Navigating Multi-Generational Trips to Hawaii with Melissa Conn— Ep 20

Planning the Ultimate Multi-Generational Trip to Hawaii with Family Voyage's Melissa Conn

In this episode of the Hawaii Travel Made Easy podcast, host Marcie talks with Melissa Conn from the Family Voyage blog about planning multi-generational Hawaii trips. This comprehensive Hawaii travel guide focuses on Hawaii family travel for extended families, perfect for first-time Hawaii visitors planning complex Hawaii vacation logistics.

Melissa, who has traveled to Hawaii multiple times with her extended family, shares insider Hawaii travel tips for choosing the right Hawaiian Islands and accommodations, navigating flight and car rental logistics, balancing Hawaii activities across different age groups, and leveraging travel rewards to save money on your Hawaii vacation.

This detailed Hawaii family travel guide discusses favorite Hawaii activities, dining strategies, and Hawaii travel tips for managing dietary restrictions and motion sickness during Hawaiian Islands trips. Perfect for Hawaii vacation planning, the episode provides a comprehensive Hawaii travel guide for families looking to plan a memorable multi-generational Hawaii vacation.

Essential for Hawaii vacation planning with grandparents, parents, and children, learn expert Hawaii travel tips for managing large Hawaii family travel groups across the Hawaiian Islands.

00:00 Introduction to Multi-Generational Travel in Hawaii

00:15 Meet Our Special Guest: Melissa Conn

00:37 Melissa's Multi-Generational Travel Experiences

03:02 Challenges of Planning Multi-Generational Trips

04:20 Accommodation Strategies for Large Groups

06:48 Choosing the Right Island and Hotel

12:57 Balancing Activities for All Ages

17:09 Favorite Activities and Memorable Moments

20:03 Meal Strategies for Large Groups

21:34 Navigating Restaurant Reservations

24:17 Transportation Tips and Car Rentals

30:05 Travel Rewards and Discounts

36:48 Final Tips for Planning a Hawaii Trip

Guest: Melissa Conn, The Family Voyage

Who this episode is for: Families planning a Hawaii trip with grandparents, parents, and kids together, and navigating the added logistics of a large, multi-generational group.

What you'll learn: How to choose islands and accommodations for large groups, balance activities across different age groups, manage meals and dietary restrictions, and use travel rewards to save money.

Activities discussed:

• Choosing accommodations for large groups
• Balancing activities across different age groups
• Managing meals for large groups
• Booking restaurant reservations for large parties
• Renting cars for a multi-generational group
• Using travel rewards and discounts

Guest recommendations (Melissa Conn):

• Choose accommodations that can comfortably house or cluster a large, multi-generational group
• Pick an island and hotel based on what works across the widest age range in your group, not just one generation's preferences
• Balance high-energy activities with downtime so all ages can participate comfortably
• Plan meal strategies in advance for large groups, including managing dietary restrictions
• Book restaurant reservations for large parties well ahead of time
• Coordinate car rentals and transportation logistics early given the group size
• Leverage travel rewards and discounts to help offset the higher cost of a multi-generational trip
• Prepare for motion sickness concerns when planning boat tours or winding drives with a mixed-age group

Related Hawaii Travel Made Easy episodes: 

• Multi-Gen Magic on the Big Island with Leslie Harvey of Trips with Tykes— Ep 145
• The Comparison Trap: When Other Families Look Like They're Having More Fun— Ep 111

Related articles: 

• How Gen Alpha is Changing Hawaii Family Travel (And What Parents Need to Know)
• Skip-Generation Hawaii Travel: The Ultimate Guide to Grandparent-Grandchild Adventures

Guest links:

• The Family Voyage (blog)
• @thefamilyvoyage (Instagram)
• The Family Voyage (Facebook)

About Your Host: Marcie Cheung is a Certified Hawaii Destination Expert who has visited Hawaii 40+ times and spent 20+ years as a professional hula dancer. Through Hawaii Travel with Kids, she helps families plan authentic, affordable Hawaii vacations that respect local culture while creating unforgettable memories.

Learn more at hawaiitravelwithkids.com

Connect: @hawaiitravelwithkids on Instagram | Book a Consultation

🌺 Join 11,000+ families receiving free Hawaii travel tips, island guides, and insider advice - subscribe now!
https://hawaiitravelwithkids.com/free-5-day-email-course-how-to-travel-to-hawaii-like-a-pro/

Transcript

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 Marcie:
Aloha and welcome back to the Hawaii Travel Made Easy podcast. I'm Marcie, your go-to Hawaii travel expert who has visited the islands more than 40 times. If you're new here, I'm so glad you found us. Today's episode is all about multi-generational travel in Hawaii and we've got a special guest. Her name is Melissa Conn and she runs the popular family travel blog, the Family Voyage, and she's done a few multi-gen trips to Hawaii. Alright, let's jump in and start chatting about how to plan the ultimate multi-generational trip to Hawaii.  Melissa, thanks so much for being here.

