Returning to One of Maui’s Most Iconic Resorts

As a kid, a stay at the Grand Wailea felt grand—and all these years later, it still does.

Staying at “the Grand,” as we affectionately called it, was like a dream vacation for us kids.

With its epic waterslides, lazy river and hidden hot tubs scattered across its pools, the resort was the ultimate destination for families—and it still is. As a 7-year-old, the hours spent in the pool were bliss, and when I needed a respite, I’d lounge around, sipping on a virgin piña colada. Even as a kid, the grandeur of the resort was apparent.

The Grand Wailea Maui, A Waldorf Astoria Resort, is a massive property, taking up 40 oceanfront acres and featuring more than 800 guest accommodations, including rooms and suites.

Within the resort is a row of shops and markets, and paths that weave through lush gardens full of tropical flora and sculptures. There’s even a chapel on the grounds, and it’s all just steps from Wailea Beach.

As a kid, I  couldn’t get enough of the resort’s pools and slides. But now, beyond all the fun memories, I have a greater appreciation for the place, its history and its vision.

During a recent stay, I discovered a little bit of the story behind the Grand Wailea Maui. And even after a multimillion-dollar renovation, that story, along with familiar touchpoints like the resort’s artwork, tie the past to the present.

Developed by Takeshi Sekiguchi, the resort opened in 1991. Sekiguchi, an avid art collector, envisioned a serene escape for travelers and locals and he adorned the property with artwork.

When guests arrive, they are greeted with lei by the resort’s staff, and among the first things they’ll notice are the impressive Fernando Botero sculptures in the Grand Wailea’s open-air atrium. The late Colombian artist and sculptor created exaggerated human figures in a distinctive, expressive way. The lobby area features nine bronze statues by the artist, and the resort’s Botero Lounge is named in his honor.

Guests can also marvel at other works by international artists, and local ones, too, including Satoru Abe, who was named a Living Treasure of Hawaiʻi in 1984 by the Honpa Hongwanji Mission of Hawai‘i. Herb Kawainui Kāne’s work is also displayed throughout the resort, and his sculpture of King Kamehameha stands at the entrance of the Grand Wailea.

The resort says it balances masculine energy and feminine energy through its artwork and design, with amenities placed in different areas to maintain harmony. The resort itself is shaped like a honu, or turtle, which can be seen from an aerial view.

A few years ago, the Grand Wailea underwent a $350 million renovation. I hadn’t visited the property in years, so I appreciated the newer modern features, but also welcomed the resort’s familiarity.

As expected, its spacious rooms feel luxe and contemporary, with touches of Hawaiian-inspired design elements and motifs, and each guest room features a private lānai.

Upon debuting its renovation, the Grand Wailea also introduced Napua, a collection of premium rooms and suites within a private space on the resort’s upper floors. Like a resort within a resort, Napua guests have access to two stunning private lounges featuring dedicated concierges and gourmet dining options. The eighth-floor lounge features a rotating lineup of special experiences, including a chef’s station and live entertainment.

In 2024, the resort launched its specific wellness-focused guest rooms. The rooms are equipped with Therabody compression boots, a Theragun massage device, a Technogym Movement Kit, meditation goggles and more. The rooms are designed to help guests find optimum well-being, rejuvenation and sleep.

As travel and hospitality lean further into wellness programs and offerings, the Grand Wailea is diving in. Along with its designated wellness rooms, the resort invested $55 million on its former spa area, transforming it into Kilolani, a 50,000-square-foot retreat. Kilolani is the Hawaiian word for stargazers, or those who observe the heavens. Rooted in tradition, many of the spa’s healing treatments, signature rituals, massages and facials are inspired by the Hawaiian moon calendar.

One of my favorite parts of the spa is the Hydrotherapy Gardens. Here, I braved a cold and stimulating waterfall shower, then decompressed in the steam room and relaxed in the saltwater pool.

By blending traditional practices and modalities with modern therapies and state-of-the-art technology, Kilolani Spa pampers guests and leaves them a little more connected to the island.

The resort has long been known for its restaurants, including its signature spot, Humuhumunukunukuāpuaʻa. With panoramic views of the Pacific, the restaurant serves ultrafresh seafood and creative cocktails in a memorable setting.

Just a year ago, Nobu Grand Wailea Maui opened in a 13,000-square-foot space. On a clear evening, I dined under the stars with a friend, enjoying the famous black cod with miso, yellowtail jalapeño, fresh sushi and an amazing lychee martini.

Whether it’s hanging out for hours at the pool with your kids, lounging at the adults-only pool, relaxing at the Kilolani Spa, or enjoying its dining experiences, guests at the Grand Wailea can build their own vacations based on whatever they’re seeking. And that’s what I’ve come to appreciate about the resort.

After dinner and a dreamy night’s sleep in the resort’s plush bed, I checked out in the morning. And  already, I can’t wait to return.

Grand Wailea, A Waldorf Astoria Resort, grandwailea.com.

Grace Maeda is the editor of HAWAIʻI Magazine.