First Timers

So, you've never been to Hawaii?

Not to worry, we have you covered.

Here is where we'll guide you step by step to actually book your own trip.

For your first trip (and trust me it won't be the last),

I'm sure you'll want to see Pearl Harbor, Waikiki Beach, Diamond Head and Honolulu.

Those historic Hawaiian sights are all located on the island of Oahu.

My suggestion, is to fly into Honolulu (HNL) and stay in Waikiki for two nights.

After you've taken your 1 1/2 day personally guided tour of Oahu,  hop on a plane for Maui (OGG).

This is where you'll spend the rest of your first trip to the Hawaiian Islands.

I do not recommend trying to see more than 2 islands in one trip.

The problem with that is, every time you switch islands means you have to repack, turn in your car, check your luggage, wait to board, fly to the next island, reclaim your luggage, get your next car, drive to your next accomodation.  That will waste half a day, and cause headaches.

The only reason I'm suggesting you stop at Oahu first, is because if you ask,

most people want to see those world famous sights.

As I said, this will not be your last trip.  You'll be able to see the other islands on subsequent trips.

Let me add this.

It seems like I've been hearing this a lot lately.

Everytime I hear of someone consulting a travel agent to plan a Hawaii trip,

they wind up taking a Hawaiian cruise.  


I don't mean that as a pirate.  That's frustration.

Let me repeat this.  DO NOT TAKE A HAWAIIAN CRUISE.

Especially on your first trip here.  There may not be a second.

Travel agents must be making one hell of a commission from Norwegian Cruise Lines.

(Norwegian is the main cruise line in Hawaii.)

If you've been on any cruise, you know your vacation is mainly about the ship.

That's where you'll spend 80% of your vacation.

You only get off the ship for 6 to 8 hours at a time.

That's no way to see Hawaii.

You will only get a taste of each island.


I'd rather be able to savor one or two islands, and go back and do it again with two more.

Don't worry, if you do it my way, you will be back.

It will be irresistable.

Here's how...


Here's what to do first.

Decide when you want to go.  Make sure you have at least a 10 day window.

For this trip, I'd rather you have at least 12.  


Once that's decided, book your Maui condo.

Yes, the Maui condo first.

 That is where you'll be spending the majority of your nights, so settle that first.

Obviously, if you've picked February 10th to the 22nd as your window, book the condo for

February 12th to 21st.  (Why not the 22nd?  You'll leave Maui on the 21st and arrive home on the 22nd.)

I would suggest you start looking for your accomodations a year ahead of time.  That way you'll have a better variety of choices.  They start getting picked over as you get closer to your dates.

Use one of these two links to find your place.  

You'll find condos across South Kihei Rd. from the ocean will be cheaper than oceanfront.  Also consider that the beach is only a 2 minute walk, and you can still have an ocean view from across the road.

After you've accomplished this (Congrats, you're going to Hawaii!!),

now find a hotel in Waikiki for our theoretical dates of February 10th to 12th.

Try here.


(Of course, you'll have to adjust dates to match yours.)

You can see I've selected hotels with a price range of $100 to $200 per night.

You'll also notice these are located away from Waikiki Beach (way too expensive).

Besides, these are all within walking distance.

 I've stayed at the Courtyard Marriott on Royal Hawaiian Ave.  

It is a very nice place with a pool and usually around $175/night.

Okay, now you have your lodging set.

Next, let's start looking at airfare.

Here's a link I've set up.  


I've set it to fly out of Toronto.

(Adjust it to fly from your airport.)


About flying from Toronto:

I've tried to make this work on 3 separate trips, because the initial airfare has been

generally $300-400 cheaper than flying from Buffalo (my home).

However, the inconvenience and add-on costs are no longer worth the initial savings to me.

You'll need to stay overnight in Toronto (because you'll be flying out before dawn).

You'll need to pay to park your car.

You'll have to drive 2 1/2 hours (from Buffalo) the day before.

And the worst: You'll have to drive 2 1/2 hours after flying 15 hours overnight.


(I didn't even mention going through Canadian customs.  Read about my adventure HERE.)


Just pay the extra money and fly out of your home airport.


You'll usually have one or two stops on your way to Honolulu (try for one).

It also includes your flight to Maui, and the return flight to Toronto.

Of course, you'll have to adjust the dates to fit yours.

If the airfare seems high (I'd say anything below $750pp/rt is good), you can set up an alert to watch.

When it drops to your liking, grab it.

Just don't wait until the last minute, you don't want to get stuck spending $1200 per ticket.

The longest I'm comfortable waiting is 4 months prior.

As far as flying out of Toronto goes, you can get a hotel there near the airport for about $150/night for the night before you leave.  The best part is it includes parking for the length of your trip!

Of course, you don't have to fly out of Toronto.  Just change the departure airport in the search.

The last thing you'll need is a car.

I use Kayak for that, also.

Don't forget you'll need one for Oahu and Maui.

Other advice I can give you, at this point, is go to the Pearl Harbor site.

You'll have to wait until two months before your visit, but you will need tickets.

They aren't expensive, it just helps keep it orderly and respectful.

I'll be adding more Oahu info as time goes by.  

But, one place I'd definitely recommend is Lulu's on Waikiki for breakfast.

© 2023 by EK. Proudly created with

  • w-facebook
  • Twitter Clean
  • Pinterest - White Circle
  • White Instagram Icon