All the colors of the Big Island of Hawai’i

On the Road: Which Hawai’ian island should you visit?

Aloha, friends! I’m approaching this On the Road post a bit differently. Instead of giving you a blow-by-blow of our recent trip to the Big Island of Hawai’i, I want you to visit the 50th state, so I’ve put together a post with some tips about how to choose the island that’s right for you.

And as the weather starts to drastically cool in the Northern Hemisphere, isn’t it time to start planning a getaway to a warmer locale? Consider this the little push you need to book a trip to our 50th state!

Why Hawai’i? I’ve long had a love for this state. It’s just a six-hour plane ride from Seattle but it’s a world away. Hawai’i offers you a unique balance — American infrastructure, familiarity, and convenience along with the richness of a different culture. My first trip to Hawai’i was 18 years ago and I fell in love. I keep going back — this was my eleventh visit. It has something for everyone — and every time I visit I discover something new.

Why are you spelling Hawai’i like that? When possible I will preserve the spelling of Hawaiian words. My college roommate was from O’ahu and I learned very quickly that I was saying the name of the state wrong. Oh Americans and our lack of curiosity about other languages! The Hawaiian alphabet has 13 letters, and the ‘ is one of them (it’s called the ‘okina). Long story short, just realize that if you say “Ha- why -ee” you’re doing it wrong.

Which islands are in the running? There are eight major islands in the Hawaiian archipelago. Let’s see which islands deserve your consideration:

Two islands are not open to general visitors:

  • Ni’ihau: Only residents, government officials, and invited guests can visit, giving it the nickname the Forbidden Isle. However, there are hints that some helicopter tours from Kaua’i are permitted to land there. You can spot it off of the west side of Kaua’i.
  • Kaho’olawe: Formerly a training ground and bombing range for the U.S. Army, it is nicknamed the Target Isle. With no fresh water, it has no permanent population; it’s only open to native Hawaiians for religious and spiritual practices. You can glimpse it from a distance from the southwest side of Maui.

Two islands are much more difficult to visit — so much so that we haven’t visited them:

  • Moloka’i: Not to be confused with Molokini (the snorkeling atoll off the southwest coast of Maui), Moloka’i is called the Friendly Isle, but most accounts from non-Hawaiians have been that residents are not friendly towards tourists. Best known for ranching and its former leper colony, it is not very developed or set up for visitors, with only one hotel on island. Still, it’s on our Hawaiian bucket list.
  • Lana’i: 97% owned by Larry Ellison (of Oracle fame), Lana’i is sparsely populated with only one real town (called, creatively, Lana’i City). It’s rugged and only accessible by four-wheel drive vehicles. But it seems incredibly beautiful and somewhat open to tourists (and can you say CAT SANCTUARY?!?), so it’s on our list. Lodging options are more or less limited to two Four Seasons resorts — at about $700/night, save your pennies for this one.
Clockwise from top left: View of Honolulu with Diamond Head in the background; Na Pali Coast in Kaua’i; Native Hawaiian settlement on the Big Island, north of Kawaihae; nothing but sand in Kihei, Maui

That leaves us with four remaining islands, all tourist-friendly and easily accessible from the mainland. From north to south, they are:

  • Kaua’i: The oldest of the main islands, Kaua’i is aptly named the Garden Isle. It’s home to one of the wettest spots on earth, which gets more than 460 inches of rain per year, as well as the “Grand Canyon of Hawai’i,” Waimea Canyon. It’s also home to an inordinate number of chickens, breeding freely after Hurricane Iniki in 1992.
  • O’ahu: With its capital, Honolulu, and more than two-thirds of the state’s population, it’s no wonder that O’ahu is called The Gathering Place. O’ahu is the island that feels most like the mainland — it comes with both incredible traffic (for the islands) and incredible food.
  • Maui: The island that has probably undergone the most transformation in the past several decades, the Maui of today is a tourist’s playground. Called the Valley Isle, it’s an easy trip for a first-time visitor. It’s also where we got married (Maui’d) in 2017.
  • Hawai’i: The Big Island is really big — 63% of the landmass of the state and the third largest Polynesian island after the two islands in New Zealand. It’s home to an active volcano (it sits upon the hotspot that created the islands) and boasts 10 of the world’s 11 climate zones.

