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Travel Arrangements

When to Go


We’re going to take this planning section step by step.  So, we’ll start here.  There really isn’t a bad time to go.  The temperature doesn’t vary all that much , and you can get better prices in the summer and fall.  That doesn’t mean I’m suggesting you go then.  But if that's your window, by all means go!  The difference between EST timezones and HST varies.  They don’t observe Daylight Savings Time.  So, they are 5 hours behind in winter, and 6 in summer.  It’ll take you a little time to adjust.  The first morning, you’ll be up at 3am, chomping at the bit, 

waiting for the sun to come up because it’s already 8am at home.  

My favorite time to go is February. Why?  

In one word, Whales.


















(Those are our friends, Bill & Tara on the boat)

The Humpback Whales migrate here from Alaska between the months of December and April, with February being the peak.  And they migrate here by the thousands.  You can rarely stand on the beach or on your balcony (which will hereby be called a Lanai for the rest of this guide) for more than two minutes without seeing one.  If you’ve ever seen one of these animals, as large as a Greyhound bus, jump out of the water 45 feet, you know what I’m talking about.  It’s mesmerizing.  We’ve literally taken 2-3 hours out of a day standing on our Lanai, spotting whales with and without binoculars.  Go snorkeling, put your head in the water, and you’ll hear them singing. 





Where to Stay


Securing a place to stay, guarantees which days you’ll be there.

It makes it a lot easier to book airfare instead of vice versa.  


BOOK A CONDO!  I can’t stress this enough.  They are relatively cheap, convenient and spacious.  The number one reason is eating.  With the full kitchens they offer, you can go grocery shopping and save a ton of money off your total food bill.  If you choose a hotel, you’re talking about eating out 3 times a day.  That WILL get very expensive.  Besides, if I eat 3 restaurant meals a day, by day 4, I'm feeling pretty crappy.  

A hotel will cost as much or more than a condo and give you a cramped homebase.  Most condos offer nice communal pool and BBQ areas.  It's a great place to mingle with other vacationers. 

It’s fun hearing where everyone is from, why they love Maui

and to hear their spin on things to do.  


A one bedroom condo in Kihei, will range anywhere from $125 to $200/night.  A two bedroom isn’t much more and I’ve seen them for $200/night.  And, this is during peak season.  (December to April)  So, if you have more than two people in your party, the savings can be substantial over a hotel (The last time I rented, it only cost about $85/night per couple).


As far as which area to stay in, there are two main tourist areas.  On the western side it’s Ka’anapali which has a good number of condos, but is the main hotel area.  It's probably the most touristy area of the island.  My favorite place to stay is the town of Kihei.  Located on the southside of Maui, it has a great balance of beaches, shopping and restaurants.  It is the Condo Mecca.  Most complexes are a two minute walk from the beach. 

And these are great beaches!  

Kama’ole I, II & III are great for watersports, sunbathing and sunsets.  


A five minute drive south takes you to Wailea, and further south is Makena.  Wailea is more upscale than Kihei.  It has a number of hotels, which are some of the most expensive on the island.  The Grand Wailea being at the top of that list, it’s worth a stroll through their grounds.  You’ll find high end stores at The Shops at Wailea.   Heading toward Makena, the hotels and condos come to an end and you’ll find some of the most amazing snorkeling/diving spots in the world.  They vary in ease of entry and accessibility, but most are easy to get to by car and a short hike.

For booking condos, one site is  In fact, here’s the link which will take you directly to Kihei.  


Here's another site to find your rental.  There are some great deals to be found here. They don't have as many listings as VRBO yet, but give it a look.  While I'm at it, at either of these sites, don't limit yourself to just condos.  There are Bed and Breakfasts, Ohanas (cottages) and whole houses.  It all depends on the number of people you're traveling with, and your personal taste.  Most of these others have kitchens, or at least a kitchenette.

But again, my most solid advice is to stay in a condo,

and I've been having better luck with prices on AirBNB lately.

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.


Getting There


Right off the get go, let me say that the flight out there sucks.  No way around it.  It's painfully long.  You can do little things to help (booking first class comes to mind).  Watch a couple movies, have a few cocktails, take a nap, get up and walk around.  But, bottom line, it still sucks to be confined in a tube for that length of time.  Keep your eye on the prize.  YOU WILL be richly rewarded!  The destination is SO WORTH the pain of getting there.


