One Week On Oahu
“Aloha Ke Akua”
You have a week to go anywhere in the world. Somewhere tropical, let’s say. A place where people live off the land and are in tune with the sea. Somewhere it is always warm. A place with the feeling of home. A corner of the Earth where it doesn’t matter what you have or what you own. All that matters is your love of life and your passion for adventure. That place for me has always been Hawaii. Now granted, I haven’t been to many places in the world, YET. But Hawaii is a special corner of the Earth I know I will always feel at home on.
I’ve first step foot on the islands when I was five and I haven’t stopped going back since. I started on Kauai, was a bridesmaid on Maui, island hopped to Moloka’i, then later my best friend at the time moved to Oahu on a whim after a visit we made. She fell in love, and then, so did I. I met my love on Oahu one night in Waikiki. Recently him and I took my roommates and one other mutual friend back to where we met. I wanted them to see the place that made my heart fully open up.
I have always been a traveler who doesn’t like to plan too much. I love to get taken by the wind in whichever direction it feels I need to go. I make sure key details such as where I will stay and what I want to see are planned, but other than that I like to have a list of options and see how I feel that day. This trip was different because I was bringing friends who had never been to Hawaii, let alone any island. I wanted them to see all the spots I fell in love with, and to get the real sense of this magical place. So, in an effort to maximize our time and fun, I made my first trip ITINERARY! One full week on Oahu and I had to make the most of it.
In this post I’m going to break down exactly what we did during our week on Oahu and give you some fun suggestions on how to make the most out of your trip. Even if you do not have enough time to get to everything, these are all great tips and ideas on where you can go and what you can do.
* Also something to note: We were on the go EVERY DAY. We all planned to go out partying every night but only ended up making it out once because we were so tired from all the activities and sun. Yes, there were moments of relaxation and downtime, but overall our schedule was jam packed to make the most of our time. I am very much an on-the-go person and love to stay active during my vacations. I am a big fan of natural and FREE activities and like to indulge as much as possible on the things that mother nature provides for us to enjoy life. With that being said look below for a great week on Oahu!
DAY 1 : Manoa Falls, Waikiki At Night
If you are staying in or near the Waikiki area, Manoa Falls is a super close trail with the maximum experience. Rent a car and head over just about 15 - 20 minutes outside of Waikiki. This trail is not too strenuous and is nothing short of “Jurassic Park” amazing. You pay a small fee to park your car which goes directly to the conservation of the paradise you are about to enter. The hike is about an hour there and back but ends up taking a little more time if you like to stop, take photos, and take in the beauty of the island. Be careful of the slippery trail, it is almost always raining a bit while you hike. At the end a beautiful waterfall awaits. *Pro Tip: Wear water shoes so you don’t slip everywhere and you can wander off the path a bit into the river and pools.
Waikiki at night is a tourist trap. It is the perfect place for dining, drinks, and shopping for souvenirs. The beach at night is a nice place to hang out and even go for a dip under the moon if you are up to it. The Queen used to love bathing under the full moon. Walk the strip at night, bar hop, and dance the night away. If you already live in a super city and are going to Hawaii for a change of scenery, you might want to cross this one off the list. It is the typical, overcrowded, commercial area of the island. With that being said, it’s fun and alive. *Pro Tip: If you find yourself in Waikiki in the morning instead, go to the Outrigger Waikiki Hotel and get breakfast at the Sunrise Shack. You won’t be sorry.
DAY 2 : Tantalus Lookout, Diamond Head Hike, Oahu Boat Party Cruise.
Tantalus lookout is one of my favorite spots on the island. Again, this drive is very closely located to the Waikiki/Diamond Head area. You spend more time driving up the mountain then you do getting to the base from these nearby areas. The road up is very windy and lusciously dripping with tropical plant life. It is as if though you are driving up the jungle towards the heavens. Along the way up there are multiple spots you can pull over and see the glorious view of Oahu and it’s city lights. This mountain is huge and the road up can take a while with it’s many twists and turns. Pull over, follow a path, explore, do a Tarzan yell while you pound on your chest, it’s just the place for it. *Pro Tip: see if you can find the hidden tree house for a great sesh/photoshoot spot. I found it years ago but haven’t been back since.
If you are an avid hiker like moi, Diamond Head is a must. Because it is on protected state land and considered like a national park, a small fee is required to enter. This is a good hike nearby Waikiki that doesn’t require getting wet and/or dirty. It is not a jungle hike, but more of a trek up one of Oahu’s most famous landmarks. During the super rainy seasons Diamond Head gets what appears to be a Hula skirt of greenery surrounding it. Hike up this path for stunning ocean and city views. *Pro Tip: See if you can find the almost hidden secluded nude beach under Diamond Head that is down a single lane street that leads right to the ocean.
