Hawaii, 30 years later

In 1996, I took my very first trip to the state of Hawaii, where I spent 5 days in Oahu to attend a wedding with my then-girlfriend (now spouse). As a kid growing up in Southern California, I remember the rich kids went to Hawaii for xmas vacations but I was always curious what the place was like.

The first thing that struck me when I walked off a plane in Honolulu was the completely different weather from where I had started. The wall of humidity I was met with felt like walking through soup instead of air. I truly was somewhere else new and exciting.

I had a lot of fun on that trip. Because of the time change, we'd get up at 6am every morning, walk down to the ocean, and swim in the waves until breakfast places opened up. We'd trek down Waikiki beach to Diamond Head and walk up the crater as a post-breakfast walk. We ate pineapples and papaya and generally had a great time.

The interim years

After moving to Oregon in 2003, the long dreary winters started getting to me, and I realized my Alaskan friends that went to Hawaii or Mexico every year weren't living some lavish lifestyle, it was a form of survival for them. I began to understand that by February each year everyone in Oregon was totally DONE with cold wet winters and desperately needed a break for their own sanity.

I think our first trip to Maui was in 2007, then we hit Kauai the next year and then did a few years on the Big Island in Kona and Hilo. 90% of the state's population is on Oahu, so we always stayed on the other islands for a more relaxed, less crowded atmosphere. Looking back at my photos, I don't think we've been back since 2012.

The 2025 trip

Kay proposed we take Fiona with us as a spring break trip. We hadn't been back to Oahu since and figured we'd heard so much about the great food there and how much had built up and wanted to see how it changed since that first trip. It's also relatively cheap and easy to get direct flights and hotels.

The good

Hawaii is amazing at delivering a sunset and sunrise at the same time of day, year round, along with 85ºF daytime highs and 75ºF nighttime lows. Getting out of Waikiki is a must, as the center of Oahu is beautiful as you drive through miles of pineapple fields and the north and eastern shores have incredible beaches you'll mostly get to yourself.

I fell back in love with snorkeling on this trip. I only get the opportunity to snorkel once every five years or so but I always have to relearn how to not freak out while breathing underwater. Once I get over that, the most relaxing thing in the world is floating at neutral buoyancy just above a shallow reef, looking down at fish you've only seen in aquariums before, but they're swimming around in the wild. It always blows me away.

We stayed at the same hotel we did in 1996, but since then it transformed into a place catering to Japanese travelers. Everything was quiet with bilingual signage, the pool area was subdued, and there was no music playing anywhere. The food options were interesting as a result and if you like a calm hotel experience where everyone goes about their day with minimal interactions or chit-chat, look for places like the Halepuna Hotel.

I forgot how incredibly useful the ubiquitous ABC Stores are. Waikiki has an ABC Store on almost every corner, and I'd hit the one below our hotel at least twice a day for bottles of water and beach snacks and sandwiches and poke from the deli. The bigger ones also stock anything you forgot to pack and we even ended up getting snorkels there.

We took a surfing lesson that was another highlight of the trip. I've spent decades skateboarding and snowboarding during my life but I'd never tried a day on a longboard in the surf before. We had private lessons from a nice place nearby and for an hour we bobbed in the waves on the reef, each of us catching half a dozen waves and we all got to stand up and enjoy at least one long ride. I gained a whole new respect for surfing as the balance point even on a stable 12' board felt tiny and twitchy. I can see how incredibly hard surfing a short board in heavy surf must be and how it can take many years to get good at it.

The bad

The most shocking thing to me was how Waikiki has turned into a giant shopping mall that stretches for dozens of blocks in all directions. Back in the 90s, there was the famous beach, but if you wanted to hit some shops, you had to walk a few blocks away from the sand (that were also easy to avoid).

These days? There are massive sprawling shopping malls on both sides of the main street, practically up to the beach sand itself. There are also baffling things like ultra high-end Tiffany and Co and Gucci stores plopped right next to a Ross Dress for Less.

What used to feel like an island paradise with some buildings nearby now feels like a Las Vegas strip dropped into the tropics. There are buskers and magicians and people holding parrots that want $20 for a picture. Walking to the main Waikiki beach felt like running through a scammy gauntlet each day. I'd strongly suggest everyone rents a car to visit the rest of the island because Waikiki felt like the least Hawaii-like place on earth.

Another shock was that almost 30 years later, the beaches and reefs around Waikiki had changed drastically. Where we remember a long low-sloped beach across the street from our hotel was completely gone, as waves were slapping against the concrete foundations of hotels and there were minimal shorelines created with a few feet of imported sand. The old Waikiki beach used to be a great place to learn to surf in waves that seemed to roll in forever, and now you had to paddle out for 5-10 minutes to reach the outer reefs to find breaking waves.

Oahu really felt like 90% of the population was there, since pretty much every place was crowded, the freeways moved at a standstill, and almost every restaurant required reservations. Also? We never got to set foot on Diamond Head because they were doing some landslide cleanup and reduced their 1-hour hiking permits to minimal amounts so much so that no permits opened up during our entire stay.

Food was expensive and I get it—it's a vacation island far away from where stuff is grown, but the quality of meals didn't match the prices where everything was $30 a plate even when I was trying to hit recommended places from Eater.

The WTF

I had heard Oahu was finally building light rail, and was curious to see what it was like, but it turns out they're in the early stages with only a fraction of track built and a train from Honolulu airport to Waikiki Beach probably won't be completed until well into the 2030s. I wish they started building it years ago since every afternoon, the drive into Waikiki from the east was choked with standstill traffic. When we landed at Honolulu, a rideshare took 40min to reach Waikiki while public transit was going to take over 90min. We noticed every Japanese airline had their own greyhound-sized buses to deliver passengers from the airport to the hotels, since public transport in the US is so far behind every other country.

Overall, Hawaii is still quite the tropical paradise offering unparalleled beaches and access to natural beauty in all the areas outside of Waikiki, but I think I'm done with Oahu and will plan future trips on the Big Island or Maui instead.