
Hawaii – who can have a bad time? Most people think that the islands are primarily for sitting around on the beach or hanging out in a pool but there’s so much more to explore and eat!

We stayed at Sheraton Waikiki which sits on the beach. If you stay here, definitely get an ocean view room to enjoy the beautiful views the island has to offer. We were on the highest floor and woke up every more to the view above. We could even spot sea turtles from the room.






The hotel offered an infinity adults only pool along with another pool for those traveling with children equipped with a waterslide. The poolside restaurant – Edge of Waikiki – offered the basics and convenient for lunch and drinks if you are spending a day lounging by the pool. There are cabanas for rent for an additional fee along with a free towel service for hotel guests. The hotel also has another restaurant – Rumfire which comes to life primarily in the evening. There’s indoor and outdoor seating and live music in the evenings. Drinks were nothing special but the live music was enjoyable. The hotel is located in the heart of the action and a quick walk across the street takes you to a multitude of high end shops and great dining options.
Day 1
First stop – coffee of course. We walked to Kona coffee which has a simple but delicious menu. They also have great pastry options and I wanted to try them all. We went back to the hotel and grabbed Poke Bowl and Poke appetizer at Edge of Waikiki at the Sheraton. It was fresh and well flavored. Next, we hit the infinity pool. After feeling relaxed and getting a tan, we headed out.



We went to Sky rooftop and barely missed happy hour which ends at 5pm. However, the bartender was nice and gave us happy hour pricing anyways. We didn’t have a reservations but they have some high top tables where you can enjoy the views. It’s a nice place to watch the sunset from 19 floors above. We tried the Spicy Tuna Roll which was much bigger than expected. Also tried tried the Truffle Honey Mascarpone which was an interesting mix of savory and sweet. It was also the first Mai Tai in Hawaii and it did not disappoint.



We then headed to House without Key where we had reservations. I would highly recommend checking this place out. The menu isn’t extensive but they have live Hawaiian music and former Miss Hawaii’s who perform. It’s outdoors and has a very laid back atmosphere. However, their fries were $18! Probably the most expensive regular fries around. The Ahi Tataki was good. I got lost trying to find the bathroom and a waiter was kind enough to walk me there since it was located a little far.


It worked out because he introduced me to Lewer’s Lounge, which a nice cocktail bar with a pianist. Usually they have a live jazz band at 8pm but it was a pianist when we were there. It was an intimate vibe but we fell in love with it immediately and even went back the following night. Their drinks were great despite being pricey but well worth it. The charcuterie boards at the tables looked very good (we were too full to try) and may be worth a shot.
Day 2
We had to wake up early to make reservations for Hanauma Bay. It is a process but recommend making the extra effort. Tickets are released at 7AM two day in advance and sell out usually in less than 15 minutes on the city’s website. Luckily we were able to score tickets for the day we wanted.









Since we were already awake, we decided to take an Uber to Diamond Head. Make sure you check the weather as there’s little shade on the hike. It is also $5/person walking in. I would highly advise avoiding driving as the parking lots fills up and there were a lot of cars getting turned around. Be ready to climb a lot of stairs (>200 in total) but it’s worth it. The views at the top can’t be beat. There were people of all ages and fitness levels on the hike so it’s definitely doable. On the second set of stairs, there is an alternate route which is slightly easier (but longer path) if the step step of yellow stairs seems daunting. After making the trek down, we went to the food truck and got a Dole Whip in a pineapple and it was delicious especially in the heat. We then decided to walk back to Waikiki (~3 miles) and it allowed us to see the residential areas which is always a plus when traveling. I love being able to see the types of homes that people have.


We were parshed so went to Hula Grill which had a large selection of beers on tap but unfortunately many were out. We opted for Crab and Macadamia Nut Wontons and Cajun Battered Fish Tacos. The food was good but nothing to write home about. There were beautiful views of the water and Diamond Head if you sit outside. We had food coma and decided it was time for a nap. We woke up refreshed and decided to head downtown. We were disappointed that we did. Downtown is about a 20 minute Uber ride and not much going on. We were hoping to get into a small bar called Bar Leather Apron but unfortunately part of the seats were closed so we couldn’t get in without reservations. It looks very inviting so it you can score reservations, definitely try. We walked around but it was deserted and most of the places were already closed although it was barely 6pm. We tried to go to Tchin Tchin but it was closed for a private event. Feeling disappointed, we actually Uber’ed back to Waikiki. If you’re debating whether to go to downtown, I think you’re not missing anything by skipping it. We went to Buho which is a rooftop Mexican place which was surprisingly empty. It has a lot of potential and we enjoyed fajitas there. Be aware of their spicy margarita because it is SPICY (coming from someone who likes spice)! As we walked down the main street, we were pleasantly surprised with the live music at multiple venues.





