Things to do in Oahu a five day itinerary
– A guest post by Laura Oxley
Whether you’re headed away with your sweet heart, your best friends or even on a solo adventure, Hawaii is never a bad idea. Last winter I opted for the middle option and found myself planning a reunion trip to meet up with my best friend for a Hawaiian adventure! We planned our trip around visiting 2 different islands, one of which being Oahu and I’ll be breaking down the short (but action packed) visit we had on the 3rd of Hawaii’s biggest islands. Known as “The Gathering Place” it was the best place for us to get back to doing what best friends do – adventuring!
So here’s the low down on top things to do in Oahu
Day 1 & 2 – North Shore Hangs, Tropical Views & Waterfalls
Our first stop when we arrived in Honolulu was the car rental office, while there is transit available the #1 thing I was told and can now recommend to anyone is that a car is a must! Being one of the bigger islands it took a fair amount of time to get from the top to the bottom and we were glad to have had the car. We looked at a lot of rental before settling on one from Discount Hawaii Car Rental but found a lot of companies had similar prices. They collected us from the airport in a complimentary shuttle and we headed over to pick up our wheels. With that we headed off in search of our home away from home for the next 5 days -destination? The North Shore.
If there is such a thing as that perfect wave, the North Shore is most likely where you’ll find it. The days leading up to our arrival had some serious weather warnings & storms off the coast resulting in some crazy swells along the island and as we got closer to our rental we started to realized just how intense the waves were going to be. I hadn’t planned to do any surfing up there (not nearly trained enough to take on those swells) but we did manage to (unknowingly) plan our arrival to the first day of the Eddie, Big Wave Invitational. This surf contest is held annually in memory of Eddie Aikau in collaboration with Quicksilver to honor the champion big wave surfer & Waimea Bay native life surfer for all he brought to the sport. We lucked out having our rental within walking distance from the breaks so coffees in hand we spent our morning watching some insanely talented surfers take on some of the biggest breaks in the country.
While we most likely could have stayed there all day we decided to move on and get our bodies moving again & take in some tropical views. We headed about 45 minutes south to the town of Kailua to check out the Lanikai Pillbox Hike. High above a resort golf course and overlooking the most incredible stretch of beach, these “pillboxes” were once used as shelters during WW II for soldiers along the coast and are now used as wicked viewing platforms for the tourists who battle the steep dry terrain to get to the top. Being sure to take our time to soak in the insanely beautiful views of the Oahu coast including the Pacific Ocean, Mokulua Islands, Kailua and The Enchanted lakes. The length of the trail isn’t more than 90 minutes return but with the amount of photo ops along the way you’ll be sure to spend far more time up there than you think.
After a day out in the sun what better way to end the day than with a swim? And even better than that? A swim in a waterfall. So that’s where we took off to next. Less than 20 minutes east of Kailua lives Maunawili Falls, hidden so well in a residential neighborhood that if you aren’t looking for the trail head you’d miss it. Round trip (without a swim) is around 2.5 hours, but you can’t visit a Hawaiian waterfall & not take a dip right? The trail itself is quite eroded & covered in roots so take care to mind your footing and tree covered the whole way along to help shield you from the mid-day sun. While the falls themselves aren’t massive, they are quite beautiful and the stream leading up to them is the perfect place to cool off after a day on the trails/at the beach.
Day 3 & 4 – Hiking the day away
When you have less than a week to discover as much of a 600 square mile island as possible your days wind up jam packed including back to back (intense) hikes! We loaded up on a great breakfast from the iconic Ted’s Bakery on the North Shore before heading down towards Waikiki/Honolulu areas to check out Diamond Head State Park. The surrounding areas were home to Fort Ruger, the first U.S military reservation on Hawaii, however now the only thing remaining of the Fort the Hawaii State Civil Defense & National Guard facility. The trail itself isn’t a long one, not even a mile one way, but beware the heat, & the steep climb will take your breath away even before you get to the views. With a 560 ft elevation gain at the top most part of the crater, you’ll be gifted with absolutely gorgeous sweeping views of the ocean & downtown Waikiki. You’ll be able to explore tunnels and artillery bunkers throughout the trail but the winner is definitely the view. If one steep hike wasn’t enough for you (like it seemed for us) then hope back in the car for another 15-20 minutes and you’ll find yourself staring at what look like marching ants up a vertical stretch of trail from the road..and soon enough you’ll see just what they are. Not ants, but people! Yep, you’ve arrived at the trail head for the Koko Head trail aka The Death Stairs as people refer to them. When you finally see it for yourself you’ll soon be asking “why am I doing this?!” and as like we did, maybe the rest of the way up. But never fear, the views at the top make up for the intense situation you’re about to enter. A total of 1,100 wooden steps will guide you up vertically to the point you may think gravity is working against you. During World War II, the military several built bunkers at the summit of Koko Head crater. They also constructed Koko Head Railway (now the Koko Head stairs) to move supplies & people up & down.
