Impressions From My First “Real” Vacation In Hawaii

Filed Under: Travel

I’ve probably been to Hawaii half a dozen times in my life, though always only for a day or two. In almost every case it was part of a mileage run. All but one of those trips were to Honolulu, while one was to Maui. This was a long time ago, back before I was even old enough to rent a car. So I remember hanging out at the Hyatt Regency for a couple of days, and that’s it.

I guess based on my exposure to Hawaii up until now it’s no surprise that I never had much of an interest in vacationing there. 😉 However, it was Ford’s birthday a couple of weeks ago, so I was a bit surprised when earlier this year he asked if we could go to Hawaii for his birthday. So we spent nine nights there, and I had a… shockingly good time.

Why I’ve avoided Hawaii up until now

It’s not that I didn’t think Hawaii had its merits. It’s a popular vacation destination for a reason. However, I also generally expected that it’s overpriced and watered down due to how accessible it is from the mainland. I guess my impression of vacationing in Hawaii was somewhat similar to how I feel about the Ritz-Carlton Laguna Niguel — people go there because it’s (relatively) accessible, and as a result they can get away with highway robbery.

For most people, having to fly 20 hours to get somewhere sounds like torture. For me that has always seemed like a feature. So in the past I’d much rather redeem 67,500 AAdvantage miles to fly Cathay Pacific first class to Bali or Thailand, rather than choose between a bunch of mediocre airlines between the mainland and Hawaii.

None of these are reasons to avoid Hawaii, but rather we all only have so much time to visit places, and my priority was just always visiting somewhere else.

We had such a good time in Hawaii

I was expecting we’d have a nice time. The more I travel, the more I think that my impression of places is formed by who I’m with and how good of a time we’re having. Depending on the circumstances you can have a great time in a not-great place, and a terrible time in a beautiful place.

However, our time in Hawaii really exceeded my expectations in just about every way. We spent four nights on Lanai, four nights in Wailea (on Maui), and one night in Waikiki. I know many have the impression that I spend all day in front of my computer, and don’t see anything, and often that’s true. However, on this trip we spent at least six hours every day exploring, and couldn’t have had a better time.

This blog is about the journey rather than the destination, though I wanted to share some basic impressions.

Impressions of Lanai

Lanai is majority owned by Larry Ellison (that whole setup is a bit confusing to me), and has a population of just 3,000 people. We stayed at the Four Seasons here, which is the only resort on the island.

Lanai was special. For one, the people were so nice and laid back. I sort of felt like I was in the Philippines — as we later discovered, Filipinos settled here several decades back, so about half of the population on Lanai is Filipino. Even though it’s just miles from Maui, the people had their own culture.

But what was surreal was being on an island with almost no other tourists. While most of the population lives in Lanai City, outside the town we’d drive for miles and miles without seeing another car. We’d visit some of the most naturally beautiful places I’ve seen and be the only ones there.

If you don’t actually want to stay on the island, you can make an easy day trip from Maui by ferry.

Impressions of Maui

This was my first time exploring Maui in-depth, and wow, what an island. Our four days here were jam-packed, and I feel like we barely scratched the surface. While Lanai felt secluded and quiet, Maui has traffic, wide roads, and a Costco, so it has a completely different feel.

But the natural beauty was the highlight. Among other things, we did the six things that Tiffany said to do in Maui. Driving to the summit of Haleakala was an adventure in and of itself, though unfortunately we didn’t luck out with weather. It rained nonstop up there and we had no visibility, so we didn’t get the view.

Fortunately we had perfect weather on the Road to Hana. I was expecting there would be thousands of tourists and bumper to bumper traffic. It didn’t end up being nearly as crowded as I was expecting.

However, my favorite part was the ride back, taking the “not recommended” way.

Overall the thing that stuck out to me about Maui is the varied natural beauty. From beaches to volcanoes to tropical areas to dry areas, it had everything. Combine that with some great restaurants (I love seafood, so Hawaii is heaven in that regard), and I can see why so many people move here.

Impressions of Waikiki

We only had one night in Waikiki on the way back. I think Waikiki is pretty polarizing — people either love it or hate it. Maybe I’m weird, but there’s something I’ve always loved about Waikiki. Partly I like how you can have a lot of fun there without renting a car and walking around, partly I like that it almost feels like the Las Vegas of Hawaii, and partly I like the number of Japanese tourists, which creates a unique vibe you’ll find almost nowhere else in the US. And having spent the past 24 hours binge-watching Hawaii Five-0, I like Honolulu even more.

