How I Plan Hawaii Itineraries for First Timers

by Mariam Beard • Last Updated: October 2022

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First off, welcome!

I have worked full-time as a concierge here in Waikiki – off and on over the past 10 years (minus Hawaii closures over COVID). I have worked as a concierge and planned THOUSANDS of Hawaii itineraries. I live on the island of Oahu and I make Hawaii videos to take the guesswork out of planning your trip. I recently had a subscriber reach out to me asking for tips on how to plan their Hawaii vacation.

If you’ve never been to Hawaii before, it can seem really overwhelming in this video I’m going to share with you exactly how I do it.

Planning Tips

This video is for you, if this is your first time planning a Hawaii vacation or if you’re the lead planner of your family or group. Let’s pretend you’re a first time visitor to Hawaii have never been here before.

My Vacation Planning Process

I’m going to take you with me through my entire vacation planning process on things that I think about towards making your Hawaii vacation as easy and worry-free as possible.

I’m going to break this article up into three sections:

  1. Intro & Planning
  2. Reservations
  3. Completed Itinerary

Now, I’ve been doing this for a long time. I can usually do this entire conversation in about 15 to 20 minutes.

Goal of Conversation:

Help you get your bearings on where the hotel is located, things to do some excursion and to have a general game plan

The Game Plan

The game plan gives you ideas and framework that leaves plenty of room for spontaneity and of course relaxation. The idea is not to plan every single minute that you’re here, but rather plan a few key things and then have options on everything else.

Concierge Example: Brunch Ideas

For example, if on the phone you’ve told me you’re a brunch person (1st off – same), I might also email you 3-4 brunch spots that are near the hotel, their menus and their hours.

Do you need to go to all those brunch places?

Of course not.

But, if you wake up one morning and you decide you want to go to brunch at least you have a good place to start that way. You’re spending more of your time on vacation enjoying your vacation instead of wasting your time in Hawaii – Googling yelping, researching when all this can be done BEFORE you even arrive.

Concierge Example: Dietary Restrictions

In addition to some suggestions that I’ll provide that are close to the hotel, I’ll typically also give you some of MY FAVORITES and a few other options, depending on your specific dietary requirements.

For example, if you have kids that are picky eaters or people in the group who are vegan or require gluten free alternatives.


For this planning process, I’m going to say the question that I would normally ask the guests explain my rationale for why that is an important question and how YOU can apply it to your own Hawaii vacation.

Let’s get into it.

Also, do you have any vacation planning tips? If so comment down below.

PART ONE: Intro & Planning

So, let’s take it from the top first.

You’re calling your hotel and you’ve been asked to get transferred to the concierge.

I’m the one who answers first.

Contact Info

I’ll ask you for your contact information:

  • First Name
  • Last Name
  • Your Phone Number
  • Your email address

Why is this so important?

The phone number is specifically important especially for disconnected. Often by the time you reach me, you’ve either called the reservation center or you’ve called the hotel, been transferred a couple of times, and you finally reached the concierge desk. So, if we’ve been chatting for a few minutes and we get disconnected, it can be hard for you to get back to me specifically – and that can be frustrating for anyone.

During the Call

While we are chatting, I’m telling you that I’ll be taking notes. I’ll let you know that I will email you a SUMMARY of everything we talked about because in this conversation will be going over a lot of things and a lot of information.

You know that I’m taking notes.

You don’t have to ask about the spelling of certain streets, the names of certain restaurants.

Just know that everything we’re chatting about, I will type out and send to you. I do this every day. I go over places for tour pickups, restaurants, activities, things to do. So for me, it’s second nature but for someone who’s never been here before, it’s a lot of information.

How to Apply this to YOUR Vacation

If you’re calling your hotel and speaking with your concierge, within 30 seconds, say just in case we’re disconnected, can I give you my cell phone number and can I also get your direct phone line.

This way, if you are disconnected you have a point of contact and a way to reach that person next what is the first and last name booked under the room reservation.

I’ll ask for the first and last name of the room reservation because a lot of hotels have similar names. I also want to tie all my notes and reservations together.