So, there you have it! Four wonderful choices for us to explore and spoiler: I recommend all of them! But first, a few more technicalities to cover…

When should I visit? The Hawai’ian islands tend to have two high seasons — summer (June through August) and winter (November through March). That leaves the two shoulder seasons (April and May; September and October) as our favorite times to go. But remember that not all months are created equal, from a weather, price, or people standpoint.

If you want to whale watch, come in winter. If you want to tourist watch, come in July.

Windward and leeward — spot the difference?

Where should I stay? Take note that you’ll experience multiple climates or microclimates in each island. Two big factors to keep in mind:

  • Windward or leeward? Do you prefer the side with the majority of the wind (and therefore weather, like rain?), called windward, or do you want to stay in the shadow of the weather and wind behind the mountains, called leeward? There is no right choice — they come with very different climates. In Hawai’i the windward sides are archetypal lush landscapes, while the leeward sides tend to be drier with most of the lush landscape brought in artificially (for the benefit of the tourists). On the islands you tend to have windward conditions on the east sides of the islands and leeward on the west.
  • What’s your elevation? In our trip last week to the Big Island we watched the temperature drop more than 20 degrees with a 2000-foot elevation gain as we drove from Puako to Waimea. Keep in mind that you’ll get cooler, non-Hawaiian feeling weather at higher elevations (it snows on the mountains of the Big Island every year enough to ski!). But during hot and humid months (say, August and September) staying upcountry can be a nice relief from beachside heat.
Many places to lay your head (L to R): Making friends with resident cats at our VRBO in Hilo; The Kahala Hotel and Resort is an older property south of Honolulu in wonderful shape — don’t be fooled by the exterior; our favorite mega-resort in the islands, The Grand Wailea in Maui.

Once you have an area, consider the different property options on offer. Though this is true wherever I’ve traveled in the world, it’s doubly-true in Hawai’i — you get what you pay for. Resort accommodations are very pricy here, and many include add-on “resort fees,” parking fees, and come with expensive on-property restaurants. That being said, we’ve had some rather magical experiences in mega-resorts.

We’ve also had good luck on the other end of the market — VRBO. We just stayed in a VRBO in Hilo and it was a wonderful experience at a fraction of the cost — and came with resident pets (5 cats, 2 dogs, 1 million geckos).

You know your travel style — be smart and do your research. Some of the islands experienced building booms in the 1970s, and while some of these properties have been lovingly tended, others haven’t. Remember to adjust your mainland prices upwards for a similar experience (my rule of thumb is to add $100–150/night to expect a similar quality of service in Hawai’i).

Which shave ice is best? Sergio’s favorite is Scandinavian Shave Ice on the Big Island. I prefer Ululani’s on Maui. But with a Dole Whip core or a haupia cream snow cap, we’ll take either, actually. They don’t make it like this on the mainland :(

What will I eat when I visit? I find island cuisine to be a delight! You have many options, from traditional (poi and pork) and new Hawaiian (think West Coast farm-to-table with a Polynesian twist), Asian and Asian fusion, plenty of mainland American food (pizza, pasta, burgers), vegetarian and vegan options, local treats (remember — it’s shave ice, not shaved) and fish, fish fish! Both of us have a number of dietary restrictions and we’ve been able to make it work. But be careful — if you’re like me, you might bring a few extra pounds back with you.