Melissa:
Aloha. Great to see you, Marcie.

Marcie:
So let's just jump right in and can you tell us a little bit about your family and who you've traveled to Hawaii with most recently?

Melissa:
Sure. I'm a married mom with two kids just like you. My, kids are 10 and 13. We live in Columbus, Ohio now, but before that we were in LA, which gives you much better access to Hawaii. Between those two locations, we actually traveled full-time for two years, which included two separate visits to Hawaii.

So obviously we love Hawaii so much. I've been seven or eight times. But we've gotten to do two multi-generational trips there. The most recent one was over winter break and we went with my husband's side of the family. At our biggest on that trip, we were 13 people. We had seven kids evenly spaced from three to 17 years old.

Five of us middle-aged folks. And then we were with grandma, who is 77 years young, and she absolutely loves Hawaii. So a lot of the impetus for that trip was that she hadn't been in many years and really wanted to get back.

Marcie:
That's awesome. And where do you guys travel from? Where are you located?

Melissa:
We're flying from the Columbus airport, so it's pretty far to get to Hawaii these days.

Marcie:
Absolutely. So I know you've done it twice. What islands have you visited?

Melissa:
On our multi-generational trips. The first one was back in 2018, and as I mentioned, my family was traveling full-time for a couple of years. We had a large vacation home through the Home Exchange Network. That was a partnership we had for my blog, and we had that house for five weeks on the Windward coast of Oahu.

So during that trip we had both of the grandmas, my mom and my mother-in-law join us for about 10 days of that trip, and that was really special to have them with us in Hawaii. More recently we were on Oahu as a group of 10 over winter break, and then we flew to Maui and picked up three more in the extended family.

And we were on Maui for six days.

Marcie:
Oh, that's awesome. Were there any favorite islands that the extended family preferred?

Melissa:
Maui is really popular for everybody in the family. You know, as, as you know, it, Maui's got something for everybody. It has tons of different options, whether you wanna hang out on the beach or do activities, hiking, cultural, cultural points.

Marcie:
Absolutely. Yeah, Maui is fantastic. I know when we do multi-generational trips to Hawaii, Maui seems to always be number one that people request, so I totally get you on that. What do you think is your biggest challenge when planning a trip with multiple generations?

Melissa:
Well, for us, the biggest challenge always is getting the dates right. And unfortunately what we have realized is that the only option that works for the whole extended family, 'cause we do these trips pretty much every winter is the second week of winter break. That's it. That's the only overlap that we have between everybody's work and school schedules.

But unfortunately, that's also the absolute most expensive week of the year to travel to Hawaii. And Hawaii's already expensive, so this is a real gut punch.

Marcie:
I know, I have been there too. That's the same week. That seems to work for our families as well.

Melissa:
yeah. And then, you know, the other, the other piece that's a challenge for us, to be honest, is that the most natural way to save money on a multi-gen trip to Hawaii is rent a big house for everybody. And then you can. Economize on your accommodations. You can use the kitchen, everything like that. But the reality is that we have a few different households coming together and everybody's got different styles.

So we thought about it for this trip as a way to save money, but it would've been really challenging to try to get everybody happily staying under one roof. So I think beyond getting dates lined up, figuring out accommodations that make sense for everybody in terms of both the budget, but also everybody getting along and having a good time together.

Marcie:
We have also encountered that, so I feel you on that. What did you guys do for accommodations on this last trip?

Melissa:
For this one, we stayed on two different properties because as I mentioned, we had a group of 10 that was on Oahu first, and then we hopped over to Maui. So on Oahu we stayed at the Hyatt Regency Waikiki in three rooms. And then we stayed at the Andaz Wailea in four rooms.

Marcie:
Nice. And did that work out for everybody? Was everybody happy?

Melissa:
Yeah, both properties were really great for, for us. Part of the motivation for staying at those properties is that as you probably know, I have Hyatt Globalist status, which gives us lots of perks when we stay at Hyatt Properties including free breakfast or club access for, for everybody. I'm able to get everybody on board with getting all of those perks and it can be a real money saver when you have lots of people traveling with you.

Marcie:
Absolutely. Yeah. I think you bring up a really good point about, it's really tempting to get a giant house for everybody, you also have to take in consideration the emotional toll maybe, and how different it is to have multiple households all living under the same roof and that it might, while you might save money, you might, it might cost you in other ways.

Melissa:
Correct.

Exactly, and, and you hit on a really great point, and, and you're right. It's, it's the emotional toll and that can be. People getting along. It could also be as simple as one family keeps their stuff a lot tidier than the other.

I don't wanna stay in a big rental house that's got 10 people's stuff strewn all over the living room.

