Island hopping in Hawaii: How to plan it + Which Hawaiian islands to visit

Even though Hawaii was already on our never-ending bucket list, our recent trip to the islands was a bit of an impromptu trip. We actually planned to head to Australia in that same period when we spotted a great flight deal for Honolulu. Without hesitation – and without preparation – we booked the tickets for a three week family travel adventure. Yay, island hopping in Hawaii! But the initial excitement quickly turned into panic when we realized the amount of research ahead. We had no idea which Hawaiian islands to visit and how to travel between islands in Hawaii. So, in order not to feel any bit as overwhelmed as we did, read this… before you book your flights.

Map of the Hawaiian islands

For your convenience, we’ve created this map showing the inter-island transportation options.

How to island hop in Hawaii

Island hopping in Hawaii by plane

Hawaiian airports by island

Let’s have look at the airports in Hawaii island by island:

• Oahu is home to the only international airport in Hawaii: Honolulu Daniel K. Inouye International Airport (HLN). Because it’s such a hub, prices from the mainland to this airport are often better priced than those to the other islands. So, it’s a great airport to for arrival and for going back home after you’ve finished island hopping in Hawaii.
• The number of direct flights from the mainland to Maui’s main hub, Kahului (OGG) is increasing which is why it’s becoming a major competitor for Honolulu airport price-wise. Again, a good choice to start off and end your Hawaiian trip. When you’re staying in Ka’anapali, nearby West-Maui’s Kapalua airport (JHM) might be a valid option for inter-island flights but you’ll likely be traveling in a smaller plane and thus spend more time in the air.
• Kauai’s major airport is Lihue (LIH) to which only a handful of (mainly Californian) destinations fly directly. Most visitors will need to transfer in Honolulu. That’s why Kauai might be the better choice as an in-between island.
• Because of its size, the Big Island of Hawaii has two airports: Kona (KOA) & Hilo (ITO). Some airlines offer direct flights to Kona and a rare one maybe even to Hilo but it will cost you. So, just like the Kauai, we’re recommend you to visit the Big Island in between Oahu and Maui.
• There are no direct flights from the mainland to neither Lanai nor Molokai, only inter-island flights.

Airlines in Hawaii

At the time of publishing this article, two major carriers offer inter-island Hawaii flights for passengers: Hawaiian Airlines (and its regional subsidiary ‘Ohana by Hawaiian Airlines) and Mokulele Airlines.

Cost of going island hopping in Hawaii?

Remember our excitement after booking that great flight deal for our family of four? Well, if only lasted until we researched tickets prices for flights between Hawaiian islands. The number of inter-island flights that are scheduled on a daily basis is surreal, we never expected it would be that many. Therefore, we were surprised to see these relatively high prices. An important Hawaii fact to consider when planning your itinerary.

Here’s the overview of our Hawaii island hopping itinerary

• Day 1: Oahu (Honolulu airport – HNL) to Maui (Kahului airport – OGG)
• Day 2-5: Maui
• Day 6: Maui (Kahului airport – OGG) to Big Island (Hilo airport – ITO)
• Day 7-14: Big Island
• Day 15 : Big Island (Kona airport – KOA) to Oahu (Honolulu airport – HNL)
• Day 16-20: Oahu

We paid a total of $249,60 (about €220) per person for these 3 inter-island flights. The second flight, the one from Maui to Hilo, was the most expensive one at $80 (about €70) per person despite being the shortest of the three. So, we finally did manage to find an okay deal but it took some figuring out the best dates, flight times and route for the most interesting Hawaiian island hopping itinerary.

Baggage fees

Before-mentioned ticket price does not include checked bags. Luckily we pack rather light because, for a family of four on a three week trip, that does significantly increase the total cost. On inter-island flights with Hawaiian, you pay $25 (€22) for the 1st bag and $35 (€31) for the 2nd bag. However, Hawaiian Miles members only pay $15 (€13) for the 1st bag and $20 (€17,5) for the 2nd bag so if you haven’t registered for their loyalty program yet, then do so before you fly!