What I’m not very qualified to speak about: Every traveler has their preferred activities and their favorite pastimes on the road and things that just don’t suit them. While there are many activities we’ve tried, there are some that just don’t factor into our decisions, so if these are important to you, research elsewhere:

  • Nightlife: My personal version of hell is going out to a dance club. First of all, my dancing is reserved for my husband, my cat, and maybe my family on a good day (think Elaine from Seinfeld). Besides, Hawai’i is an early-to-bed, early-to-rise type of place (at 19 degrees above the equator, there’s very little variation in the length of the days, quite an adjustment for someone living near the 49th parallel). I’m sure Hawai’i has some nightlife. We just don’t do that.
  • Extreme sports and adventure activities: Okay, so we’ve done some of these things. I’ve ziplined in Maui (twice!). Sergio took a helicopter tour in Kaua’i. We’ve both windsurfed (also Maui). But we’re not avid cliff jumpers or hang gliders or swim with sharks people. If that’s you, yay you! There are some pretty wild and untamed parts of the islands, so opportunities abound! Just know we love mild to moderate activities and that’s what we look for in our vacation, so I’m not going to be the best guide here.
  • Beaches: Beach, please! I can’t imagine anyone would be disappointed with Hawaiian beaches, though take it with a grain of salt(!) because I grew up in the Northwest, and a beach day means 55 degrees with a rain jacket and boots. Hawai’i has an incredible selection of beaches in a rainbow of colors (white, golden, green, red, and black, to name a few), and each island seems filled with them. I admit that I’m not an expert on beaches, but I’ve never been disappointed on any of the islands. A good beach is just a short walk or drive away, no matter where you are. If you are a beach connoisseur, consult someone else.

Long story short, there are many niche experiences in the islands, but do your research because not all islands offer the same things. For example, don’t expect to windsurf on the Big Island — the winds go in the wrong direction! Likewise, don’t expect to see an active volcano on O’ahu — that’s a few islands south. If you have a special experience in mind, make sure that you are on the right island for the experience — or adjust your expectations!

How are you so informed, anyway? I’m an obsessive travel researcher, for starters. I love to learn about the places I visit so I can get an experience tailored to my preferences. This generally starts with flight, hotel, and rental car research, but then broadens into activities and dining. While you can find much of this information on the internet, you can also find a lot of bad information. So if you take away only one tip from this blog, it’s this: Buy yourself the Blue Book(s) for the island(s) you plan to visit.

This is the ultimate guide to Hawai’i written from a local’s perspective. It will give you tips and tricks that you’ll never see in Fodor’s or Frommer or whatever other F-books there are on the shelves. The writing is funny, brutally honest, and gives much clearer directions to hidden gems. They also swing a bit on the adventurous side, so they will give you crazy-amazing hikes to try (say, an all-day hike to the top of Kaua’i) that no other guidebook would recommend.

That being said, I think my retirement career might be planning travel for other people, if that’s still a thing in 30 years…

Okay — it’s island time! Let’s find out which is right for you!

Rugged southern Kaua’i

If you love relaxation, head to Kaua’i. In need of a laid-back Hawaiian vacation? I’d recommend the Garden Isle. More low-key and less pretentious than some of the other islands, Kaua’i feels a bit rough around the edges with many hidden gems, if you just look. The smallest and least populated of the four main islands, sometimes you feel like you have places to yourself, especially during shoulder season!

Though all the islands seem ready-made for photography, Kaua’i seems even more photogenic than the rest (this from my photographer husband). We couldn’t stop pulling off to the side of the road to snap photos of plants, animals, or seaside vistas. Of all of the islands, this is the island for a helicopter tour (or so I hear, as I’m petrified of them), namely because the Na Pali coast (Kaua’i’s west side) is not accessible by car (you can take a boat tour, a helicopter tour, or rough it out on a two-day hike). In fact, some of Sergio’s amazing photos are far above Medium’s limit. Get it together, platform!

Kaua’i is also a wonderful island for hikes because they are so varied in difficulty. That being said, Kaua’i, at least in the fall, was by far the most humid of the islands, so get ready to sweat it out whenever you do something outdoors.