I just can't do it. You know, I need to get in my, get into my hotel room, unpack, put everything away in a drawer and keep it tidy. And that would be really hard when you've got 13 people in one house. And one of the other issues we encountered when we did consider that we thought about maybe doing.

A few side-by-side condos or townhouses. But particularly over the holidays, you do run into those minimum stay requirements that the complex that I really, that we had stayed at for spring break last year, we really wanted to stay at again, had I think a 10 day minimum stay over the holiday period.

Another one in the area had a 14 day minimum stay, and that just wasn't gonna work for our entire group.

Marcie:
Yeah, that's definitely a good point to always be looking at those minimum stays because I feel like. just with all of the situations with short-term rentals in Hawaii people are really it's really important just to, to read those and make sure that you're following those. But it can be frustrating when you just want it for seven days.

I get that. So how do you usually decide which island to visit and where to stay when you are dealing with people from many different generations, many families.

Melissa:
There's so many factors that go into play. We actually made a, a mid-course change for this specific trip that we did in December. In this case for us, the choice of which island to stay on and which hotel really went hand in hand. We knew we were gonna spend a couple of days on Oahu because my sister-in-law's got family there.

And you know, our immediate family wanted to revisit some old favorites from that long stay that we did back in 2018. But then my immediate family had been in Hawaii splitting between Maui and Kauai for spring break last year. And it was kind of a scouting trip and I'm really glad that we did it that way.

We had both a push and a pull involved in. Deciding where to stay. We stayed down in Wailea in March, and it was our first time in South Maui. And we really loved it. We had a condo that was right next to the Andaz Wailea and the beaches down there are really spacious and they're not crowded. It's, it's definitely a nice change of pace.

Change of pace compared with, or even Ka'anapali. But then when we hopped over to Kauai, we were staying at the Grand Hyatt Kauai in Poipu I think you've stayed there before as well, right?

Marcie:
I love that property.

Melissa:
Beautiful. Absolutely gorgeous. And that was where we had originally planned on doing this multi-gen trip. We really loved it.

Don't get me wrong at all. My mother-in-law, especially, she loves flowers and landscaping. So we thought this is gonna be perfect. And because of my global status, I would've been able to give club access to everybody in the family. So that would've covered us for breakfast and snacks. And even a light dinner from the hor d'oeuvres if need be.

Unfortunately, there are two things about the Grand Hyatt Kauai that made it ultimately not the right fit for us. One is that that hotel's really, really spread out. You know, if you think about, let's say the Hyatt Regency Waikiki is being totally vertical, right? 26 floors or something in two towers.

Well, the Grand Hyatt Kauai is exactly the opposite. Everything's very low and far apart, and. Because we knew we would want club access there and at least at the time, the club was in what they call the Poipu wing, whereas the pools are in what they call the shipwreck wing. Those are so far apart.

Even for us as a young active family, it was kind of a hike to get between our room next to the club and the pool area. And for grandma, who had a knee replacement a year and a half ago, that would've easily been a 20-minute walk anytime she wanted to get. To the room, to the club, to the pool. And so we felt like it was just gonna be really taxing on her.

You know, as I mentioned, we also have a, we had a three-year-old in tow who is not a fast walker. She's three. She gets distracted and there are a lot of things to be distracted by along the way. So that was one real concern. And then the second is that the beach at that property is not swimmable. It can actually be really dangerous, even though we were gonna be.

In the least dangerous part of Kauai for a winter trip.

it was, it's not a place where we could comfortably send, you know, a three-year-old and a five-year-old to enjoy splashing in the water. So ultimately we decided that it was gonna be easier if we were somewhere else. You know, there, there are great beaches near Grand Hyatt Kauai. Poipu Beach is awesome and perfect for kids, but when you're talking about 13 people having to get ready, get in all the different cars. Bring chairs and towels and pool to sand toys and everything with you. Then find parking across the street, schlep everybody over to the beach. It's really a lot.

So in the end, my preference was to have a property where it was gonna be a little less walking for grandma. And we had a good beach on site so that if we wanted a beach day, we could just walk right there. Andaz Wailea was perfect for that. I don't think anybody had any complaints. There was still a decent amount of walking.

I'm not gonna lie, because the, the pools there are terraced one right below the other, and then the beach is at the bottom. There are ramps to go all over the property though, which is great. But the beach there is serviced.

So, the beach not only is gorgeous and swimmable and not crowded, but they've got really wonderful team down there that is providing chairs and towels and snorkel gear and kayaks and everything that you want without you having to bring anything.

They even had beach toys for the kids. So that worked out really well for us. And, and so as I said, it, it was really the decision about the hotel on the island going hand in hand. That's how we ended up on Maui instead of our original plan of going to Hawaii.

Marcie:
That totally makes sense. It's a good thing that you weighed the pros and cons and realized what needs each member of the family would have for sure. So how far in advance do you start planning a multi-generational trip?

