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Hawaii Island Hopping: How to Do it and Best Multi-Island Plans

Hawaii Island Hopping: How to Do it and Best Multi-Island Plans

I love talking about Hawaii because it’s such a different place from the mainland USA, and island hopping is a great way to see the islands. Having spent so much time on the different Hawaiian Islands I’m excited to share how we do island hopping, and provide some of our best tips for planning an amazing trip to Hawaii. Whether you want to learn about Hawaiian culture or see science up close, let us help you plan something epic.

Hawaii island hopping is a good way to have a variety of experiences in one visit. It takes a lot of time and money to get to the Hawaiian Islands, so making it count is important. We don’t view visiting Hawaii as a vacation to just relax on a beach, because we can easily do that here on Mainland USA (and we live in Florida), but visiting Hawaii for us is all about learning on many levels. That’s why island hopping is so good for visiting Hawaii with kids: it’s the most educational and unique destination that young people will really get into!

Hawaii island hopping is a complex but wonderful way to experience multiple Hawaiian Islands. We answer how to travel from island to island, how much time to spend on each, and our favorite must-do activities across Hawaii.

Before Visiting Hawaii, Understand It

As you consider island hopping in Hawaii, or even just visiting the islands, know that it’s a complicated place. Just like how ALL OF THE USA was taken from the indigenous people (including our direct recent ancestors) Hawaii is the same, and most of it much more recent than many mainland Americans relate to. There are a lot of native Hawaiians who have stories and memories from their grandparents and great grandparents around the colonization of the Kingdom of Hawaii. With this comes a lot of hard feelings against tourism, but that is balanced with most people being exceptionally welcoming and ready to share their homeland. The Hawaiian people are gracious stewards who are willing and able to both educate visitors and work to preserve their homeland. If anything about any of this doesn’t sit right with you, stop considering Hawaii island hopping now.

Visiting Hawaii is a privilege and should be treated as such. We return to Hawaii because we have friends there and we want to share more about how to be a responsible visitor. Hawaii isn’t our go-to vacation destination, but a place we can learn and have new experiences, and do it with efforts of not having a negative impact or plundering the culture and resources of the islands.

Note: yes, Hawaii is a state in the USA and yes, it’s become very reliant on tourism, but that doesn’t mean it’s a land for tourists to run rampant. As you plan a visit to the islands, consider the choices you make and what you can give back to the Hawaiian communities you visit, and not just “sipping mai tais on a beach.” (Tips for making travel decisions that positively give back to Hawaii below).

Beach Clean up Sign at Wailea Bay Hapuna Beach State Recreation Area Big Island Hawaii 1

How to Plan Hawaii Island Hopping

If you’re thinking about island hopping through Hawaii, you first need to think about what you want to experience and why. That will guide your planning process. The islands are very expensive to visit, so set a goal with your trip and make it count. We are lucky enough to live at the beach, and I’ll proudly say that our beach (St Augustine Beach, FL) is as close to perfect as you can imagine with sand and waves and temperatures. Hawaii is NOT a beach destination for us, and I struggle to see it as such for others. Hawaii is all about science and culture, and it’s learning about the world in a beautiful and unique location. Yes, there are beaches and we do indeed visit them (there are some unique ones), but Hawaii is so much more than laying on the sand.

When we plan our visits to Hawaii, we look at what we can do that we cannot experience in the mainland USA. We plan our Hawaii Island hopping to include history, agritourism, culture and science. And guess what: in Hawaii you can visit beautiful places AND learn so much! Here’s why we like each of the islands (not including visiting family and friends).

Maui from the Air flying from Kauai 2

Hawaii Gone Wrong – Podcast Episode to Listen To

We’ve been in Hawaii when our plans drastically change without notice in addition to all of our awesome trips. With that, we’ve actually recorded a podcast episode all about what happens when you’re already in the destination and plans get cancelled.

BUT we’ve also had awesome and successful island hopping adventures, both via airplane and sailing from island to island. And we talk about that too!

How to Travel Between Islands in Hawaii

I wish it was as easy as crossing a bridge and being on the next island, but that’s not the case. And yes, I have been asked if there is a bridge between the Hawaiian Islands (you can’t fault somebody for wondering). And while you do need to fly or do your island hopping by boat, it’s not difficult and you’ll be surprised how inexpensive it is. We fly Hawaiian Airlines between the islands for the most part, and it’s so easy.

Check out Hawaiian Airlines cheap inter-island flights here!

