Hawaii for the Spoiled: Where to Stay, Play, and Splurge in the Islands

Where to Stay: Hotels That Will Ruin You for Regular Life

Four Seasons Resort Hualalai (Big Island)

Picture this: a beachfront villa, a private infinity pool, and staff who somehow know what you need before you do. The Four Seasons Hualalai is pure magic, with oceanfront golf, world-class dining, and a spa that will melt your stress like butter on hot pancakes.

➡ Book your stay at Four Seasons Hualalai here.

Halekulani Hotel (Oahu)

If you like your luxury with a side of Old Hollywood glam, Halekulani is your spot. Located in Waikiki, it’s got ocean views, a heated pool with a glass-tiled orchid design, and a legendary afternoon tea service. And did I mention the cocktails at House Without a Key? Because you need one.

➡ Check availability for Halekulani Hotel here.

Sensei Lanai, A Four Seasons Resort (Lanai)

For those who prefer their vacations with a side of wellness and exclusivity, Sensei Lanai is a private island escape designed for ultimate relaxation. Think gourmet healthy dining, guided meditation, and one-on-one fitness coaching—or, you know, just a lot of lying around in a fancy robe.

➡ Book your escape to Sensei Lanai here.

Where to Play: Next-Level Experiences

Helicopter Tour Over the Napali Coast (Kauai)

Driving around Kauai is cute, but soaring over the jaw-dropping cliffs and waterfalls of the Napali Coast? That’s luxury. A private helicopter ride will give you movie-worthy views without the effort of hiking (because, let’s be honest, we’re here to be pampered).

➡ Reserve your private helicopter tour here.

Private Yacht Charter (Maui)

Snorkeling tours with 50 strangers? No thanks. Rent a private yacht instead and sail along the Maui coast in total VIP mode. Swim with sea turtles, sip champagne, and let the crew take care of everything while you live your best luxurious life.

➡ Book your private yacht experience here.

Sunset Dinner at Mama’s Fish House (Maui)

Yes, it’s expensive. Yes, it’s touristy. But guess what? It’s also one of the best meals you’ll ever have. Fresh, locally caught fish, incredible cocktails, and a setting that looks straight out of a tropical dream. Just do it. (And book a table WAY in advance.)

➡ Reserve your table at Mama’s Fish House here.

Where to Splurge: Because You Deserve It

Spa Day at The Ritz-Carlton Kapalua (Maui)

If your muscles are sore from all the luxury (or, you know, from doing absolutely nothing), treat yourself to a Lomi Lomi massage at the Ritz-Carlton’s world-class spa. They use local Hawaiian ingredients like volcanic clay and passionfruit, so you’ll smell like paradise while being pampered to oblivion.

➡ Book your spa treatment at The Ritz-Carlton here.

Shopping Spree at Ala Moana Center (Oahu)

Ala Moana isn’t just a mall—it’s a designer lover’s paradise. From Chanel to Gucci to a luxury food court (yes, that’s a thing), this is retail therapy at its finest. Just make sure to leave room in your suitcase.

➡ Check out luxury shopping tours here.

Final Thoughts: Go Big or Stay Home

If you’re going to do Hawaii, do it right. Stay in the best resorts, eat the best food, and book the most incredible experiences. Because why settle for ordinary when you could have extraordinary?

Need help planning? Check out my top recommendations above and book through my affiliate links—I may earn a small commission, and you’ll earn major travel bragging rights.

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