The Four Seasons Maui Wailea

Rainbows Are Never Far in Maui

One of the many great things about living in Southern California is its proximity to Hawaii.  If you are a smart shopper (Hopper App, I love you), finding a palatable fare is relatively easy.   Proving that a five-hour non-stop flight to arrive in plumeria scented, tropical breezes and deceptively strong Mai-Tais paradise is within reach of a long weekend.  I mean, we Californians, don’t think anything about going East to NYC. Why should getting to Maui (especially The Four Seasons Maui) be any different?

So why do we think of this beautiful set of islands as being so inaccessible?  It’s not.  It’s worth a three-day weekend provided the airlines are running efficiently (which seems like an impossibility, these days- but that’s another post).  However, getting to the islands is the easiest part of the quick trip equation finding a room or rental can be expensive and disheartening.   Be careful of those big hotels like The Four Seasons Maui as they seem to be quantity over quality catering instead to the herd and feed lot chain hotel mentality.

Arrival to the Four Seasons Maui

The escape to Maui was direct and painless.  Even with a forecast of inclement weather, a tourist to the islands knows it will never get cold and the rains will pass.  Upon arrival to the Four Seasons Maui at Wailea you will see the “striped head” sculpture and other beautiful pieces of art originating from Michael Dell’s (Dell Computer and resort owner) personal collection.

The Four Seasons Maui Wailea

Front Lobby of the Four Seasons Wailea- Artwork from Michael Dell’s Personal Collection

The hotel is cleverly built so that most rooms have a semi-ocean view.  The lobby that you walk into is open and the roof of the lobby has a gorgeous garden with fountains constructed on top of it.

The Four Seasons Maui Wailea

The Roof of the Lobby Has Been Transformed to a Beautiful Rooftop Garden


Upon arrival, there was a line and a 30 minute wait for check-in.  The Assistant GM greeted us and apologized for the wait and offered us cooling wash cloths and fresh lemonade- nice touch.  The Four Seasons does do customer service beautifully.  Without exception, the staff at The Four Seasons Wailea is wonderful.  Every staff person we met had been employed for years.  The employees feel personally invested in the success of the property.

However, a great staff can’t fix significant management oversights. Why wouldn’t you tell guests that there is construction in the hotel and offer a reduced price? Huge crowds with every pool and the beach utterly packed, a guest is presented with limited options except to eavesdrop on conversations.  Mediocre and expensive food- do you really need to eat another Wolfgang Puck meal?   Tip: go off property for many better restaurant options- the hotel offers a diluted Polynesian cuisine trying to appeal to a mass market.


The room, booked through AMEX Fine Hotels and Resorts, was not cheap at over $1400.00 per night.  Located on the Club Floor, we discovered that this meant you could have unlimited alcohol and all meals.  If you’re a light eater or a heavy drinker you will save a bundle taking advantage of the club’s amenities.  Honestly, it’s not fancy but all the food is all from the same the DUO restaurant where you will pay 20.00 for an appetizer and 38.00 for a main course.  We had poke (sashimi salad) on the club level that was the same as the $27.00 appetizer in the restaurant- no joke.

The Four Seasons Maui Wailea

Poke Served at Duo Restaurant for Lunch – The Same Night/Same Poke in the Club Lounge

Our room on the club level was .25 miles away from the elevators which was not an issue for us but may be for some older guests or folks with mobility issues.  Down this newly renovated and sterile hallway, doors appeared with dirty fingerprints and many discarded, dirty room service trays littered the hallway.

The Four Seasons Maui Wailea

Hallway Littered with Room Services Trays

The Four Seasons Maui Wailea

Dirty Fingerprints on the Doors of the Four Seasons Wailea

Due to the on-going construction (nice to hear drills in paradise) and uncleanliness, our initial impression harkened to a Motel 6 and not The Four Seasons.

The recently renovated rooms are large and well appointed.  Smelling of fresh paint and new carpet,  I believe that there are still some decorative additions (furniture) forthcoming.  While the rooms are spacious, there was enough empty space to conduct a small yoga class in the room.  For the money you would have expected a better view of the ocean. Honestly, you had to stretch and turn your head over the railing of the balcony to see the ocean otherwise your were looking at a blank wall of the other side of the resort’s rooms.

The Four Seasons Maui Wailea

Stretch Your Neck Before Trying to get a Glimpse of the Ocean

The balcony furniture is very comfortable and it is a nice spot to read.  Reminder: the public areas of the hotel are teaming with guests so this is not the hotel for privacy or quiet.

The Club Lounge

The Four Seasons Maui Wailea

The 8th Floor Club Lounge

The best view happened to be in the Club Lounge where you could easily get a table on an outside balcony with a beautiful ocean view.

The Four Seasons Maui Wailea

View from the Club Lounge

The Property

After settling into the room and checking out the club lounge, we explored the property looking for some outside r&r.  Full disclosure, I am not a pool sitter.  I don’t really understand why folks go all the way to a tropical paradise and don’t sit on the beach.  However, it was clear that there were many, many, many little children in the hotel.  Since leaving our own children at home, we searched for a little slice of kidless heaven.  Happy, screaming little children are all well and good except when you are unrelated to all of those happy, screaming little children.

We searched for the adult pool to get some reading in and find equilibrium in our new surroundings.  Unfortunately,  only two stools at bar were vacant the pool.  In order to get lounge chairs at the adult pool, we learned later that folks line up starting EARLY (6:30am line began).  As well, The Four Seasons Maui institutes some rules around how long you can save chairs before releasing them to the general public. Really?  Is this Disneyland? Vegas?  You gotta line up?  It’s a nice pool and all, but really?

The Four Seasons Maui Wailea

It’s 6:55 a.m. and The Line is 5 Deep and Growing by the Second!


So, then rather than cursing our adult-pool-misfortune, we opted to hit the spa.  No brainer, right?  Not so much.  The massage was good, but for a great massage go to Lumeria in Makawao (no joke, just go).  The Four Season’s spa is haggard.   Like many of the jet-lagged guests, the spa looks appeared to be ridden hard and put away wet.  The layout is strange.  The woman’s changing area is poorly located forcing ladies to walk through public areas to access the waiting room.

Small Beach/Crowded Pools & Restaurants

There were too few servers in the restaurant and the food was bland and too safe.  Trust me, with how expensive the islands are due to importing you can forgo the Four Seasons Wailea and find a great VRBO, AirBNB, or smaller hotel (like Lumeria) for more bang for your buck.  Unfortunately, after sitting on the beach for a couple of hours, I learned about the ins and outs of investments, people’s sex life, complaints about the rain and critiques of my fellow beach loungers.

The Four Seasons Maui Wailea

The Tiny and Crowded Beach at The Four Seasons Maui at Wailea

To Go or Not To Go

The Four Seasons Maui Wailea

Crowded Main Pool

Most of all if I wanted the crowd, I would’ve gone to Vegas, but this is a tropical island!  For the money, you can find a far better deal almost anywhere.  If you have money to blow, blow it somewhere extraordinary.  Unfortunately, for most folks, The Four Seasons Maui is anything but extraordinary. The exception to this rule is if you have kids (young ones) this property is for you.  Appealing to younger families, The Four Seasons Maui appeals to this younger set.  Kids will love it as all the food tastes like it’s off the kid’s menu, the pools are teaming with little ones (with precariously full swim diapers), and the staff is excellent at child wrangling/entertaining.