Hawaii is one of those destinations that can be completely different depending on which island you choose. On my recent trip, I spent three nights in Honolulu on Oahu before flying across to Kona on Hawaii Island (the Big Island).
I wanted to experience more than just the beaches. I wanted to see the hotels, explore the destinations, experience some of the activities and get a genuine feel for what each island offers — so I can give my clients advice based on first-hand experience rather than simply what I’ve read online.
From inspecting four Waikiki hotels to visiting a pineapple farm, swimming with manta rays and learning about Kona coffee, this trip gave me a wonderful taste of two very different sides of Hawaii.
Hawaii offers an incredible combination of beautiful beaches, luxury resorts, adventure, food, culture, nature and unforgettable experiences. Plus it makes for a good stop over traveling with kids if your making your way over to USA. A little bit of beach, cocktails and sun on the way over and/or way home to break up the long journey from Australia.
What I particularly love about Hawaii is that it can work for so many different types of travellers.
You could spend your days relaxing beside a beautiful resort pool, exploring the island by car, eating incredible food, hiking, snorkelling, experiencing Hawaiian culture or ticking off once-in-a-lifetime experiences such as swimming with manta rays.
The key is choosing the right island, location and accommodation for the type of holiday you actually want.
And that’s where good planning makes a huge difference.
Oahu — and particularly Waikiki — is fantastic if you want a holiday with plenty happening around you.
You’ll find:
It’s particularly appealing for first-time visitors, families, couples and travellers who don’t want to be too far from restaurants and activities. Staying anywhere on Waikiki main beach, you really are a stones throw from one end of the bustling street to the other.
Kona offers a completely different experience.
The pace feels more relaxed, the landscape is more expansive and there’s a stronger sense of adventure and nature. While I did arrive 2 days after a Hurricane, there were unfortunately alot of national parks and beaches closed as it did make quite a mess!
The Big Island is particularly appealing if you want:
So which should you choose? If it’s your first trip to Hawaii and you want a combination of beach, dining, shopping and activities, I’d look closely at Oahu. If you’re craving adventure, nature and a slower island experience, Kona and the Big Island could be a fantastic fit.
And if you have enough time? I’d seriously consider combining islands. I was able to experience both in 6 nights, and honestly its very doable without feeling overly rushed to fit it all in.
We began our trip with three nights in Honolulu. Waikiki is one of those places where you can step outside your hotel and immediately feel like you’re on holiday. The beach is right there, restaurants and shopping are right on your doorstep and there is always something happening in the area.
We spent time exploring the area and getting a feel for the destination, while also inspecting several hotels that I can now confidently talk about with clients as to whats best going to suit their needs and expectations.
We drove up to North Shore which was a completely different feel. Buildings felt like they were back in time but painted like new with lots of little quirky shops along the way. From here we went to Kualoa Ranch. It was fabulous. A great down out as a couple of with the family as you can experience the park via Bus, Bikes, Horse and buggy, depending on what your comfortable doing but it is a attraction that needs to be booked in adavnce.
For me, this is one of the most valuable parts of travelling as a travel specialist. Photos and websites can tell you a lot. Being there tells you much more.
One of the main purposes of my Honolulu stay was to inspect four properties so I could better understand which travellers each one would suit. Outrigger is a big brand in Hawaii so it was the perfect chance to see how vastly different they are.
Right on the Beach. It is lively, loud and full of Entertainment. It also helps that it is home to Dukes restaurant. If you want to experience this famous restaurant, I advise booking a table in advance or you can try your luck grabbing a seat at the bar as walk up guests. Waikiki beach is going through a very major renovation and are currently sitting at 50% complete with hopes it will be finished by January 2027. The rooms are more spacious, its looking very very fresh without the tired American feel that some properties are still showing. Highly recommend Outrigger Beach for the higher end client wanting to spend a little more on accommodation.
I loved this property. Not as noisy or as Busy as Waikiki Beach. It has some wonderful room options including beach front and interconnecting. As soon as I walked into the Entrance of this property I knew it was going to be a Fave. It went through a major renovation with everything pretty much complete and has a wonderful Vibe. Plenty of in resort shops, amazing large pool with Bar, beach front and a very good choice for Families as well.
