Hawaii on Three Budgets: Your Complete Island Planning Guide

Episode Description

Dreaming of a Hawaiian vacation but not sure where to start? In this episode of All Things Travel, hosts Ryan and Julie wrap up their three-budget series by exploring the islands in three completely different ways—proving that paradise is accessible no matter your budget.

What You'll Discover

Join travel advisors Ryan and Julie as they break down three distinct Hawaiian vacation experiences for a family of four, each offering unique adventures across the islands:

Budget-Friendly Oahu Adventure (Around $155/person/day) Experience the best of Waikiki without breaking the bank. Stay at the Aqua Aloha Surf Waikiki with free breakfast, explore iconic sites like Diamond Head and Pearl Harbor, and discover why Oahu offers the biggest bang for your buck. Learn how to maximize free and low-cost activities while still capturing that authentic Hawaiian spirit.

Moderate Two-Island Experience (Around $300/person/day) Ready to see more? This 8-10 day journey combines the energy of Oahu with the relaxation of Maui. From Pearl Harbor passport tours and catamaran snorkel cruises to the legendary Road to Hana and Molokini Crater, discover how to experience Hawaii's must-do activities while staying at quality resorts like the Hilton Garden Inn Waikiki and Sheraton Maui.

Luxury Multi-Island Escape (Under $700/person/day) Indulge in 10-12 days of pure Hawaiian luxury with stays at Four Seasons properties in Oahu, plus your choice of the Big Island or Maui. Enjoy private island tours, chartered catamarans, helicopter rides over dramatic sea cliffs, VIP luau experiences, and exclusive cultural programs. Learn why the Big Island's Volcanoes National Park is an absolute must-see.

Episode Highlights

• Why Oahu is perfect for budget-conscious travelers
• The best free and low-cost activities across the islands
• Smart strategies for keeping food costs manageable in Hawaii
• Private vs. group tour options: when to splurge
• Inter-island flight planning tips
• The ultimate Hawaii activity recommendation from experienced travel advisors

Whether you're planning your first Hawaiian getaway or returning for another taste of aloha, this episode delivers practical insights and real pricing to help you craft your perfect island adventure.

Bonus: Hear where Julie's heading next—a magical Disney Christmas trip with family and clients!

Ready to start planning your Hawaiian escape? The travel advisors at Wonder and Beyond Travel are here to help create your one-of-a-kind journey.

Transcript

j_1_11-17-2025_143440: 0:00

Aloha and welcome to all Things Travel. We often work with clients who are dreaming of traveling to Hawaii. There are so many great options and activities to consider, but the islands accommodations and tying you spend there is often dependent on your budget. Today we're concluding our three budget series by discussing different ways to see Hawaii.

ryan_2_11-17-2025_143439: 0:23

Listen in with travel advisors and destination experts. Ryan and Julie. I'm your travel professor teaching you everything you need to know to have a magical vacation, and she's a Disney loving Maryland mom of three and a specialist in family travel. Whether we're discussing incredible destinations, top vacation tips or sharing personal stories, it's always all things travel. Alright Julie, so it is starting to get cold here in the Midwest. It's probably getting cold in Maryland. So I thought a great way to wrap up our three budget series is to talk about one of our favorite places, Hawaii.

j_1_11-17-2025_143440: 1:06

Hawaii.

ryan_2_11-17-2025_143439: 1:08

And Hawaii is one of those, you know, every time I plan a trip or work with a client talking about Hawaii, it's like a puzzle. And I don't mean that in a bad way, but it's like, you know, what islands do you want to see? What activities do you want to do where do you wanna spend most of your time? And really, there's a lot of choose your own adventure when it comes to Hawaii. And so it became really interesting as I started to put these three different trip options together.

j_1_11-17-2025_143440: 1:33

Yeah, I'm excited to hear about this because we both have some, in-person experience in Hawaii, but very different experiences.

