5 Days on Oahu: Beyond Waikiki!
When to visit:
Oahu is picturesque, warm, and inviting all year round. However, the waves will be rougher and rain a bit more common (mostly on the Windward side) in the winter months. Summer is full of out of school tourist families. This leaves Spring and Fall as ideal visiting seasons!
Where to stay:
Most hotels in Hawaii will cost a pretty penny. You can find the cheapest lodgings in Honolulu, but if you can swing it I would recommend staying outside the city. Here are some great options for your trip!
For the Budget Conscious:
Ohana Waikiki East:
Great location if you want to be right in the heart of Waikiki. Walk to the beach, restaurants, bars, and the International Market Place. Basic rooms and amenities, but how much are you going to be in your room anyway??
For the Eco-Friendly:
Paradise Bay Resort:
I absolutely love this resort. It is located on North Shore right on Kaneohe Bay. The resort provides complimentary yoga classes as well as kayak and paddle board rental, perfect for exploring right outside your doorstep.
For Families:
Marriott’s Ko Onlina Beach Club:
The lagoons that make up Ko Olina have shallow waters, protective sea walls that block out the surf, and lifeguards on duty. There is no better place to relax with your kids. There are a few resorts in Ko Olina, but this one’s prices aren’t QUITE as steep as the others, and the restaurants are some of my go-tos.
For Luxury Lovers:
Kahala Resort:
Sure, you could stay at the absolutely luxurious Four Seasons at Ko Olina, or at Turtle Bay Resort on North Shore (I recommend both of these as well!) but if I could choose any Oahu hotel, it would be Kahala. The location is idyllic, the restaurants are amazing, and they have real live dolphins next to the pool!
For a Home Away From Home:
Turtle Bay Condos:
The Turtle Bay Condos allow you to enjoy the same location and restaurants as those staying at the Turtle Bay Resort without paying resort prices! Win-win in my book!
Island Itinerary:
I’ve divided the days into sections of Oahu - probably easiest to start with the area closest to where you are staying!
Day 1- North Shore
Breakfast:
The Sunrise Shack will get your day started on a nice healthy path (you’re going to be eating a lot this trip!) Try the payaya bowl!
If you’re starting from another area of the island you may be driving by! If not, it’s well worth an extra trip. Coffee drinks, pastries, gifts, and a small farm plot to explore! You’ll want to take home bags of coffee as the best souvenirs.
Adventure:
The hike to Waimea Falls can be done by anyone! It’s a nice paved path through a botanical garden with historical Hawaiian structures in the Waimea Valley. Get a nature fix, your steps in, and learn about the history of Hawaii without too much strain. For those who may need a little extra help you can even get a ticket for a shuttle that’ll take you straight to the waterfall.
If you can’t vacation without some strenuous physical activity, the Ehukai is a short but steep hike that rewards you with amazing views of the North Shore!
Lunch:
MY FAVORITE! Sandwiches on an assortment of fresh baked breads, salads, juices, and do not leave without a cookie! Eat on the porch, or take your food for a beach picnic.
This is the perfect lunch spot for vegetarians, and so good carnivores will even love it.
A North Shore staple - go for the peel and eat shrimp.
You’ll want dessert after lunch! This is IMO the best shave ice spot on North Shore.
Beaches:
The waves can be a bit rough depending on the time of year, but on a low surf day it is just gorgeous here. Brave souls will want to jump off the rock!
Again, swimmable in the calmer warmer months, but may be too rough in the winter. If the surf is too high, take a seat on the sand and enjoy watching the surfers.
Usually plenty of parking, this is a great calm spot to bring the kids. There’s also a beachside restaurant and snack bar. Bring snorkel gear if you have it. There’s a reason it’s called Turtle Bay.
Dinner:
Only open for dinner on the weekend, but if you’re around Fri-Sun, go! And if you’re not around on the weekend, stop in for lunch. Try the Tuna Tartare! FYI, not a great spot for vegetarians.
An absolutely understated gem. Some of the best sushi I’ve had in my life.
Get the ahi taco salad and a margarita. Can’t go wrong with Mexican food IMO.
Day 2- Leeward Side (West Side)
Breakfast:
Eggs ‘n Things is a Hawaiian institution. Great place to try a Loco Moco.
Beloved local spot, this can fill up fast! You want to try the likikoi pancakes.
Adventure:
Drive west and keep on driving. Not there yet, keep going. Little further… and stop when you can’t drive any more. Park, and then start walking. Ka’ena Point is the western most tip of the island. It is also a nature preserve for sea birds and monk seals! Tread lightly and take in the sights. Bring water, sunscreen and a hat as there is almost no shade.
This counts as both dinner and an activity. If a luau is on your Hawaiian bucket list, this one is a great option.
West side snorkeling tour! If the season is right they also have guided whale watching tours.
Lunch:
Quick, satisfying food right next to the Ko Olina lagoons. Pop in for lunch and a cocktail, and then head back into the water.
If you’re out doing Ka’ena Point or the West Side snorkeling tour this is a great lunch option. It’s right on Pokai Bay (my second favorite Oahu beach!) so plan to stay and swim after lunch. It’s technically on an Army Rest Camp, so you will have to show id to park.
This is a farm-to-table co-op that also offers farm tours and sells fresh produce. It is an experience, and well worth the drive up the mountain. Currently the cafe is only open for lunch on Mon, Tues and Fri.
Beaches:
My second favorite Oahu beach. Bring snorkeling gear and paddle boards if you have them!
The Ko Olina lagoons are calm and inviting, the perfect spot for families or for a relaxing day on the sand. Get there early in the morning!! All parking lots fill up SO fast!