At about the halfway mark the wooden railway ties continue but the ground underneath disappears, stead your grip and climb on, or reroute yourself to the right into the bushes & you’ll find a trail for those less sturdy on the ties to continue until the ground appears under the ties once again. When stopping for breaks along the way (you’ll be thankful you did) be sure to get a look at how far you’ve come and the view down below. But to be honest the best views will come when you finally (tired & sweaty) arrive at the top. No matter which way you look the views are incredible. The ocean, the peaks & valleys of the island & even the city all look amazing from way up there.
Soak it in, catch your breath & then brace yourself for the trek back down. This might take you a little longer as it’s a little harder going back down the “ladder” style trail. Once you get to the bottom and apologize to your jelly legs it’s best to get to relaxing asap! And what better way than with sunset on the beach. Back to Waimea beach to catch the last moment of sunlight & the die-hard surf enthusiasts hoping for one last break are the best things to rest your legs to before gearing up for your last day on Oahu.
Day 5 – Historical Hawaii
And just like that your trip is coming to an end, or so it was in our case as we were headed back to Canada on a red eye that night. So one last full day, and nothing short of jam packed once again! We checked out of our cute little beach front rental & decided to check out some spots on the North Shore, including the historic town of Haleiwa on our way into Honolulu for some last minute souvenir shopping and then we made our way to Pearl Harbour. Because a trip to Oahu is complete without visiting this historic spot. Just west of the city of Honolulu lies this historic landmark, and is the headquarters of the United States Pacific Fleet. The attack on Pearl Harbour on December 7th, 1941 by the Japanese was the immediate cause of the United States’ entry into WWII and a day that will never be forgotten. Admission is free, unless you are interested in visiting the several other ships and memorials on the grounds which start at 60$ +. We opted for the free tour of Pearl Harbour which gives you access to the main grounds, a film viewing & a boat ride out the USS Arizona Memorial. Leaving every half hour we made it just in time for a new tour to begin and we were greeted by a few members of the US Navy who gave us a bit of background about the base and what had happened there some 75 years before, and from there we were ushered into a theatre for a film (about half an hour) on that fateful day in 1941. From there you’re onto a fairly small boat and taken the 10 minutes across the base to the USS Arizona Memorial with full view of the massive naval ships along the shores, and the crisp white memorial not too far in the distance.
This memorial was erected to commemorate the nearly 1200 men & women who were killed on Japan’s attack on Pearl Harbour, their bodies to rest in the ships wreckage in the ocean. From the memorial platform you are able to see most of the Arizona in the water as well as the few manta rays who now call it home. Inside there are plenty of memorial items of those who lost their lives that day, and a full wall commemorating those brave individuals. The memorial itself is a rectangular white housing with cut outs on each side allowing you to see the ship below and the battle ships on the shore.
To end our trip on an even higher note than we began we opted to celebrate by attending a luau. The one we went to was at Sea Life Park. And it was hands down the best cultural show I’ve seen. There are a few different options, including seating choices & meal service but for about 90$ (USD) you get a free drink, a huge meal, a hilarious host (The Chief) and a fantastic showcase of South Pacific culture. Before the show actually begins you get a feel that you’ve stepped into a whole other part of Hawaii being greeted by men & women dressed in traditional luau fashion and offer different stations to try your hand at basket weaving, hula dancing & even spear throwing. From there the Chief calls you around in a circle to unveil the “roast” by having a few people pull it out of the ground in true Hawaiian fashion. After that the night is filled with cheeky remarks from the absolutely hilarious Chief, great food, fantastic music & performances from multiple South Pacific cultures, including Tahiti, New Zealand, Samoa and of course Hawaii. All of the performers are the same for each act & are insanely talented putting on the show for all the spectators. An incredible fire dance closes out the show and with that our 5 day adventure on the island.
While 5 days doesn’t seem like that long, with the right mindset and attitude you can experience so much a place has to offer. And if you feel as if there is still more to be seen, Hawaii is always a good idea so leave a few things to do for the next trip over to the Aloha state.
Laura Oxley Bio
Laura is a self-proclaimed wanderluster extraordinaire who has spent the last 6 years exploring the world & her own backyard. From working in a little beach town on Australia’s East Coast, to sliding down an active volcano in Nicaragua, climbing up 1400 vertical wooden steps in Hawaii to sailing thousands of feet in the air behind a boat on New Zealand’s North Island. There is so much of the world she has yet to see, so many people she has yet to meet & she has no plans to stop exploring anytime soon.
Website – She Who Wanders
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