Hawaii's Best: Travel Tips and Guides for Your Hawaii Vacation

First Time to Hawaii? Plan Your Trip Like A Pro

• Bryan Murphy of Hawaii's Best | Hawaii Travel Tips & Vacation Planning • Episode 153

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Did you know trying to see and do everything on your first trip to Hawaii can leave you exhausted before your vacation even begins?

Planning a visit to the Hawaii is exciting, but the endless options—choosing the right island, building your itinerary, and making sure you don’t miss out—can feel overwhelming for any first-time traveler. I've been there!

If you’re hoping to plan a relaxing, memorable, and culturally respectful Hawaii vacation, this episode is for you.

👉 In this episode, you will:

  • Find out how to avoid the most common itinerary mistakes first-time visitors make.
  • Learn what sets Oahu, Maui, Kauai, and the Big Island apart, so you can pick the perfect spot for your dream trip.
  • Get practical tips for responsible travel, booking must-do tours and restaurants, and truly embracing the aloha spirit.

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Scroll up ⬆️ and hit play now to start planning your first trip to Hawaii like a pro and make your Hawaii vacation truly unforgettable.

Whether you’re looking for the latest travel tips, want to support local businesses, or hope to deepen your understanding of Hawaiian culture, this episode is your essential companion for a stress-free trip to Hawaii. We’ll cover what first time visitors need to know about Oahu, Maui, Kauai, and the Big Island, share responsible travel advice, and reveal travel hacks to help you make the most of your time as you visit Hawaii.

🎧Related episodes:

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💻Related blog posts:

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🤓Chapters:

  • 2:04 Planning Your First Trip: Duration and Itinerary Tips
  • 5:08 Dining and Spontaneity in Hawaii
  • 6:46 Exploring the Main Hawaiian Islands
  • 10:18 Embracing Hawaiian Culture and Respecting the Land
  • 12:55 Common Mistakes and Final Tips

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🤙Show Aloha

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📲Connect

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This podcast is for travelers looking to plan a trip to Hawaii. Discover travel tips, itineraries, and traveling tips & hacks with guides to help you explore Hawaii. Whether you’re planning a vacation to the Hawaiian islands, dreaming of a Hawaiian getaway, or visiting Honolulu, Maui, Kauai, Oahu, or Big Island we’ll help you travel with aloha.

Edge of the Ocean, Stick Figure (w/ permission)

Ukulele and Chill, Coby G (w/ permission)

153_First Time to Hawaii


[00:00:00] Bryan Murphy: Ever wonder how to make your first trip to Hawaii unforgettable. Well, in today's episode, we're diving into everything from the unique charm of each island to essential travel tips. Ensuring your Hawaiian vacation is as unforgettable as it is seamless. So stay tuned for this one. Let's go.

[00:00:20] Bryan Murphy: Aloha, and welcome to Hawaii's Best, the podcast Helping Travelers Plan an unforgettable Hawaii vacation with insider tips and featuring local voices. I'm Brian Murphy, a husband Data three, and certified Hawaii destination expert. Each week I share local insights, travel tips, and up-to-date news, sometimes with guests across Hawaii and sometimes solo.

[00:00:41] Bryan Murphy: All to help you plan your next trip to Hawaii.

[00:00:48] Bryan Murphy: Hello. Hi, and welcome back to another episode. Today we're talking all about what to know for your very first trip to Hawaii. Now, if you're planning to travel to Hawaii for the very first time and you're feeling a bit overwhelmed with all the choices and information out there, then my friend, you have landed in the right spot, and that's what we're talking about in today's episode.

[00:01:12] Bryan Murphy: Today is all about demystifying Hawaii. For first timers and turning what might seem like an overwhelming task into an incredible doable adventure. One of the first things to know before even booking a trip to Hawaii is understanding that Hawaii is more than just a destination. It's this blend of diverse cultures, natural beauty.

