If you are thinking about visiting more than one Hawaiian island during your trip, it’s very easy. Scroll to find out everything you need to know about Hawaii island hopping.
This Hawaii island hopping post was written by Hawaii travel expert Marcie Cheung and contains affiliate links, which means if you purchase something from one of my affiliate links, I may earn a small commission that goes back into maintaining this blog.
Okay, so someone told you that you HAVE to visit multiple Hawaiian islands on your trip, right?
Maybe it was that friend who did all four major islands in six days and came back with 10,000 photos.
Or you saw those Instagram posts of families posing at different beaches on different islands and thought “we should do that too.”
But nobody mentions in those highlight reels: island hopping with kids can either make your trip incredible or turn it into an exhausting airport shuffle where you spend more time dealing with rental car returns than actually being on vacation.
I’m Marcie, and I’ve been to Hawaii 40+ times since I was 10.
I’m a certified Hawaii Destination Specialist (yes, that’s actually a thing), and I basically consider myself a professional tourist at this point.
I’ve island hopped with my two boys more times than I can count.
I’ve also talked hundreds of families OUT of island hopping when it didn’t make sense for their trips.
So let me save you from the mistakes I’ve made.
Last year we flew from Kauai to the Big Island. My kids were SO confused about why we were still in Hawaii after a 1-hour flight. They kept asking “when are we going to get to Hawaii?”
The islands are way more spread out than they look on those cute maps in the airline magazines.
Most of my family trips now?
We stick with Oahu plus either Kauai or Maui. Those flights are only about 30 minutes. You barely have time to get comfortable before you’re landing.
Way easier than dragging two kids through long travel days.
Do You Even Have Enough Time for This?
I’m going to be straight with you about something most travel blogs won’t say: you need at least 8 days total to make island hopping worth the hassle. Ten or more days is even better.
Here’s why. Each island deserves at least 3 full days. Not 3 days where one is spent traveling. I mean 3 actual days where you wake up, do stuff, and go to bed on that same island.
If you’re giving an island less than 3 days, you’re basically just unpacking and repacking your suitcase while your kids complain. Ask me how I know this.
The Time I Totally Screwed This Up
Early in my Hawaii-with-kids adventures, we had 7 days total and I tried to do Oahu, Maui, AND the Big Island. I thought “oh, the flights are short, it’ll be fine!”
It was not fine.
We were packing every other day. My kids were cranky from all the movement. We never actually relaxed. And we barely scratched the surface of any island because we were always thinking about the next move.
I learned my lesson. Now when families tell me they have 5-6 days total, I always say pick one island. You’ll have more fun, spend less money, and actually feel like you had a vacation.
When Island Hopping Actually Makes Sense for Families
You should think about visiting two islands if:
You have 8+ days. This gives you real time on each island without feeling rushed. You can actually unpack. Your kids can settle into a routine.
Your kids are either tiny (under 3) or older (8+). Babies just sleep through flights and can be worn through airports. Older kids can manage their own backpacks and think the inter-island flights are an adventure.
But that middle zone? When they’re too big to easily carry but too small to handle their own stuff? That’s rough for all the airport shuffling.
You want completely different experiences. This is the big one for me. If you want both the “city vacation with tons of restaurants and activities” vibe AND the “chill on quiet beaches surrounded by nature” vibe, you probably need two islands.
Because Oahu can’t give you Kauai’s dramatic, empty coastlines. And Kauai can’t give you Oahu’s walkability and crazy fun downtown scene.
You’ve been to Hawaii before. If this is your first trip, honestly? Go deep on one island. Hawaii has this way of pulling people back anyway.
When to Just Stay Put (And Save Your Sanity)
Skip the island hopping if you have less than 8 days. I cannot stress this enough, and I’ve had the arguments with people who don’t want to hear it.