ryan_2_11-17-2025_143439: 1:41

absolutely. But before we do that, I wanna remind folks, if you did not listen to last week's episode and you're wondering what in the world is Ryan talking about with these three budgets? We did a great, episode about Japan, looking at Japan on three budgets for a family of four. So I did the same thing, Julie, as I did last week. I took Hawaii and I said, if we want to do this on a more economical budget, a moderate budget, and a luxury budget, how could we go about that? when I think of how do I see Hawaii? Still keep mindful of how much I'm spending. I think as an island, Oahu has the biggest bang for the buck. Would you agree with that?

j_1_11-17-2025_143440: 2:26

Yeah, because there's such a variety to do there.

ryan_2_11-17-2025_143439: 2:30

Yeah. You have anything from classic, Waikiki to the North Shore and surfing to some great landscapes. and water activities. There's so much to see now, I will say. Once you've gotten off Oahu and seen some of the other islands, you'll definitely get I think, more of the true Hawaiian sense there. but Oahu is gorgeous and I would go there in a second.

j_1_11-17-2025_143440: 2:56

Agree.

ryan_2_11-17-2025_143439: 2:57

So as I'm talking about this more budget, option, the tone here is simplicity. Classic, Waikiki vibes, think food trucks, open beaches, local culture, affordable group tours. And the good thing Julie is. Oahu and all the islands are very drivable, so you can, you can really go off and see a lot of these things on your own to match your schedule, your flexibility, and really to keep it very budget conscious.

j_1_11-17-2025_143440: 3:27

Mm-hmm.

ryan_2_11-17-2025_143439: 3:28

So this is a seven night trip for a family of four and that seven nights is exclusive of travel. And we are gonna be staying at the Aqua Aloha Surf Waikiki, and this is a great option. For the budget conscious traveler. I've quoted this for folks that are like, we don't care as much as where we stay, but we want the right location. it's clean, it's fun. It's definitely got a, a Hawaiian theme. It's just a quick walk to the beach and also has free breakfast, which is great for families.

j_1_11-17-2025_143440: 4:03

Especially when you're looking at resorts in Hawaii, if you can get any sort of food included, it really helps with your budget because the food is such a big expense there.

ryan_2_11-17-2025_143439: 4:15

So what are the types of activities that are gonna be, focused on in this trip? we're gonna do a, group, Oahu Island highlights tour, where we're gonna see the Dole Plantation, the North Shore Surf beaches. We're gonna go to nnu Poly Lookout. and that's just gonna give you a really good overview of the island. A couple things that are actually free. you know, going to Diamond Head, there is a small entry charge.

j_1_11-17-2025_143440: 4:42

Yeah.

ryan_2_11-17-2025_143439: 4:42

but it's so iconic and just a great experience. Hanah Bay snorkeling, which is one of the best snorkeling spots in Hawaii. Pearl Harbor is free. You just have to get onto the park service and make your reservations. So right there, boom, boom, boom. You've got some of the biggest things on the southern part of Oahu that really isn't costing you much of anything.

j_1_11-17-2025_143440: 5:04

You're staying in Y Kiki, so you definitely wanna have some free time

ryan_2_11-17-2025_143439: 5:09

Yes.

j_1_11-17-2025_143440: 5:10

on the beach, to explore the town there. You don't need to have, a packed itinerary

ryan_2_11-17-2025_143439: 5:16

Yep.

j_1_11-17-2025_143440: 5:16

a place like Hawaii.

ryan_2_11-17-2025_143439: 5:18

As far as food options, y Kiki is more of a city area, so you're gonna have anything from, fast food places, local places, all the way up to nice dining. You've got the Alma Shopping Center, that's not too far, that gives you lots of options. you can do a lot here by just focusing around this area. if we look at the price breakdown, Doing this budget trip here, Julie would look to be about 155 per person per day. That's gonna be your lodging, food, that's gonna be your local transportation. If you're in the city, you know, using public transportation or maybe some Ubers every once in a while and you've got then those couple of activities, I think you've got a really nice week here.