Melissa:
The earlier, the better. We've done a couple of these multi-gen winter trips. We've got another one coming up later this year. And I would say that we usually start brainstorming at least a year in advance, sometimes more. And then I'm looking to start booking cancelable hotel rooms as soon as the calendar opens.

For, for Hyatt, which is my preferred brand, that's 13 months out. The nice thing is that you can generally reprice your reservation if the price drops, but at least you've locked in those rooms. As I said, we need four rooms every now and then. We're actually doing five now because of some changes in the family, and it can be hard to get five rooms.

We're four rooms all in the same vicinity. You gotta make sure that everybody has the same type of view, so nobody feels like they're being left out.

And it's, it's certainly possible to book things closer, and especially if, let's say you just need two rooms because it's the kids, the parents, and the grandparents, that's a much easier situation to handle versus, you know, four or even five rooms.

So you, you really have to be on the ball if you've got a big group going.

Marcie:
No, I totally agree on that. Okay, let's switch gears a little bit. I know that that is another thing that people are always asking me about in emails and on Instagram and stuff. So like, what kinds of activities have worked best for all the age groups in your family where you're talking about grandma, you're talking about a three-year-old. What has worked best.

Melissa:
Cultural activities are really great. As I, I think I've told you we went to the Old Lahaina Luau, which had just reopened in March of 2024.

Everybody had a great time. It actually reopened the week after our family's spring break trip last year. So we didn't get to go last year, but we went, then we went in December January.

We also did a really great whale watching trip that was a hit. And then on Oahu, which again was only 10 people, not 13 people, we spent a half day at the Bishop Museum, which my family loves. We've been there a bunch of times. And that's really great because for the kids there's a whole science center.

And then for the adults there's a great cultural area, but there, everybody can find something to appeal to them in both areas. If you have enough people, you can get great deals on activities like Luaus and the Bishop Museum. Like at the Bishop Museum, I originally was going to purchase admission for 10 people and then the nice lady at the desk said, Hey, you know, if you buy a membership, I.

You get a certain number of guest passes and it's actually gonna be cheaper for you to become a member just for this one day visit. So that worked out really well for the luau. I, I know that they had a 14 or 15 person minimum to get a group discount, so we were just a little bit shy of that unfortunately.

But yeah, in general I would say those kind of cultural activities have been really great.

Marcie:
Yeah. That's great insight. So I know we've talked about the cultural activities

You know, beach days and full-time or whatever. How do you balance the downtime and excursions when you have toddlers, teens, and grandparents in the mix? Is there some sort of secret formula or how do you handle it?

Melissa:
I'm not gonna lie, in many ways, this is the hardest part. You and I have traveled together so you know that I always wanna be out, especially snorkeling,

but there are a lot of people in my family who like you just wanna lay by the pool and read a book. No, that's totally cool. So generally I try to come up with activities that, that my immediate family wants to do, and then I send 'em out to the whole group to see who wants to sign up.

And people have agency, they don't have to do things that they don't wanna do except my kids. They don't get a choice. But with, with such a big group I do it pretty far out to make sure that sure, that there are enough spots, because sometimes we do end up needing to have essentially a private tour, you know, if we wanna do kayaking and there are 10 people.

Well, it's not gonna work if somebody else has already signed up for, let's say, two spots, and the kayaking company can only take 10 people at a time. So, so I really have to be on the ball in terms of getting that stuff lined up to keep everybody happy. I usually try to plan for an activity or excursion every other day.

We wanna, we wanna have, you know, a balance of relaxation especially for those who aren't traveling as often as my immediate family. This might be their big opportunity of the year to sit by the pool with a book or to just enjoy a casual beach day. You know, we, we are fortunate. We get those opportunities a lot, but not everybody in the family does.

and I think that

Between a trip and a vacation too.

I am Team trip.

am as well.

One thing I wanna say that was really perfect about the Andaz in this particular area is that the resort fee there includes a lot of experiences that you would be paying for otherwise. So like we did a guided kayaking trip, we did outrigger, canoeing, we did all this cool stuff.

It's onsite, it's already included in the fee, so there's no discussion of who's paying for what. And oftentimes those excursions are early in the morning. So it was easy for me to slot those in, even on days when we didn't have plans that were off property. So we might call it a pool day for everybody, but for me it's outrigger, canoeing, a few hours of snorkeling, and then meet up with everybody at the pool.

So finding a property where you can do some of that really cool stuff without leaving. The vicinity is very helpful if you're trying to balance that trip versus vacation vibe.

Marcie:
I think that's the ultimate hack right there. I think you, you hit it on the money right there. Can you share a favorite activity or moment that stood out for your whole group? Was there anything that all of you were like, gosh, this was so amazing. I'm so glad we did it.