The thing is, the travel day between islands isn’t “just a quick flight.” The actual plane ride is short, sure. But you’ve got to:
- Check out of your hotel (usually by 11 AM)
- Return your rental car
- Get to the airport (you should budget 1-2 hours before your flight even if it’s only a 15-minute drive)
- Fly to the other island
- Wait for luggage
- Pick up a new rental car (I once waited 90 minutes for this at Maui airport during peak season)
- Drive to your new hotel
- Check in (which might not be until 3 or 4 PM depending on the hotel)
That’s basically your whole day. Gone.
And listen. If you have car seats, you’re lugging those through airports. Yes, you can bring them on the plane for free. No, it’s not fun.
My youngest is finally out of his car seat and I literally did a happy dance the first time we flew between islands without having to drag that thing around.
Here’s what to consider before deciding whether you should island hop in Hawaii.
Best Island Combinations for Families (What Actually Works)
Here’s the quick comparison of the most popular family-friendly combinations:
| Island Combo | Flight Time | Best For | Estimated Cost (Family of 4) |
|---|---|---|---|
| Oahu + Maui | 30 min | First-timers wanting city + resort vibes | $400-$1,200 flights + rental cars |
| Oahu + Kauai | 30-40 min | Families who love hiking & nature | $400-$1,200 flights + rental cars |
| Maui + Big Island | 35 min | Adventure families with older kids | $400-$1,200 flights + rental cars |
| Maui + Lanai | 70 min ferry (or 35 min flight) | Day trip or overnight escape | $240 ferry for 4, or $200-$600 flights |
| Oahu + Big Island | 40-50 min | Families wanting extreme contrasts | $400-$1,200 flights + rental cars |
Now let me break down why each of these works (or doesn’t) for different families.
Oahu + Maui (My Top Pick for Most Families)
Flight time: 30 minutes
What you’re getting: City energy + resort relaxation
This is one of my go-to recommendations because it just works. Oahu gives you Pearl Harbor, Waikiki Beach, incredible food (seriously, the restaurant scene in Honolulu is amazing), and you can walk to stuff. You don’t need a car for everything.
Then you fly to Maui and it’s totally different. Resort pools. The Road to Hana if you’re feeling adventurous. Beaches that feel less crowded even though Maui is super popular.
The flight is so short your kids barely have time to get situated before you’re landing. I usually split it 4 days Oahu, 4 days Maui if we have 8 nights total.
Real costs for a family of 4: Flights run about $50-$150 per person each way depending on when you book. So figure $400-$1,200 just for the inter-island flights.
Plus you’re paying for two different rental cars (one on each island), which adds up.
Oahu + Kauai (The Adventure Option)
Flight time: 30-40 minutes
What you’re getting: Urban + wilderness
My family does this combination a lot because we love how different the islands feel. Kauai is just… different.
It’s not built up like Oahu. There are no buildings taller than a coconut tree (that’s actually the law). The pace is slower.
If your kids are into hiking, snorkeling, and being outdoors, this combo is great. Do the city stuff, historical sites, and food scene on Oahu. Then escape to Kauai for waterfalls, the Na Pali Coast, and beaches that feel remote.
Fair warning though: Kauai can feel boring to some kids. There’s no Waikiki to walk around. The restaurant options are way more limited.
If your kids need a lot of structured activities, you might want to stick with Oahu + Maui instead.
Maui + Big Island (For Families Who Want Adventure)
Flight time: 35 minutes
What you’re getting: Resort life + volcanic landscapes
Both islands offer totally different vibes. Maui has that resort feel with Wailea and Kaanapali (those big hotels with the pools and activities).
The Big Island has black sand beaches, Hawaii Volcanoes National Park, and you can see actual flowing lava sometimes.
This works great for families with older kids who aren’t tied to resort pools all day and want variety.
One thing to know: the Big Island is HUGE. Like, bigger than all the other Hawaiian islands combined. You’re going to be driving a lot.
If you stay in Kona (the west side), it’s about 2.5 hours to the volcano on the east side. Plan accordingly.