We stayed at this property and it really was fabulous. Set across the street from the beach (literally 2 minutes walk to the beach, but right in the hustle and Bustle. Rooms are large in size and currently holding the Cirque Du Soleil event, which for me was an absolute stand out attraction. Tickets sell out every night! A perfect property for families and or couples and for people wanting to save a little more on accommodation to use for food, drinks, attractions and sightseeing. The only downside I saw to this property was a very small rooftop pool.
A great option for clients wanting more room or traveling as a family. Sitting one back back from Waikiki Beach, it too is in a very convenient location and also offers a descent size pool and outdoor area.
They have the bedrooms separate from the living room. Options ranging from standard rooms/suites to 1-2 bedroom suites and an option to interconnect. The other positive is they do have a breakfast option you can include in your rate, however me being me, I noticed how very american it was. Not much in the way of fruit, fresh juices, bakery, yoghurts. It was quite basic but a good option to have never the less.
The important thing is that there isn’t one hotel that is automatically “best”. The right property depends on who is travelling, what they want from their holiday, their budget and how they want to spend their time. That’s exactly the kind of decision I help clients make.
One of the experiences we included during our time on Oahu was a visit to a pineapple farm. It was such a great way to experience another side of Hawaii beyond the beaches and resorts.
Getting out into the agricultural areas and seeing how the produce is grown gives you a completely different appreciation of the destination. The pineapple farm goes for miles and employs all Hawaiian locals. They do keep their pineapples in country, with no longer exporting them an option. We were able to see how they are harvested, the different stages of growth and then went into the factory where they wash, cut and sort the different varieties to go to different parts of their country.
And, of course, you can’t visit a pineapple farm without sampling some pineapple! And trust me when I say, our pineapple tastes alot less sweet than the Hawaiian Pineapple. It really is beautiful
It’s experiences like this that I love including in itineraries because they give you a chance to see, taste and experience the destination rather than simply look at it. And di you know, it takes 3 years to grow 1 pineapple!!!!
From Oahu, we flew across to Kona on Hawaii Island. A quick 1 hour flight with Hawaiian Airlines. No sooner your up in the sky and then suddenly back down on land again.
And almost immediately, the experience felt different. The Big Island is huge, and the landscape and atmosphere are very different from Honolulu and Waikiki. When we landed however, all I could see was black rock and dirt, but I was quickly reminded that this is infact, volcanic rock. With a Volcano still active on one side of the island, this is from many many years or flowing Lava landing all around the island.
Unfortunately, our timing coincided with the aftermath of a hurricane, which meant some of the activities and areas we had planned to experience weren’t possible during our stay. That’s the reality of travelling — sometimes Mother Nature gets to make the itinerary! But rather than let it ruin the trip, we adapted. And we still managed to experience two incredible Kona highlights.
This was one of the absolute highlights of the entire trip. Swimming with manta rays in Kona is one of those experiences that is almost impossible to explain until you’ve done it.
Being in the water and watching these enormous, graceful creatures glide through the ocean around you was surreal. It’s completely different from a typical sightseeing experience. They are right under your body chasing the plancton from the lights they eliminate whilst your in the water.
You’re not simply looking at something through a window or from a boat. Your are in the ocean with them. However, it was very very choppy. A few ladies were sea sick, whilst in the water. I didnt even know this was possible to be sea sick whilst swimmming but I was feeling very very nauseas as well, so it is definitely possible.
Its roughly 45-60 minutes in the water with these amazing creatures and well worth the evening dip! You’re in their environment. For travellers who love adventure and want to include genuinely memorable experiences in their holiday, this is one I’d definitely have on the conversation list when planning Kona.
Kona is famous around the world for its coffee, so visiting a coffee plantation was another experience I was particularly looking forward to, but not because I like coffee, I actually despise it, but it was such a great experience learning all about the production of coffee and the environment.
