One of the most common questions people find themselves asking when planning their island vacation is should I soak up the experience of one island for a full week, or should I visit multiple islands to see as much as possible? Like anything, the answer depends on what you’re looking for. We’ll get into the “whys” for each island in just a moment, but it ultimately comes down to how you like to travel, and whether or not you think you’ll be making a return trip to Hawai’i! In this blog we’ll outline the pros and cons of island hopping, as well as the reasons to visit, or not visit, each of the 6 largest islands so you can make an informed decision and enjoy the vacation of your dreams.

 

The Pros and Cons of Island Hopping

 

To get straight into it, the main reason why you should island hop is because you don’t expect to ever return to Hawai’i, and you’d like to see as much as possible on your once-in-a-lifetime trip. The other main reason is because each island is so different, and therefore has a unique experience to offer you. Seeing just one island won’t satisfy you if you want a complete picture of Hawai’i, and it’s easy enough to travel between the four main islands (Big Island, Maui, O’ahu, Kaua’i). That’s another point in favor of island hopping: flying between islands will only take you about an hour from gate to gate on the longest routes, which means you can catch an early morning flight from one island, and start exploring your next destination by noon on the same day. On the whole, if you’re interested in seeing a variety of landscapes, geographical features, cultural sites, and lifestyles, then island hopping is the way to go. Every island has something different to offer, so why not try and see them all?

 

On the other hand, there are plenty of reasons why you shouldn’t island hop. The first, and most obvious, is that island hopping requires more travelling, and therefore more time and effort. Flying between islands, even on local carrier Mokulele, means more time driving to and from airports, going through TSA, and waiting to get on and off the plane. This is on top of packing up your stuff at whatever hotel or condo you were staying at, returning your rental car or waiting for public transportation/ride shares, and potentially getting up at the crack of dawn to catch an early morning flight. All this traveling necessarily comes with extra costs, and if you came to Hawai’i for some rest and relaxation, then the stress of additional flying kills the vibe. It’s also much harder to get a “complete picture” of whichever islands you visit, because your days will likely be jam packed with the hottest activities, leaving little opportunity to delve into what life is really like there, and leaving you with a skewed impression. So, if you’re on a budget, focused on truly unwinding, or looking to delve deep into the island experience, then you should probably do your research, pick the island that stands out to you the most, and stick with it.

 

But Which Island(s) Should I Visit?

 

Again, it truly depends on what you’re looking for. We’ll get into the broader details of what each island has to offer in just a moment, but you’ll have a different experience on every single island. O’ahu is urban and bustling, Maui is full of other-worldly landscapes, Kaua’i is lush and laidback, etcetera etcetera. With that being said, if visiting Lana’i or Moloka’i is a priority for you, you’ll need to schedule time on either Maui or O’ahu, as these are the only islands with airports that operate air services to the two smaller islands. Many people prefer to make O’ahu their first stop anyways, as Honolulu has the most direct flights from mainland airports. Now, let’s get into some of what each island has to offer.

 

O’ahu: Urban Island Life, History, Something For Everyone

 

O’ahu, home to the island’s capital and most populated city Honolulu, is one of the most popular choices for Hawaiian getaways, and for good reason!

 

Pros:

• The beaches are beautiful, and the watersports are great! O’ahu’s North Shore is one of the world’s surfing hotspots, the snorkeling around the island is great, and many beaches are lifeguarded.
• It’s a doable vacation if you’re on a budget. Because Honolulu is a big city, you’ll be able to find everything from high-end resorts, to surprisingly affordable beachfront high-rise condos. If you don’t have a lot of extra cash to throw around, O’ahu is your best bet for good food, good beaches, and good times that won’t break the bank.
• HNL airport has the most direct flights from the mainland, which makes it more affordable to get to. Especially from the West Coast, flights can be relatively cheap.
• HNL offers affordable connectivity to the other islands. If you’re planning to island hop, Honolulu airport can get you to any other island affordably, including Lana’i and Moloka’i. 
• You don’t necessarily need to rent a car. O’ahu, and especially Honolulu has some solid public transportation options, and if you’re staying in the highly popular tourist neighborhood of Waikiki then you can even get around on foot. You can’t really say this for most of the other islands.
• There are more locals on O’ahu than any other island, which allows you the opportunity to get a feel for what the Hawaiian lifestyle is all about, and dive into the culture of Hawai’i with incredible museums, cultural heritage sites, art galleries, dance shows, and more.

 

Cons:

• Traffic. Honolulu traffic is famous for being terrible. As one of our cleaners Shaylyn put it: “it’s LA on an island.” 
• Crowds. O’ahu is the most popular island for visitors, which means you should expect crowded beaches, the aforementioned traffic, a bustling city, and the occasional line to get into a restaurant/coffee shop/shave ice stand. 
• The urban environment can detract from the beauty of the island. O’ahu is highly developed, which means noise and light pollution, highrise buildings dotting the coast, and all the comforts of city living that you’re used to on the mainland. If you’re looking to “get away from it all,” this probably isn’t the spot for you.