You can fly between Hawaii (Big Island, both KOA and ITO), Maui (Kahalui OGG), Oahu (Honolulu HNL) and Kauai (Lihue LIH). There aren’t many direct flights between the Big Island and Kauai, so if you’re island hopping with them on your itinerary you’ll most likely have a layover at OGG or HNL. It’s a really easy process to fly between islands.

If you’re visiting Molokai and want to fly there, you’ll actually need to fly Mokulele Airlines from either Oahu or Maui, and it’s the same for Lanai. These are very small planes and you’ll need to provide the weights of all passengers at the time of booking. Flying Mokulele Air adds a little adventure to Hawaii island hopping.

Flying over Lihue with Air Kauai Doors Off Helicopter Tour Kauai Hawaii 1

There’s another option to travel between the islands, and that is by boat. There isn’t a state ferry service or any sort of auto ferry like in Washington’s Puget Sound area or Wisconsin’s Door County, but there is a passenger ferry between Maui and Lanai. You can reserve this in advance (recommended) and make it either a multi day visit or just go over for a single day returning in the afternoon.

The other boat transportation for Hawaii island hopping is visiting multiple islands as a part of a cruise of sorts. There are huge cruise ships that sail to the South Pacific and include Hawaii in their itineraries, or sailings from LA or San Francisco, and then there are the smaller options. Small ship sailing, like UnCruise or being a part of a charter, also can take you from island to island. The price is higher, but if that’s how you want to experience it and it’s in your budget, go for it!

Taylor Family on whale watching tour with Pacific Whale Foundation Maalaea Maui Hawaii 3

Need to Know for Hawaii Island Hopping

Besides making a schedule and plan for island hopping, there’s not too much else you really need to know about inter-island travel. If you’re flying between islands, you don’t have to do any agricultural declarations like when you fly to and from the state of Hawaii, but you still need to treat inter-island flights like any other sort of air travel. The same security processes and procedures apply, so you should still give yourself an appropriate amount of time at the airport before your flight.

For the smaller airplanes, like with Mokulele Air, check for specific carry on requirements. Depending on the airline and route, you may have to declare bringing a carryon in advance and there may be an additional charge. Also, flying out of the smaller airports like Lihue (Kauai) or Kona (Big Island), you’ll find some food options, but they’re really limited, so we always bring our own snacks for our preflight waiting.

Taylor Family at KOA Kona Airport for Inter Island Hawaiian Airlines Flight to Honolulu Hawaii 1

The last thing to really consider for planning Hawaii island hopping is whether or not you’ll need a rental car in Hawaii. If you’re visiting multiple islands via boat, whether it’s a private charter or via a cruise itinerary, you may not have enough time to drive anywhere and will most likely just be able to explore the port town on foot. For port days where you have a significant amount of time and you get to actually head up into the mountains or have time for beach hopping, you can just book cruise excursions, as getting a rental car requires taking an Uber or taxi to the airport and back.

We like to spend a few days on each island we visit, so getting a rental car in Hawaii is a must for us. At Kona (Big Island), Honolulu (Oahu) and Kahalui (Maui) it’s very easy, but each time we’ve gotten a car in Lihue (Kauai) it’s been a pain, even with rental car status. Just be patient and don’t doddle when you first land, and you should be fine. If you have more than one day on any of the Hawaiian Islands, you’ll want your own vehicle. You can book tours to get around the islands, but I like the freedom we have with driving ourselves. There are some incredible scenic drives on the Big Island and so many great things to do on Kauai!

Full Taylor Family hiking the Ohai Trail on Kahekili Highway Northwest Maui Hawaii 1

How Many Days per Hawaiian Island

I love planning travel, both to new destinations and places we’ve already been. When it comes to planning how much time to spend in a destination or on a road trip, I’ve actually got a formula I use. Check out our Road Trip Planning Tool. It’s also easy to use and has good information for planning island hopping or any other sort of trip.

For Hawaii, I think that you always need at least three days on each island you visit. You can easily spend a week on the Big Island or Kauai, but Oahu and Maui really only need a few days. Having been to Hawaii so many times, I’ve plotted out how I feel is best to distribute your time for Hawaii island hopping, assuming you haven’t been before or just need somebody to plan it for you.