We learnt more about how Kona coffee is grown and produced and even had the opportunity to make some coffee ourselves. We roasted and named our own little bag of goodness. A great little day trip with a stop on the way home for lunch at a world renowned seafood restaurant.
Hawaii offers beautiful resorts, romantic beaches, incredible dining and plenty of experiences you can share together.
Oahu in particular offers a huge range of family-friendly activities, beaches, resorts and excursions, with some accommodation options to suit families wanting more space. Plus a great stop over to USA to break up a long flight.
Hawaii has an excellent selection of luxury accommodation and experiences, and the right property can make a huge difference to the overall holiday.
From snorkelling and hiking to marine experiences and exploring the islands, there’s plenty for travellers who don’t want to spend their entire holiday beside a pool.
Hawaii’s agricultural regions produce some incredible food and drink, from pineapple to Kona coffee and everything in between.
Oahu can be a particularly easy introduction to Hawaii because you can combine beach time with dining, shopping, sightseeing and activities.
For Honolulu, I recommend between 5-7 nights if its THE destination, or as a stop over or quick trip with another Island 3-4 nights is Plenty.
There isn’t one universal answer. Oahu is often a great choice for first-time visitors who want beaches, restaurants, shopping, activities and plenty happening around them. But the best island depends entirely on the experience you’re looking for.
Neither is “better” — they’re simply different. Choose Oahu if you want a more energetic destination with lots of dining, shopping, beaches and activities. Choose Kona if you’re looking for a more relaxed, spacious and adventure-focused experience.
Absolutely. Kona is a great choice for travellers who want to experience a different side of Hawaii, particularly if they enjoy nature, adventure, marine experiences and food and coffee experiences. If it was possible when I was there, we would have got the Helicopter over the Volcano, a true Kona island experience.
Yes. Swimming or snorkelling with manta rays is one of Kona’s best-known marine experiences and was one of the highlights of my own trip. Its a draw card along with the Volcano as to why people visit this island. It is big though so a car is required in order to get around. But remember, it is America so driving on the other side of the road is required.
Very much so. Hawaii offers a wonderful combination of luxury resorts, beautiful beaches, romantic dining and unforgettable experiences, making it an excellent honeymoon destination.
Yes. Families can choose from beaches, cultural experiences, water activities, sightseeing, nature and plenty of family-friendly accommodation. The trick is choosing the right island and resort for the ages and interests of your family.
If you have enough time, yes, I think it’s worth considering. The islands have very different personalities, so combining two islands can give you a much more varied Hawaiian holiday. Oahu and Kona can work particularly well together if you want a mix of vibrant Waikiki and a more relaxed Big Island experience.
There isn’t a single answer because luxury means different things to different travellers. The best choice depends on whether you’re looking for a high-end resort, exceptional dining, privacy, adventure, wellness, beaches or a combination of everything.
My biggest takeaway from this trip? Don’t choose your Hawaiian holiday based solely on the prettiest hotel photograph. Think about how you want to feel when you’re there.
Do you want to walk out of your hotel and straight onto the beach? Do you want restaurants and shopping nearby? Do you want to explore by car? Are you looking for complete relaxation? Do you want adventure? Are you travelling with children? Is this a honeymoon? Or are you celebrating something special?
Once you know that, choosing the right island, location, hotel and experiences becomes much easier. And that’s exactly where I come in.
As a luxury travel specialist, I personally inspect properties and experience destinations whenever I can so that I can give my clients advice based on real experience — not just a hotel website and a pretty brochure. My Hawaii trip gave me a wonderful first-hand look at both Oahu and Kona, and I came home with a much better understanding of how I’d match each destination and property to different types of travellers.
Your Hawaii holiday shouldn’t be a collection of random bookings. It should be an itinerary designed around you. If Hawaii is somewhere you’ve been dreaming about, let’s talk about what you actually want from the trip and I’ll help you build it from there.
Ready to start planning Hawaii?
Let’s create a Hawaii holiday you’ll still be talking about long after you’ve come home.
Six nights was nowhere near enough to experience everything Hawaii has to offer — but that’s probably a good thing.
Because it means I have plenty more reasons to go back.