[00:01:36] Bryan Murphy: And the kind of hospitality aloha that makes you feel like you've come home, even if it's your very first visit. With that, each island in Hawaii has its own personality and its own rhythm, and we're gonna be covering that. I. A little bit. In today's episode, I dive deeper into this topic on a recent blog post that'll be linked in the description of your podcast player for this episode.

[00:02:03] Bryan Murphy: So be sure to check that out. So as we dive into this topic of what to know for your very first trip to Hawaii, one of the biggest questions is, how long should your first trip to Hawaii be? Well, here's the thing. Hawaii is more than just a destination. It's this experience and to really soak up that experience, I would recommend planning for at least 10 days.

[00:02:25] Bryan Murphy: Maybe that's doable for you. Maybe longer's doable for you, but depending on your budget, right? But if you're able to. Why do 10 days? Well, it's, I think, the sweet spot that allows you to get over any jet lag, especially, you know, traveling with Hawaii's time zone differences, especially if you're traveling from the east coast of the US continent.

[00:02:47] Bryan Murphy: That is, what is that, that's like, that could be a, a six, five to six hour, depending the time of year, uh, time difference. And that takes some time to adjust. And with the 10 days and adjusting to the time zone. That leaves plenty of time to explore, relax, and immerse yourself into the island life. Now I know what you might be thinking.

[00:03:09] Bryan Murphy: 10 days might sound like a lot. But trust me, once you're there surrounded by the amazing beauty and the aloha spirit, time just flies. Plus those extra days will give you a chance to really dive deep and explore the island that you're on, or islands if you plan on doing some puddle hopping, you know, go to between islands.

[00:03:32] Bryan Murphy: But regardless of how long you plan on staying in Hawaii. Probably the best key advice that I could give is don't overstuff your itinerary. I, I see these itineraries and they'll post their itinerary, like on a Facebook group and every single day is, you know, doing Pearl Harbor and trying to do North Shore.

[00:03:52] Bryan Murphy: I. Oh, Oahu on the same day and then heading over to Kailua for lunch. I'm like, that's not possible. So just try not to overstuff. I know maybe this is like a once in a lifetime trip and you feel like you got to get it all in, but I know it could be tempting, but remember. You're on island time now, and part of the magic of Hawaii is in those unplanned moments like stumbling upon a beach or finding the local market or a place to eat with the most amazing tropical fruits and dishes that you'll probably have ever tasted.

[00:04:25] Bryan Murphy: So what's the best approach to planning then? So I would say start by jotting down your must do activities. Maybe it's watching the sunrise of Halala. Taking a helicopter tour over to the uh, Nepali coast. We're learning to surf on Oahu. Once you have your lists, spread those activities over your days.

[00:04:48] Bryan Murphy: Mixing in plenty of downtime, resort time, pool time, beach time, just getting lost time and, and maybe finding the local farmer's market. You know, this way you can get the experience of the best of Hawaii without burning out and feeling like you need a vacation from your vacation when you, when you get home.

[00:05:08] Bryan Murphy: And when it comes to dining on Hawaii, there's so many incredible places to choose from, from fruit trucks to even chain restaurants like, like Cheesecake Factory. For some reason. That is huge. NY Kiki, I don't get it, but hey, people love it and that's totally fine. Maybe they don't have a Cheesecake Factory back where they're from and, but there's also some locations that require reservations well in advance in one of those.

[00:05:36] Bryan Murphy: Popular spots is on Maui and that is Mama's Fish House. A be sure you plan on visiting a a spot like Mama's Fish House. Make sure you have reservations sometimes months in advance. I definitely would recommend that there's nothing worse than showing up at a highly recommended spot like Mama's Fish House, only to find there's a two hour wait, or even worse, they're fully booked.

[00:05:58] Bryan Murphy: So be sure to plan for that, but also plan for the unexpected. Maybe you're driving along. And you see a, um, a spot that you, that looks great, just do it. And it could be your favorite spot. It that could be like the moment you just never know when you're in Hawaii. That could be the moment that makes a trip.

