Maui Wailea Winter Visit

Wailea for the Win

What an amazing vacation that Wailea provided for us. We had the opportunity to visit friends for the annual national Dermatologist convention of Maui Derm 2021 at the Grand Wailea Resort. COVID restrictions in place, mandatory masks, etc. made me apprehensive. In either event, we still went for it. As a result of COVID, hotel occupancy has been in the mid-teens percentage. Normally bustling with enthusiastic vacationers, the hotel was quiet, and the mesmerizing beaches were calling our names.

As a lifelong family from Maui, it is often easy to take our beautiful island and waters for granted. This invitation allowed us to have an amazing staycation and really relax as if we were on a vacation on any secluded beach. As a result, I personally gained perspective as to how Maui guests and Wailea owners view Wailea’s dreamy qualities. How can you not want to buy real estate on Maui after a Wailea experience like this?

From the Hotel

Leaving the room, we were immediately greeted by the tranquil fountains of the reflection pool on our way to the beach. Walking through the lush gardens down to the sugary sand under our feet. As a result of a few minutes in the 80 degree plus weather, we are heating up from the sun’s soothing rays. It is a treat to swim in the crystal clear water. Want a song? Dive down to listen to the sounds of whales singing underwater. It never gets old. Swimming along with different schools of fish, green sea turtles, you come out refreshed and invigorated.

Bored on a Wailea Beach

Admittedly, I got bored sitting on the warm sand beach for long periods. To each their own. Luckily we were able to snag a couple of stand up paddleboards (or there are multiple rental options) from a friend. How cool is it to paddle out, looking for turtles? Very cool. Wait… more?? Splash splash…. look up and to the horizon. With this, we are listening/watching whales breach and flap their fins on the sheet glass waters of South Maui. Being from Upcountry Maui and living on the North Shore, Wailea’s calm, clear water and beaches are a big change from the wind and winter waves of Peahi, Hookipa, and Spreckelsville. I love them all.

Apres Beach Hotel Amenities

If that wasn’t enough, we still have the Grand Wailea to enjoy. My son loves the various pools and the rope swing.  Luckily, he is often invited by friends who buy day passes or get a room for the night just for the pools. Any child and most adults beam with large smiles frolicking down the 5 slides from the top pool down to the “Lazy River” of the Grand Wailea.

In addition to the day’s fun, we still have the afternoon hour. Adults really enjoy the chance to play in the Napua Tower, the Grand’s exclusive floors overlooking the Pacific. As a result of our hosts’ welcoming lounge, we enjoyed a few libations. Our gracious servers kept the delicious pupus coming before a famous Maui sunset. Now we are off and away to dinner at one of the many fabulous restaurants in Wailea.

So Many Places to Eat in Wailea

As a suggestion, how about fresh fish at Tommy Bahama’s, mai tais, and pizza for a quiet evening from Monkeypod, sushi at Morimoto, oysters and fresh veggie dishes from Lineage at the Wailea Shops, or fine dining and tasty wines at the Bird Cage in the Hotel Wailea?? Yikes. This was only one weekend’s worth of ideas. There is a multitude of yummy spots with great atmospheres in South Maui.

A More Permanent Decision??

As a result of this trip, I really empathize with people who feel that this is the time to make a more permanent decision about visiting or living on Maui long term.  With this, I am in Kula on Maui daydreaming of warm Wailea beaches. Sorry if you are somewhere else where a plane, automobile, and/or more are required to get to Maui. Could this be the time to consider one of the many great places to purchase for an investment in your memories and life? In addition to historically low interest rates, successful stock markets, and a personal quality of life analysis, the opportunity for a  real estate purchase on Maui may be aligning for you.

There are many price points in Wailea, from condominiums to oceanfront estates. For instance, consider a Kai Malu (MLS# 390293) condo home, iconic Wailea Point, Wailea Beach Villas (MLS# 386323), brand new construction at La’iloa (MLS #390216), or a personal golf course or beachfront home like this favorite of mine in Maluhia at Wailea (MLS# 389626). I am here to help you navigate your Maui real estate decisions.

Therefore, if this calls to you, contact me.


JB Guard IV


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