 

Maui: Luxury Vacations, Incredible Landscapes, Whales!

 

Maui is Hawai’i’s second most popular island destination, and has a distinctly more upscale vibe. It’s important to note, though, that many Native Hawaiians are still displaced or rebuilding from the Lahaina fires of 2023. While enjoying this beautiful island can be a once in a lifetime opportunity for many people, we encourage visitors to be mindful of the devastation that occurred here, and respectful of the locals. 

 

Pros: 

• The ocean activities here are top notch. There are black, gold, red, and white sand beaches to choose from, the reef offers protected waters that are great for snorkeling and scuba diving, boat tours and outrigger excursions abound, and the surfing isn’t half bad either.
• The whale watching in the channel between Maui and Lana’i is some of the best in the world. During the winter months you can see whales and their calves breaching and spouting, which is truly incredible.
• If upscale beachfront resorts are your thing, then Maui is the place for you. This is an island of high-end accommodations and fine dining.
• The landscapes! The hiking here is incredible, and taking a trip to Haleakalā National Park will provide you with views of stark volcanic landscapes, subtropical rainforests, and protected species not found anywhere else in the world. Taking the iconic Road to Hana will lead you past tumbling waterfalls and lush greenery along the coast, before spitting you out at an otherworldly black sand beach in Wai’ānapanapa State Park 

Cons:

• This is not an affordable destination. Hawai’i in general tends to be pricey, and Maui even moreso. There are fewer budget accommodations here, fewer lowkey dining options, and renting a car is practically required. 
• The high prices and high end reputation means there’s a much smaller local population, and a much more “touristy” feeling. If authentic Hawai’i (whatever that may mean to you) is your goal, then Maui probably isn’t what you’re looking for.
• Traffic can be surprisingly bad, and parking incredibly difficult, especially on the Road to Hana and in Lahaina. Though nothing like Honolulu, you’ll need to budget some extra time to get around. 

 

Hawai’i Island (Big Island): Volcanoes, Star Gazing, Fewer People

 

The Big Island is just as the nickname implies: big. It’s larger than all the other islands combined, and has the island chain’s only active volcanoes, Mauna Loa and Kīlauea. Similar to Maui, the geography here is unlike anything else you’ve experienced. 

 

Pros:

• Active volcanoes. I’m not sure how much more we really need to say. They’re just freaking awesome! You can go on any number of hikes in Hawai’i Volcanoes National Park and watch as new island is created in real time. Not only is this incredibly cool, it’s deeply sacred and spiritual, and should be approached with caution and respect.
• Stargazing! While there are paid sunset and stargazing tours, you can drive to the summit of Maunakea yourself, watch an incredible sunset, and then stay for stargazing as night falls. Being so high up on a dormant volcano and watching the stars come to life above the island is an awe-inspiring experience. 
• It’s surprisingly affordable to stay on the Big Island. Accommodations can be found relatively cheaply, and there are any number of delicious local joints to grab a bite.
• There’s tons of biodiversity. Driving around the island can be an activity in and of itself, and you’ll encounter 11 of Earth’s 13 microclimates in one day. It’s one of the most climatically diverse spots on the globe!
• The term “crowded” definitely won’t apply here. You’ll still encounter plenty of visitors, but in general you can expect a laid back experience that you won’t find on Maui or O’ahu.

 

Cons:

• Travel times can be quite long. It’s a huge island, and driving between destinations can take hours. If you only have a few days to visit, this can seriously eat into activity time. 
• The beaches are not the best. Because it’s an active volcanic island, the beaches haven’t had time to erode into soft sand, and are largely rocky and unappealing for lounging and relaxing by the water. If toes in the sand relaxation is your goal, Big Island is not for you.
• Limited nightlife options can lead to boredom as night falls. If hitting the town is your idea of fun, you may end up disappointed with your time on the Big Island.

 

Kaua’i: Lush Landscapes, Laidback Living, Simpler Times

 

Kaua’i is the oldest, and smallest, of the Hawaiian islands, as well as the least developed of the four major islands. Things move slow here, and most of the island is charming and unpretentious. 

