Raise your hand if money has ever stopped you from doing something absolutely amazing.
Right.
Now assuming you’re not Larry Ellison, and everyone else has answered in the affirmative, let’s now assume that you have the opportunity to explore Maui with the ultimate ‘treat yo’self’ mantra in mind. You don’t need to be Ellison to enjoy some luxurious Maui experiences. It’s worth holding back on consistent and extravagant vacation indulging in order to enjoy one or two truly sumptuous life long memories.
While everyone’s list would obviously vary based on their specific desires and interests, we hope you enjoy the following treat yo’self suggestions! And get a +1 to join you. Ahem.
Sunset in Style
Sail from the beach at Maluaka Beach on one of the most luxurious sailing catamarans in the State of Hawaii. Enjoy pupus and craft cocktails while cutting through the waters with a blazing sunset over the ocean. We’ve been on this particular Maui sunset cruise countless times over the last few decades and recommend it to everyone looking for a better experience than you might be used to on some of the bigger boats.
Have the 5-Star Restaurant Come to YOU!
Nothing says “treat yo’self” quite like staying in your oceanview rental while someone else handles dinner, and not in a “we ordered takeout again” kind of way. Chef Matt Yakabouski cooks private Maui dinners at villas, estates, condos, and vacation rentals across the island, which means your lanai can suddenly become the best seat in the house.
Chef Matt has worked as a Sous Chef at Mama’s Fish House, so the seafood game is strong, but the real flex is the privacy. No reservation stalking. No valet line. No post-dessert drive home. Just your people, your view, and a Maui private chef making the whole night feel ridiculously easy.
Champagne & Helicopters
Yep, you read that right.
On a Maui helicopter tour, not only will you experience a helicopter tour of the whole island of Maui, including the remarkable West Maui Mountains and otherworldly Haleakala Volcano, but you can briefly land in Upcountry Maui for none other than a champagne toast before continuing onto the remainder of your full island aerial tour. Heyo!
Outcall Massage in your own room
When there’s valuable mai tai drinking and sunbathing time to be had, who wants to waste it on a drive to a massage studio? Maui’s Best Massage will drive to your hotel, resort or condo, set up their massage table in your room, set some mellow music, and melt all your cares away. They offer soothing relaxation massage, deep tissue, couples massage as well as lomi lomi.
Or, if you’re staying near Wailea, you can go to their studio at 161 Wailea Ike Place, Suite A105-2. Call (808) 426-7418 for an appointment.
Go House Hunting
Why leave?
Is there any greater treat than splurging on your very own Maui home? We think not. Mindless scrolling on Zillow will only get you so far- it’s time for an old-fashioned boots-on-the-ground house hunt. With the help of a top Maui realtor, you can make your dream of living on Maui come true. Many boast a knowledge bank of every area, subdivision, and condo community on the island. And since any medley of factors might apply to your search (location, price, climate, schools, etc.), the help of a well-informed professional is a must. After all, this is your dream home we’re talking about!
Pick Up Unique Artwork
Stop by Hot Island Glass in Makawao Town to unique, beautiful hand-crafted artwork made on Maui. Sitting and watching these talented artists wield molten glass into spectacular art is something worth visiting for, though they do sell their pieces online too.
Hot Island Glass is a mainstay of Makawao and Maui with roots known far and wide. If you talk to anyone that’s been to this sleepy paniolo town, they likely have enjoyed some time at this “hot” spot.
For visitors planning to splurge on a few memorable drives during their trip, GuideAlong’s Maui tours offer a practical way to add structure and information without booking a full guided outing. Their self-guided audio tours play automatically as you drive, sharing background, stories, and stop-by-stop tips along major routes like the Road to Hana and Haleakalā. It’s a useful option for travelers who want the flexibility of having their own car, but still want the kind of helpful commentary that makes a scenic drive feel more complete.
Spend the Night on a Sailboat
Though purchasing your own private yacht sounds more Ellison-like than anything, it also sounds like kind of a lot of work, both paper and maintenance-wise. So for purposes of a one off treat yo’self moment, we recommend hiring a private sailboat (and the skills of a private sailboat captain) for ultimate Pacific Ocean awesomeness.
Nova, a sailboat offering private tours to areas of Maui, Lana’i, and Moloka’i, also offers the option of overnight sailing tours in the comfort of its spacious cabin. With the friendly and welcoming Captain Mike behind the wheel, you’ll set sail for wherever the hell you please, enjoying amazing activities like whale watching, stargazing, snorkeling, dolphin watching, stand up paddling, eating, drinking, and more along the way. Arrange for some French champagne, freshly caught fish, and eco-friendly sparklers to accompany you – hey, it’s our fantasy! – and thank us later. Preferably with an invite, of course.
Go Shopping for REAL Souvenirs
head to The Shops at Wailea for designer boutiques, a long lunch, and a gallery stop that feels indulgent from the moment you walk in. Finish with a visit to Kush Fine Art & Jewelry, where you can choose from original paintings, signed limited edition prints, bronze or silver sculpture, or a fine jewelry piece drawn from Vladimir Kush’s signature motifs. The team will walk you through sizes, editions, and finishes, then arrange professional packing and insured shipping so the splurge is effortless. Walking out with a Kush, whether a framed print or a pendant, turns a shopping trip into a lasting Maui keepsake.
Head to a Luau
“If married couples can do it, so can we! Instead of celebrating recent nuptials, however, how about we simply celebrate life with a Maui luau? From authentic hula dancers and fire spinners to traditional Hawaiian food, an actual luau on Maui sounds like the paradise party of a lifetime. We highly suggest the most upscale luua: The Andaz Luau.
Hire yourself a mai tai mixologist to accompany the evening entertainment, and you’re set. Or, book an inexpensive Maui luau. Learn about your options and find the best luau for your group.
