Updated July 2, 2021.

Aloha! It’s a very special Where I Went Wednesday! If you’ve been following along on the blog, you know my sweet husband and I just took a big anniversary trip to beautiful Hawaii! After our first anniversary on O’ahu (the island with Honolulu, Waikiki, and Pearl Harbor), we decided to spend every anniversary on an island, for as many years as we can. Islands are great because they are reputably exotic, romantic, and relaxing–after all, there’s only so far you can go!

But once I started planning our trip to the Island of Hawai’i, I quickly found myself overwhelmed! Trip planning is something I do often and even enjoy, so I knew if I was overwhelmed, there were probably others out there who feel the same way when planning a Hawaiian getaway. So here you go, folks: your ultimate guide to planning an Island of Hawai’i getaway!

1. Understand that the Island of Hawai’i is BIG!

It’s really big, as in, all the other Hawaiian islands can fit into it twice–and it’s still growing! It would take you about an hour and a half to two hours (with no weather problems or bathroom stops) to drive from one side to the other on Saddle Road, which cuts through the middle of the island. Looking to drive all the way around the island? That’ll be about seven hours of driving time. That does not include stopping to look at and enjoy the beauty of Hawaii!

More here: What to Know Before You Visit the Hawaiian Islands

2. Plan Your Activities

Are you more interested in the green sand or the waterfalls? The hiking or the beach-going? The World’s tallest mountain (where it snows in Hawaii), or lava flowing into the ocean at 2000 degrees? Well, we were interested in it all, and perhaps you are, too! I do not get paid by or received benefits from Trip Advisor, but having traveled all over the world, I’ve found this site and its app to be the most helpful in trip planning. I searched for “Island of Hawaii,” selected “Things to Do,” and started saving everything that interested us.

When I finished with that, I selected the map view to see exactly where everything was in relation to everything else we wanted to do. Lucky us, we wanted to see things literally all the way around the island. A road trip was definitely in the cards for us! I “unsaved” several things that were not “must do” items that we would not be able to see. That helped narrow down the list.

Keep reading: The Ultimate Island of Hawai’i Bucket List

3. Pick a Side–or Not!

Now that you have an idea of what you want to do and where those things are located, it’s important to choose the best place to stay. You have two main choices: Kona side (sunnier) or Hilo side (Volcanoes National Park). Lucky me, I have a friend who lives on the Island of Hawai’i! She told me (and now I’m telling you) that Kona is the more popular town for visitors, and Hilo and the volcanoes are really not things you can see and enjoy on just a day trip. To me, that meant splitting our time between the two sides and seeing as much as possible along the way.

We thought about flying into one side and out of the other, but that got to be too complicated. Then we thought maybe we should do the Kona side this time and come back next year for the Hilo side. But you never know what might happen, and since we’d be on the island a full week, we thought we could probably fit everything in this time around. Why miss an opportunity? We opted to start and end in Kona, and spend three days road tripping our way around the island, including two nights in Hilo!

Read next: How to Road Trip on the Island of Hawai’i

4. Choose Your Flights

This is the time to book your flights if you haven’t already. When we knew we wanted to fly in and out of the same airport and had a rough idea of where we’d be staying, we went for it! If you can avoid flying on Saturday and Sunday, you will avoid most honeymooners, so flights will possibly be less expensive, and you will have more seating options (as well as more chances to upgrade if that’s something you want to do). Try to be flexible to get the best price.

More here: Surviving the Flight to Hawaii
and Inter-island Flights on ‘Ohana by Hawaiian Airlines

5. Plan Your Route

If you decided to keep to one side or the other, you will definitely not have to do so much planning. Enjoy your relaxation! But if you’ve decided to tackle a road trip, get ready to see some incredible sights!

Insider Tip! My friend who lives on the island suggested that we go the south route from Kailu-Kona to Hilo first. That way we could be in Volcanoes National Park at sunset (year-round about 6:30 pm) to see the lava glowing in the park. When she and her family do take visitors to Volcanoes National Park for a day trip, they take the southern route, spend the day in the park until sunset, drive about 45 minute to an hour for dinner in Hilo, then take Saddle Road back to Kailua-Kona so they can stop at Mauna Kea for some star-gazing at night.

We chose to take the southerly route on our first driving day, spend a day in Hilo, then take the north route to come back. I went back to my Trip Advisor map to see what sights there were to see on our way to break up the trip and see as much as possible. Check out our Road Tripping the Island of Hawai’i post for more!

More here: What to Eat on the Island of Hawai’i

6. Volcanoes and Lava

Thinking of seeing the infamous lava flow into the ocean? We debated whether to take a boat tour, helicopter tour, or simply be satisfied with what lava we could see from the land inside Volcanoes National Park. Since we would be so close, and you never know if you’ll go back to a place or not, we decided to treat ourselves to a more elaborate lava viewing experience.

The pictures people had posted from the helicopter tours honestly weren’t all that impressive. There were far more waterfall pictures than lava pictures, and the lava flowing into the ocean creates so much smoke and steam, the views from the air really didn’t seem that great. However, the lava boat tours boasted many impressive pictures from the boats! So we opted for that. It was $200 each if we paid cash, but more if we paid by credit card, so we chose cash.

Keep reading: How to Have an Unforgettable Lava Boat Tour

7. Choose Your Accommodations 

We like to choose our accommodations a little bit late in the planning game. If we choose one before we start making plans, we sometimes end up much farther from the things we want to do than we might have if we’d waited. We chose the Courtyard King Kamehameha Hotel in Kailua-Kona because it seemed fairly centrally located in relation to some of the sites we wanted to see in town, and there’s a beach and place to snorkel nearby as well. For Hilo, we chose the Grand Naniola by Hilton because of its proximity to the water and walkability to sites in town. Hotels, vacations rentals, and more are all available!

More here: Your Ultimate Guide to Accommodations
and How to Earn and Use Hotel Reward Points

Still have questions about planning your trip? Ask me in the comment section below! For more trip planning information, check out my Hawaiian Islands Page!

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