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

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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. 

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. 

Mai Tai Bar

This beachfront bar at the historic pink Royal Hawaiian hotel is one of several places that claims to have invented the mai tai. Maybe we’ll never know the truth, but this is such an iconic spot.

They have several different varieties of mai tais and whichever one you choose you’ll be feeling good as you sip it underneath those famous pink umbrellas. 

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. 

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. 

Here’s a few places that I haven’t made it to yet, but I’ve been hearing great things about…

La Mariana Sailing Club- Not in Waikiki (about a 15 minute drive), but one of the best Tiki Bars in Hawaii.

Tommy Bahama- Okay, okay, okay I know…no chains, BUT I always hear such great things about their rooftop vibes and coconut shrimp. 

DECK. – Amazing views of Diamond Head with a great happy hour. Above the Queen Kapiʻolani Hotel.

P.S. I travel to Hawaii multiple times a year, and let me tell you a secret…I do most of it for FREE using credit card points and miles. 

I have a somewhat intricate system that I’ve fine tuned over the years to maximize earning points and how I cash them in, but the short version is:

I use THIS Marriott Bonvoy Boundless card for free Marriott nights. The sign up bonus alone on this card will get you 3 (sometimes 5!) free nights at hotels in Hawaii like the Sheraton Maui, Royal Hawaiian (Oahu), Sheraton Kauai Coconut Beach Resort, and the Waikoloa Beach Marriott (Kona). 

And I use THIS Southwest Premier Rapid Rewards card for free flights on Southwest. The sign up bonus will get you at least one round trip flight to Hawaii (possibly two depending on where you’re flying from). 

The combo of these two cards will have you most of the way to a free trip to Hawaii right out of the gate. Again, you can sign up for the Marriott Bonvoy Boundless >> HERE and the Southwest Premier Rapid Rewards >> HERE
And if you’re really serious about getting into the travel hacking game, read this post for a more in depth look at how I maximize credit card points to book travel.

P.P.S. Here’s one more really important thing you need to know before your Hawaii trip…

You’ve got your airfare, hotel, rental car and your big activities booked, so you should be good to go, right? Wrong!

Travel is BOOMING in Hawaii and a lot of state and national parks have instituted reservation systems at some of the island’s most popular spots to help manage the crowds and make things a little more sustainable. 

That means that there are now over half a dozen sites (beaches, trailheads, etc.) that require advance reservations. And some sell out well before you arrive on the island so you really need to have some sort of a plan. 

I recently saw somebody in a Hawaii travel group post in a panic that they didn’t know they had to make reservations for things in advance…they thought they could just show up and “go with the flow.” I was tempted to say, well, “as long as the flow doesn’t take you somewhere that requires reservations, you can!” ; )

But I don’t want YOU to be that person, so I’ve pulled together a list of all the places you need to reserve entry in advance (plus all the details on booking windows, price, links, etc.) and a handful of popular tourist hotspots that book out really far in advance too. 
Get that info >> HERE