the buildings and mountains to the west.  I couldn’t miss a sunset, so I hopped in the car and took a quick drive around the north tip of the island and found this beach.  I was in a hurry, so I snapped a few quick pictures and raced back, arriving just in time for the start of the “Ha: Breath Of Life” show.


#20 – “Pillbox Peak”

Pu’u O Hulu Summit

Aahh, finally a day to do absolutely nothing!  And by nothing, I mean sit at the pool all day and relax. I turned to the internet for suggestions on where to watch the sunset, and discovered that hikers who make the 500 foot ascent to the top of Pu’u O Hulu are greeted by several abandoned military pillboxes and incredible views all along the western shore of Oahu.  I knew this “off the beaten path” location would be the ideal spot for a completely unique view of the setting sun without all the crowds, and it was totally worth the short, but strenuous climb.  I opted for the “hard route” which bypasses the switchbacks, and scales nearly straight up the side of the mountain.


#21 – “Magic Moments”

Magic Island Lagoon, Honolulu

Our week on Oahu was coming to a close, and my mom and sister still hadn’t had their fill of shopping, so we took a trip down to the Honolulu and Waikiki shopping areas so they could pick up a few last-minute, must-have souvenirs.  Tacky tourist shops aren’t really my jam, but I was happy to oblige, as long as I could take pause to watch the sunset.  I had read that Ala Moana Beach Park has good views of the setting sun, and we happened to be right in that area, so we made a pit stop for the nightly show.  I ended up walking out to the end of Magic Island Lagoon to catch this shot.


Culture shock set in immediately when I arrived on Oahu after Molokai.  The crowds, traffic, and skyscrapers were a stark contrast to the quaint little island I had just come from.  I love all of the Hawaiian islands, but if I were forced to rank order them, Oahu would sit behind all the others.  Don’t get me wrong, we had a fantastic time and we were able to do things that the other islands don’t offer, but I think we had our fill of Oahu for a while and we look forward to trips back to the smaller, less crowded islands in the future.  As my mom and sister boarded their plane back to the mainland, I continued my trek westward on a flight to Kauai, where several friends would be waiting for my arrival.



#22 – “Mountains On Fire”

Marriott’s Kauai Lagoons

The sun was hidden behind heavy clouds and light rain when I arrived on Kauai. My personal chauffeurs for the week (aka the friends who arrived before me) met me at the airport and we headed for the nearby Marriott which we would call home for the week.  As everyone was unpacking and getting settled in on our first evening, the mountain range across from our balcony lit up orange, as if to be aglow with fire.


#23 – “Sunset Sail”

Blue Dolphin Charters Sunset Dinner Cruise

The stunning views along the Napali Coast never get old, so one of my must-do experience on this trip to Kauai was a sunset dinner cruise along the coast.  The crew on our Blue Dolphin boat was awesome, and watching the fading sun glisten off of the waves behind us as we sailed back to port was stunning. When we reached our turnaround point, near where the Kalalau Trail ends, I was surprised to find that the beach didn’t have a single tent or person on it.  At the end of the week, I was supposed to backpack this trail and camp on this beach, something didn’t feel quite right…


#24 – “Sandy Glow”

Kiahuna Beach, Poipu

After exploring the McBryde Botanical Gardens and checking out Spouting Horn Blow Hole, we ended up at Poipu Beach to relax for the afternoon.  As the sunset crowds descended on Poipu Beach, I walked west past several resorts and found this secluded spot.  I loved how the low angle sun light skipped across the sand on this beach illuminating it in an intense orangeish glow.


#25 – “Waimea Hills”

Kekaha Lookout, Waimea Canyon

After soaring over Kauai with Jack Harter Helicopters, we spent the afternoon exploring Koke’e and Waimea Canyon State Parks by car and foot.  While hiking back from swimming in Waipo’o Falls, the suns light was quickly disappearing behind the mountains and shadows shroud the path.  Once we made it back to the car, we raced down the mountain towards sea level, stopping at several lookouts along the way in hopes of catching a view of the setting sun.  We found this clearing and incredible view just seconds before the sun fell out of view and the color faded from the sky.


#26 – “Pounding Waves”

Hokuala Golf Course, Hole 14 (Overlooking Ninini Beach)

Hurricane Lane wasn’t alone in stirring up the Pacific. Hurricane Olivia followed in his footsteps and brought more wind and rain to the already drenched Hawaiian islands.  Fortunately for us, by the time Olivia made it to Kauai, she had been downgraded to a tropical storm.  Despite the weakening, she still battered Kauai with pretty intense wind and rain on and off all day, sending huge waves crashing towards the lava rock cliffs that line the shore and the usually calm “secret” beach tucked at the base of them that we like to swim at.  Determined to capture the moment, I ran out into the storm, yet again, right as the sun would have been setting.


#27 – “Pool Guard”

Marriott’s Kauai Lagoons

Tropical Storm Olivia graced us with another wet and rainy day.  We braved the weather to venture up to the north shore for the afternoon, and ended up back at the resort just in time for another cloudy sunset.  This awesome tiki had been carved out of a palm tree and stood guard ominously over the pool area.  The only color in the otherwise dark sky came from the torches blazing across the pool.


