Waikiki Perfect Weekend, Pono Guide to Waikiki

Waikiki Perfect Weekend, Pono Guide to Waikiki

So you want to pop over to Waikiki for a weekend…here’s the perfect setup. I wrote this for a friend who was staying on the diamond head side of Waikiki.


Waikiki is great for what it is, but if you are envisioning deserted palm tree lined beaches, it’s certainly not that.  All depends on expectations.  Not sure if you’ve been to Honolulu but it’s basically a big city stuck on one side of the island with Waikiki being a small section of mainly tourist hotels etc.  My first time here I was disappointed because I had visions of deserted beaches, Mai Tais and hula dancers : ).  There’s also a bit of a homeless problem at the moment…it’s seems to have gotten worse from the pandemic but usually they keep to themselves…even when they’re tweaking.


That said, Waikiki has some great things going for it.  Waikiki has some of the best restaurants etc in close proximity….walkable or a cheap Uber.  Beaches are nice w/ calm water to the shore so you won’t get pounded...and a lot of shops for whatever you’re looking for.


I would recommend getting a car for at least a day as I feel like you miss what Oahu really has on offer if you just stay in Waikiki or just the close surrounding areas. Prices are ridiculous right now so you might double check….that said, I’d probably pay it as you’ll forget the price for a day eventually but you won’t forget where you’ll go.


Another thing to remember…the early mornings and the sunset times are the most magically epic in Hawaii…you’ll probably have a bit of jet-lag which helps…just get up and take a walk around Waikiki in the early morning…and over to Kapiolani park...it’s beautiful.  If you keep walking and stick to the ocean side, you’ll go up the ocean side of diamond head which is fun and has some nice overlooks.  Some of the most amazing houses are along this route as well…always fun to dream.  You can walk the trails down to the beach there as well..   Sunsets are great from anywhere in Waikiki so just make sure not to miss that.  Not much happens at night so you can go to bed early without “FOMO"


Make reservations early for dinner…like now…or whenever they allow you to.  Hawaii is super conservative when it comes to the pandemic…masks everywhere and they restrict the numbers in restaurants …this means they fill up quick.  Add in cheap flights and hotels and we had an explosion of tourists…it seems to fluctuate now between empty and packed.



Here’s some restaurants we like close by to Waikiki or in Waikiki….everything’s expensive compared to the mainland but these are a bit better or you at-least get what you pay for...




The Deck…on the diamond head side of Waikiki…has great breakfast with a view of Kapiolani park and diamond head. I haven’t had lunch or dinner but it would be nice anytime of day.  We had breakfast for Mother’s day and it was wonderful...It’s not cheap but well done and the view of iconic Diamond head is as close as you can get.


Bogarts…breakfast and lunch.  I used to go here after surfing in the mornings…you could get coffee and their breakfast bagel which is amazing for pretty cheap.  It got featured in a Japanese tour guide and got way too crowded but no one is here from Japan now because of their travel restrictions.  It’s a 10-15 walk from your hotel or a 2min uber…. At the foot of diamond head outside of Waikiki.  If you wanted to hike diamond head (epic view of the city and island), the trail head is a bit further up the street or Kapiolani park is fun to stroll through as well which is just down the street (toward the ocean and Waikiki).


Island Vintage Coffee.  This is one of our favorites…they have really good breakfast and lunch items… and coffee. It’d be a bit of a walk deeper into Waikiki from you and there is now usually a long line but good.  If you decide to go to N. Shore, there’s one in Haleiwa and that would be a better bet.


Honolulu Coffee Company (experience center)…. This is right at the gateway to Waikiki just outside by the Ala wai canal.  You’d want to uber but it has good food for surprisingly cheap and the cappuccinos are really good…ask for the full boat.  The fried rice with kalua pork and an over easy egg is the jam…so are the breakfast sandwiches.   Acai bowls are the kids favorite.  The store has a bit of a museum vibe as they grow the coffee on the big island and distribute. Cool concept.