[00:06:15] Bryan Murphy: You strike up a conversation with maybe the local owner there at a, at a local spot. Uh, so just be open to that. Be open to the spontaneity. Leave room in your schedule for those unexpected adventures. Maybe you'll hear about a local festival or a can't miss hike from a, you know, someone else who's traveling or a friendly local.

[00:06:35] Bryan Murphy: Those spontaneous experiences often end up being the highlights of your trip, and that's something that myself and my family have experience as well.

[00:06:46] Bryan Murphy: So let's just go ahead and give a brief overview of each of the Main Islands. So first, there is Oahu, or known as The Gathering Place, a blend of urban and peaceful country landscapes. So imagine transitioning from the vibrant streets of Honolulu to the relaxed North Shore. Which is famous for its surfing like at pipe, and along that stretch of coast AHU is also a mix of modern city and historic sites like Pearl Harbor, which is a living piece of US history.

[00:07:17] Bryan Murphy: And the next is Maui or the Valley Aisle. A top pick for many first timers, both Maui and Oahu are. Kind of the top picks for first timers, but, uh, Maui beautifully balances modern comforts with island magic, if you will. It's incredible. Beaches and food scene are compliment to its national wonders like Haleakala National Park, which offers, like I mentioned, breathtaking sunrises and sunsets Also, if you're able to do that.

[00:07:48] Bryan Murphy: Kui or the garden aisle is at Adventures Paradise with lush rainforest, dramatic cliffs and stunning trails. It's less developed. So Kui is rich in unspoiled natural beauty, perfect for outdoor enthusiasts. There's a couple small towns across the island, um, so there isn't a large. Uh, nightlife seeing it, the town is pretty sleepy.

[00:08:13] Bryan Murphy: It, it'll close pretty early, so just be aware of that if you're looking to, to go out late at night and great for if, you know, if you're retiring and wanna celebrate that. It's a great island for just being able to unwind. An unplug, and especially maybe if you're getting married, is also a great island to just kind of get lost together and start that new adventure together.

[00:08:39] Bryan Murphy: And then lastly, the big island of Hawaii Island is just huge. It offers everything from black sand beaches to volcanoes at Hawaii Volcanoes National Park. Its diverse landscape provides a sense of space and variety, and I think you'll notice that each island offers its own vibe and experiences from.

[00:08:58] Bryan Murphy: Urban and beach relaxation to adventure and tranquility. So when choosing, think about what you want from your trip, but also think about those that are going with you too, right? So think about your group, your family, whomever you're going with. Think about their wants, their needs, uh, for the island that you're choosing.

[00:09:16] Bryan Murphy: I would recommend if you're a young family, maybe look at, uh, Oahu. There's. Lots of diversity on Oahu, on the different sides of the islands, especially if you're staying in the Colina Resort area where Alani and, uh, Marriott are over there, out of Waikiki, out of Honolulu. Um, it's a great launching pad into going to the North Shore, visiting Honolulu, making your way all the way, all the way over to the east side in Kailua Town.

[00:09:45] Bryan Murphy: We love staying in the Colina area, but if you're staying in Waikiki and um, just, you know, have some time in Waikiki, is is cool to get that experience and see Diamond Head and Waikiki Beach and the whole thing, but also plan for some time. I. Out of Waikiki as well, especially getting up to the North shore and getting some country in is also a good refresh.

[00:10:08] Bryan Murphy: So as a young family, I would highly recommend Oahu, but really you can't go wrong in any of the islands. I mean, you're, you're in Hawaii. Come on, it's amazing. Delving into the heart of Hawaiian vacation also means. Embracing and respecting its rich culture, which can transform your trip into a truly unforgettable experience.

[00:10:27] Bryan Murphy: Hawaii is deeply rooted in vibrant traditions and customs, offering a unique blend of history and culture. Engaging with this culture enriches your experience and shows respect for the local community. So before your visit, take some time with yourself to learn about Hawaiian and Polynesian culture history and some basic Hawaiian phrases on this podcast.