Bottom line

I knew we’d have a nice time in Hawaii, though the islands as such exceeded my expectations. I can see why people flock to Maui, and am happy I had the chance to see Lanai. Ford and I are already excited to go back sometime soon, especially since it’s not that far of a trip from the west coast.

I only have two general reservations with Hawaii:

  • As someone who works while traveling and likes to work in the morning US east coast time, it’s probably the worst timezone in the world for me
  • While Hawaii is beautiful, you won’t get nearly the value or quality you’d get from hotels in other parts of the world, especially in Southeast Asia

Still, I intend to return very soon, and really can’t emphasize enough how much more enjoyable our vacation was than I was expecting.

  1. Hopefully you make time to check out Kauai. The Grand Hyatt is top notch, and Kauai seems to overwhelmingly be everyone’s favorite island. We go every year from southern California using our annual Alaska companion passes. Hawaii is fantastic.

  2. Lucky,

    I wonder if you could do a quick post on your drive back from Hana the ‘not recommended’ way. I’ve seen warnings about not taking rental cars – so I’ve never actually done that route.

    It would be very interesting to hear just how forbidding the road actually is.

  3. where did u stay on maui and oahu? hope u stayed at the Halekulani on oahu and the four seasons on maui?

  4. Ben, I think the real joy of Hawaii is the scenery off the beaten track, so for a blog interested in Sheratons and Hyatts, there’s a danger you’ll gravitate towards unremarkable resort areas. I’m glad you loved it this time, and you might think about Kauai north shore next. Hanalei Bay is incomparable, and the Na Pali coast totally jaw-dropping. But mostly it’s rental houses rather than hotels up there, apart from the St Regis Princeville.

  5. Lucky, really glad you guys enjoyed the trip.

    I think Hawaii gets written off as “too accessible” or “basic” by bloggers and expert travelers. I think that’s a huge misconception. Sure, places like Waikiki are a huge tourist trap and not my ideal spot.

    But Kauai has to be one of my favorite destinations on earth. Absolutely stunning and worth the higher prices. And getting off the beaten path in Hawaii is essential.

    Plus, you won’t catch me staying in a chain hotel in Hawaii. A unique rental property via Airbnb or VRBO is the way to go.

  6. @Mike: The southern route back from Hana is interesting, but after awhile the desolation (scorched grass, black rocks) makes it feel like you’re driving through Mordor. Some of the roads are also really narrow, there may be no guardrail at points, no paved road and limited to no cell reception. For me, I could’ve done without it!

  7. We just did the road back from Hana on the non recommended way.

    It was beautiful but I can’t say that it was that much more beautiful than other parts of the island

    The ROAD wasn’t that bad. The issue was the width. It is 1.5 car widths wide in many areas with a cliff drop off on one side

    Thus, if someone is coming towards you it gets pretty hairy very quickly. [think pull mirrors in and go inch by inch, while having passengers get out of car to direct, and for safety in case a car goes over the side]

    It’s doable on a sunny day. Not rainy season.

    I just didn’t think it was worth it
    I’d rather just go back the normal way and eat banana bread

    The Kahekili road past Kapalua and Kahakuloa is worse. (Other side of Maui, beyond Kana’apali). It is 1 car wide and switchbacks along a cliff. People commonly have to drive backwards up a twisty mountain road for 1/2 mile or so as it is impossible for two cars to make it by each other
    But there is a cool art gallery at the endow that road at least

    I found both roads to be stressful
    I don’t go to Maui to be stressed

  8. Lucky,

    I hope you’ll consider traveling more (not just flying and staying in hotels) and I’d love to see you start doing expanded trip reports including this information
    (For instance, a trip report about the road to Hana)

    As for Hawai’i
    try the other islands.
    Hawai’i and Kaua’i are nothing like the islands you’ve been to.

    That’s one of the marvels of Hawai’i!

    Heck, Hawai’i island has 10 of the worlds 14 climate zones… all on one island!

