If you’re not sure which Hawaiian Island to visit, I’m here to help you decide. Having spent three months flitting between the islands, I crammed in as many sights and activities as I could and although I have my personal favourite (more on that below), each island offers different experiences depending on the kind of trip to Hawaii you’re planning.
Understanding the Hawaiian Islands: An Overview
Prone to disorganisation, I didn’t have clue about Hawaii when I boarded my last-minute flight. I picked up a guidebook in San Francisco during a 4-day layover and left it neatly unopened in my bag until I boarded my flight to Oahu. But even when I started to read about the islands of Hawaii, I couldn’t quite grasp Hawaii in the same way I usually do with new destinations. Perhaps it was the number of islands and the differences (and similarities) between them or maybe I was having a mental block, but it took me more a bit more research online (and then 3 months in the islands) to truly figure things out.
So, with that in mind, I’ll start with the overview of the Hawaiian islands I wish I’d had before I arrived.
There are eight Hawaiian Islands in total but from a tourism perspective they can be categorised as follows.
The Main Hawaiian Islands: Oahu, Hawaii Island (Big Island), Kauai and Maui – these are the ones you’re most likely to explore.
The Smaller Hawaiian Islands: Molokai and Lanai – you’re most likely to visit these islands if you’re looking for adventure away from the tourists or are splashing some serious cash at one of the remote Four Seasons resorts.
The Islands Off-Limits to Tourists: Ni’iHau and Kaho’olawe are the remaining two islands and, for the reasons explained below, you’re highly unlikely to step foot on them.
Looking for a cheap flight to Hawaii?
Being from England, Hawaii was always a bit of a pipe dream because of the prohibitive flight costs. Until I found myself in Mexico (Yucatan) perusing the Skyscanner website, as I’m prone to do on a regular basis. Fo under $200 I found a one-way ticket to Hawaii.
$92 to San Francisco. And $96 to Honolulu.
What?! It seemed too good to be true but I check, checked, cleared my cookies (here’s why) and checked again. It was legit so I booked it.
My best tip for finding cheap flights?
- First, use Skyscanner. I never find flights cheaper using any other website.
- Use open dates – ideally whole months if you can.
- Don’t be afraid to use different airlines – my two flights were not with the same airline and that made it a lot cheaper
- Check often but keep your cookies clear (see above for why – basically, airlines hike prices when they see you’re keen)
Which Hawaiian Island to Visit: The Highlights
Here’s the fact that impressed me most about Hawaii – the Hawaiian islands have 11 out of 13 of the world’s climates. Beaches, jungles, snow-cloaked mountains, desert, Hawaii almost has it all. It’s a staggering amount of diversity packed into a relatively small area. For that reason it’s difficult to condense the variety of Hawaii into a small number of highlights, especially when everyone has a different list of what they’re looking for. With as much objectivity as possible, and a small sprinkling of my personal favourites, below is a summary of each of the visitable island’s highlights.
The Main Hawaiian Islands
I’m not going to slap a label on each island (Best for Romance, Best for Hiking etc.) because – thanks to Hawaii’s diversity – you can pretty much find what you want on each island – it’s perfectly possible to find romance watching the surf or add a hike into a romantic star-gazing trip – that’s the beauty of Hawaii. Plus, as remote exotic islands go, Hawaii has got to be one of the most family friendly places you can go, if you’re treating the kids to the trip of a lifetime.
Which Hawaiian island to visit might be answered, in the first instant, according to your inbound flight. While O’ahu may not be the biggest island (Big Island takes that title, if the name didn’t already tell you that), it does serve as the landing point for most visitors to Hawaii who touch down in Honolulu International Airport.
While it’s perfectly possible to bounce in and out of Oahu without leaving the airport, it would be a shame not to spent at least a couple of nights exploring what the island has to offer.
Things to do in Oahu
Step on famous Waikiki Beach
If not THE most famous beach in the world, Waikiki is definitely in the running for the prize. I’ll be honest, I’ve seen better looking beaches both within Hawaii and worldwide but that didn’t stop me galloping like a small child to dig my toes into an (overcrowded) patch of this iconic beach’s sand. Plus, there aren’t many places in the world where the sunset is so fantastic that people look up from their cameras and phones and actually applaud nature’s performance.
How to do it:
If you only have time for one trip to Waikiki beach, visit at sunset. If you can’t hit that time, a visit at any time of day is still good. And with the boardwalk littered with shops, cafes, bars and restaurant, you can literally spend the day hopping on and off the beach.