j_1_11-17-2025_143440: 6:02

Wow, that itinerary is simple. It's easy to put together. easy to follow, and it's so affordable.

ryan_2_11-17-2025_143439: 6:08

Great. We'll talk about, a moderate Hawaii option where we actually do two islands in our stay.

j_1_11-17-2025_143440: 6:16

So this is a really popular combination of Oahu and Maui. A lot of times Oahu

ryan_2_11-17-2025_143439: 6:23

Okay.

j_1_11-17-2025_143440: 6:24

kind of that introductory and, and there's more activities to do, and Maui is the more relaxing side of a trip like this. At least that's how I

ryan_2_11-17-2025_143439: 6:33

Yep, absolutely.

j_1_11-17-2025_143440: 6:36

This trip is gonna be anywhere between eight to 10 days, and it's gonna be that classic Hawaiian vacation, but with better hotels, with more resort pool options. You're getting the two islands, like we mentioned. There's some group tours as well as a few options to splurge on some meals. So we're gonna start in Oahu and we'll be there for four to five nights, staying at the Hilton Garden in Waikiki Beach. This is a really solid mid-range hotel. You're still close to the beach, close to the restaurants, in that really great location.

ryan_2_11-17-2025_143439: 7:08

Yeah, I actually have stayed at this hotel, Julie. it's a really good location to walk down to the beach. this was the first hotel that I was ever introduced to one of those fancy, Toilets with all the different settings and options and, and all that stuff. So there you go. that's part of the fun. maybe that's part of the attraction of this itinerary.

j_1_11-17-2025_143440: 7:29

All right, so here's some activities we want to include here. The first one is the

ryan_2_11-17-2025_143439: 7:33

I.

j_1_11-17-2025_143440: 7:34

Pearl Harbor Passport Group experience, including tours of the USS, Arizona, USS, Missouri, the Aviation Museum. And this is great because it's a full day, it's really educational and it's also great for families. So you have that one day where you do this big history lesson and then you can stay in the area, grab some lunch, Another activity we're gonna include is the group catamaran, snorkel crews. And here's my favorite part, you can do turtle watching, which are my favorite animals. There's shallow reefs here, so it's easy to see a lot of, ocean life. And this is like a really classic y Kiki experience. Whenever I have clients, I'm planning a trip to Hawaii I wanna make sure they have an option to snorkel, get on the catamaran and see the coast from that viewpoint.

ryan_2_11-17-2025_143439: 8:21

Yeah, I love that.

j_1_11-17-2025_143440: 8:22

And the last activity we're gonna include on Oahu is a group surf lesson. This is like iconic Hawaii, right? Learning to surf. this is really fun for the whole family to learn something new together. All right, so then we're gonna fly over to Maui. the itinerary we have is gonna include your flight over to Maui. It's a short flight, and you're gonna be there for four to five nights, staying at the Sheraton Maui Resort and Spot in Cali. This is a beautiful beach front resort. It has a great pool. They offer nightly cliff diving. Just a really great place to be. We're gonna include a couple of what I like to call the iconic things

ryan_2_11-17-2025_143439: 9:00

The must dos. Yep.

j_1_11-17-2025_143440: 9:02

The must dos. The first one is The Road to Hana, and this is a group tour. And I do recommend this as a group tour because it can be a stressful drive to take, if you're gonna do it yourself. you're gonna drive down the road to Hana, pass the waterfalls. You're gonna see the rainbow eucalyptus trees make a stop at the Black Sand Beach. This is just one of those really iconic sites to see.

ryan_2_11-17-2025_143439: 9:25

Very cool.

