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3 Days in Oahu

After a long, blissful summer of exploring new cities like San Francisco, St. Louis, and Chicago, I couldn't wait to escape to somewhere with a more diverse landscape and less and hustle and bustle to end the season. Back in July, I had planned and detailed out a week-long trip to Puerto Rico, which I looked forward to for weeks as I continued working in NYC and New Jersey.

Unfortunately, August and September turned out to be one of the most devastating months in natural disaster history, with multiple hurricanes and earthquakes that destroyed many parts of Mexico and the Caribbean. We monitored the hurricane situation closely for weeks leading up to the trip, and ultimately decided two days before the flight to reroute our destination to Hawaii instead. I actually have never been to Hawaii before, but quickly added it to one of my top destinations after Melissa went on a 12-day trip last May and raved about how it was her absolutely favorite destination after a very long summer of traveling (Read her incredible Hawaii posts here). Based on her recommendations, we decided head to Oahu and Kauai for a total of 6 days, and we can confidently say that it was the best decision we could have made given our situation! If I had the flexibility, I easily would have chosen to stay in Hawaii for a week or even more, since there is so much to see and enjoy here. Given how long it takes to get here from New York, spending a few extra days is definitely worth it!

Below is an itinerary detailing what I was able to see and capture in 3.5 days in Oahu! I hope this helps you in your trip planning for a visit to Hawaii or if you are just looking for inspiration because you have constant wanderlust like me. All are welcome!


The Sheraton Waikiki

Waikiki has one of the greatest selections of hotels and places to stay when it comes to the island of Oahu, and it is a quick (depending on traffic) 30 minute drive from Honolulu International Airport. We stayed at the Sheraton Waikiki, and although it was super crowded the entire time, we had an incredible view of the beach and pool from our room, and we thoroughly enjoyed the gorgeous infinity pool.

Waikiki Beach happens to be the backyard of the Sheraton Waikiki, and because it is one of the most popular beaches on the island, there are always a ton of people around. We did get a chance to watch the gorgeous sunset on our first night at the beach, and the next day with a duck floatie in the morning before the late morning crown came, but it definitely wasn’t the most relaxing beach. I do recommend checking it out earlier in the morning though since the beach sits along some of the most beautiful hotels in Waikiki.


Watch Fireworks at the Hilton Waikiki Beach

Every Friday Night, the Hilton in Waikiki puts on a beautiful fireworks display right on the beach. They begin at 7:45 pm, and it seems like the entire island flocks over to get good view of the show. Although I wouldn’t recommend spending too much time camping out for a good spot (the display only lasts about 10 minutes), I do recommend going a bit early since you will probably find it difficult to even walk around in a herd of people. Since we walked to the Hilton, I was able to snag a spot right in front of the base of the fireworks, though you can get a great view from Waikiki beach and at the beach bars further East.

Lanikai Beach

Lanikai beach is about a 30 minute drive from Waikiki, and is easily the most beautiful beach we visited in Oahu. Although the water wasn’t as calm as it could have been, it was quite the backdrop for a quick photoshoot with the fresh haku I picked up from a local flower shop along the way. For those of you looking to get that Hawaiian Goddess look with your very own flower crown, I recommend placing an order early for pickup since many places only take custom orders. If you're lucky enough, a local flower shop may have some ready-to-buy, but usually this is not the case. Lanikai is consistently ranked among the world's top beaches, and I certainly would have to agree. I wish I had more time to frolick around this beach, but coming here gave me the perfect taste, and I can't wait to come back in the future.

Drive along the Northern Coast

Driving along the coast of one of the most beautiful coastlines in the world is hardly a chore, and I would highly recommend renting a convertible for the full cruising experience. Many people recommended visiting North Shore in Oahu for more quiet and relaxing beach time, so we made the drive after visiting Lanikai in the early afternoon. Sometimes, the most beautiful places are discovered when you're not really looking for anything at all, so if you do have some extra time to wander without a particular final destination, I would suggest hopping in the car and just driving around. Practically every corner of Hawaii is beautiful, so you can't really go wrong. Stop along the way for food, shaved ice, and plenty of photo ops! One of my favorite spots was this juice shack we spotted since we were able to pick up a couple of coconuts for an afternoon treat. I also got to take the pineapple photo (see below) that I had been meaning to take on this trip.

