Oahu is Hawaii’s most populous and built-up island. As such, this island often gets poo-poo’d for being too crowded, modern and over-run with tourists. While it certainly lacks the more rustic and authentically Hawaiian feel of some of the other islands, don’t miss out on all Oahu has to offer. It is a stunningly beautiful island with tons of stuff to do and see. Just don’t sit on touristy Waikiki beach the entire trip if what you’re really looking for is wooden huts and grass skirts and an authentically secluded Hawaiian vacation.
If you like to golf and have a military connection, DO NOT leave Oahu without playing Klipper which is located on the Marine base in Kaneohe. It’s $35 for active/retired military and has three of the most beautiful water holes in the world on the back 9.
Between great golf courses, the famous Waikiki beaches, restaurants, bars and shops, some pretty amazing hikes, shark cage dives, The North Shore, Kualoa Ranch, Pearl Harbor and a bunch of other cool tourist attractions you won’t be at a loss of things to do and see. And, despite the amount of people and modern construction, Oahu is one of the more beautiful islands in the Hawaiian archipelago.
Waikiki
Waikiki has tons of upscale restaurants, bars, clubs, shopping and a really nice beach. It is the only area in all of Hawaii that has any type of proper night life. It is, however, totally touristy. Make sure not to neglect the other side of the island which I, personally, think is much nicer. Consider staying in Kaneohe, Kailua or Lanikai instead. Lanikai beach is the nicest beach on Oahu. There are tons of airbnbs on that side of the island near the beach. Much nicer than Waikiki and away from all the tourists.
If you’re dead set on staying at a hotel on Waikiki beach there are no shortage of hotels for you to pick from. The nicest I’ve found after staying at a couple in that area is by far The Hilton Hawaiian Village.
On of the first things I recommend doing when getting to the Island of Oahu is taking a morning hike. My favorite hike to start with is the famous Pill Boxes Hike over Lanikai Beach.
The Pill Boxes Hike
This is a great little hike with a fantastic view. It’s super easy, I’ve done it in sandals, my mom, who’s over 50 and certainly not in the best shape, was able to do it without too much problem. And, ultimately, it has one of the nicest views of any hike on the island. It’s a great hike for beginners and it’s an excellent hike to begin your vacation with. Sunrise is the best time to go and due to the jet lag you’ll probably have no problem getting up early and doing this hike during sunrise.
Jump in your rental car (side note: splurge for the convertible Seabring or Mustang, it’s a couple extra bucks and it makes all the driving around and site seeing that much better) and from the Waikiki side of the island take the Pali Highway over the mountain towards Kailua/Lanikai. The drive is approx 20 min. Do not turn stay straight on the Pali Hwy, it will eventually change names to Kailua Rd and you’ll hit a T in the road. Make a Right at the “T” onto Kalaheo Ave. You’ll go over a man made canal, Kailua Beach park will be on your left. Stay next to the beach as the road turns to the left, you’ll go up a small incline past a big stone marker that says Lanikai. The road will bare to the right and you’ll make a quick right (it’s the second right onto Kaelepulu Dr). There will be a golf course to your right and homes to your left. Just past the last house on the left is a sign that says “Pill Boxes” This is the starting point of the Hike. The hike is well marked and easy to follow, and most likely you’ll see some other locals doing the hike as well. The hike to the top only takes 20 min, but you get a breath-taking view of Lanikai Beach, Kailua, Kaneohe and the Marine Base. There’s two islands off Lanikai beach and the sun rises right in between them, which makes this a fantastic sunrise hike. Highly recommended for one of your first hikes on the island. Either way, make sure to do this hike while visiting Oahu. The other well known hikes are either really difficult or kinda lame in comparison.
At the top of the hike you can see all of Lanikai and Kailua, two of Oahu’s best beaches and residential beach front areas. There are also old WWII defense outposts or pillboxes that allow for some great photos and a place to sit up on top of and overlook the gorgeous views.
After your hike, head to Cinnamon’s in Kailua. (315 Uluniu St, Kailua, HI 96734 (808) 261-8724). It’s one of the best brunch places anywhere let alone Hawaii. Their Kalua Pork and Spinach Eggs Benedict is life changing as are their special Macadamia Nut, red velvet pancakes. There might be a small wait later in the morning so you might want to call ahead for reservations.
After Breakfast, relax off the eggs benedict and pancakes on Lanikai beach for awhile before heading back to wherever you’re staying.
If you’re heading back to Waikiki, don’t take the same route back on the Pali Hwy (the Pali is the quickest route over the mountain but definitely not the most scenic). Instead, head back on Kailua Rd (make a right onto Kailua Rd) and make a left on Kalanianaole Hwy. Then just stay on this Hwy. It will take you through Waimanalo which is really local. If you’re not staying in Waikiki still take this drive around the Waimanalo (pronounced Why-Man-Aloo) side of the island. It’s a beautiful drive in either direction and there’s plenty of places to pull off to the side of the road and explore the rock formations and take photos.