There are tonnes of beach-activities you can do from stand up paddle boarding to boarding a boat. Honestly, I think there are quieter beaches to enjoy these activities in Hawaii but let me know in the comments if you had a great experience with one of the activity tour operators in Waikiki.
Catch the Hop on Hop off Trolley in Waikiki
Ever since I bust my knee in the British Virgin Islands (cue: surgery), I’ve become a huge fan of the Hop on Hop off buses around the world. They’re one of the best ways to get the lay of the land in a new city or area and – yay – there is a Hop on Hop off bus in Waikiki. Ok, it’s called a Trolley, which just makes it more cute. If you’re there for a few days, multi-day passes are likely to be a good deal. You can book tickets here.
Pay your respects at Pearl Harbor Memorial
If you’re in Hawaii on romantic business, then a trip to Pearl Harbor may not be top of your list, but the historical significance and poignancy of this memorial makes it worth dragging your sun-drenched butt from the beach for half a day.
How to do it:
Intent on spending 3 months in Hawaii, I was keeping to a tight budget. Which is how I figured out that you can visit Pearl Harbor for only $5 if you take the local bus. I’ve written about how to do that here.
If you’re short on time, want more luxury or prefer a guided tour of Pearl Harbor, check out this tour. It includes skip-the-line access to USS Missouri (the USA’s last battle ship) and well as a tour of downtown Honolulu, Punchbowl Cemetery and a few other of the nearby sights.
Hike up Diamond Head
Dominating the right side of Waikiki beach (with your back to the waves), the volcanic tuff cone (technical term!) of Diamond Head is perfect for walking off too much loco moco and offers views that are unparalleled (absent the expense of a helicopter tour or adrenaline of a sky-dive).
How to do it:
You can hike up Diamond Head off your own steam. It honestly took a bit of a walk from Waikiki and a lot of map interrogation to find the trail head but then the route up was clear as day.
If I went again, I’d take a guided tour – I did this for other volcanos in Hawaii and it really enriched the experience, knowing a bit about what I was walking on. Plus, you’ll get driven to the trail head and returned back to your hotel afterwards. You can book a guided tour here – this is by far one of the most popular tours on Oahu and gets impressive reviews.
Is Diamond Head a difficult hike? The climb is to 760 feet/228 metres with good, steady stairs and a well-paved trail. There’s even a ‘quick and hard’ ‘slower but easier’ route to choose. I’d therefore say it’s one of the easier hikes in Hawaii and definitely family friendly – in fact, the kids are likely to race you to the top.
Surf, skydive or eat shrimp on the North Shore
Wave sliding, as surfing was once known, was born in Hawaii and its popularity just never seems to grow old in the islands. North Shore with its big waves (especially during winter) is the place to be if you want to watch the experts at play. The waves here were bikini-stealing-aggressive so definitely not for amateurs like me, but I could sit and watch this wonderful sporty art-form all day long. Splash! It’s also one of the best places to skydive and visit a shrimp shack (though these activities should not be performed at the same time).
How to do it:
Getting to North Shore is pretty simple, especially if you have a car. I took public transport and it was easy enough but took a looooonnnnnnggggg time.
Otherwise, this tour from Waikiki will take you to North Shore, get you some views of the surf-famous Banzai pipeline and even throw in a trip to a shrimp shack.
Thinking about getting really adventurous? You can read about my Skydive over North shore and how to do it here.
Prefer to be at least a little bit tethered to Mother Earth? Try a zip-line adventure over North Shore.
Want to see see the highlights of Oahu in a day?
Ultimate Oahu Circle Island Adventure will take you on an 11-hour small group tour around Oahu showing you the islands best sights including Diamond Head and plenty of bays, coves and waterfalls.
What about a Luau?
Oh, sure it’s touristy but an evening of cultural entertainment, a big buffet and free Mai Tai? Why not? You can book a Luau at the popular Paradise Cove here.
Hawaii Big Island
If you really forced me to answer the question, which Hawaiian Island to visit, it would be this Big Island. Why? Hawaii’s Big Islands really does offer everything – nature operates at its most dramatic on Big Island (where else can you witness new land being spewed forth from the earth’s core?), the beaches are not just pretty but also rare (Big Island has one of the few green sand beaches in the world). And that’s not to get me started on the coffee plantations and local brewery.