Laniakea Beach (a.k.a. Turtle Beach)

I was thoroughly excited to see sea turtles spread out along the beach on North Shore, so I am slightly disappointed that I didn't spot any when we visited Laniakea Beach during sunset. I am convinced we went to the wrong beach entirely, but that is another issue in and of itself haha. To avoid what happened to us, I recommend reading about Laniakea and prime sea turtle season here. Regardless, we watched a beautiful sunset (no crowds!) and ate delicious chocolate mousse pie from Ted's Bakery, which is only a few minutes away. Ted's is an institution in Oahu, so make sure you pick up a sweet treat for the prime sunset watching experience.

Kualoa Regional Park (View of Chinaman’s Hat/Mokoliʻi)

Kualoa was actually not on the Oahu itinerary at all, and we happened to stop by this beach since it was on our drive to Laniakea in the early evening. LIttle did we know, we happened to cross off seeing Chinaman's Hat from the beach, which was absolutely breathtaking. Mokoliʻi is a basalt islet in Kāneohe Bay, and is part of the Kualoa Regional Park about 1/3 mile off shore of Kualoa Point, Oahu. I believe you can actually visit the island via kayak or boat, so I recommend adding this to the list if you have extra time on your hands to explore.

Hanauma Bay Nature Preserve

The Hanauma Bay Nature Preserve is one of the top things to do in Oahu, so we made it a mission to get there early to avoid the giant crowds that I read about on TripAdvisor. Even though we made it there by 8:30, there were already tons of people waiting in line. Admission into the Preserve is $7.50 per person, although it will cost you an addition $15-$40 for snorkeling gear depending on what equipment you want to rent for the day. We spent about half an hour snorkeling, although we were disappointed by the lack of fish we saw and how cloudy many parts of the water was. Although I did enjoy getting a bit of sun after being in the water, I would have enjoyed it more with less crowds, so I recommend getting there right at opening time (7am).

Halona Blowhole Lookout Fun Fact: Halona means “lookout” in Hawaiian! The Halona Blowhole is a cool stop along the Kalaniana’ole Highway, located at Halona Point. The rock formation reminded me Geysir in Iceland (read my posts here), where crowds gather to watch the natural phenomenon of thousands of gallons of boiling hot water erupt up to a few hundred feet into the air. The Hawaiian version, however, is a natural occurrence formed by molten lava tubes from volcanic eruptions thousands of years ago. Because the lava tubes run to the ocean, large waves crashing against the coast can cause water to shoot through the tubes, and the blowhole will shoot up to 30 feet of water into the air! It’s actually pretty cool, and if you don’t watch intently for a few minutes, you might just miss it! There is actually pretty ample parking, which I found surprising, but you may have to fight with others for a spot during high-peak times. If you have more than just a few minutes on your drive (the Blowhole is best coupled with the Hanauma Bay Reserve and Koko Crater Trail), I recommend checking out the Halona each Cove, also known as the “Peering Place”. I didn’t get a chance to enjoy it, but this small sandy beach at the cove would be a sweet spot for an early morning picnic.

Tip: The blowhole is best captured on video vs still photo.

Lanai Lookout

The Lanai Lookout is one of Oahu’s greatest gems, and I highly suggest adding this stop to your drive, since it is also a lookout point along the Kalaniana’ole Highway, just a few minutes drive away from the Halona Blowhole. Oahu’s southeastern shore is one of the most beautiful coastlines I have ever seen, and is definitely underrated, in my opinion. The parking lot is carved into the seacliff, and on a clear day, you can see the islands of Lanai, Molokai and Maui! I really couldn’t get over how beautiful the cliffs are, and it easily makes one of my top 5 destinations for taking photos on the entire island. If you happen to be visiting during whale watching season (from December to April), the Lanai Lookout is a prime spot for spotting a humpback whale.

