We Visited All 4 Hawaiian Islands in 2 Weeks
(Here's What We'd Do Differently)
When people dream about Hawaii, they usually picture choosing one island and spending a relaxing week on the beach.
My family did the exact opposite.
Over two weeks, we visited Maui, Kauai, the Big Island, and Oahu. We rented a car on every island, packed up our luggage every few days, and even traveled with my two-year-old son and his car seat.
Was it an incredible trip?
Absolutely.
Would I recommend it for everyone?
Not at all.
My family loves staying busy and seeing as much as possible, so this style of travel fit us perfectly. But looking back, I think most travelers would enjoy Hawaii even more if they slowed down a bit.
If you’re trying to decide whether to island hop—or wondering which island is right for you—here’s what our experience taught us.
Why We Decided to Island Hop
One of the things that makes Hawaii unique is that every island has its own personality.
Rather than picking just one, we wanted to experience as much of Hawaii as we could.
That meant:
• Flying between islands
• Renting a car on each island
• Staying in multiple hotels
• Experiencing completely different scenery every few days
It was fast-paced…
…but also unforgettable.
Is Island Hopping Difficult?
Honestly?
Not at all.
Inter-island flights are surprisingly easy.
Airlines like Southwest and Hawaiian Airlines operate flights throughout the day, and most flights are only about 30–45 minutes.
The biggest thing to remember is to plan your route carefully. Even though flights between the islands are easy, not every island has the same nonstop flight options. Choosing the right order can save you both time and money. For example, an itinerary that zigzags from Kauaʻi to the Big Island, then to Oʻahu, and back to Maui usually isn’t the most efficient use of your vacation. Planning your route thoughtfully means spending less time in airports and more time exploring.
As a travel advisor, this is one of the biggest ways I help clients. Sometimes simply changing the order of the islands can save hours of travel time.
It’s even possible to visit another island as a day trip. There are organized excursions that handle all the transportation, or you can book flights yourself if you’re comfortable planning the logistics. Personally, I think that’s a very long day, but it can be a great option if you only have a week in Hawaii.
Maui: Waterfalls, Scenic Drives & Black Sand Beaches
Maui was our first stop, and it immediately reminded us why Hawaii is on so many bucket lists.
The highlight for us was driving (most of) the Road to Hana.
We didn’t make it all the way to Hana, but we experienced countless waterfalls, lush rainforest, and one of Hawaii’s famous black sand beaches.
The black sand beach was beautiful to see and absolutely worth stopping for, but it’s more of a sightseeing destination than a beach I’d spend an entire day relaxing on.
One thing I’ll mention for anyone planning to drive the Road to Hana…
The road isn’t difficult because of traffic—it’s the narrow curves and steep drop-offs.
I was perfectly comfortable driving the beginning and end of the route, but once the road narrowed with those incredible cliffside views, I happily handed the keys over to my mom. She’s much more comfortable with those types of roads than I am!
If winding mountain roads make you nervous, don’t let that stop you from experiencing the Road to Hana. Just consider letting someone else drive or booking a guided tour so you can relax and enjoy the scenery.
Kauai: The Island That Completely Surprised Me
If I had to choose a favorite island…
It would probably be Kauai.
Not because it had one standout attraction, but because every day felt completely different.
One day we were standing at Waimea Canyon—often called the “Grand Canyon of the Pacific.”
The next day we were flying in a small prop plane over the breathtaking Nā Pali Coast, which ended up being one of my favorite experiences from our entire Hawaiian vacation.
We also spent an evening at a luau hosted on a local ranch. Before dinner, we rode a train through the property, seeing horses, tropical plants, and fruit growing around the ranch before settling in for an evening of Hawaiian music, dancing, and food.
That variety is what made Kauai so memorable for me.
Within a couple of days, we experienced beaches, mountains, dramatic coastlines, canyons, and Hawaiian culture—all on one island.
The Big Island: Hawaii’s Most Unique Landscapes
Our next stop was the Big Island, which feels completely different from the rest of Hawaii.
This is the island of volcanoes, lava fields, waterfalls, and black sand beaches.
Our favorite stop was Hawaiʻi Volcanoes National Park, where we explored lava tubes and experienced landscapes unlike anywhere else we’d visited.
We also found a beautiful beach to relax and watch the sunset—one of those simple moments that ends up becoming one of your favorite vacation memories.
Oahu: The Perfect Way to Finish
Our last island was Oahu.
Because we were traveling with a toddler, we made a few different choices than we probably would have otherwise.
Instead of hiking Diamond Head, we chose a guided city tour that let us see many of Honolulu’s highlights while learning the history behind them.
We also toured Pearl Harbor, visited a macadamia nut farm where we cracked fresh nuts ourselves and sampled local coffee, and spent time at the Waikiki Aquarium, which was a huge hit with my son.
One funny memory was arriving at one of the nearby beaches only to find it closed because a seal had chosen it as the perfect place to give birth. While we didn’t get our beach afternoon, it was a pretty incredible reminder that Hawaii’s wildlife often has the final say!
Would I Visit All Four Islands Again?
Yes.
But it’s not right for most people.
Most travelers don’t vacation that way.
If I were planning a first Hawaiian vacation today, I’d probably recommend choosing one or two islands and really settling in.
Every travel day means checking out of your hotel, catching a flight, picking up another rental car, and checking into your next hotel. While inter-island travel is easy, it still takes time away from enjoying Hawaii.
That said…
Experiencing all four islands gave me something incredibly valuable: the ability to truly appreciate how different each one is.
They’re all Hawaii—but they each have their own personality.
And choosing the right island can completely change your vacation.
(In my next Hawaii guide, I’ll break down exactly which island I recommend based on your travel style, whether you’re planning a honeymoon, family vacation, adventure trip, or first visit.)
Jenny Even
As I grew up, my main bucket list item became to visit all 50 states (which I just completed in 2023 with an island-hopping trip in Hawaii)! When asked what my favorite type of vacation is I never have an answer – I love to do it all! And now being a mom of two young kids it has been fun getting more into the family vacations for our own family.I plan vacations because I love to help people have the best experience and make unforgettable memories.