There are a couple different companies that offer that Oahu Boat Party Cruises in Waikiki. We got our deal on Groupon, a two for one coupon, that was good for a two hour party boat cruise. This is a cruise that sets off by the Ala Moana mall, very close to Waikiki, and you can bring your own booze on the the boat. Blasting music, dancing, and jumping off the boat into the ocean are all fun activities you can expect when on the cruise. *Pro Tip: they don’t allow you to smoke anything on board. Also make sure to take some dramamine if you get seasick because the boat will be anchoring in the moving waves while you party.
DAY 3 : North Shore Day, Giovanni’s Shrimp Truck, Dole Plantation, Lahaina, Sunset Beach, Turtle Bay
The North Shore of Oahu is a special place and probably my favorite area of Oahu. It has a completely different vibe then the Waikiki area and I could easily spend more than one day here. If you are not staying in the area, this is definitely something that you would want to dedicate the an entire day to. Depending on what you are more into there are many ways that you can schedule your stops. If food is a priority, Giovanni’s Shrimp Truck and Dole Plantation are going to be your major stops. If beaches and scenery are at the top of your list, map out your stops and make sure Sunset Beach, Lahaina and Turtle Bay are priorities.
Giovanni’s shrimp truck has two locations, both in North Shore. They are world famous for their garlic shrimp, rice, and macaroni salad. Truly a Hawaiian staple and a must have. The lines for the trucks usually get really long so either go early or prepare to wait anywhere from 20-60 minutes depending on the time of day you go. So worth it though.
Dole Plantation is a place I have been to twice but would still like to go back and explore some more. This is the location of Dole farms that harvest the famous golden Hawaiian pineapples shipped all around the world. You can walk around the gardens where exotic flowers and different types of pineapples are growing. You can take a tour of the grounds on a train that runs throughout and end in the cafeteria/gift shop that serves an amazing selection of Dole Whip, pineapple desserts, and all the typical Hawaiian dishes that you love.
Oh Sunset Beach, what a beaut. This is by far one of my most treasured beaches on the island. Known for it’s wide beach perfect for watching sunsets, it is a great way to end your day on north shore and gather with the crowds to say bye to another day. Now mind you, there are many, many beaches that I prefer to swim at on the North Shore. Different beaches along the highway with some trees for shade, or more gentle waves to bask in. I can’t remember any names off the top of my head which is why I am definitely suggesting to at least hit up this beach for the “North Shore” experience. This side of the island is best for cruising and stopping at different beaches until you find one that speaks to you.
Turtle Bay Resort was on our list but we didn’t end up stopping. I wouldn’t say this is a must see but it is a fun place to stop if you are an avid movie watcher. This is the resort where Forgetting Sarah Marshall and other movies were filmed. A bougie spot known for it’s incredible turtle watching, Turtle Bay is a great place for a drink and a swim.
DAY 4 : Sunrise Hike @ Pillbox Hike, Lanikai Beach, Luau in Waikiki
This hike is an adventure all on it’s own. If you are traveling with a crew, make sure you guys go to bed early the night before because this sunrise hike is no joke. Sure, you can go at any time in the morning, but if you really want to soak it all in I highly suggest you make it a priority to hit the trail as the sun is rising. About 30-45 minutes down the H1 from Waikiki, the East side of the island is on a calming vibe. You have to drive over the mountain through long tunnels until you reach Kailua. Find a spot to park right next to Lanikai Beach and walk up into the neighborhood until you find the sign that leads you past the fence and up into the trek. This hike is straight up, and although it doesn’t take too long to get to the top, it is going to take some time for sure. At the top is one of Oahu “pillboxes” that were positioned up at the peak of the mountain as an army lookout back in the day. The pillbox is covered with art and graffiti and overlooks one of the most beautiful beaches, not only on the island, but in the world. If you do make it at sunrise you are in for a treat. *Pro Tip: Go to Cinnamon’s in Kailua for breakfast after your hike and before the beach. Must try: Guava chiffon pancakes and the Kailua pork eggs benedict with purple potatoes. You won’t be sorry.
After your hike and some breakfast head on over to Lanikai Beach. Not only is the one of the most picturesque beaches on the island, it is also one of the best to relax and swim at. The tide and the waves are very calm and you can swim or paddle board out very far with ease. Park in the neighborhood and walk on over.