This beach is referred to by locals as “Pray for Sex” beach, which I am told originated from it being called “Pray for Sets” beach by surfers. Regardless, it’s a lovely beach for sunning, swimming, surfing, and fishing.
Dinner:
This is where I first met my husband, so it’s a bit sentimental for me… but the food and drinks are really very good. Most evenings there is live music and the ambience is lively and romantic. Get the strawberry pie for dessert.
This one is a splurge. But if you want to push the boat out for a REALLY great meal, this is it.
This is a more affordable option, but no less delicious. We love Kalapawai in my family! Delicious fresh salads, sandwiches, and hot entrees, with great coffee in the daytime and cocktails in the evening.
Day 3- Windward Side (East Side)
Breakfast:
Need another açai bowl fix? Here’s the Windward spot!
If you need something a bit more substantial in the morning, here you’ll find eggs, potatoes, rice, and more.
Adventure:
Kaneohe Bay is a clear, turquoise paradise. Take a catamaran or pontoon boat out for a party on the sandbar! Kaneohe Bay is perfect for sandbar volleyball, paddle boarding, kayaking, tubing, or some chilled out sunbathing.
Kualoa Ranch is stunning, which is probably why it’s been used in many tv shows and movies. Choose your own Kualoa adventure from the Hollywood bus tour, a boat journey out to Secret Beach, zip lining in the mountains, or an ATV ride.
Another great spot for hikers! This has another pillbox at the summit with spectacular views.
The trail up to the Makapu’u Lighthouse is a much more accessible trail for most fitness levels. It’s still a trek mind you! But it is paved and gently sloping. Highly recommend!
Lunch:
I told you I love Kalapawai. This is the original location and right behind Kailua Beach Park.
Hawaiian plate lunches, specialty pastas, saimin, and more. This is really good comfort food.
Beaches:
Floury beach sand, bright blue waters. This is one of the most picturesque beaches on the island.
Perfect for a dip, great place to bring kids.
This is my Windward Side go-to beach and probably my 3rd favorite beach on Oahu.
Dinner:
This restaurant has gorgeous valley views. Get there before sunset to fully enjoy them (and because they don’t take reservations!)
Great Hawaiian brew pub. Take some beers to go after your meal.
Day 4- Waikiki
Breakfast:
If you haven’t tried a Loco Moco yet here’s your chance!
Part of the Royal Hawaiian (the big pink hotel!) this is a memorable spot to enjoy pink royal pancakes.
Perfect for a coffee and a quick bite, or a takeaway breakfast.
Adventure:
If learning to surf is on your Hawaii must-do list this is a great, accessible way to do it.
I’m almost embarrassed to admit how many times I’ve taken the Maita’i Tradwinds sail. Sail around Waikiki bay with views of Honolulu and Diamond Head while sipping a cocktail. Heaven! Pro tip: check Groupon a few weeks before you go. They almost always have HUGE discounts for this company!
The best place on the island to learn about Hawaiian history and royalty, and how the Kingdom of Hawaii was illegally overthrown by the US government.
Lunch:
Musubi are a Hawaiian power food. Don’t leave the island without trying one!
If you love seafood this is a great spot.
Be prepared to WAIT IN LINE! But well worth the wait.
Beaches:
This span of beach is iconic. It is the most well-known and photographed spot on the island. Great for swimming, though it can get very very crowded (especially at sunset)
A little separated from Waikiki Beach, this beach park is a peninsula perfect for walking, jogging, and swimming with little kids. It’s also an amazing spot for watching the Friday night fireworks display.
Dinner:
My husband’s favorite! It is far less crowded than Duke’s downstairs, with better food and better views IMO. Get the Hula pie for dessert.
I was SO impressed with the food here! Cocktails are great as well!
Another splurge, but right on the water and an excellent meal.
Day 5- East Honolulu
Breakfast:
A historic building that opened as the Waioli Tea Room in 1922, it is now an amazing breakfast spot. This cafe provides vocational training for individuals released from incarceration and those who have graduated from substance abuse treatment. Support the social good work they do over banana macadamia nut pancakes.
Hawaiian style diner fare not far from Diamond Head trail.
An amazing spot for breakfast, brunch or lunch! Park in the resort parking structure, get your parking ticket validated, and bring beach gear to relax on the pristine, perfect beach after you eat. Don’t forget to say hi to the dolphins next to the restaurant!
Adventure:
Personally I think this climb is mad, but hikers love it. It is over 1000 steps made from abandoned railroad tracks!
This hike is more my speed, but will still be a work out and will reward you with sweeping views. Parking can fill up so go early.
I think this is the most scenic waterfall hike on the island. It’s an easy-to-moderate level jungle hike. It can get quite slippery in the rain so try for a dryer day.
A pristine protected nature preserve. The snorkeling is unreal! Reservations are required and it’s a $25 entry fee. This is a bucket list experience for sure.
Lunch :
Our fav Mexican spot on the island. Unassuming but so good!
An absolute local favorite. Fuel back up after climbing Koko Head (Or not if you’re not a mad hiker! I kid…)
Beaches:
Pristine. Resort bougie beach for sure! There’s a beachside bar that’s part of the Kahala resort you can enjoy while you sun and swim yourself.
A local beach, somewhat difficult to reach, but hardly ever busy.
Dinner:
Another great Hawaiian brewery for the beer lovers.
Roy’s is known as THE special occasion restaurant on Oahu.
If you haven’t been able to leave Kahala Beach since lunch, and are getting hungry again, here’s another great option at the resort.
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