A guide to Island Hopping in Hawaii

When we booked our tickets to Hawaii, the first thing we did was go to Barnes & Nobles and buy the Hawaii Fodor’s Guide. Best guide around by the way. It helped me so much through the trip preparation and it was a life saver before and during our vacation.

I was really confused as to which island to pick and visit for our first time in Hawaii. For those who don’t know, Hawaii is an archipelago of 8 main islands ( Hawaii – big island, Maui, Kauai, Oahu, Molokai, Lanai, Niihau, Kahoolawe). They all seemed very beautiful and unique but, being there only 12 days, we needed to make a choice. Reading about each island in the Fodor’s guide was the first step of my travel research.

1. How we chose our islands

To pick our islands, we had to proceed by elimination. Before you read this, you should know Bobby and I deal with severe cases of FOMO (Fear of Missing Out) when we don’t “do it all”. We hate not being able to see everything we want in a destination. We care to taste all the foods, see all the views and walk all the paths. Hence, choosing our islands was one of the hardest part of the trip planning.

Amongst all of them, a few small islands seemed better suited for another trip : Molokai, Lanai and Kahoolawe. We were at peace knowing they are not places you see on your first visit. Also, Niihau is basically impossible to get to, except if you’re the rich guy who owns it or you have a hunting permit. This one was equally easy to take off the list.

But then, in 12 days, how many of the 4 remaining islands could we visit ?

Our tickets were cheap enough through Honolulu with American Airlines, so we knew we had to start and end the vacation on the island of Oahu. If I had listened to myself at the time, I would’ve said I’d rather go to the Big Island and forget about Oahu. But Oahu was a fantastic surprise. I really thought it would be too touristy and not have enough adventure and nature. Boy, was I wrong! I’ll get back to that on my Oahu’s article…

The Big Island is very well-named as it is 10,000 square meter (4,000 square feet) and it is large enough to contain all the other Hawaiian islands. It is home to 11 different climate types but also beaches, jungle, volcanoes… It’s big and it’s varied and I really think you need to spend at least 10 days there to really enjoy. That’s why we decided to keep it for another time (soooon hopefully!).

We were sure 100% we wanted to visit Maui, because it is a romantic destination (we were going there for our honeymoon after all) but it also has everything we imagined of Hawaii ie. volcanic views, tons of waterfalls, a lush jungle, long sand beaches, natural wildlife…

Now the challenge was to know if we were going to have time to squeeze Kauai – the embodiment of natural beauty, myriad of waterfalls and untouched land – into our vacation. Kauai is actually one of those places where you can drive to one side of the island in just under an hour and to the other side in just over an hour. Knowing 80% of the island is only visible by boat or by helicopter, we were confident we could see everything we wanted to see in 48 hours.

We ended up allocating time to 3 islands as follows :

  • 2 days in Oahu
  • 6 days in Maui
  • 2 days in Kauai
  • 2 days back in Oahu

2. Island Hopping in Hawaii, what you need to know

A few things are important to know when you decide to island hop :

  • First, allow at least 2 days – 2 nights on each island or there is no point in island hopping. You will leave more frustrated than anything if you are really there to discover and explore like we did.
  • Second, consider that going from one island to the other by plane is VERY EASY 🙂

We went from island to island with Hawaiian Airlines. It’s a great airline not only because they have good prices (take your tickets as soon as possible and you won’t spend that much) but also because they rock their logistics.

From Honolulu, you can find connecting flights to other islands almost every half hour. Each flight lasts between 30 min to 1 hour. The airport is never that busy and quite efficient. If you travel with carry-ons like us, it won’t take you more than 30 minutes to go through security and find your gate. So basically, you can leave the city 2 hours before your flight without any worries.

Funny story : We woke up at 2 am on the third day of our trip because we had a flight from Honolulu (Oahu) to Kahului (Maui) at 5am. We wanted to be there early enough to drop our rental car at the airport and then go through security and find our gate. We arrived at 2:40am at the car rental centre and then at 3:00 am in front of the doors of our terminal. Well, the terminal did not open before 4:15am. So we waited outside for more than an hour. I wish someone had told me this before – we could have used an extra hour sleep haha!

-> So, make sure you don’t go to the airport too early, especially in Kauai and Maui because they will board your flight only 20 min before departure. That applies to any time of the day.

3. A few extra tips

  1. If you DO arrive extra early to the airport, ask to be on “stand-by” for a sooner flight. Not all flights are full and you might be able to spend more time on the next island.
  2. Go online and check the times of sunrise and sunset on your travel days. Then pick flights around those times. If the sky is clear, you will enjoy some of the most beautiful views above the islands and the ocean.
  3. Rent a car to explore the island on your own when you stay for 2-4 days. There is no better way to visit Hawaii than to get lost in nature and allow yourself to go off the beaten paths.

Those tips are for travellers who really want to get the most out of their island time. If you are traveling for just one week in order to enjoy some laid-back time, some resort fun and chill at the beach, I would definitely advise to stay on one island and not worry about island hopping.

NB about Kauai : I do believe you could go to Kauai only 1 day and do a helicopter tour + a drive up-north. It is totally possible if you REALLY want to go while on another island. But you would miss on one of the coasts and they are both extraordinary and different. The South shore is dry while the North Shore is wet – The south Shore also has the Grand Canyon of the Pacific (Waimea, see pictures above) while the North Shore has more jungle and hosts some of the most beautiful beaches in the world… Allow yourself to stay one more day and see it all 🙂

Are you thinking of island hopping while in Hawaii ? If you have any questions or concerns and can’t make up your mind, I’d be happy to help!

More to come on our honeymoon soon…

Love, Coco

COPYRIGHT: All pictures belong to Fanny Cohen Sanchez, @fannychn on Instagram, Three Times Nine 2021.

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2 responses to “A guide to Island Hopping in Hawaii”

  1. I hate to say it, but you did too much and crammed too many places into too short a time. Especially on your honeymoon! The whole idea of coming to Hawaii is to slow yourself down, not speed yourself up. Who gets up at 2am for an inter-island flight? And it’s kind of funny that you said you wish that someone had told you about early-morning hours at car rental dropoff and airport locations. Perhaps you could have looked into that yourself online in advance? There are some very informative blogs out there, and some very good threads on Trip Advisor that give you the opportunity to ask questions and get answers and advice from locals. But at least your whirlwind tour included Hanalei. I think you kind of dropped the ball by not mentioning the various flood-related road closures in Hanalei, especially around the Pier….that have impacted both locals and tourists. The big storm happened a year and a half ago and locals there are still trying to recover from the various problems. Anyway, hope you enjoyed your honeymoon. Next time, slow down. Do less.


    • Hello Mark! Thanks for dropping by and the piece of advice. I think however that it’s a bit subjective. We loved our honeymoon and had plenty of time to just sit at the beach and enjoy. The point FOR YOU to go to Hawaii might be to do less but for us, it was to explore and see as much as we could.

      As said in the article, this is advice for people who -like us- enjoy a high pace even on vacation.
      Also, I am not really here to talk about the floods in the northern area of Hanalei as this article focuses on island hopping and not on Kauai.
      We DID really love our time on the 3 islands and would do it all over again 🙂


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