Choose the scenic side

Flight times and infrastructure

Traveling between islands in Hawaii by plane will take anywhere from 30 to 50 minutes. Out of the 3 inter-island flights we took, 1 was delayed and 1 was canceled (we were rebooked after a 2 hour wait).

The airports of Kahului and Hilo were pretty decent and staff were very kind and helpful but Kona airport seemed very basic. We had to walk barefooted over a disgusting carpet – luckily, disinfectant wipes are part of my standard equipment – and were treated with anything but the aloha-spirit. At least the gate was the cutest we had ever seen.

Hawaii island hopping vacation packages

For those visitors who don’t have the luxury of spending three weeks on the islands, like we did, the one-day Hawaiian island hopping packages are a great alternative. It saves you the fuss of packing and planning and most importantly… it saves you precious vacation time! Check out some of the packages at our branded Viator site.

Island hopping in Hawaii by boat

Ferry between Hawaiian islands

Prior to our research, we had expected there to be ferries for island hopping in Hawaii. Turns out there have been in the past but the only one remaining today is the Lanai – Maui ferry (from/to Lahaina harbor). At the time of publishing this post, it operates five times daily. We can’t talk from personal experience but we do imagine the views from aboard the ferry to be very impressive.

Hawaii island hopping cruise

Another option to travel between Hawaiian islands, is by cruising. Can I make a confession? We’ve never taken a cruise before. Those giant vacation ships remind us of those massive, all-inclusive, loud resorts we once visited (a looooong time ago). That’s just not how we like to travel anymore. So, we would prefer prefer small-vessel cruises, comparable to low-key, boutique style hotels with personal service. The UnCruise Hawaiian Seascapes adventures, for example, really appeals to us.

Which Hawaiian islands to visit and for how long

The Hawaiian archipelago consists of many islands but only six of those islands are inhabited. Out of those six, these four islands are the main vacation islands:

Oahu

‘The Gathering Place’ is Hawaii’s most popular island and home to state capital Honolulu. Apart from the famous tourist sites, such as Waikiki beach and Pearl harbour, Oahu is actually surprisingly rural. But since many tourists are keen on exploring the island’s attractions, it can get quite busy. If you prefer to see the true soul of the island, then these top things to do in North Shore Oahu are a great place to start.

We barely got to see the highlights in the four days that we spent on Oahu. Okay, I admit that we had a hard time leaving our superb Alohilani resort at Waikiki beach too but still…. If you want to explore the Honolulu area and you’re ready to book your attractions in advance, then four days will do. However, if you really want to discover what Oahu is all about then we would advise you to stay a bit longer, like we will next time. With 100 things to do on Oahu, you have plenty of exciting sightseeing options to choose from.

The Big Island of Hawaii

Often referred to as ‘Hawaii’, this island is all about purity and authenticity. This is the best Hawaiian island for families with a sense of adventure, nature-lovers and thrill-seekers. The landscape is incredibly diverse:

• It offers some of the best hikes in Hawaii in and around Hawaii Volcanoes National Park featuring the famous Kilauea volcano.
• You’ll find the most gorgeous scenery near Hilo.
• The colorful Big Island beaches are mind-blowing, especially the rare Papakolea green sand beach.
• Its picture-perfect Hawaii waterfalls are often easily accessible.
• Culture buffs will take pleasure in visiting the many cultural sites, such as Puʻuhonua o Hōnaunau National Historical Park.

This is the youngest island out of all six inhabited ones and also the biggest, almost twice the size of the other three vacation islands combined. Therefore, it is recommended to divide your time over the two inhabited coasts, the lush east coast (Hilo area) and the sunny west coast (Kona area) with its white beaches. Check out our article on where to stay on the Big Island to find your perfect spot.

You should at least spend a week on the Big Island to take in all its beauty. If you want to add a few days to relax too, as you should, then you’re looking at 10 days.