What’s in a name? Big island’s official name is “Hawaii” – confusing, given that it is just part of the larger state of Hawaii. With that in mind, the island has been answering to the nickname “Big Island” for years (for obvious reasons if you look at a map). But some locals are not happy with this nicknaming process and are returning to an amended version of the traditional name – “Hawaii Island”. Got it? Good, because I’m not sure I have!
Things to do in Big Island
Visit Hawaii Volcanoes National Park
Despite its beaches, jungle and agriculture, Hawaii is most simply a chain of volcanoes and that fact resonates nowhere more so than on Big Island. Home to the world’s biggest and newest volcanoes (yes the island boasts two of the beasts), walk through lava tubes, feel the heat underfoot when you descend into an inactive crater, try not to breathe in the steam vents (trust me on this) and toast marshmallows on fresh-flowing lava. I could play for days in this national park.
How to do it:
Updated 2019: After the eruptions in 2018, Hawaii Volcanoes National Park has seen some dramatic changes and these changes are likely to be ongoing. You can read about my visit to Hawaii Volcanoes National Park here. You should also check out the latest information about visiting the park which you can do on the official National Park Service website here.
Want to visit but don’t want to risk getting it wrong? Take a tour. This one seems to have it all – as well as Volcanoes National Park, you get to visit a Kona coffee farm (see below), search for sea turtles on Black Sand Beach and finish with a spot of star gazing. You can also take a day-long tour of Big Island that includes the park, details here.
Gaze at the stars atop Mauna Kea
Holding another world record, Mauna Kea is the world’s largest mountain (measured from the base, which sits under the Ocean), but that’s not the only reason to wind to the top. So perfectly positioned for clarity that NASA has its telescopes up there, this is one of the world’s best spots for star-gazing. Don’t worry if you don’t know Saturn from Uranus, there are patient guides who will stand with you until you can make out the cheese craters on the moon.
How to do it:
Update 2019: it’s all kicking off on Mauna Kea and this time Pele (Goddess of Volcanoes and Fire) isn’t to blame. In July 2019, the state closed the summit, access road and visitor centre to start construction of a giganormous telescope. Protests have followed. The downside for tourists, it’s no longer possible to just drive up and take advantage of the free star gazing sessions.
All is not lost. A handful of tour companies are still taking small groups up the volcano via alternative access routes and operating their own stargazing evenings. Bonus: they’ll take you up in a vehicle that is fit for the road and they’ll handle the altitude change/rest times to get you up there fit and well.
This is the most popular tour and includes a warm park to wear which, trust me, you’ll need but would be forgiven for not having packed one…to Hawaii.
Travel tip: the combination of altitude and nightfall means it gets very cold very quickly – pack layers so you don’t end up buying overpriced fleece jackets in the gift shop as I saw one poor honeymoon couple do.
Scramble down to Green Sands Beach (Papakolea)
Just when you thought Big Island couldn’t be any more impressive, you hit the south coast and discover Green Sands Beach. (Olive) green in colour, there are only a few places on earth where this unique sand is found (the other places are the Galapagos and Norway). There’s a fun hike and down slope scramble to get there, making it a more rewarding visit all round.
How to do it:
Not wanting to put you off but most people aren’t going to get to Green Sand Beach. You either need a good 4×4 or the legs to carry you 2.5 miles from the parking area to the beach (I did the latter) and then you need the head and legs for the steep scramble down, and back up again. There aren’t any tours that take you there. But you can find the location here on Google maps.
Please be responsible and don’t take any of the sand from the beach.
Get your coffee and craft beer fix in Kona
Nature works its magic in Kona. Not only are there some pretty impressive beaches (and maybe the chance to swim with mantas), the earth’s soil delivers up the raw ingredients responsible for two of the island’s greatest tastes – Kona coffee (try Hula Daddy) and the range of beers from the Kona Brewery. Music to my taste buds – both the coffee plantations and the brewery can be toured and tasted.
Kona is also the place where the Iron Man World Championship is held – something I was lucky enough to see during my trip to Hawaii.
How to do it:
You can easily enjoy the delights of Kona without straying far from the centre, which makes a nice change if you’ve been zipping around the Hawaiian islands.
You can walk to Kona Brewery from the town and either take a brewery tour or just hit the restaurant and enjoy a tasting flight of beer. Details and tour times on the Kona Brewery website here.
For coffee tasting, I’d definitely recommend Hula Daddy, which has a free plantation tour and tasting. Details and opening times here.
