I have always put off visiting Hawaii for fear it would be overrun by tourists and overpriced food and drink. While it is a tourist hot spot, there are plenty of places to escape the crowds and find reasonably priced meals. Plus, it’s almost an all-year-round kind of place. I was there in February, which is technically winter, but the weather was perfect for swimming. I really would have liked to have had more time to put my feet up. But if, like me, you only have a few days my Oahu 3 day itinerary is the perfect plan for you.
Oahu 3-Day Itinerary
This Oahu 3 day itinerary has a little taste of all of the amazing things to do in Oahu.
From hiking, shopping, snorkeling, and swimming to dining on some delicious healthy food, we’ve got you covered for your Oahu vacation.
Oahu 3 Day Itinerary: Day One
Shop at the Waikele Premium Shopping Outlets
I don’t know about you, but I treat shopping as exercise. It’s hard work. And the shopping in Hawaii certainly leaves nothing to be desired.
On the first morning of your Oahu itinerary, I would suggest getting the Waikele Premium Shopping Outlets out of the way.
You can find everything from skincare to designer shoes, handbags, sunglasses, and clothing, all at incredible prices.
Think of a Coach bag paired with a pair of Michael Kors shoes for under $300. Yes, really.
Spend a few hours here. You can catch the bus (US$15 return) from Waikiki – it leaves from a number of designated hotels. Check with your concierge for your closest departure point.
After you’ve done some damage to the credit card, you can head back into Waikiki for an afternoon of walking and swimming.
Work up a bit of sweat with a walk all the way up the Waikiki esplanade.
Aside from plenty of spots to jump in the ocean, you can also spot the famous statue of Duke, the Hawaiian dude who invented surfing.
There’s no doubt, after all this action, you’ll be hungry, so head to Bills for dinner.
It’s the same Bills as in Sydney, which is a favorite for yummy breakfasts, but at the one in Waikiki, there’s no need to fight for a table and the dinner menu is outstanding.
It’s inspired by fresh, tropical produce and a fusion of a whole bunch of cuisines. The coffee is also pretty damn good.
Oahu 3 Day Itinerary: Day Two
Try and get an early start on Day Two. You’ll need it to beat the crowds.
Today, you’re heading for Diamond Head; formed by a volcanic eruption more than 100,000 years ago.
It was originally used as a strategic military outlook but is now a popular 1.1km hiking trail with an incredible view of Waikiki and the south shore.
Hike the Diamond Head Trail
You can get to Diamond Head by bus, taxi, or walking/running if you’ve got the energy. If you’re like me, you will enjoy running all the way up to the top.
The trail is a fairly tricky one and obviously all uphill, but if there aren’t too many people around, it’s a nice way to work up a sweat, and the reward once you get to the top (via two sets of steep stairs & a dark, underground tunnel), is well and truly worth it.
After making your way down (the crowds will likely have built up by now) the hill and back into Waikiki, jump in the ocean to cool off and then grab a feed.
Gorilla in the Café
Gorilla in the Café might not look like much, but you can tell a place is good when there’s a line of tourists out the door.
It also actually does the best Australian-style coffee along the main drag, in my opinion.
Not a filtered coffee in sight. I’m talking smooth, creamy milk and strong coffee shots.
The café also does green smoothies, and a decent Acai bowl (it actually comes in a cup), filled to the brim with banana, strawberries, and muesli.
SUP in Waikiki
Spend the rest of the day SUP-ping in Waikiki.
The cheapest SUP (stand-up paddle boarding) board hire rates I found were at Koa Board Sports where it’s US$25 for an hour.
If you don’t feel up to more exercise, you can grab some rays by your hotel pool. Remember: Happy Hour usually starts at around 3-4 pm.
Sunset Drinks at Duke’s
To top the day off, you can’t go past watching the sun go down over Waikiki beach while sipping a cocktail at Duke’s.
I can recommend the Coconut Mojito and the Tropical Itch (which conveniently comes with a back-scratcher you can take home).
