To plan a multigenerational family trip to Hawaii, pick one island and one home base, agree on who is paying for what before anyone books, and plan a few things for the whole group while leaving the rest optional.
This post about planning a Hawaii trip with Grandparents 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.
Grandparents, parents, and kids don’t have to do every activity together to have a great trip.
I’m a Hawaii travel consultant for families and host of the Hawaii Travel Made Easy podcast, and I’ve done this kind of trip a few different ways.
My husband’s parents hosted our whole family at the Ilikai in Waikiki in 2011, and at Honua Kai on Maui in 2013 and 2015. In June 2021, there were 12 of us at the Ê»Alohilani in Waikiki. I was a guest on the first three trips and picked the hotel for the last one. My mom also lives on Kauai, so she joins a lot of our trips.
None of those stays were hosted by the hotels.
For a Big Island version of this trip, listen to my conversation with my friend Leslie Harvey of Trips with Tykes. Her family does their multi-gen trips at the Mauna Kea resort, and her last one had kids from 3 to 17.
What should you agree on before anyone books a flight?
Agree on who is paying for what and who is making the decisions.
On all three trips with my husband’s family, my in-laws hosted. They covered the lodging, the rental car, the big family meals, and the activities we did as a group. If one of us went off and did our own thing, like a tour or a meal, we paid for that ourselves.
I know that’s not how every family works. Whatever your family’s version is, talk about it before anyone books.
It also helps to know who the planner is. My mother-in-law picked the island and the meals every time. For the Ilikai trip, which was right after I got married, she picked the hotel too. By 2021 I was the one choosing the hotel.
Once you know who is covering what, figure out the actual numbers. Lodging taxes in Hawaii total about 19% in 2026, and you pay that on every room. My free Hawaii budget planner has a spot for each category, so every family in your group can fill in its own share.
Which Hawaiian island is best for a multigenerational trip?
Oahu is my pick for a first trip where everyone wants to do the iconic things, and Maui is my pick when the point is hanging out together at a resort. The right island depends on the family.
| Island | Best for | Where I’d base the group | What to know |
|---|---|---|---|
| Oahu | A first trip to Hawaii with a list of iconic things to do, and grandparents who don’t want to drive | Waikiki | You can walk or get a ride to most things, so nobody is stuck at the hotel |
| Maui | Families who mostly want to hang out together at a beach resort | A beach resort area like Kaʻanapali, where we stayed | A lot more beach resorts to choose from, at different price points |
| Kauai | Groups that want bedrooms and a kitchen at a resort | Koloa Landing Resort in PoÊ»ipu | PoÊ»ipu is usually the sunnier side, but it’s a long drive to the North Shore |
| Big Island | Groups happy to stay put at a resort | The Kohala Coast, where my friend Leslie’s family stays at the Mauna Kea resort | The drives are long. Kona to Hawaii Volcanoes National Park is 2 to 2.5 hours each way, depending on where you stay |
If it’s a first trip and the group wants to do all the iconic things, I usually suggest Waikiki, especially if the grandparents don’t want to deal with driving. The parents and kids can go off on their adventures without stranding the grandparents.
That’s how our June 2021 trip went. My in-laws had been to Oahu many times and had no interest in touring around. Our family of four drove up to the North Shore for the day, and everyone else hung out by the pool and in Waikiki.
If the trip is more about hanging out together at a resort, I suggest Maui. It has a lot more beach resorts to choose from, at different price points.
On Kauai, I recommend Koloa Landing Resort in Poʻipu for multi-gen trips because the villas have bedrooms. I stayed there in a one-bedroom villa with my mom and my two kids, which I wrote about in my Koloa Landing review. As of October 2026, the two-bedroom villas sleep 6 and the three-bedroom villas sleep 8.
I haven’t done a big-group trip with my in-laws on the Big Island. My friend Leslie told me on the podcast that her family does their multi-gen trips at the Mauna Kea resort on the Kohala Coast.
If you’re choosing from scratch, my guide to which Hawaiian island is best for your family goes through all four.
I’d also keep a big group on one island unless you have at least 10 days. That’s the minimum I suggest for island hopping with any family.
Should you book hotel rooms, a condo resort, or one big rental house?
I usually recommend hotel rooms or a condo resort over a rental house, because of all the illegal vacation rentals in Hawaii.
| Option | It works when | The trade-off | Where we did it |
|---|---|---|---|
| Hotel rooms near each other | Everyone wants their own space and teens want some independence | No shared living room, and connecting rooms aren’t guaranteed | Ê»Alohilani, Waikiki, 2021 |
| Condo resort | You want a kitchen, a washer and dryer, and one unit where everyone gathers | Somebody has to shop and cook | Ilikai, Waikiki, 2011, and Honua Kai, Maui, 2013 and 2015 |
| One big rental house or villa | Everyone wants to be under one roof | You have to verify it’s a legal rental, and not everyone ends up happy sharing a house | We haven’t done this in Hawaii |
At the Ê»Alohilani, we had three rooms. Our family of four had one, my mother-in-law and father-in-law had one, and my teenage niece and nephews shared one. If we did it again, I think we’d try for connecting rooms. I tell the whole story in my Ê»Alohilani review.