We don’t generally have big lunches because you're on the go and we don’t normally stay in Waikiki all day so I don’t have too many thoughts on this.  I think your better off just snacking for lunch...


Happy’s at the Hale Koa hotel…it’s cheap and quick grab and go style…good if you want to save room for dinner and drag it down to the beach.  This areas is one of my favorite to go in Waikiki…it’s on the other side from where you are so you might uber but the Hale Koa is the military hotel and their grounds are beautiful and open to the public.  The beach out front is a nice spot and they have “the barefoot bar" so you can grab drinks instead of having to bring them or go to a restaurant.  The “super” mai tai…will get the party going quickly…it has a kicker of 151 in it. But you have to ask for it.  As far as I know, that’s the easiest way to get drinks on the beach from a bar…there aren’t really any “beach bars” except for this one.    I would link this up with Azure for dinner…that would make an epic day..


Tucker and Bevy… down on your end...I actually haven’t been here but they sell to the supermarkets as well and it’s tasty.  This would be good for grabbing and taking down to the beach..


ABC stores… this is like the 7-11 of Hawaii…they have great snacks and good place to buy water or beer or whatever.  Try a Spam Musubi as it’s a local thing and worth a try.  Also a Manuapua is a unique local eats that’s fun to try.  If you want to bring drinks down to the beach…everybody does it but it is technically illegal.  Just bring a yeti or something to use…I’ve never seen anyone get in trouble unless they are having a full on beach rager. 






Signatures... in the Alamoana hotel…this is one of our favorites.. it’s a high end restaurant at the top of the tower with views for miles.  It’s great for dinner but it is pretty expensive…say 200 for couple.    We found that they have a happy hour which starts at 430…you need to be there a little early as a line usually forms and there isn’t a ton of seating for happy hour…. They have 1/2 price pupus (appetizers) and it’s great for trying a bunch of stuff.  Ahi tartar, shishito peppers, steak plate are my favorites…we found you’ll still spend 100 bucks but it’s so worth it.  It’s down by Alamoana beach park…I’d walk around there after dinner…nice spot and alamoana mall is right there as well…don’t think id waste the time shopping but could.


Maui Brewing…great beer…if you like IPA’s try the big swell…it’s a bit too good. Food is decent and beer is great.  It’s not on the beach and doesnt have a view so would only go here if you really like beer …or go when it opens for a happy hour and then move along to another joint.  You can buy their beer about anywhere so might be a better bet to just buy a 6er and head to the beach.


Sansei…down on your end.  Great for sushi and they have an amazing crab truffle ramen…it’s ridiculous…. They used to do a 1/2 price thing early on Sun and Monday but not sure if they still do it…they shut down for the pandemic and not sure how open they are now.  Also had an Ahi roll which was amazing…I didn’t like sushi at the time and even I liked that one.


Dukes…this is one of the first places I went when I moved here when people came in town.  It’s a bit touristy but you cant beat it as it’s on the beach and hits all the right notes.  They have a good happy hour during the day.  That said, I haven’t been down there in 15 years but you’d have fun for sure.




If you want to go higher end…and I’d recommend doing it one night…these days you’ll need a reservation for sure.  Since it’s just you and your wife, it shouldn’t get too pricey…it’s always annoying bringing the kids as the bill balloons.


Azure… I’d probably do this one if you could only do one high end place…it’s location is amazing (although on the other side of Waikiki from you) and on the beach…. The royal Hawaiian hotel is fun to walk through as it’s one of the oldest hotels in Waikiki and they have some of the history on display.  It’s close to the Moana surfrider which is worth a walk through as well because of the history.  If you can’t make dinner, they have a bar outside and is magic at night…


Hy’s Steakhouse has been around since the beginning of time…no view but neat place..when I first moved here, I live in the tower above it and had to smell the steak being cooked everyday while I ate my can of tuna and bagged ramen.. I still go here to celebrate stuff but it’ll set you back a bit. You should get the flambe for desert…it’s an experience…the kids still talk about it.