If you love feral cats and/or chickens, you’re in the right place. They. are. everywhere.

Some fantastic attractions on Kaua’i that might tickle your fancy:

Visiting Waimea Canyon: Ten miles long and three miles deep, consider it an island-sized Grand Canyon. What I appreciated about Waimea Canyon is that there were a variety of hikes for different levels, but if you didn’t want to hike there were many pull-outs that were accessible to people of different physical abilities. The upcountry areas were positively charming.

Minimal hiking, maximal payoff

Visiting lush gardens: The McBryde Botanical Garden was phenomenal, and that’s considering that I’ve never been that hot and sweaty in my life outside of Yucatan, Mexico (going to Merida in May = big mistake). You’ll park and catch a shuttle up a valley into the gardens and can wander to your heart’s content. It’s the largest collection of native Hawaiian plants in existence, and the self-guided tour materials were highly informative.

Visiting sacred sites: Whether you’d like to visit a Hindu monastery, a Hawaiian heiau, or temple, or a Catholic mission, religion and spirituality are a big part of this island. Get curious about a faith tradition other than your own!

Heiau ruins on the east side of Kaua’i

Finding a place to read and relax: Natural wonders abound, but there are plenty a hammock or a park bench with an ocean view waiting for you. If you’d like to simply clear your mind and watch the waves, you won’t be bothered.

L: Dinner at Red Salt, the only (but delicious) restaurant on property; R: Obligatory hotel balcony shot

Where to stay: We’ve been to Kaua’i only once (we hope to return in 2019!), but we would head back to Ko’a Kea Resort in Poi’pu without a second thought. Unlike the Marriott or Grand Hyatt just down the road, this is a much smaller property, so don’t expect the mega-pool, kid’s club, or giant spa. However, the service here was unreal, as were the ocean views with dramatic sunsets every night.

Ko’a Kea sunsets — magnificent every night of our stay.

What to pack: Bugspray, bugspray, bugspray. Also, patience, as Kaua’i doesn’t have any major highways — you’ll be driving at the speed of the person in front of you. Patience is not my virtue, so this made it a little tough for me, a fast-lane driver.

If you’re not ready to entirely let go of the mainland, visit O’ahu. You know, I think O’ahu gets a bit of an unfair rep, but I’ll admit that I fell into the same trap. “How different is it, really?” I asked myself. But having visited O’ahu, I can promise you that it has plenty to offer, even if it might not feel as removed as the other three islands.

Touristy AF in Hawaii Kai

If you’re heading to O’ahu, you have to embrace that you’re a tourist. It’s touristy! But it’s not entirely a bad type of tourism. You can get your kitsch on and experience old-time Hawai’i in Waikiki or soak up Hawaiian history at the state capitol or the Iolani Palace. Interested? Here’s what you can look forward to on O’ahu:

Visiting the largest range of historical sites: I have to admit — I thought Pearl Harbor or the National Military Cemetery of the Pacific would be a bit overrated. Untrue — they were both fascinating places to learn about and appreciate WWII military history. You could make a week out of all of the military sites, but we just did two — the boat tour to the U.S.S. Arizona Memorial (closed then and currently closed due to damage, so you just sail by it) and the submarine the USS Bowfin. There is a large museum at the site that provides further information about Pearl Harbor and the Pacific Theater. But that’s not all — there are ships and aircraft and other things to see. I’m not exactly a rah-rah military hoo-rah lady, but these were powerful and important sites to see.

L: Cemetery of the Pacific; R: Aboard the USS Bowfin

And like all of the islands, O’ahu has many important sites to native Hawaiians. It forces Americans to confront the facts — that we took over the land of native peoples and did not treat them well.

Speaking of traditions, this is a replica of a Japanese Buddhist Temple on O’ahu. It was a fantastically fun place to visit.