I've had a few friends, while walking off the jetway in Maui proclaim,

"There is no way this place will be worth that flight."  


Within two days, they're ready to move there.

My favorite travel site currently, is  It searches all the airlines flying to Hawaii and allows you to set up alerts, which are invaluable.  You can set alerts for the dates you want and you’ll receive an email either daily or weekly with the current rates.  You can even set it to only alert you when the price drops below an amount you pick.  Once you find your flights, however, proceed directly to the airlines' website for booking.  Most times Kayak will take you there anyway.  But, you want to make sure you book with the airline, instead of a third party.  That way, if there are any changes or cancelations in your itinerary by the airline, you’re covered.  Not always the case in third party vendors.  In all the times we’ve flown out there, we’ve never paid more than $1000 pp/rt.  Most of the time, it’s been around $850.  The lowest was $560, including insurance, in 2012.  Trend?  Probably due more to great luck, and perseverance.   The week previous to finding that rate, I couldn’t find anything below $1100.  I guess they wanted to fill that plane.  

There are some great deals flying out of Toronto recently.

We have some friends who got $500 fares from there with only one stop in Chicago.

We have flown out of Toronto twice now.  

We found flights with just one stop for just over $600/pp/rt once and $700 the second time.

With the relatively shorter travel time of 12 ½ hours, we arrived on Maui at 2:30pm.

We had never managed to get there before 5pm in the past.

I'd say the cost savings and shorter travel time justified the added inconvenience of

driving to Toronto from Buffalo.

Click HERE to read more. 

Update: We just grabbed a fare out of Buffalo for $800/pp/rt with one stop in Chicago. 

So, our travel time is only 12 1/2 hours including the layover.

That makes flying from our home airport the better deal (In my humble opinion).

 There are a few different routes to take.  Most of the time, I’m flying out of Buffalo and there are no direct flights.  If you're also flying out of a smaller city in the Northeast, the best you can do is fly to Chicago, and then directly to Hawaii.  However, last year we flew Jet Blue to JFK, then Hawaiian Airlines all the way to Honolulu (That leg was 11 hours.  Which is too long in my book.  But, on the return it was only 9 due to the jetstream).  And yes, the big planes land on Maui, too.  I would also settle for Buffalo-Chicago-Honolulu-Maui.  I’d rather get the big Chicago to Hawaii leg (8 to 8 1/2 hours) out of the way, without any stops. 


(If it's your first trip, click the link to read some info just for you.

But basically, fly to Honolulu first

and plan a two night stay to see Pearl Harbor, Waikiki and Diamond Head. 

Here you can book a hotel in Waikiki and rent a car for a day.

But, don’t lose sight of the main objective: Maui.) 


The worst thing and unfortunately most airlines try to do this, is herd you into a layover in Los Angeles.  LAX is a massive airport which all the airlines use as a hub, so it saves them money by putting as many people through there as possible so they can fill all their connecting flights.  I’ve never had a lay over there that wasn’t almost three hours.  That’s a long time after flying all day to get to LA, especially, when you still have another 5 ½ hour flight staring you in the face.  Flying to Chicago is 1 ½ hours.  If you take a direct flight from there, you’ll be in the vicinity of your first Mai Tai in another 8 ½ hours.  Your goal is 12/13 hours travel time, including layovers.  I’ve only accomplished it three times.  

Most of the time, it’s 14 or 15.    

(Or 20.  Click here and I'll tell you the story)


Beware of some recent fares with 21 hours and 3 layovers.



Chicago- O’Hare airport code: ORD

Honolulu airport code: HNL

Kahului, Maui airport code: OGG


Okay, let's stop right here for a moment.  Do this right now.  

Order the book, Maui Revealed.  


This will be your bible out there.

A final note:

I want to strongly advise you AGAINST taking a cruise of the Hawaiian Islands.

I understand some people just love cruising, because they find it easier to let the cruise line lead them around.

I get it.

But, if you've been on a cruise, you know that 80% of your time is spent on the ship.

So, it's more about the ship than the destination, no matter where you go.

You should understand that you will only get a small taste of your destination(s).

I'd rather spend less money and see more.

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