  9. Every time I go to Hawaii (Kauai mostly) I wonder why I don’t go more often. Last time we took a couple of pit bulls from the local animal shelter for the day and spent most of the time swimming with them and avoiding the wild chickens (a delicacy for the dogs).

  10. Big resorts with huge pools are great, but I love staying in B & B’s seem I go. You always very free parking, wifi and of course breakfast. You get inside inside information from your hosts and feel a part of the island. I’ve stayed in magnificent en suite rooms with antique furniture and four poster beds for $155/night all in. In places like Oahu you can’t even get a Motel 6 for that.

  11. Kaua‘i is beautiful especially area around Hanalei. The hotel to stay is St Regis which is super dated and in a desperate need of remodeling. But of course they won’t remodel as long as people keep on flocking to the hotel due to its gorgeous view despite their high prices for crappy product. Hyatt is on the dry side of the island and beach is gorgeous. But it’s a Hyatt and let’s just leave it at that.

    Four Seasons on Lanai is gorgeous. Larry Ellison’s vanity project made this THE island to go to imo. I mean how many hotels in the world put Neorest Toto toilet in their cheapest room? Their Alii Royal suite is breathtaking in every way. I can stay in that suite and never leave.

    Four Seasons on Maui is also quite pretty but it’s a huge resort which means service will not be nearly as personalized as one got on Lanai. And honestly, the only rooms worth staying at are ocean front suites imo. The finishes at their Elite suite is not as nice as the suites at Four Seasons Lanai. But then again, Maui Four Seasons is own by Michael Dell who isn’t exactly as wealthy as Ellison.

    Of course going to Southeast Asia and staying at places like Amankila is a lot cheaper than staying at suites in Hawaii, but five hour flight and three hour time difference is easier on one’s body and time.

  12. I love Maui. Not as into Waikiki. So is the consensus that a day trip from Maui to Lanai is worthwhile?

  13. You are looking at the time zone the wrong way. I live on the us east coast and love hawaii because of the time zone. I get up at a decent time in the morning and go through emails, phone calls, etc that are waiting for me but by lunch time in hawaii the east coast business day is over leaving me free to enjoy the entire afternoon and evening free from my phone and emails.

  14. Wow, can’t believe no one has brought up the Big Island! My favorite of them all it has. Aton of stuff to do – Diving, hiking, go to the top of a 14K mountain (and sometimes ski), see a live volcano, visit an enormous ranch, waterfalls, touristy Kona, old Hawaii Hilo, sleepy rainforest Hamakua coast, super off the grid live-in-a-yurt Puna and Ka’u, zip lining, and so much more. Big Island mo betta!

  15. You should have tried the Big Island. The Mauna Kea Beach Resort has the friendliest staff and the best beach in the islands.

  16. I think Hawaii (or Kabuha’iiiii or whatever we’re supposed to call them these days) is a great choice for some people. I hadn’t expected you and Ford to be in that demo, gotta say.

    When I visited, I had a feeling I was in water-Vegas. Same people coming there, just with less clothes on.

  17. Next time you’re in Honolulu checkout The Modern hotel. It’s a really cool place with a great ambience.

    It’s our “go to” hotel whenever we’ve stayed in Honolulu and is far less crowded than the chain-hotels in Waikiki and there’s never a problem in managing to get a chair by the pool.

  18. I agree with Eric Webster! The Big Island is incredible! Maui has gotten much more crowded and our beaches on the Big Island (some of the best in the world) are world class and more secluded.

    You can stay at the Four Seasons on the Big Island, see the volcano, travel to the top of Mauna Kea (bigger and higher than Haleakala and usually much better weather). It’s one of the few places where you can snow ski and surf in the same day!

    We now have nonstop flights from Kona to Kauai (so you could do both islands). We also have nonstops to Japan from the Big Island so you can access Asia without going through HNL.

    My partner moved to the Big Island a couple of years ago and I go as often as I can. Come see us (we are big fans of OMAAT)!!!

  19. So how much time did you spend on all fours??? 😉

    Anyways, how do they pronounce Lanai? 2 syllables or 3? Is the patio 2 and island 3?

  20. We live in SoCal and have been all over the world…and still enjoy Hawaii.

    While we aren’t as fond of Honolulu and Waikiki, we have enjoyed times on Waikiki at the Halekulani and often have enjoyed Oahu’s North Shore–away from the tourist hordes in Waikiki.

