A Maui Vacation For Those Who Like To Indulge

Money can’t buy happiness – unless you’re planning a trip to Maui.

Sure, Maui’s greatest splendors might be free (i.e., beaches and sunsets), but this one is for the high-fliers, the big spenders, the ones who’ve never met an ATM withdrawal they couldn’t handle. From luxury oceanfront suites to Porsche rentals, here’s how we would plan a Maui vacation where money is no object.

STAY

Fairmont Kea Lani

With an all-white castle-like design (complete with domes and spires), the Fairmont Kea Lani certainly looks fit for royalty. But the elegance extends beyond the resort’s architecture. In keeping with the palace-like vibe, Fairmont Kea Lani is Maui’s only all-suite hotel. Even the smallest rooms are a whopping 860 square feet, and luxe details abound.

But for true opulence, book a stay in one of Fairmont Kea Lani’s multi-bedroom oceanfront villas. These white-washed abodes look like they’ve been plucked from a Greek isle and perfectly placed steps from the sand at Polo Beach – private plunge pool and all.

Wailea Elua Village

Sure, Maui’s beachfront resorts can certainly be luxurious. But if you value peace and privacy more than fancy amenities and room service, then you’ll enjoy a stay at Wailea Elua Village.

Spread across 24 acres, this gated condo community features palatial units ranging from one to three bedrooms – hello, peace and privacy. Beyond Wailea Elua’s luxurious digs, you can explore the nearby Shops at Wailea, soak up the sun in the quiet oceanfront pool, or say ‘what up’ to the sea turtles that frequent the reef at Ulua Beach out front.

Makena Surf

Exclusivity reigns at Makena Surf – a gated condo resort just south of Wailea. Perched between the shimmering Pacific and the (mostly) undeveloped southern slopes of Haleakala, Makena Surf is a serene escape.

Opt for a first-class oceanfront condo where the golden sands of Poʻolenalena Beach beckon just steps from your door. When you’ve had enough of the beach, disappear into the property’s garden-like ten acres for a quiet dip at the pool or game of tennis.

Although void of restaurants, the gourmet kitchens in each of Makena Surf’s units practically beg to be utilized – maybe not by you, but certainly by a private chef.

PLAY

Private Sail

Few things are more “baller” than chartering a boat. Don’t believe me? Hop on a private charter with Maui Custom Charters and set sail on a personalized adventure.

Whether aboard the 47’ S/V Artemis sailing catamaran or the 42’ S/V Nova monohull, you can explore hard-to-reach reefs, search for humpback whales (in season), or savor stellar sunsets with a side of silver service. So kick back, snack on a board or charcuterie, pour yourself a glass of champagne, and toast to the lifestyles of the rich and famous.

Maui Roadsters

From the waterfall-studded road to Hana to the undulating Upcountry roads, every Maui vacation deserves a road trip. But few opt to drive in style.

Infuse some flair into your Maui road trip. Rent a flashy Porsche from Maui Roadsters. This local company boasts a fleet of professionally reproduced 1957 Porsche Speedsters. Take Pele – the bold red ride – on a drive out east. Or maybe rent sleek and showy Lani for an Upcountry cruise. You’ll be turning heads no matter where you end up.

INDULGE

Spa Day

For the cream of the crop of Maui indulgences, head to Spa Montage. Nestled steps from the surf at Kapalua Bay, Spa Montage offers an unparalleled luxury experience – and the promise of ultimate relaxation.

From lomi lomi massages to seaweed body wraps and traditional Hawaiian healing therapies, each treatment is designed to restore balance and invigorate your senses.

Just stepping foot in the lavish facilities is enough to make you feel like royalty — with outdoor treatment bungalows, a hydrotherapy circuit, and an infinity pool with A-plus views.

One thing is clear: every moment at Spa Montage is a reminder that, on this Maui vacation, money truly can buy happiness.

Maui Singing Bowl

A date with the world’s only giant singing bowl epitomizes the essence of a no-expenses-spared vacation.

Not sure what to expect? Here are the deets on Maui Singing Bowl. You’ll settle into a cozy hammock suspended over the bowl. A practitioner will strike the bowl every 15 seconds for 20 minutes — and you’ll be bathed in resonant sound and harmonious vibrations, said to promote deep inner healing and send you into deep relaxation. See for yourself how the Singing Bowl’s sonorous sounds elevate your mind, body, and soul.

MauiWine

Wine lovers, rejoice. Maui boasts one of Hawaii’s only wineries, set on the verdant slopes of Haleakala. A wine flight at MauiWine will run you less than $15. But why not rock up like a VIP to an already luxurious experience?

Book the Under the Camphor Tree experience for a private wine tasting. You’ll be welcomed onto MauiWine’s stunning, historic property with a sparkling toast and led to your private seating area—nestled beneath the largest camphor tree in Hawaii. Enjoy five four-ounce tastings of MauiWine’s premium wines, a large grazing board, and a dessert wine and chocolate pairing. Oh, and personalized, private service.

DINE

Kō

Hawaiian culinary excellence is epitomized at Ko at the Fairmont Kea Lani. This gleaming restaurant presents a renewed take on island cuisine. Diners can tuck into elevated Pacific plates like pancit, lau lau (a traditional, ti leaf-wrapped Hawaiian dish), and other fresh seafood and locally sourced dishes. Whether indulging in dinner or brunch, Kō celebrates Hawaii’s melting pot of cultures and Maui’s vibrant flavors.

Marlow

Restaurant Marlow might not be the most exclusive or expensive restaurant on Maui, but its chic interior, craft cocktails, and delicious wood-fired pizza appeal to all demographics. Owned by a renowned Maui chef, Marlow highlights locally sourced ingredients, with farms listed directly on the menu. The restaurant even features beers brewed next door at Mahalo Aleworks—can you say hyper-local?

The Treehouse at Hotel Wailea

Have you ever had a private seven-course dinner? Okay, what about a private seven-course dinner in a mango tree?

The Treehouse at Hotel Wailea is one of Maui’s most exclusive, sought-after dining experiences. A personal chef will lead you through seven exquisite courses while you savor the sunset from your private treehouse. Elegantly crafted dishes, seasonal ingredients, a personal chef, and outstanding sunset views—what else could you ask for?

So there you have it, ballers. Of course, there are other creative ways to plan a Maui vacation where money is no object — but this is a good place to start. Cheers to a life of luxury.