Melissa:
I would say that whale watching on Maui was a big hit for everybody because we got to see I think they call it a heat run where you have all of these whales circling. So we, we get to see tons of whales. We were there in January, which is perfect time for whale watching in Maui. But I am gonna cheat and I wanna share a favorite from me personally.

So we were actually on Oahu for my birthday,

and I got to do all my favorite things with my favorite people. So this is why this is like, you know, for more personal for me. We started off visiting the gardens at way Maya Valley, and then we went up to Turtle Bay and Snorkeled and played at the beach, and we wrapped up with dinner at the beach house in Haleiwa, sitting at a huge table.

And I got to be surrounded by most of my favorite people in the whole world. One of my favorite places in the whole world. So how can you beat that

Marcie:
Amazing. I love it when you get to celebrate your birthday somewhere else and you get to do all your favorite things with your favorite people. I think that that's the ultimate right.

Melissa:
Exactly, but especially if you get to celebrate that birthday in Hawaii,

Marcie:
Well, we talked about good things, but are there any excursions or activities that didn't go as planned or weren't a good fit, and you heard a bunch of complaints about it?

Melissa:
No big complaints. I think honestly we did pretty well in that realm and I think it, part of that is because my husband, Ronnie, and I have spent so much time in Hawaii. And we also know our travel crew really well. We know what's gonna, what's gonna fly and what's gonna flop. The biggest hiccup was that we did book one guided kayaking trip that most of the group did.

But my sister-in-law and her daughter are both really prone to motion sickness. They know that and we know that, so, so we always are a little bit hesitant on small watercraft experiences, big boats. They're fine. They both took some Dramamine and they thought they were gonna be okay. But in the end they did have to paddle in early with the guide.

But because we had what amounted to a private tour, since we were 10 people, it worked out okay. There was nobody else on the trip that was inconvenienced. Our guide was able to just pause the tour, take care of them, get them back to shore safely, and then hook back up with the rest of the group and continue the experience.

Marcie:
Nice. Well, and I think part of that is probably that you guys have done these multi-generational trips other places before, so this isn't your first time doing it, but I think it would have been a different experience had this been the first time you guys were all traveling together.

Melissa:
Yeah. And it was also not the first time that we've had a challenge with, with those two in particular, having motion sickness when we're on small boats. Lots of funny stories about those kinds of things happening in Mexico. S you know.

Marcie:
Totally. I know it's so unpredictable sometimes, or predictable, I guess, if you know that they're. Prone to it.

Melissa:
Exactly. Yeah.

Marcie:
Right, let's switch gears and talk about food. This is another big concern with groups for sure, and especially with meal dietary restrictions and things like that. So what is your strategy when it comes to meals?

Like do you mostly eat out or cook your own at a rental or do a mix? What works for your family?

Melissa:
So hard for us. Not gonna lie so hard. As I mentioned before, I thought that for this trip, a hotel was gonna be the best option because. We didn't all wanna stay under one roof. We did end up eating all of our dinners out. Breakfast was included for everybody thanks to my status with Hyatt.

And if you haven't stayed at Andaz Walea, or at least gone for brunch, you've gotta do it once because the spread is. Amazing is incredible. And there were some days that we got away with just giving the kids a snack in the middle of the day and then having an early dinner. By the way, also the Andaz brand, they give you free mini bar.

They have tons of snacks and drinks and stuff included in your room and you just take what you want. And then they refill it later in the day,

Marcie:
amazing.

Melissa:
We were, yeah, so it's a really nice perk. The Andaz brand has been great for us. So we were able to get away with not necessarily having like a sit down lunch every day.

There were some days that we did but it was kind of catch as catch can we'd maybe get the kids some food, food poolside or walk over to the shops that way. Leia, or, you know, one time we had an excursion in a different part of the island, so we got lunch. And then on those days we just planned for an early dinner.

But then dinner we did out at restaurants every night.

Marcie:
Nice. And then when you were eating out, were there any restaurants that worked really well for having a larger group?

Melissa:
This again, was one of the hardest things. My husband is such a trooper. He started working on dinner reservations more than a month out. And I think I was messaging you about some of the challenges that we were encountering because even a month of lead time wasn't enough for such a big group visiting over.

The peak holiday period, we were only able to get, I think, two reservations on Maui. One that I wanna highlight 'cause people might not know about, it's called Gather on Maui, and that is a newer restaurant that's at the golf course in Leya. That was really great. If you go shortly before Sunset, they have a beautiful view.

Really, really had a, a great meal there. Then on Oahu, we ate at Tommy Bahama in Waikiki. That worked really well. They're great for big groups. They have a beautiful rooftop with a nice view as well. Oh, you have a city view, not a, an ocean view there. But they were happy to accommodate our big group.

And they had a lot of options for all ages. You mentioned dietary restrictions. My daughter has celiac disease. She was diagnosed in between our March trip to Hawaii and our December trip to Hawaii. So we had two very different experiences. You know, going back with, with that really serious dietary restriction.