The Quick Ferry to Lana’i (From Maui)
Ferry time: 1 hour 10 minutes
What you’re getting: A day trip adventure or overnight escape
If you’re already based in Maui and want to add something different without dealing with airports, there’s a ferry to Lana’i. It leaves from Maalaea Harbor (not Lahaina anymore – that changed after the 2023 fires).
The ferry is $30 one-way for adults, $20 for kids ages 2-11, free for kids under 2. It runs a few times a day. Takes about an hour and 10 minutes.
Most families do Lana’i as a day trip. The island is super small and quiet. Two luxury resorts, one main town, that’s about it.
It’s cool for a change of pace but probably not worth spending multiple nights unless you really love golf or seriously want to unplug.
Ferry schedule (as of 2026):
From Maui: 6:30 AM, 11 AM, 3:30 PM
From Lana’i: 8:30 AM, 1 PM, 5:30 PM
(Note: The 11 AM from Maui and 1 PM from Lanai get cancelled on the second Thursday of each month for Coast Guard drills)
How to Actually Island Hop (The Logistics)
Flying Between Islands
You’ve got three main airline options:
| Airline | Best For | Typical Price | Key Perks |
|---|---|---|---|
| Hawaiian Airlines | Most routes & flight times | $50-$150 per person | 170+ daily flights, Boeing 717s, Alaska miles now work |
| Southwest Airlines | Budget-conscious families | $50-$150 per person | 2 free checked bags (huge for families) |
| Mokulele Airlines | Smaller islands (Molokai, Lanai, Hana) | Varies | 25% kids discount ages 2-11, infants free |
Hawaiian Airlines has the most flights. They fly big planes (Boeing 717s) and have 170+ daily flights between the islands. Prices usually run $50-$150 per person depending on when you book.
Side note: Hawaiian Airlines was acquired by Alaska Airlines in September 2024, so if you have Alaska miles, you might be able to use those now. The integration is still happening, but worth checking.
Southwest Airlines is the budget option if you can snag a good fare. The big perk is two free checked bags (for certain guests), which matters when you’re traveling with kids and all their stuff.
Some news reports say they might reduce Hawaii operations in 2026, so definitely check flight availability before banking on Southwest.
Mokulele Airlines flies small planes (like, 9-passenger small) to the less-visited places like Molokai, Lanai, and Hana. They have a 25% Keiki Discount for kids ages 2-11, and infants fly free.
This is great for adventure-seeking families, but know that some kids (and adults) get nervous on tiny planes.
Actual Flight Times
This is the time you’re actually in the air, not including getting to the airport early or waiting for bags:
| From → To | Flight Time |
|---|---|
| Oahu → Maui | 30 minutes |
| Oahu → Kauai | 30-40 minutes |
| Oahu → Big Island (Kona) | 40-50 minutes |
| Oahu → Big Island (Hilo) | 45-55 minutes |
| Maui → Kauai | 45-50 minutes |
| Maui → Big Island | 35-40 minutes |
| Kauai → Big Island | 50-55 minutes |
Even the “longest” inter-island flight is under an hour. But remember: you still need to get to the airport way earlier than that.
What Island Hopping Actually Costs
Let’s be real about money. I see a lot of blogs that gloss over this part.
For a family of four doing two islands (let’s say Oahu + Maui for 8 days):
Inter-island flights: $400-$1,200 total (varies wildly based on when you book)
Rental cars: You need one on each island. Budget at least $60-$100 per day per car. For 8 days split between two islands, that’s roughly $480-$800 total. Prices have been nuts since the pandemic.
Hotels: Two different hotels means two different resort fees, two different parking fees (if you’re staying in Waikiki, parking can easily be $40+/night).
In Waikiki, decent family hotels run $200-$400/night. In Maui resorts, you’re looking at $300-$600/night depending on where you stay.
Gas and rental car returns: Returning rental cars can eat up time and money. Make sure you fill up the tank before returning or you’ll get charged premium rates.
Car seats: If you need them, either bring your own and lug them through airports, or rent them from the car company (usually $10-$15 per day per seat).