j_1_11-17-2025_143440: 9:27

You are also gonna go to the Molokini crater and go snorkeling. This is one of Hawaii's best snorkel sites, so you're back on that catamaran, but this is a whole different area of Hawaii to snorkel on the Maui Ocean Center. This is a self-guided activity and great for families. Kind of a more relaxed day, but a little bit of marine education for your little ones. if we break down the pricing here, and we are gonna include our lodging, the food, inter island flight, the local transportation, and some of those tours, this comes to close to about$300 per person per day. And I think that's, that's actually like overestimating being generous with that budget because like we mentioned before, with the food, you can kind of upscale it or. go more quick service route. This is amazing to be able to

ryan_2_11-17-2025_143439: 10:21

Yeah,

j_1_11-17-2025_143440: 10:21

both Oahu and Maui and do some of those classic experiences.

ryan_2_11-17-2025_143439: 10:25

You've got a rental car your entire time on Maui. You've got it for partial time on Oahu. You've got your inner island flight taken care of. Boom. so before we talk about the luxury option, where in the world is wonder and beyond travel

j_1_11-17-2025_143440: 10:40

This is a fun one because when this comes out, I am on my big Disney trip.

ryan_2_11-17-2025_143439: 10:47

really?

j_1_11-17-2025_143440: 10:48

my family, we love to travel to Disney. The first week in December, that's when we do our big trip focused around the holidays. I love seeing all the Christmas decorations. So it's my personal family. My in-laws are coming with us, and then I actually have five client families going. that same week.

ryan_2_11-17-2025_143439: 11:09

Holy smokes.

j_1_11-17-2025_143440: 11:10

A lot of the things that we are planning on doing are the same things I'm planning for my clients to do. Mickey's very merry Christmas party at Magic Kingdom, the candlelight processional at Epcot. I've got a whole list of the snack items to try at the party and then at the festival, the holidays. I love the decorations at Hollywood Studios for Christmas. They're so nostalgic. It's just gonna be. A lot of fun. I'm sure I'm gonna have some great photos and my kids are counting down the days until we get there.

ryan_2_11-17-2025_143439: 11:43

I am super excited and I have been, um, told by Jasmine that we are doing Disney next Christmas. so we can experience all of that because we both love Christmas. He loves Christmas a lot. and neither of us have been to Disney for Christmas, so that'll be a lot of fun to experience so we'll be getting your help for that trip.

j_1_11-17-2025_143440: 12:04

It's so magical.

ryan_2_11-17-2025_143439: 12:06

Well, we love celebrating where our clients are headed, even when it's us. and we can't wait to hear about their trips. so, who knows, maybe your trip will be featured next. All right, Julie. So two great trips, budget, moderate, and now we're gonna focus on the luxury when it comes to Hawaii, and we're gonna have some options here. Okay. We're gonna start in Oahu, and then you can decide where we're headed next. this is a 10 to 12 day trip. The tone here, it's gonna be more exclusive with private, options, top tier resorts, private chartered experiences, premium dining, great service.

j_1_11-17-2025_143440: 12:47

Point.

ryan_2_11-17-2025_143439: 12:48

And because of that 10 to 12 days, you've got a slower pace, which is really nice. So we're gonna start with five to six days in Oahu, and we're gonna stay at the Four Seasons Resort, Oahu at Colina. Now, you and I love Colina because Ani a Disney resort and Spot is there, and right next to it is the Four Seasons. What a fabulous spot to start your Hawaiian vacation.

j_1_11-17-2025_143440: 13:14

It is so lovely.

ryan_2_11-17-2025_143439: 13:16

So that is a five star oceanfront luxury community. There's great dining there. There's other resorts you can take advantage of the dining and the, and the activities there. You've got lagoon access, kids Club, private beach sections. Just get there and unwind, right.

j_1_11-17-2025_143440: 13:36

Yes.

ryan_2_11-17-2025_143439: 13:38

So here are the activities we're gonna be partaking in. We're gonna have a private island highlights tour, that's gonna tailor our stops based on where we want to go. You're gonna have a private guide with your vehicle and you're basically gonna be able to say, these are the places in Oahu. I want to see. Let's go do it. You're gonna have a private catamaran charter where you can snorkel, you can dolphin and sea turtle spot your drinks and your snacks would be included in that. And you're gonna have a VIP experience at a luxury luau. So you're gonna have front row seats, table service, crafts, all that kind of stuff to really get in that luau experience. After our five to six days on Oahu, we can decide to go to Maui or to the big island of Hawaii. What would you like to do? Well, we're gonna talk about both of them, don't worry, but what do you want? Which one do you wanna talk about first?