Maui

‘The Valley Isle’ forms the perfect introduction to Hawaii. The island offers an excellent combination of gorgeous resorts, lush nature and the best beaches around. There are no cities, only some small towns so it never feels crowded (except when you’re driving the Road to Hana but that’s another story). Everyone will feel right at home in Maui.

• Sports enthusiasts for one, since the island is ideal for snorkeling and hiking. We’ve dedicated an entire article on the most spectacular Maui hikes.
• But also families with young children have plenty of options on the Valley Isle since it’s just as perfect for little adventures. Just check out our ultimate list of things to do in Maui with kids.
• With all this activity, you’d almost forget that the island also counts as a prime honeymoon destination.

Since our stay was just a day or so too short to see all highlights (and to make a second attempt to drive the Road to Hana), we’d recommend you to spend a week on Maui.

Kauai

‘The Garden Isle’ is the one that got away… this time! We’re already making plans to return to Hawaii in a year or two and then this little gem will be the first we’ll visit. Kauai is the youngest of the Hawaiian islands but also the wettest one (more on that later). This island is often described as the most beautiful Hawaiian island. From what we’ve researched, it has the same adventurous soul as the Big Island but is a bit less accessible. That was also the reason why we chose not to include it in our planning. This actually turned out to be a good decision because the island of Kauai suffered some severe flooding when we were in Hawaii (april 2018).

We believe that 5 days would be a minimum to spend on this beautiful island.

Molokai and Lanai

The other two inhabited islands, Molokai and Lanai, may be great for day trips but also for visitors who have been to Hawaii numerous time and are ready to travel deeper and more off-grid. Or maybe for the unconventional tourist who’s looking for unspoilt beaches and rolling green hills untouched by tourism.

Suggested itineraries for first time visitors

10-day Hawaii itinerary

A two island combination of either Oahu, Maui or Kauai would be ideal to explore the best of the chosen islands but it won’t allow much time for relaxation. We would personally suggest to start with Maui. It’s the perfect place to recover from a jetlag and very well-connected to the mainland which might save you a layover.

2 week Hawaii itinerary

Again, a combination of two of the above islands would be ideal because at this pace you’ll have plenty of time to spend to relax on one of the beautiful beaches. If you’re more of an active type, you could try and squeeze in a third smaller island (just not the Big Island) or book a one-day island hopping package. Again, start in Maui and build up from there.

3 week Hawaii itinerary

Three weeks is just enough time to combine the Big Island with two smaller islands, like we did. Or you can take spend your days on the three smaller islands at a slower. Whatever option you choose, after three weeks of island hopping in Hawaii you’ll have explored some pretty amazing places.

Best time to travel to Hawaii

The weather can also be a deciding factor in selecting the islands for your Hawaiian island hopping itinerary. After all, rainbows and waterfalls wouldn’t be there without the occasional shower. Each of the Hawaiian island boasts several climate zones, one more humid than the other. Hawaiian summer runs from May to October and has an average day temperature of 85° F (29.5° C). The winter months are November to April with an average day temperature of 78° F (25.6° C).

Also the trade winds are a big factor in Hawaiian weather. Coming from the north and east, these pick up moisture from the warm ocean waters and bring heavy rainfall to this side of the Hawaiian islands. That’s why these northeastern sides are called the windward sides. This picture was taken on the Road to Hana adventure which is clearly located on the windward side of Maui. We gave up after a while since it got too dangerous…

Now you know why you’ll find most of the lush nature and waterfalls on this side of the islands.
Tropical storm season typically runs from July through November.

When will you go island hopping in Hawaii?

It’s an ambitious adventure, especially when you’ve traveled over 35 hours to even get to Oahu like we did. Oh yes, we did: a 3 hour drive to Amsterdam, an 8,5 hour flight to Washington DC, waiting at immigration for 2,5 hours, a 16 hour stopover and a 10,5 hour flight to Honolulu. Was it worth it? Totally! Would we do it again? In a heartbeat because it was our most epic travel adventure so far. Would you up for it? Let us know in the comments!

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Credit: The Kauai image (which is also the used as a featured image) is courtesy of a Pixabay photographer

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