Actually there, there were two other people in our extended family who were also diagnosed with celiac disease in that same time period. So it was, that was really something that we had to get used to. But Hawaii has was great about that. I think more than a lot of destinations in America, people understand and are willing to accommodate the, the needs of a strictly gluten-free diet.

Other than the, those fewer, we were able to get reservations. We did a lot of quick service type restaurants you know, popular spots like Paia, fish Market, coconuts, fish Cafe, both really great,

favorites.

but, but man, over the holiday period, those lines can be crazy. We're talking like an hour long wait at Paia.

So because we, I think one thing we're gonna talk about in a few minutes is the vehicle strategy. We did have multiple cars, spoiler alert. So sometimes we would send one car, whoever was ready first over to get in line at Paia Fish Market or coconuts, and then the other two cars would follow behind once their people were ready.

That helped a little bit, but definitely a struggle to accommodate such a big group. And you know, thing you're talking about having multiple tables, so you have to figure out how to break things down. Kids table, grownups, table. Definitely a big, big, big challenge.

Marcie:
Yeah. So let's go ahead and talk about the vehicle situation. So it sounded like you were renting cars for each individual family, is that right?

Melissa:
Yeah. Multiple cars, no question at all. We had, we had three cars for 13 people. Grandma doesn't really drive, so she would just go with whomever had a spot for her. And that worked out well because there were times that we split up based on interests or based on who was ready first, usually my family.

And, and that worked out well.

Marcie:
Nice. Okay. And then were there any transportation tips that have made things easier for your group?

Melissa:
Well, I'll tell you one of my few regrets on planning that trip is that I didn't book a bigger car for my household. We have, we're a family of four, and then we, we knew we'd be bringing grandma from the airport to the hotel, but then we figured I. The other folks would be transporting her around because she doesn't see them as much as she sees us.

She lives down the street. We see her all the time. So it's an opportunity for her to spend time with the other parts of the family. So I figured, alright, a standard sedan is gonna be fine, and I have the top tier Avis status. So typically when I book a standard sedan. I'm able to get into something bigger, usually in SUV, sometimes a minivan, but unfortunately, because it was that peak holiday period, they were totally sold out and it just didn't happen.

We had a really cramped sedan. I don't even know why this standard sedan was so, so tight. More than more cramped than any other sedan I think I've been in. And it was, it was a challenge because. While in theory we had enough seats for everybody across all the cars, sometimes it didn't line up perfectly or comfortably with where people wanted to go at different times or who they wanted to ride with.

You know, it's an opportunity for extended family from around the country to get together. So there's a lot of trading of kids, trading of, you know, middle-aged folks as we wanna spend time with people from different parts of the country. And then, you know, one other thing that. I wish I had done differently.

It's a little specific to our family, but as you know, I'm a car seat technician, so I'm always weighing which safety device to bring for my daughters since she still rides in a booster seat. And for this trip, I brought a super compact booster seat because we're team carry-on and I could just slide it right into my carry-on.

What I didn't think about is that my niece and nephew are still too small to ride in that specific booster seat.

They ride in boosters, but that one has higher, higher minimum requirements. So the kids all wanted to play musical cars because. Sometimes the brother and sister wanna ride together.

Sometimes they wanna trade off and do boy car, rental car. Sometimes we have to put a teenager in the middle, whatever. But because I had a different booster seat that the younger kids couldn't use, we were constantly having to swap car seats if the kids wanted to ride in a different vehicle than they had the last time.

And if I had just brought the same one that my niece and nephew were using, which is in my garage it would've been a lot easier. For, for everybody. And would it kind of streamline that? So like if you're traveling with younger kids, if you have a bunch of cousins that still ride in, harness car seats, I would say to think about a flexible option that's lightweight, but that you can also easily adjust for the different kids.

So something like a Greco contender is a great choice for that situation. If all the kids are under 40 pounds, just put it in rear facing, move the headrest up and down for whoever's gonna ride. Or if all the cousins are. Five, six older bring a flexible booster, like the Kiko Go Fit or the Greco Turbo Booster, and then the kids can ride wherever they want.

You know, you don't have to worry about switching car seats every other minute.

Marcie:
I think that that is such great insight. I'm so glad that you brought that up because I think a lot of families, it wouldn't even occur to them to check with their you know, brother-in-law, sister-in-laws and stuff to see. What kind of car seats people are bringing because that would really save people a lot of stress. And then I wanna ask you a question that I know the answer you're gonna give, but should people bring their own car seats or should they rent something when they land in Hawaii?

Melissa:
They should definitely bring their own, because boy, you never know what you're going to get. I mean, I have, as a car state technician, I have had the experience of helping. I. Basically stranded grandparents at the airport who rented a car seat and discovered that it was missing parts. It was missing the lower anchor strap.