The total for island hopping (flights, rental cars, hotels) can easily add $500-$1,000+ compared to staying on one island for the same number of nights.
Is it worth it? Sometimes absolutely yes. Sometimes absolutely no. Depends on what you value.
Common Mistakes Families Make (Don’t Be These People)
Trying to See Too Many Islands
I get messages from families planning 10 days who want to hit all four major islands. Please don’t do this. You’ll be exhausted and you won’t actually enjoy anywhere.
Two islands is the sweet spot. Three max if you have two weeks and one of those islands is Lana’i or Molokai for just a day or two.
Not Building in Buffer Days
Things go wrong. Flights get delayed. Kids get sick. You find an amazing beach and want to go back.
Don’t pack your itinerary so tight that one weather delay ruins everything. If you’re doing 8 days and two islands, split it 4-4 or maybe 3-5, but leave some flex in your schedule.
Underestimating the Rental Car Shuffle
I already mentioned this, but rental car returns on both islands can suck up WAY more time than you think.
I once waited in line at the Maui airport rental counter for over an hour during peak season. Not in the car. In line to GET the car.
Budget time for this. Don’t book your inter-island flight too early in the morning if you’re trying to squeeze in one more beach day before leaving.
Forgetting About Jet Lag
Even though the inter-island flights are short, you might still be dealing with jet lag from your mainland flight. Give yourself at least one day to adjust before you start the island-hopping shuffle.
My kids are West Coast, so Hawaii is only a 2-3 hour time difference. But if you’re coming from the East Coast, that’s a 5-6 hour jump. Your kids might be waking up at 4 AM for the first few days. Not ideal for early flight connections.
Random Tips That Actually Matter
Book the first inter-island flight of the day if you can handle it. Less likely to be delayed. Gets you to the next island with most of the day ahead of you.
Pack a change of clothes in your carry-on for the kids. I learned this after bags got delayed and we showed up at our Maui hotel with zero clothes except what we were wearing.
Bring snacks on the inter-island flights. They’re so short that they don’t serve food, and if your flight gets delayed, hungry kids turn into monsters.
Check if your hotel offers free parking. A lot of Waikiki hotels charge $30-$40 per night for parking. Some Maui resorts charge even more. If you can find a hotel with free parking, that saves real money over several nights.
Consider a travel consultation if you’re feeling overwhelmed. I help families figure out which islands to visit, where to stay, and how to avoid the common pitfalls.
Sometimes it’s worth paying someone to just tell you what to do instead of spending hours researching.
Is First-Timers Better Off on One Island?
Short answer: usually yes.
I know that’s not what you want to hear if you’re excited about island hopping. But every single Hawaiian island has enough to keep you busy for a week or more. You could easily spend 10 days just on Oahu and not run out of things to do.
If this is your first time, pick one island and really experience it. You’ll be back. Everyone comes back.
First-time families: Oahu is usually the best choice. It has the most activities, the best food, it’s walkable (Waikiki area), and you’ve got Pearl Harbor, Hanauma Bay, the North Shore, hiking trails, great beaches, and everything is closer together.
If you really want two islands on your first trip: Do Oahu + Maui with at least 9-10 days. That gives you enough time to actually enjoy both without feeling rushed.
Questions Families Always Ask Me
Which island is best for toddlers?
Oahu. The beaches in Waikiki are calm and protected. There are tons of family-friendly restaurants. Everything is close together so you’re not driving for hours with cranky toddlers.
Can we island hop in 5 days?
Technically yes, but I don’t recommend it. You’d get maybe 2 days on each island after losing a day to travel. Just pick one island and enjoy it.
Is the ferry better than flying?
The only ferry is Maui-Lana’i. For that specific route, I think the ferry is actually more fun than flying, especially if you have kids who might get seasick (the crossing can be choppy). But for Oahu-Maui or Oahu-Kauai, flying is your only option and it’s really easy.
Do the inter-island flights fill up?
During peak times (summer, Christmas, spring break), yes. Book early. But there are so many flights throughout the day that it’s usually not a problem if you’re flexible on timing.
