Waikiki gets a lot of hate (yes, it’s a big city…yes, there are way better places to a “real” Hawaii experience) BUT. NOTHING is more iconic than sunset drinks in Waikiki. It’s just a vibe. 

Whether I’m staying elsewhere on the island and popping into Waikiki for a day or doing a few days in Waikiki at the beginning of a trip as a basecamp for some long days of exploring, these are my go to spots for an evening drink (and bite) in Waikiki…

Best Places for Sunset Drinks in Waikiki

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.

House without a Key

If I only have one night in Waikiki, this is where I’m coming. Hidden away in the luxurious Halekulani Hotel at the quiet, older end of Waikiki, this place feels like old Hawaii. 

It’s sophisticated, the views are as good as they come, and there’s nightly live music and hula dancing. 

I don’t know about you, but sipping a mai tai on the lawn while watching a hula dancer silhouette at sunset is as “Hawaii” as it comes. 

Make reservations in advance if you want a table and full menu. Otherwise, the smaller tables up around the stage are first come first serve. They serve a drink menu and smaller selection of food (however I’ve always been able to order anything off the main menu). 

Their mai tais are legendary. I’m always pleasantly surprised by their pizzas. And they’re famous for their coconut cake. 

Live music is from 5 PM – 8 PM with a hula dancer from 6 PM – 8 PM. 

Monkeypod

I’ve been a Monkeypod stan for well over a decade now, and I never feel like I’m in Hawaii until I have one of their famous mai tais with the lilikoi foam. 

So I was over the moon when they finally opened a location in Waikiki. Situated beachfront in the Outrigger REEF Waikiki (there’s more than one Outrigger hotel in Waikiki), this is your typical Monkeypod experience (lively atmosphere…their motto is “a party every night”) but with even extra Waikiki energy. 

Like I said, they’re famous for their mai tais which have a lilikoi foam on top, but they’re REALLY famous for their happy hour. Double check the hours seasonally (and by location) but it’s usually 3:30 PM to 5 PM and covers half priced appetizers (no seafood options though), $14 pizzas, and $4 off craft cocktails. 

Honestly everything on the menu is really good but I’ve found that 90% of the time when people aren’t impressed with this place it’s because they ordered the margarita pizza ; ) 

I love their kalua pork and pineapple pizza, potstickers, lobster deviled eggs, garlic truffle oil fries, and seafood pasta. Also, I ALWAYS get a side of their broccoli. It’s so good and SPICY!

Mai Tai Bar at the Royal Hawaiian 

It doesn’t get any more iconic than the Royal Hawaiian. 

I firmly believe that even if you’re not staying here, you NEED to visit this hotel.

Mai Tai Bar has prime beach front real estate, and it’s allegedly the first place Trader Vic brought his legendary mai tais in Hawaii (they were invented in California). 

Their White Wash mai tai is my favorite. 

I also had the braised beef shortrib ragu for dinner one night and it was very good. 

Duke’s

Okay, let’s talk about Duke’s. This is easily the most recommended restaurant in Waikiki, and maybe in Oahu overall. Is it really the best restaurant on Oahu? No. BUT. It is right on the beach with AMAZING views of Waikiki Beach and Diamond Head. 

It’s a pretty large restaurant with a first come first serve bar section (a lot of tables) that serves the full menu. 

The food is decent (not outstanding, but not bad by any means), and on par with Waikiki prices. 

And that’s a recipe for a ton of buzz. You cannot underestimate how crowded this place gets…reservations are hard to come by, and it’s in a high traffic area. But if you can get a table in the bar area with a good view, it’s pretty dreamy. 

The mai tais are okay. Not the best, but pretty festive. Their coconut shrimp, fish tacos, etc. probably won’t be a culinary highlight of your trip, but they’re not disappointing. Their Hula Pie is a yummy tradition and I think it’s a must if you’re coming here. 

For me, Duke’s is one of those places where “the whole is greater than the sum of its parts.” The drinks and food aren’t particularly outstanding and the service isn’t anything to write home about, but the setting and the “buzz” make it feel pretty special. 

I personally probably wouldn’t come here for a full dinner, and it wouldn’t be my top pick (even top 5) for drinks), but I LOVE stopping by mid afternoon for a slice of Hula Pie at a table on the rail. Classic Waikiki. 

***Want to save major $$$ on your trip to Hawaii? I get asked ALL the time how I’m able to travel so often to Hawaii and stay at really nice resorts. Well, my favorite travel hack is cashing in points to score free airfare and free nights at some of Hawaii’s most high end resorts. Read my full guide on the exact system I use to max out credit card rewards here. Seriously, it’s going to save you soooo much money. 

Hau Tree

Hau Tree in the Kaimana Beach Hotel (at the far less hectic end of Waikiki) is one of my new favorite spots on the island. 

I’ve actually only been for brunch, but their dinner and cocktails are supposed to be amazing. 

It’s about a 15 minute walk from the heart of Waikiki and totally worth it! 

The Kaimana Beach Hotel has just been totally renovated in a really chic way and the restaurant is about as close as you can get to toes in the sand dining. 

You’ll get those coveted Waikiki views, but without the crowds and masses tooling around. 

HeyDay

This is one of the cutest pool bars in Waikiki and definitely worth a stop at happy hour. The bar has swings!

Tommy Bahama

I don’t normally do chain restaurants in Hawaii, but the rooftop bar is nice, the coconut shrimp is yummy and they have a great frozen mai tai which is unique.

Hideout at the Laylow

It’s not beachfront, but this has got to be one of the coolest places in Waikiki. The rooftop bar at the Laylow (one of my absolute favorite hotels in Waikiki) has such a cool vintage Hawaiian vibe and their drinks are top notch. 

They don’t rely on Diamond Head views to serve weak drinks ; ) 

I always go with the mai tai, but their old-fashioned is highly recommended. 

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 map and itineraries here.