A Baller’s Guide to Maui


You know how people who don’t travel live vicariously through those who do? Well, this post is dedicated to the people for whom money is no obstacle. The people for whom casual trips to the ATM do not result in an immense amount of wincing accompanied by a solo pity party. Whoever said money can’t buy happiness was probably never poor.

resort life maui


Maui: A Baller’s Guide

Where to Stay

If I had a budget that had nothing to do with making a budget, I’d stay in one of three places:

If getting in tune with nature— in an ultra-exclusive setting— sounds like your cup of tea, then stay at Makena Surf. This gated community is spread across 10 acres of mesmerizing, meticulously landscaped tropical grounds with ocean views that command attention. Just minutes from Wailea and all its plush offerings, Makena Surf sits between two out-of-the-way beaches on a husky lava point: and the snorkeling out front is first-rate and uncrowded. Digs here are palatial, with multi-bedroom suites and stately lanais overlooking the sparkling Pacific Ocean. And you’ll have full reign of Makena Surf’s tennis courts, workout facility, pools, and jacuzzis.

Makena Surf

Oceanfront Villa at the Fairmont Kea Lani: Want to live like royalty while on Maui? Then it’s only fair you stay in a castle. Enter the palace-like Oceanfront Villas at the Fairmont Kea Lani. These dual-level 2-3 bedroom villas feature both the comforts of home and top-notch resort amenities. Only here will you have to decide between whipping up a meal in your kitchen or ordering room service. And as if living in a sleek oceanfront villa isn’t enough, you’ll also have your own private plunge pool, complimentary all-you-can-eat breakfasts, and a welcome basket waiting for you when you arrive. Talk about the royal treatment.


The “Maile” Presidential Three Bedroom Suite at the Four Seasons Maui at Wailea – This 4,000 square foot stunner is home to a private full-size sauna, penthouse views from an expansive lanai, private catered dinner service, a customized premium bar, private transportation, a personal assistant, and many other awesome things that I don’t know about. The Four Seasons is my favorite resort on the island. The adults-only pool has an underwater sound system (say whaaa?!), a swim-up bar, and private cabanas with TVs and ceiling fans, and the rest of the resort is equally as impressive. Also, they spritz you down with Evian water by the pool. Because sure.

The Four-Bedroom Presidential Villa at the Andaz Maui at Wailea Resort – They also offer two and three-bedroom villas, but we’re not shooting for silver and bronze here, folks. At 4,070 square feet, the villa includes five bathrooms, a media room, private plunge pools, a full kitchen, and beachfront access to Mokapu Beach, among other lovely things. The Andaz is the newest resort in Wailea, and it’s absolutely beautiful inside and out. I bet you could even pay someone to give you a piggyback ride to their Mokapu Luau.


Where to Eat

I know Mama’s Fish House gets all the attention, and probably for a very good reason, but I personally think there are more interesting choices on Maui. For the average Maui baller, I’d suggest the following restaurants and bars. When all else fails, hire your own personal chef. The world is your wealthy oyster.

Feast at Mokapu – Those of you staying at one of the mega luxury resorts in Wailea will be able to walk to the Andaz Luau, held every Tuesday and Sunday.  This is the high-end Maui luau everyone has been asking for!  Really quality dishes served to your table, fewer people, an incredible show, and a view that can’t be topped.

feast at Mokapu Maui luau

Cane and Canoe – Oceanfront scenery, chef-curated menus, a refined wine list, and locally sourced ingredients- it’s safe to say that the best of the best is reserved for guests at Cane and Canoe restaurant at Montage Kapalua Bay. With chef Ryan Ferguson at the helm of operations, Cane and Canoe’s 7 oz. filet mignon, freshly caught fish, farro risotto, and other gourmet entrees are sure to please even the most particular bon vivant. Of course, the restaurant’s elegant design and decor are on par with the dining. Constructed to resemble a traditional Hawaiian canoe hale, the restaurant features spacious, torch-lit outdoor seating and unique Hawaiian-inspired focus pieces.

The Sunset Luau – For some, luaus aren’t regarded as a particularly luxurious activity. Visions of guests packed like sardines, hokey activities, and below-average buffets might come to mind. However, before you turn up your nose at the mention of a luau, The Sunset Luau at Kapalua Bay is redefining what a festive Hawaiian celebration might look like. Rather than hosting hundreds of people, The Sunset Luau welcomes a maximum of 40 guests to enjoy top-notch Polynesian entertainment, a quality Hawaiian culinary experience, and intimate hospitality. The family-style dining, relatively small attendee size, and hospitable service at The Sunset Luau are distinctly different from what larger luaus typically offer.

Beach Club Luau Maui

The Restaurant at Hotel Wailea (formerly Capische) – If you’re a fan of delicious cocktails and food, head to Hotel Wailea’s restaurant. The farm-to-table approach to the menu is appreciated and the service is always outstanding. Grab a table on the upstairs lanai or in the downstairs garden and make sure to try the Bonnie & Clyde bourbon cocktail.