The top tethers had been cut off by, probably by an airport, airline, or a car rental employee who didn't know how to uninstall it. You never know what you're gonna get if you're in a a peak period when the car rental agency is sold out. They can't even guarantee that they're going to have a car seat at all.

Well, and you never

And,

for your child either. That's something that they can't guarantee.

Absolutely, and what you may not know, you probably know this Marcie, but your listeners may not know. Hawaii actually has pretty stringent car seat requirements, which I think is awesome. They require kids to ride in a car seat or booster seat until they're 10 years old, or four foot nine, and most kids are not four foot nine at age.

Seven or eight whenever people frequently stop using a booster seat. So you should plan on bringing a booster seat for your kid until at least age 10 in Hawaii. And then they do require a harness car seat until at least four years old, which is pretty standard, but usually it's safest until five or even six years old to stick with a harness car seat.

these are

So definitely bring your, bring your own from home. If you need help choosing a lightweight car seat, I'm definitely your expert on that.

Marcie:
You definitely are. All right, so I wanna switch gears again, and I know that you are like the queen of miles and points and everything, so like have you used any travel rewards points, group discounts, whatever, to save money? I know we touched on this a little bit, but I wanna like really talk about it now.

Melissa:
Absolutely. You know me. You ready to get into the weeds?

Marcie:
YES.

Melissa:
Okay. So the group of us flying from Ohio, there are five of us total, including grandma flew on Southwest. We don't have great options on any airline for getting to Hawaii. It's far. We have to stop no matter what. And those tickets were basically the same price as what all of the other airlines charge.

And the schedules were pretty much the same. But my husband and I both have the Southwest Companion passes, so that means our kids fly essentially free with us anytime we fly. It's just the cost of taxes, which is five, or the mandatory government fee, which is $5 and 60 cents each way. So for the round trip flight for each of my kids, it was $11 and 20 cents to island hop from Oahu to Maui, $5 and 60 cents.

We can use that over and over. Southwest Companion Pass is like the best thing since sliced bread.

The companion Pass has not changed, at least thus far. Southwest has made a lot of changes. They've announced a lot of changes in the last month or two. I don't love all of them, but they still are not really gonna impact our travel pattern. One of the big changes they made is they are gonna start charging for check bags.

We don't check bags. However, the way that most people get the companion pass is by holding Southwest Credit cards and Southwest credit card holders are still gonna get free check bags,not only for the credit card holder, but for their family members traveling on the same itinerary.

Marcie:
Perfect.

Melissa:
If you wanna go to Hawaii and you're in a city that is served well by Southwest, I definitely think you should look into that.

Companion pass. Total game changer. Another thing that was a big savings for us is that as a small business owner, I have a discount arrange with Hyatt. Lots of these, lots of travel companies have small business programs that you can sign up for, and Hyatt's is nice because. You can sign up for it just by having the Hyatt business credit card.

There's no minimum amount of business that you have to do with them every year as long as you have that world of Hyatt business card. So we're able to get discounts on our room rates, including at the Andaz Wale, and we're, I'm also able to stack my globalist benefit on top of that. Globalist is highest its top tier status.

Yeah, it and it provides some really amazing benefits. Free parking on award stays. Resort fees are waived, whether it's a cash stay or an award stay. My family gets free breakfast or club access, but then I also have Guests of honor awards that I can apply to the other rooms that are traveling with us.

So it's really an amazing perk that is, it's in the realm of points and miles. But saved us tons of money. In fact, we had initially planned or talked about staying at the Yle, a beach resort next door. And that's a super family friendly Marriott property. It's got a game room, it's got water slides, it's kind of got everything.

But when I crunched the numbers of getting everybody at least a partial ocean view at the Yle Beach Resort and getting everybody breakfast, 'cause I wanted to start the day off easy. The Oex came out to $12,000 cheaper for the four rooms that we booked. Thanks to all of the discounts I was getting and globalist benefits, yet, $12,000 is huge.

Obviously it's an expensive trip, but that's really meaningful savings. So we actually opted to use a thousand dollars of that savings to purchase resort paths for Yle Beach Resort. And we used that on our last day and that worked out great. So we got, we got some cabanas there and, and had a really fun day, but we still had the massive $11,000 in savings from staying at the Andaz.

Plus, we got all of these great benefits. Okay. I had to make notes on this 'cause I, I wanted to make sure that, to give your, your listeners all of the inside track on the aboard travel aspect.

you.

oh. Since, since the Andaz Walea, it was a cash stay. We didn't, we didn't use points to stay there, but it did kick off a ton of points.

Especially since as a globalist I get a 30% bonus on any points earnings. I also put it on my Hyatt credit card, so I got extra points for doing it that way. So we're, we're doing a cruise this coming winter as an extended family. Again, same group of people and I'm able to use those points that we generated in Hawaii to cover everybody's hotels, both before and after the cruise.

