Trip Planning-Maui

We had planned to do something big for our ten year anniversary, but work was hectic and we couldn't find the time nor the extra money to do it. Two years later we found the time and made the decision. This year for year 12, we do something. Something different. It was important to me that before we headed out to Thailand, Japan, Europe and take advantage of our passports, we wanted to make sure we took the time to enjoy everything that our homeland had to offer. Somewhere tropical filled with waterfalls, reefs, and beautiful national parks.

In February we will flying to Maui, Hawaii for 8 days!

Why Maui? Well, why not? I think it's a big goal of almost anyone living in the USA to eventually visit one of the islands of Hawaii. We choose Maui out of the other islands because it wasn't the major tourist site where everyone would be, but it also wasn't a completely secluded island where there would be nothing to do.

We spent some time looking at the various hotels Maui had to offer. There's a certain amount of time to see X amount of things, and if you consider the possibility of us ever going back to Maui again, it was likely very low, so we wanted to see as much as possible in the time we had, and the best way to do that comfortably would require us to stay at different locations. Lucky for us, I learned a new tip this year from my always traveling friends

For those of you who aren't familiar with it, is an online service that matches people seeking vacation rentals and other short-term accommodations with hosts who have an unused space to rent. is an amazing service as it allows you to find accomadations that suit your traveling style. Don't want to spend money, as you'll be out and about all the time? You can rent a bed in a den for as low as $30 bucks (probably less if you hunt around). You can also rent a private Gated Estate with a pool if you have the cash for the low, low, low price of $950 a night. FYI that was sarcasm.

That just covers Maui. Airbnb could be used for almost any location on the planet earth. Are you a Frank Lloyd Wright fan? How about fulfilling that childhood desire of sleeping in a REAL treehouse? If you have the time, and the coin of course, anything is possible.

But that's enough of that. Let's get back to the whole point of this post. The main attraction we had to see was Hana, home of the 7 sacred pools.
Seven Sacred Pools

We spent a few days looking through the offerings of Airbnb and comparing them to the local hotels. There's a criteria when renting from people you don't know.
  • Do they have reviews?
I wanted to make sure enough people had a good time before taking the plunge.
  • Do they have pictures?
Pictures speak much louder than words and give you an idea of what you are buying.
  • Is it a private room or an entire house?
Since this was a relaxing vacation trip we didn't want to have to worry about dealing with the personalities of the owners on a nightly/daily basis so we opted for an entire home/apt.
  • Was this a property manager or a private owner who lived on the property? 
Dealing with property managers is dealing with a professional who most likely rents out multiple locations for a living. We opted for one of each to see how each experience went and to compare. Now before you read any further a disclosure. The pictures you see in this post were NOT taken by us. We haven't been to any of these locations, nor Hawaii for that matter. They are taken from the galleries advertising the locations and we did this so that we can show what we were being sold. Once we return from the trip we hopefully have the exact same picture taken by us. Then we can see if we did indeed receive what we thought we were paying for and compare the two. Expectations vs Reality.

Our first location was going to be unrelated to airbnb. A big hotel. It would be near the airport and easy. Dealing with a car rental, luggage, possible flight issues, it would probably be the best bet to have a professional handling us while we are dealing with everything that goes with arriving in a new land. The hotel we choose, Hotel Wailea located in Wailea-Makena.
"A" the airport of our arrival to "B" our destination in Wailea-Makena about a 35 minute drive according to the Google Gods.
Hotel Wailea
Nice comfy room, but something tells me it's not going to look like the picture.
The Garden

Once bored with our room we plan to set off on a nice drive around the West side of Maui to check out Napili-Honokowai and check out what that has to offer. We have two nights at the Hotel Wailea so three days of exploring is available if necessary.
The west side trip. Total drive time around 3 hours but this will most likely be split over three days. After two nights there we would be on our way to Hana. With the help of we located a gorgeous ocean front location on 7 acres with epic views into a secluded bay and is about one mile from Haleakala National Park's Seven Sacred Pools. The location was Halemano and can be found on airbnb by going here.
Wailea-Makena to Hana about 2.5 hours
7 acres of secluded private property
The Yurt
Yoga House
the Communal Kitchen
the bathroom
Views from the porch

Once our time there has been completed we will be on our way to Haiku-Pauwela.
We picked this place because it was in the middle of everything. Close to the airport for departure and a short driving distance to both Hana and Wailea-Makena allowing us to head back to either destination if we need one more day to check things out. It's also a whole new place to explore. This location was also a fraction of the cost of the other properties. I was actually pretty amazed at the deal we got with this one. The location is Modern Studio Apartment and can be found on airbnb by going here.

Modern Studio Apartment
Simple studio. If I was to take a guess I would imagine the owners converted a detached garage.
Views were clear but a bit boring. Not sure how that matters as it's Hawaii and you only have to drive down the street to be at the beach.

The point of all this, mostly is expectations vs reality. We picked locations with overwhelmingly positive reviews that we felt each hit a price point that almost anyone could afford.
  • How will they turn out? Just like you we have our doubts and concerns.
  • Will the private owners be as friendly as the reviews say?
  • Will the transactions go smoothly?
  • Did we pick good locations that ended up syncing with our plans?
It will be fun to follow up and go over everything. A review of our planned trip vs how things eventually unfolded. Big corporate run hotels vs private owner accommodations and of course HAWAII!

We took our trip! Read about our Maui adventure by going here!