[00:10:50] Bryan Murphy: We've had some of those and we've had some Hawaiian teachers on, so you go back and listen to those as well. I'll link those in the episode description, but also. Uh, just take some time, like a simple aloha, Mahalo can make a significant impact. And throwing up the chaka and just taking time and not using your horn and just letting the island time do its thing, uh, can go a long way.

[00:11:15] Bryan Murphy: And experiencing Hawaiian culture through its music and dance, and art, especially at a luau, is also a recommendation. It's not just. About the entertainment of the luau. It's a journey into Hawaii, and it's a journey into Hawaiian cuisine. A mix of traditional dishes influenced by diverse cultures. So try dishes like Poque, KAA Pig to connect with the culture and support local businesses.

[00:11:41] Bryan Murphy: You know, the food is culture and culture is food. So be sure to try some of those dishes maybe that you haven't tried yet or don't have at home. And also remember that Hawaii is more than just a tourist destination, so respect the land. It's, you know, one of the sayings is malama ina care for the land by caring for the environment and leaving no trace wherever you go, whether whatever hike you do.

[00:12:04] Bryan Murphy: Wherever you go, just leave no trace, pick up, you know, trash rubbish along the way. This approach ensures that the islands remain pristine for future generations, for your children, your, your children's children. These islands are better than we found it, so that's a huge topic right now, as I'm sure as you have done any research on traveling to Hawaii.

[00:12:28] Bryan Murphy: Is making sure that responsible travel is at the forefront of everything and anything that we do. Now, I was gonna cover some of the things to do on each island, but I just think that's just gonna get a huge episode and too much info. I'll have to do separate episodes about what to do on certain islands and especially what to do with certain.

[00:12:53] Bryan Murphy: You know, months of the year. I wanna talk a little bit about some mistakes to avoid, and one of those key mistakes to avoid is, like I mentioned, overt stuffing your itinerary. It's tempting to fill every day with activities, but remember, the essence of Hawaii is in the experience, not just in the doing.

[00:13:11] Bryan Murphy: So rushing from one activity to another can be overwhelming. So slow down. Savor each moment go a little bit easier on your budget. Whether it's relaxing on a beach, hiking, enjoying a simple meal, these things can help you to avoid overt stuffing your itinerary. Regarding weather, don't let unpredictable forecast deter your plans.

[00:13:33] Bryan Murphy: Hawaii's weather can change rather quickly, and a brief shower can often be followed by sunshine. So also leads me to a next point, kinda goes together, but also never underestimate the Hawaiian sun. It's closer to the equator and even on cloudy days. Be sure to protect yourself with reef safe sunscreen.

[00:13:51] Bryan Murphy: So stay hydrated. Wear protective gear like hats and sunglasses, and if you're looking for a list of some reef safe protective sunscreen, we also did a post on that, and I'll be sure to link that. In the episode description on your podcast player, and finally, avoid making the mistake of not planning ahead.

[00:14:11] Bryan Murphy: I know I mentioned about restaurants can book up fast, but also some of the tours can book up quickly. If you have dates on the calendar that you're gonna be going to Hawaii. Get those down, get your your accommodations and get your flights booked. And then immediately as quickly as you can, try to get a list together of what you wanna do, what your group wants to do.

[00:14:30] Bryan Murphy: Book those tours, book those luaus just so they don't book up. Or you have some fomo like, I wish I would've done that. But be sure to book in advance as best as you can. So there you have it. A high level overview of what to know. For your very first trip to Hawaii and to dive deeper into what to know for your very first trip, go to the show notes, also links to the articles I mentioned such as a blog post that goes into deeper what to know, uh, for your, for your very first trip to Hawaii.

[00:15:05] Bryan Murphy: Alright, until next time. As always, live with Aloha

[00:15:13] Bryan Murphy: Mala for listening to this episode of Hawaii's. Best to stay up to date on future episodes. Hit follow on your podcast app. Hawaii's Best is a production of shore break media group with editing by easy podcast solutions and music courtesy of our friends. Stick figure.


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