I’ll make the lead passenger/guest for your activities the SAME NAME as the name thehotel room is booked under.

Another reason for doing this is to make sure you are calling the right hotel and that all of your reservations are booked with the correct pickup location if you’re booking a tour or excursion.

3 Hyatts

For example, there are three Hyatts
1. Hyatt Regency
2. Hyatt Place
3. Hyatt Centric
That’s 3 different hotels in 3 completely different areas of Waikiki. All 3 hotels start with “Hyatt.” If you’re staying at Hyatt Centric and you quickly type in “Hyatt” in Google, it’ll typically send you to the Hyatt Regency – which is the wrong hotel. This is a great reason why it’s important to double check the hotel and room name reservation.

Multiple Outriggers

Similarly for Outrigger properties, there is a:
1. Outrigger Waikiki Beach Resort
2. Outrigger Reef Waikiki Beach Resort
3. Waikiki Beachcomber by Outrigger
There’s even Outriggers on the island of Maui, for example. If your first call was to the Outrigger reservation center, you may be transferred to the wrong Outrigger hotel when you make the call.

Multiple Hiltons

The same can be said for Hilton properties. There is a:
1. Hilton Hawaiian Village – which is oceanfront
2. Hilton Waikiki Beach – which is on Kuhio Avenue (and NOT oceanfront)

The Hilton Waikiki Beach Hotel and the Hilton Hawaiian Village are on two completely opposite ends of Waikiki. This is especially important if I’m booking a tour excursion for you with a hotel pickup. If I didn’t know that you were staying at the other hotel by the time that we figured it out, there’s a chance that the shuttle pickups that you need from the Hilton Hawaiian village might be full.

Now, this is a really easy mistake to make. Oftentimes when you’re staying at a property you type the name in Google and often just click the very first one. Some hotels also have similar sounding name. For example, there’s the Halekulani hotel, which is oceanfront, which at first glance may sound very sim to the Hokulani hotel, which is a block away.

How to Apply this to YOUR Vacation:

When you call your hotel and work with your concierge, double check that you’ve called the right property.

It’s often helpful to have the ADDRESS handy.

Similarly, if you booked your own airport shuttle service or are using a taxi to get to/from Waikiki, having your HOTEL ADDRESS is helpful. This way you won’t be dropped off at one similar sounding property…waited in the check-in line for a bit…only to realize you’re at the WRONG HOTEL. Yikes!

PART TWO: Reservations

For activities/tours or any reservations, I’ll make the LEAD PASSENGER name match the HOTEL ROOM RESERVATION name.

This makes it easier for the activity/tour to reach you, if necessary. If the activity/tour is unable to reach you on your cell phone (ex. if your phone is an international phone number), the activity/tour can also call the hotel. Hotels will ask for the FIRST and LAST NAME of the guest. If the activity/tour name does not match the hotel room name, the front desk would be unable to transfer the call – as they would not know what room you are actually in.

Reconfirm your phone number.

PART THREE: Completed Itinerary

Things to take note of:

  • Any block parties or festivals on your arrival/departure date (road closures & traffic)
  • Specific activities or points of interest?
  • Reconfirm check-in & check-out dates at the hotel, especially if booked with a 3rd party site
  • Time Zone differences – Early start Pearl Harbor tours are best for East coasters in the beginning of your trip when you are already +5 hours ahead.
  • No activities/tours your 1st full day on-island (in case of any travel disruptions or flight delays)
  • Activity pricing can vary by ages (ex. Luaus often have adult, teen, and child pricing)
  • Age minimums (ex. Kualoa Ranch ATVs require drivers to be 21 years old)
  • Any activities that require a reservation from the State of Hawaii (ex. Diamond Head)
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2 responses to “How I Plan Hawaii Itineraries for First Timers”

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Aloha! I'm Mariam.

I'm an Oahu resident sharing my adventures here in Hawaii to help take the guesswork out of planning your trip to Hawaii.

I've worked full-time as a concierge for a decade and have planned thousands of itineraries for travelers like you!


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