Should we stay at resorts or vacation rentals when island hopping?
Hotels make more sense when you’re moving around because check-in is usually easier and they’re more flexible with luggage storage if your flight doesn’t line up with check-out/check-in times.
Vacation rentals are great if you’re staying put on one island for the whole trip.
How early should we get to the airport for inter-island flights?
I always tell families 90 minutes, especially if you’re returning a rental car. The TSA lines can be long, and rental car returns can be slow.
What if we only want to see one specific thing on another island?
This is so common. “We’re staying on Maui but want to see Pearl Harbor.” Book a day trip flight. Fly over early in the morning, spend the day on Oahu, fly back to Maui that evening. It’s doable. It’s not relaxing, but it’s doable.
Can kids handle all the travel between islands?
Depends on the kid and their age. My boys thought the inter-island flights were cool. They’re short enough that even my antsy kid could handle it.
The hard part is the rental car returns and hotel check-ins/check-outs. That stuff is boring for kids.
Which island has the best snorkeling?
Maui and the Big Island both have incredible snorkeling. Kauai and Oahu are good but not quite at the same level. If snorkeling is your top priority, Maui is probably your best bet.
Here’s What I’d Actually Do
If you gave me 10 days in Hawaii and said “pick the best plan for a first-time family with kids ages 5-12,” here’s exactly what I’d recommend:
Fly into Oahu. Stay in Waikiki for 5 nights. Do Pearl Harbor, spend days at the beach, eat all the good food, maybe drive to the North Shore one day. Let your kids get comfortable.
Then fly to Maui. Stay in Kihei or Wailea for 4 nights. Do resort pool days. Hit the beaches. Maybe drive the Road to Hana if your kids are up for it.
Fly home from Maui.
That’s it. Two islands. Enough time on each to actually relax. Different enough that the trip feels diverse. Easy enough that you’re not stressed.
And honestly? If someone told me they only had 7 days, I’d tell them to skip the island hopping and just do Oahu. You won’t be bored. I promise.
Want More Help Planning Your Hawaii Trip?
I get it. This is a lot of information and you’re probably still not sure what’s right for your family.
I’ve got some resources that might help:
If you’re trying to decide between one island or two, I recorded a whole podcast episode on this exact question. It’s Episode 70 and it goes into even more detail about how to make this call.
If you’re leaning toward island hopping, Episode 9 of Hawaii Travel Made Easy covers the island-hopping basics with more specific tips.
If you want someone to just tell you what to do, I offer personalized Hawaii travel consultations. We’ll talk through your specific situation (your kids’ ages, your budget, what you want to see) and I’ll build you a plan.
If you want to learn at your own pace, I’ve got detailed travel guides for each island:
- Maui Travel Guide for Families
- Oahu Travel Guide for Families
- Kauai Travel Guide for Families
- Big Island Travel Guide for Families
Or if you’re feeling overwhelmed, I have some free email courses that walk you through the planning process step by step:
- How to Travel to Hawaii Like a Pro (5-day email course)
- How to Save Money in Hawaii (5-day email course)
So Should You Island Hop or Not?
Can you do it? Absolutely.
Should you do it? Depends.
Will it make your trip better? Sometimes.
Will it stress you out? Maybe.
The real question is whether the extra logistics, extra costs, and extra travel time are worth it for what you specifically want to see and do.
For some families, island hopping is the perfect way to see more of Hawaii and experience different vibes. For others, it’s an unnecessary complication that takes away from the relaxation factor.
I’ve done both. Some of my favorite Hawaii trips involved island hopping. Some of my favorite trips were spent entirely on one island where we found our rhythm and didn’t want to leave.
There’s no wrong answer here. Just different trade-offs.
And honestly? You’re going to love Hawaii either way. It’s pretty hard to have a bad time in paradise, even if you spend half a day in a rental car line.
Now go figure out which islands you’re visiting and when you can get me back there for trip number 43.