So that's working out really well. Yeah. The other aspect of savings that I wanted to make sure I told you guys about is rental cars. Because rental cars can be, can be really expensive. You're looking at during holiday period, probably a hundred bucks a day. Once you include all the taxes, airport fees for Oahu.

I used my Capital One Venture X card and I took advantage of the $300 annual travel credit that comes with that card. You have to book it through their portal and they have an exclusive partnership with Hertz. To provide status benefits. So you can book any company through the Capital One portal, but you're only gonna get status benefits if you book through her.

But that's fine because that card gives you Hertz President Circle. So. Which gives you all the upgrades and all the extra points and everything. So that was how I booked our car for Oahu, and I saved $300 on that. And then on Maui, I used my Avis small business discount rate. I also have top tier status with Avis because I had them match that Hertz status that Capital One gave me for free with my card.

In theory, I should get a double upgrade, but as I told you, if they're completely sold out, there's nothing they can put you in. They can only put you in the class of car that you've reserved. So I would say that didn't work out as well as I would typically hope. And then, you know, it's not quite in the points realm, but obviously you could look at group savings for things like luaus and kayaking.

If you're not gonna be able to get a group discount, sometimes it's actually cheaper for you to book through an aggregator, like get your guide or via tour. And stack that with portal savings through Rakuten. You know, there's all sorts of little hacks to, to save money, get some cash back, or get some points back.

And then you can use that for your next trip.

Marcie:
These are all great tips. Thank you. So I have one final question for you and it is, what is your biggest piece of advice for someone planning their first big Hawaii trip with extended family? I.

Melissa:
I am glad you asked, and I'm glad that this is coming right after the question about points and miles because they, they kind of relate to each other, you know, the, in the big picture, I would say start planning early, like before the hotel calendars and flights are even open. 'cause you need to have a handle on what the options are that are gonna fit your budget and everybody's needs.

And also where the opportunities are to book those options while minimizing your costs by using points and miles. I really try to leverage those rewards to decrease our travel costs, but I'm getting those pieces into place 15 to 18 months in advance to make it possible. So I'll give you an example that's really tangible.

If I wanted to spend five nights at the Grand Hyatt Hawaii next year on points. I know that I probably have to book it a year out in order to find that award availability. 'cause that hotel books up. So that means a year before my travel dates, I need 200,000 points in my Hyatt account and I'm gonna get them through transferring from my Chase.

Ultimate Rewards I. How am I gonna get those Chase points? Well, if I don't already have them, probably my husband and I are gonna open a new credit card or two, or maybe three. And then we're probably gonna use the Chase shopping portal to top things off. But I have to get that lined up way in advance, right?

I need to be opening those credit cards 15 to 18 months before our travel dates. And even if you're staying in a condo, of course the bigger units are gonna get snapped up quickly for school breaks. And the same rule of thumb is gonna apply to grabbing flights on points, right? There's limited availability for award travel.

You've got a little more time there because the carriers that go from the US to Hawaii usually open their schedules 11 months out, and Southwest is six months out. So you've got much more time there to get things into place. But the cool thing about doing a trip like this with your extended family is that if you're all trying to pay for it together.

And you wanna maximize those rewards, you can collaborate a little bit, right? You can refer each other to those award credit cards to rack up even more points. So like if I looked and saw that American had the best schedule for everybody to go to Hawaii, I could refer my husband and my mother-in-law, and my brother-in-law and my sister-in-law, all to the Chase Sapphire Reserve.

They'd each get the current a hundred thousand point signup bonus, and I'd get another 40,000 points in referrals. So in total, we, that gives us a big bank of 440,000 points to use. And after checking availability, we could say, right, we're gonna transfer them to British Airways where we can pool our household points and get those really competitive rates to Hawaii on the American Airlines flights.

It takes a lot of research and strategy and time to put all that into place. I know that kind of stuff makes you a little crazy 'cause there's so many moving parts. But you know, just like with those quick little examples, you can make Hawaii an attainable destination for a multi-gen trip. You just really have to give it some advanced thought and, you know, do your, do your research.

Marcie:
No, absolutely. This was fantastic. So that is a wrap on today's episode. Thanks so much, Melissa, for chatting with me today. How can my listeners find you?

Melissa:
They can find me primarily@thefamilyvoyage.com. I love to write long form content, as you know. And I've got a, a whole page full of Hawaii articles that can help them plan their own destinations. Of course, they can get expert advice from you as well. And then they can also find me on Facebook and Instagram at the family voyage.

Marcie:
That's awesome. If you found this episode helpful, I'd so appreciate it. If you'd subscribe, leave a review or share it with a friend who's planning their Hawaii trip. It helps more travelers find this show, and I'm always so grateful for your support. Thanks so much for hanging out with me today. Until next time, Mahalo for listening and I'll see you in the next episode. Aloha.