I’ve never booked connecting rooms in Hawaii, and clients who requested them were told the hotel couldn’t guarantee them. As of October 2026, a few Hyatt resorts sell connecting rooms as their own room type, which is the closest you’ll get.
At Honua Kai, we had about 13 people spread across three condos. We were in a two-bedroom, and my in-laws took a three-bedroom that became the gathering spot. Every unit has a full kitchen and a washer and dryer, which I cover in my Honua Kai review.
We haven’t rented a house together in Hawaii. We have for other destinations, and it’s really hit or miss. Not everyone ends up happy with the arrangement.
If your group really wants one house, I have a list of Hawaii villas for big multi-family trips. Make sure whatever you book is a legal rental.
On Oahu, any stay under 30 days counts as a short-term rental, and as of October 2026 those are only allowed in resort-zoned areas and a couple of apartment-zoned areas. You can look up an address on Honolulu’s short-term rental compliance map.
I’ve had three North Shore Oahu rental homes with a 30-day minimum ask me to promote them. They told me guests didn’t have to stay the whole 30 days. That’s a red flag.
On Maui, Bill 9 phases out short-term rentals in apartment-zoned buildings by January 1, 2029 in West Maui and January 1, 2031 in the rest of the county. It isn’t an immediate shutdown. My post on Hawaii’s vacation rental rules explains how to check a listing on any island.
I prefer VRBO and Booking.com over Airbnb.
Do three generations have to do everything together?
No. The mistake I see is one person assuming the whole group wants to do every activity together.
I recently had a client who was treating her whole family to a Hawaii vacation. She has two grown children who each have kids of their own, so it was 10 people total. Her grown kids were “too busy” to help her plan.
She hadn’t been to Hawaii in more than 30 years, and she had no real concept of how much travel there has changed in three decades. She was making a lot of assumptions about what her kids would want for the room setup, the activities, and the itinerary.
I told her she needed to talk to each of her kids and make sure they were on the same page about doing every single activity as a big group.
That’s why I usually tell big groups to book the 90-minute version of my Hawaii travel consultation and get all the key decision-makers on the call. I can bring up the questions you need to figure out as a group before anyone books. That’s much easier than booking something that doesn’t end up working for everyone.
What activities work for grandparents, parents, and kids together?
A luau, big family meals, shopping, and pool time all worked for our three generations. Those are the things our group of 12 did together in Waikiki in June 2021. Everything else was optional.
We all went to the Experience Nutridge luau in Honolulu, because my niece and nephews had never been to a luau. It’s a small one. There were about 60 guests the night we went, and it took us about 25 minutes to drive there from Waikiki. I wrote about the whole evening in my Experience Nutridge review.
A luau is easy for a mixed group. Everyone sits down, and dinner is included. One thing to know with grandparents is that the Nutridge property is hilly. As of October 2026, the luau says it has a golf cart for guests who need help getting around. Tickets start at $170 per adult, and a round-trip ride from Waikiki is $26 per person.
Most of the group also did Dolphin Quest at the Kahala Hotel, which I cover in my Dolphin Quest review. It wasn’t hosted. My youngest was too little, so we went to Sea Life Park instead and rode the Waikiki Trolley.
As of October 2026, the Encounter Deluxe at Dolphin Quest is for ages 5 and up and starts at $295 per person. Check the age minimums before you promise the kids a group activity, and have a backup for whoever can’t go.
We all went to Ala Moana Center one day. We ate together at a Chinese restaurant there, and my father-in-law mostly hung out at the restaurant and then a bar while the rest of us shopped.
My niece and nephews were teenagers, so they got a lot of freedom. They walked around Waikiki by themselves, went to the beach in the afternoons, and did nighttime pool swims. They were all on swim team.
With everyone in one place, it’s also worth booking a photographer for a group photo. Flytographer has a $20 discount.
What works for grandparents who don’t want to drive or walk far?
Pick a home base where the grandparents can have a good day without getting in a car, and arrange the rides when they do go out.
My in-laws mostly enjoy family meals and cabana time at the pool. They didn’t want to be in the car for very long, and they didn’t want to drive or walk far. When we went out as a group, we got them an Uber or drove them in a big van. If you need a minivan or something larger, compare prices at Discount Hawaii Car Rental.
In Waikiki, the Waikiki Trolley is another way to get around without anyone driving. As of October 2026, its Pink Line goes to Ala Moana Center.
At the pool, we rented a large cabana with food and drinks and just hung out. I go through the costs in are Hawaii pool cabanas worth it.
