This Stunning Hawaiian Island-Hopping Itinerary Showcases the Best of the State in One Unforgettable Vacation

As far as American states go, Hawaii is about as good as it gets. Because the Aloha State is a tropical paradise, it offers some of the best scenery and attractions in the world. So, if you’re looking for a fabulous vacation destination, any one of the islands in the chain would be a perfect option.

But what if you could visit them all and see every major highlight on each island in a single trip? That’s the concept behind this island-hopping adventure that takes you from a hidden Hawaiian gem on the Big Island’s west coast to a friendly beachside city on Kauai. 

Whether you’ve been to one or multiple Hawaiian islands before, this trip allows you to explore everything the state has to offer and more. That said, if you really want to appreciate the majesty of each stop, we recommend taking two weeks to make this trek, but it can be completed in one if you have a time constraint.

Depending on where you’re coming in from, you’ll likely have to fly into the Daniel K. Inouye International Airport in Oahu, known as the best airport in America for winter travel. From there, you can take small island-hopper flights to the other islands in the chain. So, you can either start your trip in Oahu or finish here, depending on how you want your itinerary to go. Keep in mind that some of the most populated cities are located on this island, so be wary of crowds wherever you go, including beaches, resorts, restaurants, and shops.

Despite the crowds, Oahu offers several unique spots that you can’t experience anywhere else in the state. The first is the Pearl Harbor National Memorial, which is just a quick drive from the airport. Another is the world-famous Waikiki Beach, which is something to cross off your bucket list, even if the sand is covered in tourists. Other highlights include the Iolani Palace and the Dole Plantation for some fresh Hawaiian pineapple.

If you’re into surfing, Oahu’s north shore offers some of the best surfing spots in the world. Hale’iwa and Waimea Bay are particular hotspots, with the latter being the birthplace of big wave surfing. That said, if you’re just a casual surfer, these breaks may be a bit too intense. Generally, experienced surfers love these sites because the waves are huge, but they can be quite dangerous for newbies.

Although Maui is still recovering from the devastating wildfires of 2023, much of the island remains open to tourists. You’ll fly into Kahului on the northern side, likely on a nonstop from Kona International Airport, and from there, you can head to your first destination. Much of the devastation was in the historical city of Lahaina on the western side. Although the city isn’t back to normal at the time of this writing, the businesses that are open are happy to greet visitors.

One of the main attractions on Maui is Haleakalā National Park, home to the Haleakalā volcano. If you want one of the most impressive views in the world, reserve a spot to hike to the summit before dawn and watch the sun rise. It’s truly a life-changing experience. Another main attraction is the Road to Hana. Book a shuttle ride around the eastern edge of the island, stopping at waterfalls, rainbow eucalyptus trees, and various small villages along the way. Although you can drive the route yourself, there are numerous spots where the road narrows to a single lane, so it’s best to trust a professional instead.

Maui is home to some incredible beaches, including a black sand beach in Hana. If you want pristine white sands, check out Makena Beach in Mākena State Park on the southern tip or Kaanapali Beach on the western side, just north of Lahaina.

Last, but certainly not least, is the small island of Kauai, also known as the Garden Isle. You can get here from Maui through an airline like Southwest, which offers nonstop flights from Kahului to Lihue. Once you’re on Kauai, you’ll understand its nickname as you explore lush landscapes and unspoiled natural beauty. Most of the island is full of nature preserves, with much of the infrastructure relegated to the eastern side. You’ll fly into Lihue, and you can either go north toward Princeville or south to Old Koloa Town, where you can browse cute boutiques and feel the magic of Hawaii’s rich history.

Kauai is an excellent option for winding down your inter-island vacation, as it allows you to rest and relax. While other islands have outdoor activities and attractions, Kauai focuses on botanical gardens and gorgeous beaches. Some of the best beaches are Poipu Beach, Shipwreck Beach, Kealia Beach Park, and Kekaha Beach.

But if you get tired of lounging by the waves and soaking up the sun, Kauai is also fantastic for hiking and exploring. The island is home to one of Hawaii’s most remote areas, a little-known coastal valley with unparalleled views. Because most of Kauai is preserved, you’ll get to see more of the local wildlife here than you can on other islands in the state.

If you’ve been on a road trip before, you know that it’s relatively easy to get from one city to the next. However, in Hawaii, moving between islands can be much more challenging, especially if you haven’t been to the state before. To ensure you can maximize your vacation, follow these tips.

First, separate travel days from exploration days. Although flights between the islands are pretty short (less than an hour on average), you don’t get to decide when a flight is scheduled, and delays can happen for various reasons, such as inclement weather. Additionally, since you’ll be on a new island, you’ll have to check into a different hotel or resort, and check-in times are usually in the afternoon or evening. So, trying to add attractions or stops in the middle of traveling can add a lot of extra stress and create missed opportunities.

Once you’re on an island, you’ll need a rental car to get around. It’s best to familiarize yourself with different routes, as you’ll likely have to cut across islands and use major highways. Smaller roads can take longer, and they may get backed up with traffic, depending on the time of day and the season. Finally, since you’ll be hopping from one island to the next, keep your luggage to a minimum if possible and create a checklist for everything. This way, you won’t forget small items like phone chargers or bathroom essentials as you travel.