If there’s one thing I take very seriously in Hawaii, it’s sunset drinks. I will plan my entire day around where I’m going to be when that sun hits the water.

And Maui? Maui delivers. Between the West Maui mountains, the channel views toward Lana’i and Moloka’i, and that perfect golden hour light…it’s just unfair, honestly. Almost every spot on the west and south sides of the island is going to give you a decent sunset view. But some spots are MUCH better than others, and after a lot of dedicated research (someone’s gotta do it), I’ve got my favorites locked in.

Here’s my roundup — a little something for every vibe, from barefoot-in-the-sand casual to full-on fancy.

This post may contain some affiliate links, which means I’ll make a little money on anything you choose to purchase. But of course, I only recommend my absolute favorites to you. Thank you for supporting the brands that make HulaLand possible.

Four Seasons Lobby Bar — Wailea

Elite. That’s the word. Just…elite vibes from start to finish. The Four Seasons does everything well and the lobby bar is no exception — they’ve got a really fun mai tai menu with the most gorgeous glassware, plus live music and a hula dancer while you watch the sun go down. Even if you’re not staying at the Four Seasons, you can absolutely come here for drinks, and I highly recommend it. It feels like a special occasion even when it’s just a Tuesday.

Ocean Vodka Distillery — Kula (Upcountry)

This is my FAVORITE under the radar spot on the island and I love putting people onto it. The Ocean Vodka Distillery is up in Upcountry Maui, which means you’re elevated above everything and you can literally see the whole island spread out below you. The views are absolutely insane — like, stop you in your tracks insane. It’s not the typical “feet in the sand” sunset experience, but it might be the most spectacular one on this list. If you haven’t been, go.

Monkeypod Kitchen — Ka’anapali or Wailea

Best happy hour on Maui, full stop. The mai tais here are LEGENDARY and the happy hour deals are great. There are two locations — Ka’anapali and Wailea — the Ka’anapali location has the better views. 

Side Note: If you’re looking for a rental car for your trip, I LOVE Discount Hawaii Car Rentals. They’re seriously the only company I ever use. They’ll give you the very best prices, you don’t have to reserve with a credit card or pay until you show up, you can cancel and re-book anytime if you find a better rate, and they usually have a special that adds additional drivers for no fee. It’s a no brainer. Click here to check rates for your trip.

Honu Oceanside — Lahaina

I love coming to sit at the bar at Honu. Great atmosphere, right on the water, exactly the kind of place you picture when you imagine having a drink in Maui.

Mala Ocean Tavern — Lahaina

More of a “settle in for a nice dinner” spot than a quick drinks stop, but honestly that’s not a complaint. Mala is cozy and charming and right on the water, and if you go, you HAVE to get the “Rosemary Me” cocktail. It’s so good. 

Aloha Mixed Plate — Lahaina

This one’s for when you want something a little more lowkey. Aloha Mixed Plate is right on the water on Front Street in Lahaina — super casual, great for a laid back meal with a cold drink while the sun goes down. No pretense, just good food and a great view. 

Hula Grill — Ka’anapali

Awesome views right on Ka’anapali Beach, and here’s the thing — if you sit on the Barefoot Beach Bar side of the restaurant, you literally have your feet in the sand. It doesn’t get much more Maui than that. Great spot for an early evening drink before or after a walk down the beach.

The Birdcage — Wailea

Perched up above Wailea, The Birdcage has this amazing hideaway quality to it — upscale and a little tucked away, like you’ve found somewhere not everyone knows about. It’s got a really cool, intimate vibe that feels different from the big resort bars. If you’re looking for something that feels a little more special and a little more grown-up, this is your spot.

I’ve made it my job for the last 10 years to explore Maui.

And after hundreds of beach days, rainforest hikes, snorkeling trips, and reconnaissance missions to find the best hotels… and mai tais… I put everything I know into one place.

This is my Maui Digital Map — hundreds of my favorite spots. Beaches, snorkeling spots, hikes, farm tours, scenic drives, places to eat.

Yes, I share hidden spots I don’t talk about so much on social media…but also—tourist doesn’t have to be a dirty word. Popular places are popular for a reason.

So I break down what’s worth it, what’s not, where to spend your money, where to save it, and how to avoid crowds at some of Maui’s most popular (and best) places so you actually enjoy your time.

I’m also sharing all of my travel guides on when to go, where to stay, detailed hotel reviews…plus dozens of itinerary options based on where you’re staying and what you love to do.

It’s everything you need to see the best of Maui and actually relax. A Vacation in a box…all YOU need to do is pack your suitcase. 

Get access to my Maui digital guide and map here.