We decided to stop in at the Gallery Bar which is a coffee shop by day and bar at night. They have live music every night and we enjoyed listening to _dotdotdots. There’s also cool artwork on sale around the place which is fun to check out even if you’re not going to buy anything. Best of all – they have FREE popcorn!
Day 3
We decided we needed one water day while in Honolulu and today was going to be it. We started the day at Island Village Coffee which is a very cute second floor restaurant. The main line was long but behind it was Island Village Wine Bar which was serving breakfast and shared their kitchen with the coffee bar without the wait.


I had the Mushroom Brioche and my husband had the Loco Moco. Both were absolutely delicious and I loved the nutty taste of the Island Latte. After bruch, we jumped into the ocean but it was freezing so decided to spend most of the way in the pool. It was much more crowded and drinks took forever. So we went to the marketplace right behind the pool and picked up a couple beers for a fraction of the price!



That night, we took an uber to a speakeasy called the Blind Ox. Surprisingly it wasn’t crowded but it was a cool place. The food was great and the drinks as well. There was a bull as you entered too. On our walk back to the hotel, we stopped by HideOut which is another rooftop bar with live music. We didn’t have reservations but were able to grab a quick drink at the firepit. I would have gone back for another drink if we had more time.
Day 4
Today was our day of exploration. Hawaii has a car share service called Hui which is very convenient. You download the app, input your information and can see a map of cars near you. You can rent for as little as one hour or for the entire day. By the time we checked out the app, the cars closest to us were unavailable but we were able to walk about 0.5 mile to pick one up. Your phone serves as the key and it’s super convenient.



Our first stop was Hanauma Bay. It was breathtaking and known to be one of the best places to snorkel around the island. If you’re driving, try to reserve an earlier entry so you can snag a spot. You then wait in line per your entry time and have to watch a short movie about conservation before you can get in. The whole process can take 20-30 minutes but well worth it. It is a short hike down or you can take the shuttle. I advise walking because you can catch aerial views of the reefs. We rented snorkel gear and headed into the cold waters. Surprisingly, it warms up quickly. I was a little disappointed at the lack of fish we saw but it was fun nonetheless. There is a small spot to eat at the entrance but we headed to a strip mall nearby to get some food.


I was pleasantly surprised to find a Malasadamobile (Leonard’s food truck), and we were able to try Malasada Puffs which were yummy! They are warm donuts without the hole and you can get them filled as well. I personally liked the plain ones.



We then drove around the island and made various pit stops for pictures: Halona Blowhole Lookout –> Pete’s Chair –> Makapu’u Point Lookout –>Waimanalo Beach –> Lanikai Pillbox (didn’t do the hike but it’s supposed to be nice) –> Kuala Ranch (if you’re a movie buff – spend some time here and go on the tours) –> Bodhi Temple. It does cost $5 per person to go into Bodhi Temple the backdrop is gorgeous. We were going to continue around the island but decided to cut it short. We ran into Waiahole Poi Factory which seemed like a random place to eat along the drive but it had a huge line so we stopped and tried some delicious Hawaiian food. There’s no where to sit there so you can drive a couple miles and enjoy your food on the beach.


That evening, we went to Tommy Bahama’s for some appetizers. Surprisingly, their tuna tartare was great. They also had a berry spicy Palamo which I could have drank all night (but don’t worry I only had one). We then checked out Cuckoo Coconuts because who wouldn’t be curious with that name? It’s a cool Tiki Bar with live music and they even have a drink in a real pineapple!
Day 5

Last day on the island and we couldn’t leave without getting some Hula Pie at Dukes. But we had to get some last minute pool time to build up an appetite. If you’ve never had Hula Pie, I would suggest indulging in this sugary deliciousness. It has oreos, ice cream, macadamia nuts and whipped cream – what else could one want?! With our bellies full, it was time to say good bye and head to the airport.