#28 – “Luau Lagoon”

Smith Family Garden Luau

We ended the week with a celebration of the local culture at the Smith Family Garden Luau, complete with a feast followed by traditional song, dance and story telling.  I ran out to this lagoon between my first and second plates of food to catch what I could of the sunset.  Despite the sun being obstructed by the mountains and clouds in the distance, the purple glow reflecting off the water made for a stunning sight.


Another amazing week was coming to an end.  My companions were heading back home, and I was supposed to be gearing up to spend three nights backpacking the Kalalau Trail along the Napali Coast before returning back to the mainland myself.  After seeing the empty beach on our boat ride, I discovered that the road leading to the trailhead, and parts of the trail had been damaged and were indefinitely closed.  As far as bucket list hikes go, this was a close second to Haleakala crater, and once again I was defeated.  I was NOT leaving Hawaii having accomplished neither of those hikes!  Haleakala National Park had reopened after Olivia and they were issuing back country permits.  As soon as I confirmed this, I booked the first flight I could back to Maui, I was determined to get in that crater!



#29 – “Desert Daze”

Lahaina Pali Trail

I landed back on Maui that afternoon and set out to pick up last minute supplies for my backpacking trip as well as chase the sunset before settling into a cheap hotel near the airport for the night.  Maui has such diverse climates and landscapes across the island, so I wanted to find a sunset to show a different perspective on its beauty.  I left behind the beaches and palm trees to hike into the desert like mountains near Olowalu.  After hiking two miles up, I turned around to head back down as the sun sank behind the island of Lanai.  It may not look very tropical, but it’s every bit an authentic Maui sunset!


#30 – “Summit Sunset”

Haleakala Visitor Center

I spent the morning triple checking all the gear in my backpack and was on the road to Haleakala by mid afternoon.  I picked up my permit at the visitor center and continued the drive up to the summit to watch the sunset.  People tend to crowd at the true “summit”, but I prefer to hike the short Pa ka’oao Trail (White Hill Trail) to a different vantage point that usually has fewer people and just as amazing of a view. I slept in my rental van at the trailhead and prepared for a very early morning start.  PS: This was a fantastic spot to watch the sunrise the following morning as well, it was much less crowded than down at the visitor center overlook.


#31 – “In Da Crater!”

Paliku Campsite, Haleakala National Park

After watching the sunrise at the summit, I began descending to the crater floor.  It took 4 hours to hike the 9.5 miles from the summit to the Paliku camp.  I setup camp and spent the afternoon trying to avoid the brutal heat of the direct sun, shade was hard to find.  The temperatures cooled off quickly as the sun faded behind the summit wall, but the twilight glow in the sky seemed to last forever after the direct sun light was blocked by the tall peaks of the crater. 


#32 – “Split The Gap”

Kaupo Gap, Haleakala National Park

I spent the day relaxing around camp, reading, meditating, writing in my journal…and trying to stay cool once again.  The sunset looking to the west was identical to the night before, so I waited a bit longer and then turned to the south to catch the sun refracting off of the clouds visible through Kaupo Gap.


#33 – “Silence…”

Houla Campground

After hiking 7 miles back across the crater floor, I setup camp here at Houla Campground and then set out to find a “secret” cave near by.  Being at the base of the towering 2,000 foot crater walls, the sun disappeared from view even earlier in the afternoon.  This campsite has a view out to the sea through the Ko’olau Gap to the north, so I waited until the low hanging clouds in that direction began to glow orange from the setting sun to snap this pic on my final night in the crater.  After the sun went down, the air became perfectly still, the birds and insects became quiet… an absolute silence fell over the crater.  I wont soon forget the peace that washed over me looking up at the millions of stars that lit the sky that night!


#34 – “Grand Finale”

Kahana Beach Park

The morning sunrise was my cue to begin the 4 mile hike back out of the crater.  The first mile was downhill, and the last three were a relentless grind up steep switchbacks that rose 1,500 feet in elevation.  I powered through the climb and made it to my waiting car at the Halemauu trailhead in about 2 hours flat.  I headed straight to the closest restaurant, at the Kula Lodge part way down the mountain, to have my first real meal in days.  After that I stopped at Baldwin Beach Park to go for one last swim in the ocean and then returned to Aloha Massage to relieve my sore muscles before hopping on a red-eye flight back to Vegas.  My flight home left just barely late enough that I was able to visit the beach that’s adjacent to the airport to catch my final sunset of the trip as the the sun dipped behind the west mountain of Maui.


I am so fortunate and grateful for the time I got to spend in Hawaii, and for the friends and family who joined me along my trek.  They made an already incredible trip even more memorable and special in ways I cannot express.  These pictures give me a visceral connection back to the exact moment I took them, and it was a joy to relive the trip as I told the story of my journey through them.  I hope you found some inspiration in this post… to go to Hawaii if you’ve never been, to go for a hike and watch the sunset, or to check something off of your bucket list!  Life is short, being surrounded by nature is magical, get out and enjoy it.  I’d love to hear which picture was your favorite!



  1. Susan says:

    They’re all beautiful, Matt! The different colors of the clouds, the rays of the sun breaking thru….I really can’t pick a favorite.

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