    We absolutely love Kauai, as so many others have shared, enjoying how Hawaii was 40-50 years ago and largely without the tourist hordes. The St. Regis Princeville is an old building with renovated interiors, still in need of a refresh, but with excellent service, food, and the best view in Hawaii and one of the best views in the whole USA. Just gotta avoid it in the winter when it rains the most. The Grand Hyatt is nice but not nearly as luxurious, though its location is drier and sunnier.

    We also love Maui, Lanai, and the Big Island of Hawaii. They all offer something quite distinct. Maui, as you saw, has almost all of what Hawaii offers on one island. You just have to get away from the touristy parts: Hana and Kapalua are not nearly as touristy as the main and very touristy drags of Kaanapali or Wailea. The Big Island is another with tremendous variety in environments, which you can enjoy the moment you head north out of Kona, and particularly when you cross to the rougher, more Kauai-like Hilo side.

  21. I feel the same way way about Waikiki and Honolulu and, more generally, Oahu. Yeah, I get it that it’s not “real” Hawaii, but it’s exactly as you describe: Las Vegas of Hawaii. It’s got great beaches if you’re willing to venture a bit further out, but it also has every mod-con you could want. And it’s still Hawaii. It does get a bit old after a while, but as a restless-on-vacation guy I get bored with just sitting poolside and drinking every day to “relax”. I like that there’s other stuff to see and do in Waikiki. Of course there’s a lot of great nature scenery on the other islands – and I love that – but I’m neither a botanist nor a super “let’s experience nature for nature’s sake” kind of man; I can’t take that for 3 or 4 days on end. I gotta get up and move. And Waikiki is perfect for that. I’ve done the FS on Maui and I love it, but I’ll always enjoy rounding up a trip in Waikiki for a day or two just to take it all in.

  22. Nice that you have yet to hit the best of Hawaii. Take a look at Kauai as well as the Big Island Hawaii. And on Oahu you still have the North Shore which frankly is the only part of Oahu that I enjoy.

  23. Hey Ben – yes it’s funny how your impressions of somewhere differ by who you’re with or if you visit. Try visiting more places.stsying one night at the Park Hyatt (it somewhere similar) doesn’t do the place justice. I’m glad you and Ford enjoyed Hawaii. My partner and I love it.

  24. “how do they pronounce Lanai? 2 syllables or 3? Is the patio 2 and island 3?”

    3 syllables for the island. You know it because if the Okina. (The apostrophe thing)

    The okina forces a “guttural stop”
    So o’o sounds like “oh-oh”)

    The island is Lana’i. (Lah-nah…eee) where “…” is a pause

    In Mau’i (mow…eee) people always get Ka’anapali wrong
    It’s not (kah-nah-pah-lee). 4 syllables
    It’s (KAH…ah-NAH-pah-lee). 5 syllables with guttural stop at the …

    Just pause whenever you see the okina!

  25. I try to go to Hawaii every month for a few days per visit. I never tire of it. There is something extremely appealing about being able to go to one of the most remote locations on the planet. Seeing so many people there of various ethnic backgrounds fascinates me. Hawaii’s history is chockful of human interest stories. And, there are many activities to choose from available on each island. Scenic views everywhere, all the time. I’ve never regretted any dollar spent in Hawaii and I’ve been going there since the early 1980’s. Just wish I’d gotten there earlier in my life. I’m so happy, Ben, you’ve begun your acquaintance with Hawaii. It’s a hard place to leave.

  26. Maune Kea Resort on the Big Island. It’s our go-to resort now when visiting. In fact, it’s the only resort we go to as the staff are amazing (go enough times and they actually remember you by name). Plus the location, the architecture, the beach. You just can’t ask for more. The island has so much to offer as well. I highly recommend visiting some day.

  27. Lucky – so glad you and Ford had a great time. My first weeklong trip was to Kauaii. It’s rustic and beautiful with the Napoli coast, helicopter tours of “Fantasy Island” and amazing scenery, but I like a little more action myself. Waikiki has been my destination on the last 3 trips and I always find something new to do on that island – tour Doris Duke’s home, the Dole plantation, the north shore, etc. Friends of mine love the Big Island. I think there’s always something to do in Hawaii. I agree on the miles redemption but I must admit 5-8 hours is better on my body and time clock than 20+.

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