Hawaii Island Hopping – Nights per Island
7 days / 6 nightsHawaii – 3Kauai – 3XXXX
9 days / 8 nightsHawaii – 3Oahu – 2Kauai – 3XXX
11 days / 10 nightsHawaii – 3Maui – 2Oahu – 2Kauai – 3XX
15 days / 14 nightsHawaii – 5Maui – 3Oahu – 2Kauai – 4XX
21 days / 20 nightsHawaii – 6Maui – 4Molokai – 2Lanai – 2Oahu – 2Kauai – 4

Clearly you can see from how I allocate time that the Big Island of Hawaii and Kauai are my two favorite islands. I think based on the available activities, learning opportunities, beaches and unique sights, these island hopping schedules are perfect for anyone heading to Hawaii. There is room to move with the above schedule, because as you price flights and hotels, you’ll sometimes get better deals by adding a day here or leaving a day earlier there.

Also, if you are planning something big one of the islands that will eat an entire day, you may want an extra day. For example, as fully guided tour of Hawaii Volcanoes National Park or a whole day sailing from Kauai to Ni’ihau. (here’s the tour to Ni’ihau – it’s on my Hawaii bucket list)

Full Taylor Family driving on Kauai Hawaii 1

Highlights of Each Hawaiian Island

I love talking about each of the Hawaiian Islands because each is so different and you’ll have unique experiences on each one. As I said at the start, it’s important to understand what being a visitor to Hawaii is and to be thoughtful in your time there.

That said, if you’re ready to dig in an plan Hawaii island hopping, there are so many wonderful things to do on each island and if you want to be sure to do some of the more popular tours and experiences, book them in advance. We use Viator for booking snorkeling, sightseeing and anything else to do in Hawaii because of their cancellation policies and since they vet the experiences. Check out Viator for Hawaii activities here!

Big Island (Hawaii) Highlights

The Big Island is my favorite of all the Hawaiian Islands. I love it for its unique geology (active volcanoes), its agriculture and its well preserved cultural history. The Big Island is the best island to visit with kids of any age because it’s not covered in resorts, but has many cultural sites and incredible places to see science at work. There are also lots of fun, free things to do on the Big Island of Hawaii.

Hawaii, aka the Big Island, is where you should start your island hopping. You can fly into Kailua-Kona (KOA) from many mainland airports (we usually fly from PHX or LAX), it you can get many different connectors from Honolulu (Oahu, HNL) or Kahalui (Maui, OGG). If you are connecting via Honolulu you can also get flights into Hilo (ITO) on the west side of the island. And no, you can’t do Hawaii Pride island hopping, as the different Pride celebrations take place in different months. The Big Island does Kona Pride in September while Honolulu (Oahu) and Maui do October or June.

Full Taylor family at Akaka Falls State Park Hilo Hamakua Coast Big Island Hawaii 3

Since we visit Hawaii always looking to learn something more, the Big Island is perfect to get educated on so many different things. Here are our top picks for making a trip to the Big Island and making the most to start your Hawaii island hopping:

There’s much more to the Big Island, but these are just some of the reasons to start your Hawaii island hopping here. Add snorkeling with manta rays to the list of unique things to do on the Big Island and you’ll be set up to start your Hawaiian adventure on the right foot.

Rob Taylor on Zodiac with Kona Coastline Tours Kailua Kona Big Island Hawaii 3

Where to stay on the Big Island

We have stayed several places on the Kona Coast including the King Kamehameha Courtyard Marriott, Royal Kona Resort, the Club Wyndham Kona Hawaiian, the Holiday Inn Express Kailua Kona, the Ka’awa Loa Plantation, AirBNBs… The Ka’awa Loa Plantation and the Kamehameha Resort are my two favorites on the Kona Side.

On the Hilo side we have only stayed at the SCP Hilo Hotel… three times. It’s our favorite because it’s so mellow, it’s in the perfect location and they provide bikes and paddleboards. I love it THE MOST! Book the SCP Hilo Hotel here!

Taylor Family in Two Queen Room at SCP Hilo Hotel Hilo Big Island Hawaii 1

Find a Big Island stay that’s right for your trip:

Why Maui is so Special

Maui had been built up to us SO MUCH by our friends and family prior to us visiting. In all honesty, it’s my least favorite of the main Hawaiian Islands to visit and I think is worth adding to your Hawaii island hopping only if you really want to visit more than two islands. To me, Maui is dry, very developed, over-touristed and not as welcoming to visitors as other islands. Maui has had a hard burden to bear over the years being the most popular island and facing devastating fires, and it shows.

While Maui has some incredible sights to see and some lovely beaches, it’s much more a place that locals would like to try to save/recover for themselves, and I can’t blame them. As you explore the Northwest loop and Road to Hana you’ll find many places that the Internet has made famous that locals DO NOT want visitors to impact. From secluded beaches to unique hikes, many insta-famous spots have signs asking visitors to respect the locals and not proceed. Sometimes this is because of private property, sometimes due to danger, and sometimes to keep just a few things sacred for the Hawaiian people.

