Better Than A Daydream

By Melissa Milakovic
Photos: Grand Wailea Maui, A Waldorf Astoria Resort

Returning to the resort with her husband, writer Melissa Milakovic notes, “Grand Wailea Maui was better than we remembered and as dreamy as you might expect.”

The first time my husband and I stayed at the Grand Wailea Maui, we fell in love. We were a new couple when he invited me to join him at a medical conference in Hawaii. For obvious reasons, I enthusiastically said, “Yes, of course, where do I sign?”

When we finally arrived at the Waldorf Astoria property, our mouths slightly parted in awe of the lush surroundings and grand, open-air atrium, he playfully noted that this was the nicest hotel he’d ever stayed at, so “Please, don’t expect this going forward.”

Nine years later, we made it back. This time as a married couple, exhausted by the past two years, determined to revel in luxury — the hotel, the landscape and, it must be noted, the ability to take the time to travel once again. We were there for it.

Surrounded by 40 acres of lush grounds with picture-perfect palm trees lining the west-facing beach, staying at the Grand Wailea is a fairytale at every turn — Botero sculptures, water fountains, winding paths through lavish gardens. The details, both palatial and subtle, work together to create a true five-star experience.

The town of Wailea, as described by our cab driver, is the Beverly Hills of Maui; Oprah is a neighbour and we soon discovered oft visited by celebrities and their families. Flanked by the Fairmont Kea Lani and the Four Seasons on one side and a Marriott Beach Resort and Luxury Villas on the other, the location leaves you wanting for nothing more than extending your stay.

I spent most mornings sauntering down the Wailea Oceanfront Boardwalk, a 5.5 km walking path that extends from the Fairmont to the Andaz. With a coffee in hand, I was determined to get my steps in before languorous, lazy days on the beach or reading by the pool. The early morning soft-hued pinks and purples reminded me of the Hawaii I imagined as a teen; kids from school would come back from vacations wearing pastel tie-dyed tees with ‘MAUI’ boldly printed shoulder to shoulder. On these walks, I understood the inspiration for the colour palette.

While my husband got his workout in at the fitness centre (they have two Peloton bikes for the ultra committed), I would end my walk by heading straight to the beach or the pool to secure us a spot to relax the day away. On days we chose to hang out on Wailea Beach, I made sure to ask for the front row to allow fo prime people-watching and, even better, whale-watching. January to March is peak whale-watching season in Maui, when humpbacks migrate between Alaska and Hawaii to give birth and find new mates. On our first morning we witnessed a remarkable display of whales breaching, playing and diving at a distance so close there was no need for binoculars. It was spectacular. Every day to follow, whales were nearby.

We rented a car and used it twice in ten days. The first time, we took the Kahekili Highway to the Nakalele Blowhole, a geological formation that erupts like a geyser every few minutes. The most riveting feature wasn’t the display of erupting water but the group of people standing on the edge near the blowhole. Multiple hand-painted signs down the path warned of certain death if you stood too close. We kept a healthy distance, took a few photos and headed back to the car.

The biggest decision each day at the Grand Wailea Maui was where to have dinner to catch the sunset.

The drive was breathtaking, in more ways than one. The road is narrow, tightly wrapped around the mountainside. You drive up a two-way road that feels more like a one-way backroad. I found the ratio between enjoyable and stressful leaned heavily toward the latter, but ultimately it was exhilarating to see more of the island. After finding a kitschy restaurant in time for sunset and a double Mai Tai, we headed back to the hotel for a soak in the hot tub and another round of cocktails.

The second time we used our car was only to pass the time between check out and boarding the plane to go home.

On this return to paradise, we felt little need to leave the property, and were happy not to. We easily devoted each day to reading, chatting, napping, ordering snacks and drinks from the comfort of our loungers. Our skin was grateful for an abundance of vitamin D, our bodies loose and relaxed. The biggest decision each day was where to have dinner to catch the sunset.

The Grand Wailea offers a handful of fabulous restaurants, not to mention the long list of award-winning restaurants at neighbouring resorts. There is truly enough selection to ensure a singular culinary experience every night of the week.

Open-air, thatch-roofed, overlooking a beachfront lagoon, one of our favourite spots for dinner, steps from the pool and a few more from our room, was Humuhumunukunukuāpuaʻa, named after Hawaii’s state fish. We enjoyed complex dishes sourced locally, by sea and land, while taking in an unbeatable view of the sunset. On the other side of the bar, a young Hawaiian musician would sing sweet songs in his native tongue as we were captivated by the candy colours on the horizon: oranges, yellows and reds shapeshifting to the music like whistling at the Northern Lights.

As frequent travellers, my husband and I are not typically lounge-by-the-pool-all-day kinds of tourists. We prefer to explore our new surroundings. When we skipped plans to explore more of the island to spend more time on the beach, we realized how deeply we needed to decompress; how long we’ve been holding our breath, clenching our teeth and our shoulders, standing guard for the unknown.

This vacation was about fully melting into the warm, sweet air of Maui. It felt easy to climb into a routine of morning walks, quiet conversations watching whales and sipping coffee, warm poolside naps, and early nights to bed with the screen door wide open to welcome the lulling sound of crashing waves. An absolute beach vacation cliche and we were there for it.

We were so grateful to find our way back to the place we fell in love; the Grand Wailea Maui was better than we remembered and as dreamy as you might expect