Tip: Bring binoculars and good shoes for climbing up and down the rocks if you want to venture

Koko Crater Railway Trail Hike

If you're looking for a StairMaster workout, then look no further than hiking the over 1000 steps of the Koko Cater Railway Trail. This abandoned railroad track at KoKo Crater is a super fun and steep hike with some amazing views. Due to time constraints, I only climbed half of it before beginning my descent, but I think the climb up to the top would have been so worth it!

Tip: Alot 1-2 hours for the duration of the hike since it takes more time once the path becomes extra steep. Coming down is also a bit tough so be careful not to slip!

Diamond Head

Diamondhead Crater is one of Hawaii's most well-known landmarks, and walking up the side of an extinct volcano is indeed as exciting as it sounds! Apparently, it is the lasting remnant of an volcanic explosion that occurred about 500,000 years ago. Crazy right?

The trail up to the top is easy to moderate, and probably one of the most enjoyable hikes of my entire trip. Although there aren’t too many steep inclines for most of the way, there are many stairs to climb once you reach closer to the top, so make sure you are prepared to walk up. Diamond Head is probably one of the best places to catch the sunset with an incredible view, so time your hike accordingly and begin about an hour before the anticipated sunset time.

Tip: Hydrate or cool off after your hike by grabbing a fresh coconut or rainbow shaved ice at the bottom of the trail!

Chief’s Luau

A luau is a traditional Hawaiian party or feast featuring classic island cuisine and is often accompanied by entertainment. I have been to themed luau parties in the past, but was particularly excited when I realized during the very last minute planning that I couldn’t finally go to a real one in Oahu!

Chief’s Luau is one of the most popular luaus on the Island and was definitely a one-of-a kind experience that you must do when visiting Hawaii. For those interested in this particular Luau, there are three tiers of seating at different price points: Aloha, Paradise, and Royal (least expensive to most expensive). There are different benefits for choosing the latter two options, including priority in entering the luau, better seating arrangements, getting food first, and getting extra drink tickets. We went with Paradise, which allowed us to get into the luau area at a great time to join the festivities before dinner. However, with the Royal option, you get to try to roasted pig and also the purple flower lei (I magically got my hands on one of them though…) From coconut leaf crown making and bamboo shoot javelin throwing to temporary tattoos and the sacred pig prayer, there was plenty to keep us entertained before our dinner buffet. The show, of course, was the highlight of the experience since we were wowed by the music and dance from different Polynesian islands including Tonga, Hawaii, Samoa, and Tahiti. Chief’s Luau without a doubt has a crew of incredible talented singers, dancers, and fire entertainers, and the Chief himself is quite a hilarious guy. You’ll be sure to laugh the entire night!

Tip: Although we rented a car for the trip, we decided to book round-trip transportation directly from Chief’s Luau since we were planning to have a few drinks there. For $16, you get picked up from a central location near your hotel and dropped off at the same spot. The ride is only about 30 minutes from Waikiki and the bus ride is really comfortable and convenient.

Pearl Harbor

It’s safe to say that you simply cannot come to Honolulu and not visit Pearl Harbor, which is one of the defining events in our nation’s history. Tickets are free and can be reserved online, but time slots are quickly taken, even months in advanced, so make sure you book as soon as you know you will be visiting. For those of you who could not snatch tickets, 1300 are reserved for day-of visits and are a first-come, first-serve basis. Pearl Harbor opens at 7am, so go early to avoid disappointment since it gets very crowded (as you can expect from the most popular place to visit on the island). Tickets include a ferry ride over to the U.S.S. Arizona and Missouri memorials, which I unfortunately was not able to visit due to time constraints. I did get to walk around and ready the details about the attack and events leading up to the devastation, which really jogged my memory about what I learned back in history class in high school. It really was incredible to be able to visit a place that I have read about in my textbooks throughout the years.

