My Guide to Hawaiian Island Hopping

The Hawaiian islands are one of the most remote populated landmasses on earth. The next closest land is over 1000 miles away, and the nearest significantly populated areas, California and Alaska, are over 2000 miles from the small island chain. That being said, visiting Hawaii is a trek.

For us, it took nearly 9000 miles of traveling (round trip) to reach the tropical paradise of Oahu. This involved almost 24 hours in airports and on planes, each way.

Lol, yikes. But it’s well worth it! 


And, as you can imagine, plane tickets are not cheap. (However shout out and thank you to my AMAZING in-laws, because full disclosure, We did not pay for the large majority of our trip, but that’s another post).

Given the isolation of the Hawaiian islands, and the cost to even reach one island, it’s important to get the most out of your experience when visiting.

One way to do this, is to island hop.


fun fact: after I took this picture, I realized there was a lady pooping right under this bush. Nature is gr8. 

I highly recommend island hopping. Because of the islands’ general isolation and unusual geography due to volcanic activity, visiting multiple islands is a great way to see each island’s unique landscapes and species, as well it’s spirit. Plus the islands are all decently close, so a day trip is totally do-able.

On our trip, we island hopped from Oahu to Maui, but that was a tough decision to make! There are 7 primary Hawaiian islands: Molokai, Lanai, Hawaii, Oahu, Maui, and Kauai. Each one is different. Unless you are moving to Hawaii or can somehow afford a 3 week vacation there, you want to get the most of your island hopping experience and choose the best island for you.

Here is my guide: 

1. Determine the island(s) you want to see: 

We stayed in Oahu, which was perfect because it is truly mix everything. This being a family vacation, that was ideal. For our island hopping excursion, we decided to visit Maui. It had many attractions we wanted to see, namely natural beauty like black sand beaches and rugged mountains. We were so glad we chose Maui but it wasn’t an easy choice! The island of Hawaii is known for Volcanoes National Park, Kauai has iconic rugged mountains and shoreline, Lanai and Molokai are known for their low-key and authentic island experiences and natural beauty. Do your research and prioritize what you want to see most.

2. Determine a time frame:

After you have researched islands, keep in mind what you want from your trip and how long you plan on spending on the island. Consider if it will take multiple days to see everything you want, or if one day is plenty.

3. Research How to Get There:

There are many ways to island hop: pricey private helicopter tours that bop from one island to another, tours that are inclusive and include airfare, itinerary and guide, ferry’s that cross to islands that are nearby (such as Maui to Lanai). There are a LOT of options. In my opinion, the most cost effective option, that maximizes freedom and flexibility, is booking a flight and renting a car. If you go on google flights, you can research the cost from flying from one island to another. Usually flights do not exceed 150 dollars round trip. Many flights take off early in the morning and leave late that evening, so flying for a one day excursion is totally reasonable (and exactly what we did.) Rental cars also allow for single day use. For multiple day trips, make sure to book lodging well in advance and consider options other than hotels, such a Airbnb, for cheaper and less crowded accommodations. 

4. Plan for the details of the trip:

If island hopping overnight, on a short trip, see if your primary hotel can store luggage, then bring only a carry on to minimize cost. For day trips, still bring a change of clothes, a jacket and a few toiletries just in case. Make sure you bring items for all planned activities, such as a bathing suit, towel , hiking shoes, etc. Hawaii is about going with the flow and being spontaneous, for us, that meant running around mountains in the pouring rain. I’m glad I had extra shoes when my first pair were DESTROYED by mud.

 5. Be realistic and enjoy : There is SO much to see on every island. Although they may be relatively small, one area of an island might be totally different from the other in culture and landscape. Each island in hawaii is a beautiful place with so many things to see and do, and even if you had 2 weeks, there is no way to see everything. Keep that in mind, make a list of things you would LOVE to see, but don’t get to caught up in your expectations. On our trip to Maui we hiked in Ioa Valley, completed half of the road to Hana, drove around (not near, just around) Haleakalā Crater and had a wonderful dinner at Mamas fish house. It was a perfect day, probably one of the best days of my life. However if I expected that we would complete the road to Hana, see all the stops along the way, drive to up to Haleakalā Crater and have a beach day, I would be super disappointed because that was just not possible in our time frame. Embrace the island time and forget the FOMO.


 So, that’s my guide! I will link some helpful island information below as well as the link for google flights. I hope you find this useful for planning your upcoming trip to Hawaii or inspiring if you are dreaming about going someday. 

A dream

A dream