Otherwise this small group tour focuses on the sights around Kona and includes a coffee tour.
Want to see Big Island in a day?
This tour will take you to Volcanoes National Park, Akaka Falls, Rainbow Falls and Black Sands Beach.
Why Kauai? In short, adrenaline…and peace in equal proportions. The island may be a 5 million year old dormant volcano (what?) but its unique and diverse topography will find you scrabbling for your hiking boots, snorkelling mask or kayak paddle all in the same breath. If you’re less keen on activity, you can still take a boat, ‘copter or car to explore things more leisurely.
Things to do in Kaui
See the staggering Napali Coast
I conquered my cliff-edge fears to take in the sight of the Napali coast and I don’t regret it. This 17-mile stretch of green-cloaked cliffs and inversely dramatic valleys is one of the most photographed sights in the whole of Hawaii. Only the toughest trekkers tackle the entire trail but sea-level sailings at sunset are a popular alternative.
How to do it:
I hiked it independently without a tour, which is easy enough but if you really want to get the best view, get in a plane. You can book a sightseeing tour that takes in the coast and the canyon (below).
Compare Waimea Canyon to the Grand Canyon
It’s been compared to the Grand Canyon in Arizona and although this Pacific-side gorge is not as vast, it’s definitely more colourful, photogenic and, perhaps most importantly, thinner tourist crowds make it way more peaceful.
How to do it:
Again, I visited independently, by car. But flying over the canyon would be amazing.
Kayak the Wailua River
For all of the Ocean that surrounds Hawaii, there is very little by way of navigable inland water, which is part of what makes the Wailua River feel so special. That and the fact there is so much to explore – waterfalls, fern grottos and swimming holes to jump into. I was so keen to see them all that my arms ached for days after kayaking this patch of water.
How to do it:
Meditate at Kauai’s Hindu Monastery
While this Monastery isn’t likely to feature on many lists of Kauai’s highlights, a morning of meditation at this retreat up in the hills near Wailua was one my most memorable on the islands. If sitting and “ohmmm”-ing isn’t enough for you, the Monastery also happens to be home to the world’s largest six-pointed quartz crystal, which is over 50 million years old! Kinda impressive!?
How to do it:
You might be interested in that time I took a 100-hour silent meditation retreat in India.
Psychedelic rainbow eucalyptus trees, fresh-baked banana bread, moonscape volcanic craters and the opportunity to listen to the eerie sound of humpback whales singing, Maui definitely felt the most surreal of all the islands. Which is why it seems strange to me that so many people visit Maui for resort relaxation, missing much of what makes it so special. Do yourself a favour – if you do book a beach break, make an escape from the manicured boundary of your resort, even if only for a while.
Things to do in Maui
Drive the Road to Hana
The most beautiful drive in the world. It’s quite the claim and I’m confident it could be true. Waterfalls to swim in, Pacific ocean panoramas at the end of tumbling coastal cliffs, those trippy rainbow eucalyptus trees and a distinct 60’s vibe lingering around the organic banana bread and coconut shrimp shacks, its only travel sickness from the unrelenting hairpin bends that will stop you doing this drive again and again and again.
How to do it:
Funnily enough, I didn’t actually drive the Road to Hana – I actually took a guided tour. Why? Experience on some of the most beautiful roads in the world have taught me that being a passenger is way more fun than map reading, route researching and not being able to take pictures along the way.
Of course, you can drive it but tours will get you to the most amount of stops/viewpoints in a day and that’s the way I’d recommend doing the Road to Hana. This one includes over 10 spots as well as lunch and this one is a luxury version of the same road trip.
Hike Haleakala National Park
Made most famous when Arnie (Schwarzenegger) rolled down the slope that represented Mars in the movie Total Recall, the day-long walk into the crater and back up the switchbacks of the volcano face of Haleakala is an experience you won’t forget quickly…especially not after photographing the silver plants you’ll see along the way. Being able to watch the sun set above the clouds after the hike is the kind of finale you come to expect on Maui.
How to do it:
Once again, I took a tour and this is an occasion where I wouldn’t recommend going it alone, especially if you’re doing a hike – exploring the crater floor then slinking up the switchbacks to return to the stop definitely needed a local, expert eye.
I booked locally and it was pretty cheap (sorry – can’t remember the name of the tour company) but if you do want to book ahead, this is an option. The hike took several hours and requires a head for heights and sheer drops.