Taylor Family at Olowalu Beach Maalaea Maui Hawaii 1

With that, you can add Maui to a Hawaii island hopping trip and visit respectfully and have a positive impact. Here are our picks for what to see and do on Maui that are not invasive or further the issues Maui currently faces.

  • Visit Haleakala National Park – amazing place to see science at work, including endangered bird species
  • Kihei and its beaches – this town has many public beach parks that are not intruding on private land, and there is the infrastructure to support visitors here
  • Maalaea town – another town that’s ready for tourism and is a good place to learn, Maalaea is where you’ll find the Maui Ocean Center and the Pacific Whale Foundation, both of which are active in conserving Maui’s unique ecosystems. This is THE place for whale watching out of Maui.

Beyond these three picks, Maui has many resorts that visitors tend to flock to. You could do that, and yes it supports the local economy, but know that there are better ways to give back to the locals than staying at an internationally owned conglomerate resort.

Note: we are not perfect travelers and do sometimes opt for resort stays when we’re in Hawaii. When we do that, we still are exploring and being active beyond the resort and are careful about where we spend our money and the activities we choose to do. Maui is the perfect place to stay at a nice resort and then intentionally explore the island.

Taylor family at Summit of Haleakala National Park Maui Hawaii 4

Where to Stay on Maui

There are lots of options for where to stay on Maui, but for the easiest spot that’s between the different sections of the island, staying in the Kihei or Maalaea is our pick. Staying at the buckle of the island makes it so you’re centrally located for visits to each area. Kihei itself has great beaches, and then it’s easy to go from here to the Northwest loop or to Haleakala. We’ve only stayed in vacation condos, but as soon as we stay at a Maui resort or hotel, we’ll share our thoughts!

Unique Oahu

Oh Oahu, it’s a beautiful island and an easy place to start your Hawaii island hopping since you can fly into Honolulu from nearly anywhere. Oahu is a broad mix of city, history, nature and resorts. It’s where you’ll find Pearl Harbor, Disney’s Aulani, the Waimea Valley (not canyon, more on that below) and the Dole Pineapple Plantation. The Polynesian Cultural Center is also here on Oahu. Oh, and Koloa Ranch where a good deal of Jurassic Park was filmed. These are all great ideas if you’re planning Oahu with kids.

Taylor Family swimming in waterfall at Waimea Valley North Shore Oahu Hawaii

What I like about Oahu is how you can easily get there from the mainland and then there are lots of options for the type of experience you can have. There are simple hotels, resorts, and lots towns you can be based out of, and there is so much good food on Oahu, both restaurants and food trucks. We have friends on Oahu and enjoy getting to explore and hang out with them. Some of the top picks for your time on Oahu when you’re island hopping in Hawaii include:

For anyone visiting Hawaii for the first time, Oahu is a really good introduction to the islands. Visiting Oahu gives you a sample of Hawaiian culture and history, and some really beautiful nature, but it’s much more developed than the Big Island or Kauai. I like Oahu as being a par of island hopping.

Taylor Family at Sharks Cove Oahu North Shore 8b

Where to Stay on Oahu

Visiting Oahu is different for everyone because it’s such a busy place. There are a LOT of resorts on the south shore and in Honolulu. On the North Shore, there are some smaller inns and rentals, and then the grand Turtle Bay Resort. For a first time visit, I would recommend a couple of nights in Honolulu and then a few nights on the North Shore. You’ll find better swimming beaches on the East and South shores of Oahu, so if your goal is to wake up and swim in the ocean, choose one of those areas. We’ve stayed at Disney’s Aulani and vacation rentals, and have friends that live around Honolulu, so we don’t have any Waikiki recommendations at this time.

Nature on Kauai

Kauai is my favorite hiking destination in Hawaii. We have hiked all over the island and really enjoy the amazing views on all sides. There are also great beaches on Kauai with really good, county maintained beach parks with parking. For being much less developed than Oahu or Maui, Kauai is much more visitor friendly for people that want a quiet Hawaiian trip. We’ve stayed in both Kapa’a and Poipu, and both are great locations for having beach days or exploring the mountains. Check out our Hawaii podcast episodes!

On the south short, you’ll find Koloa, Poipu, Hanapepe and Waimea, all of which are lovely places to stay and great for a multi-day visit. If you’re Hawaiian island hopping gives you more than three days on Kauai, spend a few nights on the south shore and then move up to Kapa’a, Princeville or Hanalei. These towns have more beautiful beaches and even more incredible hiking nearby. Kauai is all about nature, so wherever you choose to stay during your visit, you’ll have a wonderful time.