Eating is your thing. The food in O’ahu? Daaaamn. It was fantastic! I’ve never had such wonderful Japanese food in America before, or tried so many fantastic fusion cuisines I had never thought of (say, Mexican-Korean-Italian, and I’m not even kidding). I’m a little embarrassed that we took so few photos on O’ahu, but after a week full of photos at our wedding I think we were just done. This is also the best place to get malasadas, and if you have never had these little fried dough balls you’ve never really lived.

Surfing and beach life is your jam. The North Shore and Waikiki are two of the most recognized names in the world for surfing and sunning, respectively. O’ahu is most certainly a beach island, with wide, magnificent sandy beaches as the perfect place to throw down a towel.

L: Balcony views (it was worth the upgrade); R: Resident honu that will be released once they are large enough

Where to stay: We eschew the party scene and knew we didn’t want to stay in Waikiki (also — why would you come to Hawai’i to stay at a Disney resort? this baffles me entirely), and the North Shore felt a little too quiet. We settled upon the beautiful Kahala Resort in south Honolulu, just a short drive from all the action. We chose a lagoon room, complete with dolphin views (we have mixed feelings on the dolphins, but that’s another post). The hotel also has rescued honu, Hawaiian turtles, and small rays. The resort has a phenomenal spa, one of the most service-oriented spas I’ve ever visited.

What to pack: Just don’t eat for the week prior to your trip and you’ll be prepared. Also plan to pack extra money if you wander into the ritzy shopping districts and want to pick up something for yourself.

Lunch in Lahaina with Lana’i in the background

If you’re a first-timer, and/or a bit nervous, Maui might be your speed. I want to be skeptical about Maui, but I just can’t. Yes, part of that is because we got married there last year, but even though it’s a little too touristy in my least favorite ways it’s still so fun to visit! We picked Maui for our wedding destination because it would be easier for our families to navigate, it’s more child-friendly, and it is easier to get to that Kaua’i or the Big Island. And there are so many things worth doing, like:

Family time at Ululani’s Shave Ice in Kihei and welcoming my sisters at the Grand Wailea

Driving the Road to Hana: With hundreds of twists and turns and waterfall after waterfall after waterfall, this is the Hawai’i of your wildest dreams. We especially enjoyed the Garden of Eden and the many banana bread stands, as well as the black-sand beach in Hana itself, a reward well worth the drive.

Hot tip: Start early, and never, ever ever drive it on a weekend :)

Clockwise from top left: Rainy road to Hana; Sergio at the black sand beach near Hana; waterfall view from the Garden of Eden; Sarah making friends with ducks and geese at the garden

Kids are a part of your travel party: Maui feels ultra-accessible to families with family fun centers, an aquarium, baby beaches, and kid-friendly shops. The resorts in particular cater to families with kid-friendly menus and kids-club programs, and kid-friendly pools. Because most of the tourist sites are relatively close to one another, that means less car time for little ones. Our three-year-old and seven-month-old nephew and niece were huge fans!

L to R: Ocean kayaking; Maui Ocean Center; touch tanks

If you are planning an event (say, a wedding…): I’m a little biased because we got married on Maui in September 2017. Maui was a great place to plan a wedding remotely because the venues and vendors are such pros. We can’t recommend Merriman’s Kapalua enough — and if you want recommendations for a score of great vendors, happy to share them with you!

Even if nuptials aren’t part of your plan, Maui is home to our favorite Hawai’ian luau — The Old Lahaina Luau. I’ve been to a fair numbers of luaus over the years, but this one is heads above the rest. It would be a perfect night out for a couple or for a family reunion. Hot tip — pay extra for mat seating for not only a front-row seat, but first in line to the buffet.

Our favorite mega-resort: The Grand Wailea

Where to stay: Confession — We are mega-fans of the mega-resort the Grand Wailea. It’s home to my favorite Hawai’ian spa, a mega pool complex complete with water elevator (not kidding), acres of lush gardens, and warm, welcoming service. This one is a splurge, but I promise you, it’s worth it!