Granted after all these activities you are going to be tired. If you do it right, you will rest at the beach and leave enough time for a possible nap after when you get back to your hotel. The last suggestion for this fun filled day would be to end the night at a traditional Hawaiian Luau for dinner and a show. There are a couple options on the island, and some offer discounts through Groupon. I have only been to one Luau in Waikiki and it was amazing. My suggestion would be to go to the Waikiki Starlight Luau at the Hilton Hawaiian Village. It is a rooftop luau at night with traditional Polynesian dancing, and a delicious dinner buffet to go with the show. Again, this is a super tourist activity, but one that I believe really showcases the culture of where you are visiting.
DAY 5 : West Side of the Island, Aulani, Makaha, Pray for Sex Beach
The West side of the island is more for locals. In my experience you don’t really come to this side of the island unless you know someone, or are looking for the real Hawaii experience. With that being said, if you find yourself going towards the West side, Aulani Disney resort is a cool place to check out. I wouldn’t stay here unless I won the lottery, but it is a beautiful place to walk around and experience as a visitor and not a hotel guest. The Disney resort is along a stretch of very nice places to stay. Equipped with beautiful private beaches and bays, you are able to enjoy, swim, and even eat and drink in their super fun Disney themed locations. This is definitely not a must on your authentic Hawaiian itinerary, but a fun addition if you have time and want to see what all the hype is about.
Makaha is the quintessential super “local” Hawaiian part of the island. No resorts or hotels on this side, when you head over there you see how the real Hawaiians live day to day. Makaha has nice beaches that are great for swimming and having bbq’s with the ohana. *Pro Tip: Stop by here on your way to Pray for Sex beach and grab some spicy pickled mango along the side of the road.
Pray for Sex beach is a world of it’s own. It’s also kind of hidden. You should totally be able to put it into GPS and find it, but this is why I mentioned it is good to go over that way if you know somebody who knows the area. I was first taken to this beach years ago by some friends and I fell in love immediately. The best way I can describe to get there would be to just keep going almost all the way to the end of the highway, where you can’t go anymore. You are going to pass all of the cities on the West, past Makaha, past it all until you come to a somewhat secluded area on your left (beach side). There will be a gate, and an area that will be blocked off. There is no sign and it’s kind of hard to find. GPS should help with this but you basically have to go in towards the parking area and then you will see this huge glorious beach with grass and trees towards the back of it. I have swam at this beach, and have also attended amazing overnight camping parties under the full moon here. This beach is so out there and secluded that it is a common place for huge parties, bbq’s and get togethers. Some say the real name of the beach is Pray for Sets instead of Pray for Sex, but I prefer the latter and so it shall remain.
DAY 6 : East Side of the Island, Koko Head or Makapu’u Lighthouse Trail, Halona Blowhole Lookout, Sandy Beach
At this point you must be all Hawaii’d out. The days have been jam packed full of fun and adventure. Or you are like me and ready for another day of new sights and sounds. Th trip is almost done and if you have it in you the itinerary for this sixth day is a fun one. This side of the island is between Waikiki and the Kailua side, the southeast corner of the island. This area is widely known as Hawaii-Kai area and is known for it’s nice neighborhoods and upscale homes. You got two options: a) hit up Koko Head if you are looking for one of the workouts of your life. I haven’t done this one yet and I’ve been meaning to conquer it every time I go. This is a huge, steep mountain with a staircase that runs all the way up. This is a very famous workout on Oahu that is considered very strenuous.
The second option I suggest if you are not looking for a crazy workout would be the Makapu’u Lighthouse Trail. This is a view point of the island ideal for amazing pictures and incredible views of the vast Pacific Ocean. This is a trail with free parking and no admittance fee that is family friendly. You can go down towards the beach and hit up the various tide pools that the area has to offer. Or you can go up towards the old lighthouse and see the curvature of the Earth. Makapu’u is a great place for whale watching during the winter as well. While this hike is uphill, it is easily accessible in regular clothes to just take photos.
Depending on which option you decided on, the Halona Blowhole lookout is between the two right off of the road. It is a unique place to park and see the power of the ocean blow through this tiny hole.
Sandy Beach is famous for it’s surfing. Also home to many “locals” in the area, this is another wide beach easy for relaxing and taking in the tide. Check out the food trucks right outside the parking lot. *Pro tip: Get yourself a tropical smoothie inside of a pineapple.
DAY 7 : A week in Hawaii, you made it. This was our travel day back so we didn’t have anything planned. If your flight is at night I would highly suggest taking a last nap on whichever beach you liked the best. Pack your bags the night before so you can take advantage of any last free time you may have. Hope you had a good time in one of my favorite places in the world.
Stay tuned on the rest of this periplo chapter.
DDA