Full Taylor family at Oceanview Forest Preserve Kokee State Park NaPali Coast Kauai 4

Be sure to check out our five day Kauai itinerary if you’ve got the time, or just pick the plans for the days that you like. In the meantime, here are our picks for the must-do activities on Kauai:

  • Hiking at Waimea Canyon or the NaPali Coast from Haena or Koke’e State Park
  • Beach days at Glass Beach, Poipu Beach (often with honu!), and Hanalei Bay
  • Kayaking around Kauai, or doing the boat tour on the Wailua River to the Fern Grotto
  • Doors-off Helicopter tour around Kauai – this is a big ticket item but one of the most incredible things we’ve ever done; it’s expensive but very worth it (in my opinion)

There are tons of fun, beautiful things to do on Kauai. If island hopping sounds nice, but not what you’re thinking at this time, heading to Kauai for the duration of a Hawaii trip is a great plan too.

Chris and Rob Taylor on Hanakapi`ai Beach Na Pali Coast on Kalalau Trail Haena State Park Kauai Hawaii 2

Where to Stay on Kauai

Despite Kauai feeling less developed than Oahu or Maui, it seems like there are way more resorts and hotels here. There are for sure more national travel brand hotels, like the Sheraton and Hyatt. When you’re planning where to stay on Kauai, think about the activities you want to do. The eastern side, which includes Kapaa and Lihue, has the most options and then you can check in and explore anywhere, returning to the middle of the coast each nice. Staying in Hanalei or Princeville on the North Shore give you the chance to be close to the NaPali Coast and some beautiful beaches, but FAR from Waimea Canyon and that hiking.

For the best time on Kauai if you’re there for more than 3 nights, do two or more nights on the South Shore (Poipu or Waimea) and then 2 or more nights in Kapaa or Hanalei. This will balance your experience and you’ll be closer to your accommodations after long days of exploring. We’ve stayed at the Kauai Shores Hotel and Sheraton Coconut Beach Resort in Kapaa, and at the Sheraton Kauai Shores Resort Villas in Poipu/Koloa. We have friends who swear by the Waimea Plantation Cottages… So many options, you can’t go wrong!

Find a Kauai stay here:

Visiting Molokai, Lanai and Niihau

The lesser known islands of Hawaii are still beautiful and unique, but they’re more difficult to add to your plans. For visiting Molokai or Lanai, it’s easiest from Maui. You can fly to Molokai and spend a day or two (flights for about $150 RT), exploring the beaches and towns. Also, Kalaupapa National Historic Park is on Molokai and it’s very unique (must be permitted; over 16 years old only). If you just want to take in the views of Molokai’s cliffs and bays, do a helicopter flight from Maui.

Lanai you can visit by taking the ferry from Ma’alaea or you can fly. I think visiting Lanai is great for a quiet break in a longer island hopping trip. If you’re visiting, the cat sanctuary is a must-visit (unless you’re a dog person), and then beach time too. Lanai is not set up for lots of tourists, and some of the best sights, like Keahiakawelo (Garden of the Gods) are far from the ferry dock, so if you’re really aiming for a visit, be sure you’re staying on the island and have coordinated you plans with somebody on the island, like a concierge. Keep it easy while still seeing the sights off-shore of Lanai with a beautiful snorkel tour.

The last island to visit, Ni’ihau can only happen via tour from Port Allen on Kauai. While exploring the island itself isn’t an option, as it’s privately owned, there are a few options for tours that go out to this beautiful preserve with towering cliffs and awesome snorkeling. Holoholo Charters is the top pick for exploring Ni’ihau. It’ll cost ya, but wow.

Vintage Map of Hawaii with Pins showing port areas

Island hopping around Hawaii can be a really wonderful experience. It’s one of the most unique trips you can do in the USA and you’ll experience so many different landscapes and culture that’s truly beautiful. As I’ve said, we’re very intentional with our visits and strive to be respectful visitors, whether we’re visiting on our own or visiting friends. Check out all Hawaii articles here!

If you have any questions about planning travel to the Hawaiian Islands, need recommendations for where to stay or are curious about how our kids enjoy certain things in Hawaii, please leave a comment or send us a note. We’re happy to share more and help others plan their travels!

Hawaii island hopping is a complex but wonderful way to experience multiple Hawaiian Islands. We answer how to travel from island to island, how much time to spend on each, and our favorite must-do activities across Hawaii.