What to pack: Sunglasses to protect your eyes from the windy west side of the island, especially if you stay near Kihei.

Upcountry views northwest of Waimea

If you want a bit of everything, the Big Island is for you. Okay, okay, I hate to pick favorites… but if I were to pick a Hawai’ian island favorite, it would be the Big Island. It has the chill of Kaua’i with the variety of all of the other islands combined… and with a fraction of the tourists. If you want history and great food and some nice spas to boot, you can’t go wrong with the southern-most island in the chain. Here are some reasons why you should pick the Big Island:

Clockwise from top left: Koia’e, an ancient Hawai’ian village; native Hawai’ian marker on the “Saddle Road;” temple at the Place of Refuge; petroglyphs near Puako

History is your jam: While there is plenty of history on O’ahu, I think some of the actual historical sites on the Big Island are more interesting, especially as the native Hawai’ian sites are generally well-preserved. You can find hundreds and hundreds of petroglyphs dating from the 1600s near the resorts in Puako/Waikaloa (they’re fun to decipher) or tour an authentic Hawai’ian fishing village, first settled in the 1300s. But our favorite stop is certainly Pu’uhonua o Honaunau (The Place of Refuge), a literal refuge where you could escape death if you made it there without being hunted down and killed. And the first Christian church in the Hawai’ian islands still stands in Kona Town (it began in 1820), and visiting Kona Town helps you gain an appreciation of the impact of missionaries, both good and bad.

Clockwise from top left: Western shores on the Kohala Coast; Mauna Kea observatories above the clouds; lush streamscapes at the Hawai’i Tropical Botanical Garden north of Hilo; friendly horses east of Kapaau

Wandering brings you joy: If there’s one thing that characterizes the Big Island, it’s scenic drives and open, country roads with small roadside fruit stands or hole-in-the-walls. So if you love to put the top down and just drive, drive, drive, you can spend days circumnavigating the island, stopping at every roadside pullout to drink in the views. Because the landscapes are so varied, in a matter of minutes the scenery changes and your eyes are treated to something new. I’m not always a big fan of driving around and looking at stuff, but this island certainly converted me to the benefits of that particular activity.

Clockwise from top left: Sergio at Brown’s at the Farimont Orchid; me with Pumpkin the cat at our Hilo VRBO; me ready to snorkel at the Fairmont Orchid; rocky beach walk in Puako

Where to stay: We’ve had good luck in different places, but know that there are fewer mega resorts on this island, especially in Hilo, where VRBO seems to be a much better deal (and ours came with cats!) Big Islanders seem to be extra friendly, so if you have the chance to stay near locals take advantage of their kindness.

On the west side of the island we are in-love with the Fairmont Orchid, a medium-sized resort more catered to adults than to families (for us, a feature). It’s also home to the famous Spa Without Walls, the perfect place to get an outdoor massage topped of by a hot coconut oil hair treatment.

What to pack: Gas money — this island is BIG. Also as the climate is so much more varied here I strongly recommend a wider range of clothing as we’ve found the weather the most varied (rain, wind, sun, cold wind and rain upcountry).

So there you have it! Ready to book that trip yet? Here’s to wishing you a Hawai’ian trip filled with the aloha spirit!

Aloha, Sarah

P.S. While I want to keep my blog primarily focused on mental health advocacy, I’ll still share some travel posts from time. I’m working on a new post about why we decided to travel to Oklahoma and Kansas and how I think travel can help us come closer together. And since the holidays are fast approaching, expect a bit of Christmas-y cheer too, including next week’s annual book recommendation post, just in time for your holiday shopping push!




NW native blogging about life’s struggles and triumphs. Balancing career, family, hobbies, and health. Fierce advocate for mental health. And chocolate lover.

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Sarah Carr

Sarah Carr

NW native blogging about life’s struggles and triumphs. Balancing career, family, hobbies, and health. Fierce advocate for mental health. And chocolate lover.

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