The Maui Cookie Lady – OK, so you don’t have to be a baller to enjoy The Maui Cookie Lady’s delightful cookies (thank goodness). But these epic confections are good enough to make you want to buy up the store’s entire inventory— and doing so requires a certain level of baller status. Seriously, these cookies are the real deal. Made with the finest (and most innovative) local ingredients, The Maui Cookie Lady’s unique treats have earned several prestigious accolades and been featured in noteworthy outlets like Forbes. The Maui Cookie Lady’s shelves are also stocked with hard-to-find local goodies that make excellent souvenirs for friends and family back home.

best cookies ever 

Ka’ana Kitchen  – Located at the Andaz Resort, Ka’ana is a beautiful, modern restaurant with delicious food. Open daily for breakfast and dinner, this family-style restaurant utilizes local ingredients from Maui farms and encourages sharing. Try the Kalua Pork Benedict, Lobster Ceviche, or Abalone Risotto.


What To Do

Charter a Boat Maui Custom Charters is my favorite sailing company, simply for the fact that their boats only seat up to 6 guests and they absolutely rule. Choose from the S/V Artemis, a 47′ sailing catamaran, or the S/V Nova, a 42′ sailing yacht, both fully loaded and ready for adventures. Captain Anna offers many different options for private sailing tours, so hop on and enjoy a day of snorkeling, sunset sailing, whale watching, or whatever ocean activity suits your fancy. Visit popular areas like South and West Maui, or go for gold and book a full-day tour! Fact: Everything is more fun on a sailboat.

Ballers Guide To Maui Private Sailing Charters

Unwind at the spa – There are few better ways to treat yourself than spending a day at the spa, namely, at Spa Montage Kapalua Bay. Located near the oceanfront in heavenly Kapalua, every aspect of the Spa Montage is designed to emanate tranquility. Beyond the luxurious, foliage-fringed outdoor treatment rooms, the facilities at the Spa Montage boast a cedar wood sauna, outdoor co-ed infinity pool, bamboo waterfall, cascading whirlpool, and fitness room. What’s more, Spa Montage Kapalua Bay integrates island-inspired therapies into treatments, from the traditional Hawaiian Lomi Lomi massage to body polishes using bamboo and local fruit enzymes. If you’re going to spring for a spa day, Spa Montage Kapalua Bay is the obvious choice- and while they’ve got the credentials to prove that they’re the best of the best, why not stop by and find out for yourself?

Kick back in a waterfront rental – Many hotels, condos, and rentals describe themselves as “oceanfront,” but you can’t get any closer to “oceanfront” than at The Cliff House. This extravagant, two-story event rental (or hang-out space, if you’re so inclined) is nestled on the cliffs in Kapalua, perched above the resplendent turquoise waters at Namalu Bay. Simple kitchen, restrooms, ocean access, a large screen TV, outdoor grill, a large deck, and space for up to 30 guests, The Cliff House is typically used for weddings, corporate events, or other family gatherings. However, there’s nothing that says you can’t rent the space out for a baller day on the water. After all, this is the baller’s guide, no? So, grab some friends, pack some drinks, food to grill, and snorkel gear, and spend a day in the most sought-after, alluring rental on Maui.

Cliff House

Take a Helicopter Tour – Ever since my first helicopter ride on Maui, I can’t wait to go again. Although I definitely enjoyed the complete island tour, if money were no object, I’d go for Doors-Off Maui and Molokai option, which takes guests up and through the West Maui Mountains before crossing the channel to see the towering sea-cliff waterfalls along Molokai. Hell, for the right price, you could probably hire a helicopter to take you to lunch. Dream big.

Treat Yo’Self – Whatever that means to you. Spa days, driving a Porsche Speedster, yoga classes, exploring the neighbor island of Lana’i, kitesurfing lessons, buying art at local galleries, shopping, golfing, professional vacation portraits, you name it. There are a ton of amazing things to do on Maui, especially when budget isn’t an issue. Just don’t forget to show some aloha!

luxurious activities maui


Where to Settle

Sure, money can’t buy happiness. But it can buy you an expansive luxury vacation home on Maui, and that’s pretty darn close. While it’s true, that the housing market on Maui (or any beautiful place in the United States, for that matter) is nothing short of pricey, there are some sprawling vacation estates on the island that are reserved for the well-to-do. Just ask Jeff Bezos, who recently purchased 14 acres on Maui for a whopping $78 million.

Jeff Bezos Maui Home

If you have the dough to drop on an extravagant Maui vacation home, then the number one thing you’re going to need is a trusted realtor- especially if you’re buying the place sight unseen. That’s where a Maui realtor is crucial. And while it’s hard to be disappointed with any luxury home on Maui, having straightforward communication and attention to detail leaves no room for any unanswered questions- what you expect is what you get.

Happy spending! If anyone needs more baller tips, I’ll be the one wincing at the nearest ATM. Aloha!

2 thoughts on “A Baller’s Guide to Maui”

  1. Life, size, chess board, cause that’s the first thing that comes to mind when you
    think of Maui, lol. The Tropical Plantation is such a beautiful location; if I was a little bit taller, if I was a baller, I would definitely try it. Great post Kelsey, enjoyed the writing.

    • Ha! I know, such a random assortment of things going on in that estate. And yes, we love the Tropical Plantation, too – the whole property is so gorgeous. Mahalo, Laura! Here’s to being taller and baller(er) in 2016…


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