Dole Plantation

Pineapple has always been one of my favorite fruits, and it totally slipped my mind that the Dole Plantation was based in Oahu until we passed it one evening driving along the coast back to the hotel.

In the past, I’ve visited the Coca Cola Factory (Atlanta), Zotters Schokaladen Manufactur (Austria), and the ever so popular, Hersey Park (Hersehy, PA), which were great experiences to see how some of my favorite foods are made! I was especially excited to see the world of Dole, learn about the history of the pineapples that I buy all the time, and most importantly, try a Dole Whip! There are three different activities that you can do at the plantation - the 1) Pineapple Maze Garden 2) Plantation Tour and 3) Pineapple Express Train. You can purchase each separately, or choose a combination of any 2 or all 3 for a discounted price. We decided to skip out on the maze and ended up doing the 25 minute train tour around the plantation. It was most surprising to see how many different types of fruit Dole grows, including avocado, lychee, and watermelon. Make sure you stop by the souvenir shop and visit pineapple paradise on your way out . The shop also has a food section, where you can choose what how you want to eat your Dole Whip (a cream frozen pineapple dessert). From banana splits and pineapple floats, to whip in a cone or in a plastic pineapple cup, there’s plenty of ways to enjoy it!

Tips, Tricks and FYI's

  • Rent a convertible in Oahu, it adds to the island experience...and photo ops

  • The Sheraton Waikiki is quite central to restaurants and the pool amenities are fantastic but if you're looking for something less busy and more remote, an Airbnb in North Shore will serve as a better location. However, if you're into shopping, city life with an accessible beach, a beach front hotel in Waikiki is perfect for you.

  • Don't expect night life. Last call is at 1145pm (haha)

  • Haiku stairs - before putting this on your itinerary of things to do, make sure you understand the risks. It's illegal to hike the stairs and getting caught can lead to hefty fines and possible felony charges. However, it is a once in a lifetime experience, so hike at your own risk!

  • Sit back, drink a coconut, and relax! Drive along the coast and put that convertible on cruise control and enjoy the blue water sights and mountain backdrops. Be sure to stop off at beaches for a quick dip or picture

  • Hawaii sun can burn- sunscreen up...

  • Download an offline copy of the maps of oahu and Kauai. You can also download offline trip advisor for each city. You will lose service at certain points on the island

  • Don't be surprised to sit in traffic in Waikiki and allow extra time to get to your destination because you never know how log you'll have to wait around for

  • Set up for a nice sunset view around 6pm in North Shore with dinner and snacks!




Ono's Seafood

Ono’s Seafood Products made the 2015 Yelp's Top Places to Eat in America List, coming in at a #5! It’s safe to say that our ahi tuna poke bowls overlooking the sunset at Waikiki beach was the absolute best meal we had on the trip. The fish here is SO fresh and buttery, and there are plenty of different flavor options when it comes to picking your ahi or tako. Prices are unbeatable for the monstrous portions you get, and is a must-visit food spot on the island.

Leonard’s Bakery

A malasada is a Portuguese confection made of egg-sized yeast balls which are deep fried and covered with granulated sugar, and they are absolutely DELICIOUS.

Leonard’s opens at 5:30 am, and although is isn’t exactly necessary to go at such an ungodly hour, it does add to the experience to wake up early and grab a hot coffee and pastry for breakfast to start the day. There are about 6 flavors you can choose from, including vanilla or chocolate custard-filled ones, and plain cinnamon sugar. The local favorite is the Li Hing, which is covered in sour and sweet sugar. The taste is unexpected but definitely very unique and unlike any other flavor doughnut I have ever tried. I highly recommend picking up a half dozen and trying out all the different flavors with a cup of Joe.

Ted’s Bakery

Rainbow House Shaved Ice

Cafe Kaila

Thank you so much for reading my Oahu Diaries! Can't wait to share Kauai with you guys!


#Oahu #UnitedStates #Hawaii

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