j_1_11-17-2025_143440: 14:31

The big island.

ryan_2_11-17-2025_143439: 14:32

What are we thinking of when we think about the big island?

j_1_11-17-2025_143440: 14:35

Volcanoes.

ryan_2_11-17-2025_143439: 14:36

Volcanoes. So now we're gonna head over to the big island of Hawaii and we're gonna stay four to six nights at The four seasoned resort Holloway, and this is a premier Hawaiian lecture resort. Beautiful black lava, turquoise water, you know, Hawaii, the island is just so completely different than Oahu that I think this is a really good pairing. What are we gonna be doing? We're gonna be doing a private night, manta ray snorkel. So you'll have a private boat, a guide, a private volcanoes national park tour where you're gonna see the lava tubes, the steam vents. You're gonna have private hiking, to go to some of the best scenic routes. You're gonna have a private cultural program at the resort where you can do things like learn how to, like, make lays, take ukulele lessons. you're gonna be doing coconut frond weaving. Very cool. Right? mean, imagine as a family getting to do all those, all those special things.

j_1_11-17-2025_143440: 15:39

the thing that I really like about these activities is that a lot of these are very specific to just this island.

ryan_2_11-17-2025_143439: 15:45

Yes, absolutely. definitely the volcanoes, And because it's over four to six days, it's not rushed. you can still have time to relax, enjoy. So let's think about the second option, which is Maui. if we stayed in Maui for four to six nights, we're Gotta stay at the Four Seasons Resort, Maui at Yle, which is known for their legendary service. Huge rooms, beachfront, perfection. This is A prototypical Hawaiian resort. What are we gonna be doing here? A private helicopter tour, Julie, a private helicopter tour on the West Maui Mountains and the Molokai Sea Cliffs. One of Hawaii's most dramatic flights. You're gonna be doing a private road to Hana. So on their last, option, we had A group one. Now it's private, customized stops. The driver takes care of all the driving. You're gonna be in a luxury SUV and you're also gonna have a private beachfront photography session. you can spend the time getting pictures with the adults pictures, with the kids, and really have those memories there. we've got our lodging. our food that's a combination of resort dining and tasting menus. We've got our private tours and charters. our private transfers and luxury rentals when it comes to transportation. And we also have our inner island flights. Julie, we're looking at less than$700 per person per day, and that's on the high side.

j_1_11-17-2025_143440: 17:18

Wow. I've just so enjoyed seeing like the variety in the itineraries and how much you can really do this is the part of our job that's just fascinating to me and, and what makes it so much fun.

ryan_2_11-17-2025_143439: 17:33

What is a must do activity? If you're going back to Hawaii and somebody's putting together a trip like this that you say you have to do this, what do you think?

j_1_11-17-2025_143440: 17:46

On any island volcanoes, national Park,

ryan_2_11-17-2025_143439: 17:51

You know, I have been there and it is unbelievable. It is just other worldly. it is so unique the whole island of Hawaii, and the two sides of the island. I just think you haven't seen Hawaii till you've seen that.

j_1_11-17-2025_143440: 18:07

Yeah. How incredible.

ryan_2_11-17-2025_143439: 18:09

The world is full of wonder and your next great adventure is waiting at Wonder and Beyond Travel. We work with you to create a one of a kind journey, taking the stress off your plate so you can focus on the joy of exploring and the memories that will stay with you forever. If you're ready to start planning or you just wanna dream a little bigger, head on over to Wonder and beyond travel.com. We'd love to help you get started. We look forward to talking to you next week on all Things Travel, when we discuss cozy winter getaways.