If you prefer to visit via car, you can do that too. Definitely time it for either sunrise or sunset. You can plan your trip on the NPS website here – don’t forget to book your sunrise or sunset spot. You can book up to 60 days ahead.
And if you want to see the sunset under the expertise of a local, this is an incredibly popular tour that does all the booking and planning for you.
Explore Lahaina Whaling Town
One of my biggest reasons for visiting Hawaii was the chance to see whales in their natural habitat as they migrate to the warm winter waters of paradise and I wasn’t disappointed. Watching the mass of a whale under the water followed by the flick of a tail and water spouting into the air from a blow-hole, my trip to Hawaii was complete.
How to do it:
Unless you’ve packed your own boat, you’re going to need a tour to go whale watching. My tip – book for the first day you’re in town and keep booking if you don’t see them first time round. This is the tour I did by the Whale Foundation and would highly recommend it. It is a pretty big boat, which was fine but if you want something smaller, this tour gets great reviews.
Watch Windsurfing on Hookipa Beach
Reputed to be the windiest place on earth, there’s a reason Hookipa Beach attracts the world’s best windsurfers. And you thought Hawaii was just about the surf (I did too). It’s not an activity I’ve tried (yet) and Hookipa isn’t for beginners but if you want to catch the experts in action, here’s the place to do it.
How to do it:
Windsurfing is a year-round activity on Hookipa so just stroll on up and watch. If you want to try your own hand (and legs and nerve) at windsurfing in Hawaii, you can find out more here.
Snorkel around Molokini
Many of Hawaii’s best sights are found in the water so it’s worth getting into the Pacific Ocean at least once. And my suggestion is to take a snorkelling tour around Molokini. Personally, I can’t scuba dive (ear issues) so a day in a snorkel mask is the closest I can get but that is good enough, especially when you’re snorkelling around Moloki – a half submerged volcano crater and paddling through Turtle Town, teaming with green sea turtles.
How to do it:
The Smaller Hawaiian islands
If you have time, an adventurous spirit and/or the money, there are two more islands you may meet in Hawaii. Although I didn’t make it to either of them during my stay in Hawaii, I definitely have plans to do so when I go back.
Regularly described as “Real Hawaii”, Molokai is a place where Hawaiian time has stood still. Traffic and traffic lights have not yet infiltrated the island, no property is higher than a palm tree and the beaches are best explored with snorkel gear. In short, Molokai hasn’t made it onto the tourist circuit, and the sights are all the better for it. Halwa valley with thick, luscious greenery and ribboning waterfalls is a huge highlight.
The main stumbling block you might find on Molokai is the lack of accommodation where beach houses, condos and villas are the main places to stay and hotels few and far between, but if you can make that work for you, you’ll be in for a nice slice of seclusion.
How to do it:
Chances are, you’re not going to have time to explore Molokai unless you specifically stay there. If you do want to catch a glimpse, why not take to the sky? Helicopter rides are incredibly popular in Hawaii and if you’re going to throw down the money to do it, you definitely want to soar over paradise instead of a city. My sky-dive was my sky-high view but I’ll be trying out a helicopter tour next time I’m in Hawaii.
Lanai is another of Hawaii’s less tourist-touched islands. The top sights include the rugged Munro Trail, lined by Cook pines and offering views out to the Pacific Ocean, which will be on my list when I finally get to the island. Golf (yawn…sorry), untouched bays and plantation history are also prevalent.
How to do it:
Honestly, I’d just go and deposit myself at the Four Seasons…if that were within my budget. Otherwise, there’s enough going on on the other Hawaiian Islands to keep you occupied at a much more affordable rate.
The Islands Off-Limits to Tourists
And then, for the sake of completeness, there are those islands you’re simply not going to step foot on – unless you’re local or the recipient of an invitation.
Ni’ihau is a private island accessible only by native Hawaiians, the owners, the US Navy and guests – please, please, please can someone invite me? This is the place where the sacred Hawaiian culture apparently exists untouched. It’s no surprise it’s known locally as the “Forbidden Island”. Sigh.
Uninhabited (for spiritual reasons) and also presenting a risk of unexploded ordnance, Kaho’olawe is most definitely off-bounds.
You might like my other article: Where to stay in Hawaii on a budget
Have you been to Hawaii? Any recommendations to share? Let me know in the comments below.
Want to read more travel planning tips for Hawaii? Click below.
Or if you want something to immediately drool over, have a look at an article I wrote about for TravelMag.com about Hawaiian food.