Duke’s sits right on the beach at the Outrigger Resort and is so popular it’s best to get there around 5 pm, otherwise you won’t get a table, especially one outside on the beachfront.
The food at Duke’s is also really yummy. I can vouch for the fish tacos.
Oahu 3 Day Itinerary: Day Three
Day three of our Oahu 3-day itinerary was probably my favorite.
We took a full-day Oahu road trip around the entire island. It involved a lot of delicious food and swimming in the glassy water (which of course are the things Hawaii is known for).
First, wake up to an early alarm and hire a car (preferably an iconic Mustang convertible). If you’re in need of a wake-up in the form of caffeine, grab a really, incredibly good coffee from Brue Bar in downtown Honolulu.
Then head into Waikiki and drive east, taking the coastal route. Drive past Diamond Head and head to Hanuama Bay for some of the best snorkeling you might ever experience. This glassy, blue bay is full of thousands of tropical fish, but be aware – it gets busy! It’s best to get there before 9.30 am otherwise the car park is full and you’ll get turned away. (Note: it is closed on Tuesdays).
Your second stop is a quick one at Lanai Lookout, just past Hanauma Bay. On a clear, winter’s day, you can see humpback whales splashing out at sea. Interesting fact: President Barack Obama scattered his grandmother’s ashes here in 2008.
By now, you’re probably feeling like another quick dip in the ocean. Head straight to Waimanalo Beach; it’s isolated and peaceful, so perfect for reading a book or taking selfies while no one can see you.
Between Waimanalo and the next stop, there is a stack of beautiful, pristine beaches you can stop at for swimming – e.g. Kailua, Lanikai, and Kahaluu (which has decent snorkeling).
But if you’re like us and are ready for some food after Waimanalo, I would suggest putting the top down and driving straight along the coast all the way up to Kahuku. It is here where I had the best shrimp scampi (garlic prawns) of my life, at Giovanni’s.
You can’t miss it – it’s a food truck right on the side of the road with swarms of hungry people waiting for food. But, God it’s worth the wait.
There is a bunch of other food trucks in the vicinity of Giovanni’s.
You absolutely cannot leave without trying Uncle Woody’s BBQ Corn. There’s also a truck that serves yummy salad wraps, green juices, and fresh lemonade.
After lunch, head for some relaxation at Kuilima Cove at Turtle Bay Resort. By now you’re on the famous North Shore.
The resort is actually where ‘Forgetting Sarah Marshall’ was filmed. The water is perfectly clear and really good for snorkeling.
From here, of course, you’ve got the famous Sunset Beach and Pipeline where, at the right time of year, you can see world-champion surfers riding massive waves.
Unluckily (or luckily) for us, there was no surf so all comps had been called off, but it meant we could take yet another dip at Pipeline and it actually turned out to be the best ocean swim of my life. Clear, calm water with not a soul around – perfection.
Unsurprisingly, more beautiful beaches are dotted along the coastline as you continue along; Waimea Bay and Laniakea Beach.
Before you take a turn onto Highway 99 to head back into Honolulu, no stop on the North Shore is complete without getting a traditional shave ice in Haleiwa – a groovy little Hawaiian town with a huge surfing history and relaxed vibe.
We took advice from the locals and hit Matsumoto’s (you can’t miss it – there’s always a huge line out the door) for “the best shave ice in town”. Who would’ve thought flavored ice could be so delicious?
Now, it’s only just over an hour’s drive back into Honolulu. Follow the signs from Haleiwa onto the highway.
If you’re anything like us, you’re probably feeling a little sun-drenched and full of shaved ice and prawns, but that’s never stopped us from eating more food! I can recommend Goofy Café in Honolulu for a light, healthy dinner. The focus here is on eating locally.
They have delicious, fresh salads, tapas, pasta, and cocktails. They also serve an all-day breakfast.
This Oahu 3-day itinerary really is just a taster of all the incredible things to do in Oahu Hawaii. But, we hope it’s a good start for those planning their first Oahu vacation.
Sophia Lazarides is a journalist and public relations professional based in London. She is on a mission to live a stylish life.