House without a Key …pricey but a unique spot and a beautiful experience.  … we went down here recently after dinner elsewhere to have a drink and watch the live music and Hula show…I think they do it every night…and it’s a former miss Hawaii which is fun.  drinks are expensive but you get a show…think we had 3 drinks for $60…but I’d do it again for a special occasion.


Plumeria Beach House…this is a bit of uber on the other side of diamond head from Waikiki. It’s a beautiful hotel that feels miles away from Waikiki.  Plumeria beach house is the cheaper of the restraunts in the Kahala hotel but we really enjoyed it as it was on the water.  It wasn’t cheap by any stretch but was a wonderful experience…especially if your over the crowds. There’s a dolphin pool on the grounds and its fun to poke around.  This is where the “high makamaka” folks stay (high rollers)...




Perfect days… these are on the way to each other so you could do it efficiently.


1.  I’d get up early and go for a walk around waikiki… get picked up by uber from wherever you get tired and go to Honolulu coffee company experience center for breakfast…then uber down to a beach day around the Hale Koa…bring all your towels etc from the beginning.  Have some drinks and super light lunch at the barefoot bar and Happy’s…float around the afternoon (sailing catamaran booze cruise would be perfect) in the area and then head to Azure for dinner and walk the hotel grounds…. That’d be a long day but relaxing and lots of beach time…if you were really going for it…you could hit House without a key for drinks, music and hula for a night cap before passing out.  It would also be really fun to go on one of the catamaran sailing beach charters…they are down on this side and are a cool way of seeing Hawaii from a different view…id check a coupon site to see if you could get a deal


2. If you're able to get a car…I would head to N. Shore…Haleiwa is my favorite spot on the island…it’s the perfect surf town and probably what you envision when you think of Hawaii.  The trip up is part of the fun.  It takes about an hour to get there depending on how much traffic is in “town” (what everyone calls Honolulu).  On the way you can stop at Dole plantation,..it’s a tourist trap for sure but is nicely done.  Their dole whip is pineapple flavored soft serve…we still stop and get it. It’ll probably be closed however if you go in the morning..  Continue up into Haleiwa town the poster child for surf towns…nothing opens until about 10 except the coffee shops.. you can hit up Island vintage coffee for breakfast.  Then I’d roll up to the beaches…you can stop at Waimea Valley…it has a nice gift shop and has beautiful trails that are easy to walk…it does cost to go back to the waterfall but they have historical spots that are worth the admission.  Then I’d head to Pipe…the beach park is called Ahukai and there is parking but you’ll probably have to park on the road.  If the waves are going off…it’s the best place to watch surfing…it breaks close in towards the beach and is super fun to watch.  It all depends on swells and wind etc but usually somethings going on there.  Then head back to Haleiwa for lunch…we keep going to The Beachouse and it’s nice…not amazeballs but nice place to rest.  I like Haleiwa Joes a bit better but they have strange hours now and I think only open after 3.. it’s great to get a seat close to the outside…perfect.  Another option is to just keep going and stop at Turtle Bay Hotel…this is one of my favorite spots on island…great to get a drink and a something to eat…it’s hotel prices but the grounds are beautiful. There’s actually hikes on either side of the property which are fun too.  I take the boys fishing up here.  You can either continue going around the island the same way and will eventually find your way back home or can backtrack…it’s probably about the same time either way.  The road follows the ocean all the way to the windward side and is a beautiful drive.


3. Get up early and walk around Kapiolani park…could go down to diamond head if you were feeling spry.  Head back to The Deck for breakfast…beach day around that end of Waikiki by your hotel.  If you walk towards diamond head…there’s some beaches without as many people. If you walk all the way down to the “War Memorial” there’s a nice beach called Kaimana…it’s more locals and a neat spot.  Could do lunch at bogarts which is over on this side…might be a little annoying to walk it all but it’s close.  I’d book a surf lesson as well…there are a few over on this side.  It’s the hardest sport I’ve ever tried but is amazing and worth the effort.  Uber to Signatures for happy hour…and then walk around Ala Moana beach park.




Alright…that’s my novel : ).