If someone in your group uses a wheelchair or can’t manage sand, Oahu has free help. As of October 2026, Honolulu’s parks department lends all-terrain beach wheelchairs at Ala Moana Regional Park and Hanauma Bay. They’re free for 2 hours, first come, first served, and the person using one needs to bring someone to assist. Several beach parks also have access mats over the sand, including Kuhio Beach Park in Waikiki. The details are on the city’s beach wheelchair page.
Should you expect the grandparents to babysit?
No. Ask them before the trip instead of assuming.
My in-laws do not babysit, as a rule. The one exception was on Maui, when I was pregnant with my youngest. My mother-in-law watched my oldest so we could have a dinner out, and again so we could go on a luau date. That was very rare. She was the one who insisted before the trip, so we took her up on it.
I always tell my clients to check and double-check that the grandparents are okay with babysitting. Then do something nice for them, like bringing them coffee the next morning.
Trips with my mom are different. She lives on Kauai, and she doesn’t only see us when we visit her there. She flies over to meet us on Oahu, Maui, and the Big Island too.
She’s a resident, so she doesn’t really want or need to do anything in Hawaii. It’s more about hanging out with us. She always offers to watch the kids while my husband and I go do something.
If the grandparents are taking the kids without you, that’s a different trip. I wrote about it in my post on skip-generation travel in Hawaii.
How do you handle meals for a big family group?
Give the job to the people who like doing it, and plan on big shared meals.
At Honua Kai, my mother-in-law and my husband shopped for all the groceries and figured out the meals. It’s kind of their thing. My mother-in-law even packed spices, and I think rice, to cut down on some of the costs.
My in-laws are Chinese, so we also did a lot of family-style Chinese meals at restaurants. We do big restaurant meals as a family anytime we get together, so it wasn’t awkward at all.
If your family doesn’t normally eat that way, decide before the trip how you’ll split the grocery runs and the restaurant checks.
What would I skip on a Hawaii trip with grandparents?
I’d skip any all-day drive for the whole group. Send the people who really want it, and let everyone else have a pool day.
My last Road to Hana day, in 2022, took 13 hours. My in-laws have no interest in being in the car that long. On two-island trips, I already tell families to skip the Road to Hana and Haleakala unless they have a strong desire to go, and that goes double with grandparents who don’t want to be in the car.
I’d also skip moving a big group between hotels every couple of nights. I had a client whose itinerary switched hotels every two days, and the drive times surprised her. That’s even harder with three households.
And I wouldn’t book a big rental house just because it sleeps everyone. If you can’t confirm it’s legal, book the hotel rooms.
FAQ
How do you plan a multigenerational family trip to Hawaii?
Pick one island and one home base, and agree on who is paying for what before anyone books. Then plan a few things for the whole group, like a luau and a couple of big meals, and leave everything else optional. Talk to every household before you book rooms or activities so nobody is planning on assumptions.
Which Hawaiian island is best for grandparents and kids?
Oahu is my pick for a first trip, because the group can stay in Waikiki and the grandparents don’t have to drive. Maui is my pick if the trip is mostly about hanging out together at a beach resort. On Kauai, I recommend Koloa Landing Resort in PoÊ»ipu because the villas have bedrooms.
Is a hotel or a vacation rental better for a multigenerational trip to Hawaii?
I usually recommend hotel rooms or a condo resort, because Hawaii has a lot of illegal vacation rentals. A condo resort gives you a kitchen and a unit where everyone can gather. If you book a rental house, verify that it’s legal before you pay.
How many days do you need for a multigenerational Hawaii trip?
For one island, I recommend 7 to 10 days if you can swing it. If you want two islands, 10 days is the minimum I suggest, and 12 or 14 is easier. With a big group, one island is usually less stressful.
Should grandparents be expected to babysit on a family trip to Hawaii?
No. Ask before the trip, and then check again. My in-laws don’t babysit as a rule, and my mom always offers, so it really depends on the grandparent. If they do babysit, do something nice for them the next day.
Who pays on a multigenerational trip to Hawaii?
There’s no rule. On our trips, my in-laws hosted and covered the lodging, the rental car, the big family meals, and the group activities, and we paid for anything we did on our own. Just make sure everyone knows the plan before anyone books.
On our trips, my in-laws mostly enjoyed the family meals and the cabana time. A trip with grandparents doesn’t need a packed schedule.
If you’re organizing a trip like this and want help sorting out the island, the rooms, and the questions your group needs to answer first, book a Hawaii travel consultation. It’s a one-on-one video call, $149 for 60 minutes or $199 for 90 minutes, and you book everything yourself afterward.
 | About the author: Marcie Cheung is a Hawaii travel consultant for families who has visited Hawaii more than 40 times. She is the founder of Hawaii Travel with Kids and host of the Hawaii Travel Made Easy podcast. She offers one-on-one Hawaii trip planning consultations and itinerary reviews for families, couples, and honeymooners. |