 

Pros: 

• Kaua’i is an outdoors enthusiast’s dream. From the stunning scenery along the 26 mile Kalalau Trail, the Martian feeling of Waimea Canyon, and the number of botanical gardens and preserves on the island, you’re guaranteed to experience the natural landscape in ways you won’t find anywhere else, even on the other islands. 
• It’s very relaxed. Kaua’i has a small population, and no buildings taller than a palm tree, which makes everything feel like a slow-paced, small town, which it pretty much is! If true rest and relaxation is what you’re after, there’s no better place than Kaua’i.
• It’s more affordable than Maui, and there are fewer crowds. Popular beaches will of course be decently full, but you’ll never be fighting for a spot in the sand. 
• The stargazing is just as incredible as on the Big Island. Dark sky ordinances to protect endangered Shearwater birds make sure that you can see thousands of stars, and even bands of starlight that make up the Milky Way.

 

Cons:

• It’s less developed. If fancy, new accommodations are what you prefer, you’ll be disappointed here. Buildings and homes are older, and new development is uncommon and slow-paced.
• Things shut down pretty early. Being such a small island, most bars/restaurants/shops are shut by 9pm. This makes for early nights, and if you’re not the type who enjoys that, you’ll probably end up bored.
• It rains more than any of the other islands. It takes a lot of water to make a garden, so naturally it takes a lot of rain to make a Garden Island. While it typically stays warmer and drier on the South Shore, rain is a near constant companion on other parts of the island.
• You’ll need to rent a car. Unless you’re staying in certain pockets in Lihue, Kapa’a, or Koloa getting around the island without your own transportation will be difficult.

 

Moloka’i: Untouched Landscapes, No Crowds, Off the Beaten Path

 

Moloka’i is the least visited island of Hawai’i, and has a bit of a mysterious reputation. Tourism does not reign supreme here, and locals have worked hard to maintain Hawaiian traditions and ways of life. 

 

Pros: 

• If you’re looking for unspoiled land, miles of empty beaches, and a deep connection to the people and history of Hawai’i, then Moloka’i is the place for you. It has remained intentionally undeveloped, and you’ll get an experience here unlike any other.
• The living is simple. There’s one hotel on the whole island, a handful of restaurants, and pretty much all of the visitor infrastructure is in the town of Kaunakakai. This makes trip planning pretty simple, and allows for plenty of time for relaxing.

 

Cons:

• It’s pretty hard to get to, and to get around. Mokulele Airlines, the only interisland carrier that flies to Moloka’i, is notoriously flaky with their service, and if you do happen to successfully make it there, you’ll pretty much have to rent a car.
• The living is simple. Yes, this can be a con too. With few dining and lodging options, few excursions, and a small population, there simply aren’t a lot of typical “vacation activity” options to entertain yourself with. If you’re not interested in local culture, local people, and the beautiful landscape, you should look elsewhere for your island adventures.
• There are mixed attitudes towards tourism on the island. While some recognize that the majority of visitors will be respectful, others are deeply protective of their way of life on Moloka’i. If mindful tourism is a new term to you, this probably isn’t the right destination.

 

Lana’i: Catered Experiences, Ultra-Luxurious, Small Crowds

 

Finally, we come to Lana’i; the only privately owned island in Hawai’i. Known for its exclusive resorts, this island is sometimes seen as the playground of the wealthy.

 

Pros: 

• The secluded environment. Crowds are few and far between, and the lodging options are fairly exclusive. This means no fighting over beach space or for restaurant reservations.
• Many of the resorts will tailor your experience to your unique desires, and arrange itineraries full of excursions and wellness retreats. This makes for a customizable luxury experience. 
• You can take the ferry from Maui! The only operational ferry in Hawai’i runs between Maui and Lana’i, which can add another unique aspect to your trip.

 

Cons: 

• The price can be prohibitive. You don’t get a reputation as the wealthy’s go-to island if you’re offering budget experiences, and the lodging, dining, and activity options all come at a high price point. 
• There’s not a lot of room for doing things your way. Since the resorts typically help tailor your itinerary, and because activities are limited, this can lead to fairly strict schedules that don’t leave a lot of time for your own exploring, or simply relaxing on the beach.
• Similarly to Moloka’i, there isn’t a ton to do, especially after dark. Everything is clustered in little Lana’i City, and if you’re lucky there may be a local concert or farmers’ market during your visit. 
• Transportation can be difficult. While you can catch the ferry from Maui, if you’re coming from O’ahu your only option is to fly. The same flakiness problems with Mokulele Airlines apply here as well, and you’ll probably want a car on Lana’i as well.

 

To Hop or Not to Hop?

 

So, now you’re armed with a wealth of information on each island, and can decide if your vacation allows for multiple island visits. Generally, if you’ll be in Hawai’i for fewer than 10 days we don’t really recommend island hopping, and if your goal is to see all four main islands in one go, you should expect to spend at least two weeks here. Either way, you’re sure to see and do things in Hawai’i that you wouldn’t get to anywhere else, and meet some of the friendliest people along the way. Wherever you decide to visit, be sure to be respectful, and remember to pack your aloha spirit! Safe travels