You’ll see a guy and his cousin sitting in the back of their pick up truck selling fresh coconuts on the right side of the road. Stop and have them crack you guys open a couple fresh coconuts and ask him to shave out the inside local style. Nice guys, they’re there every day and the coconuts are really good.
There’s lots of gorgeous sites on this drive. Stop at the tide pools and take pictures. There’s always places to pull over. You’ll eventually come to Hanauma Bay Park. Make sure you stop at the park one day on your trip (except Tuesdays it’s closed Tuesday), lots of good snorkeling and a gorgeous natural volcanic crater, with a reef. If you have time, stop this day, you can see the main crater and take some pictures in 15 min or you can definitely spend an hour or two snorkeling if that’s your thing. It’s $1 to park and go see the crater and take pictures and then another $10 or $15 if you want to go in and snorkel.
After Hanauma Bay you’ll come over a hill. On your right, you’ll see Hawaii Kai, which is an upscale residential area with a few great restaurants on the water. If you’re hungry I recommend Kona Brewing Company for beer and good food (7192 Kalanianaole Hwy), The Shack (377 Keahole St) for cheap but good burgers and such, there’s also a few really good sushi and seafood places in the marina if you’re looking for something a bit more upscale.
Kona Big Wave is by far their best beer if you ask me. It’s a delightful golden ale that has a hint of flowery sweetness from it’s honey roasted malt with perfectly balanced hops. Definitely give it a try while in Hawaii.
The North Shore
The drive to the North Shore is certainly a highlight of the trip to Oahu. Don’t go all the way out to Oahu without driving up to the North Shore. Again, a convertible makes all the difference. This is the most beautiful drive on the island and there are plenty of places to stop and enjoy along the way.
You’ll again take the Pali Hwy, if you’re coming from Waikiki, over to the northeast side of the island. This time when you come down off the mountain into Kailua, make a LEFT onto Rt 83 (also called Kamehameha Hwy) it’s essentially the first stop light/major intersection you’ll hit coming off the mountain. Stay straight on Kamehameha Hwy. It will keep the name Kamehameha but will change to Rt 830. As you start to drive through denser and denser jungle, you’ll see a sign for the Macadamia Nut Farm (49-227A Kamehameha Hwy., Kaneohe, Oahu).
DEFINITELY stop here. It sounds stupid, but it’s pretty awesome, and the tours they give ($10 with military discount, $15 without) are fantastic. They give you a short bus tour through the macadamia nut farm with stops to sample local fruits ect, they take you on a short boat tour around the lagoon on the property and then they do an entire Hawaiian cultural show, showing you how to start fire, crack coconuts and do other Hawaiian themed stuff as well like the Luau Fire Dance, ect.
They do everything that they do at the Polynesian Cultural center only the one at the Cultural Center is like $50, it’s far less personable, the guides are not as funny and you actually get less. Plus the Macadamia Nut Farm tour is so hilariously ghetto local Hawaiian that it’s simply a must see. There’s only 1 tour on Tuesdays at 1045 (apparently Hawaiians have something with Tuesdays), otherwise the tours run hourly from 1045 to 6pm every other day of the week.
Shortly after the Mac Nut Farm, as you continue down Kamehameha, the island will turn sharply to the left and on your immediate left is Kualoa Ranch. This is the location where they filmed the classic scene from Jurassic Park where the Dinosaurs stampede through that giant valley. It’s a gorgeous area and many movies have been filmed here. You can see famous locations from Lost and even Godzillas footprints. Definitely worth stopping. They run ATV tours, horseback riding tours, ect. If you’re into ATVs or Horseback riding, I highly recommend stopping here. Definitely book in advance.
After Kualoa Ranch, continue on Kamehameha, the drive is gorgeous. Stop at any of the many shrimp trucks for lunch. Their overpriced, but the shrimp are great
If you want to see amazing surfing, stop at Pipeline. It’s the famous huge wave that all the professional surfers ride on the north shore. It’s right off Kamehameha across from Sunset Beach Elementary School. Don’t try to go in the water though, the wave is really nasty, but not nearly as unforgiving as the surfers if you get in their way.
Other stops of interest on the way to the North Shore: Be sure to stop at Laniakea better known as Turtle Beach where you can see green sea turtles lounging on the beach almost any day of the year. It’s located a little over two miles past Waimea Bay and about 1.5 miles before you get to the signs for Haleiwa town. Look for signs for Pohaku Loa Way on your right and you’ll know you’re there. About a mile further down the Kamehameha Highway, you’ll see signs for Papailoa Road. Drive to the end of the road, park and take the narrow path to the beach. Turn left and walk for about 15 minutes and you’ll come to Police Beach, which was used for the beach camp of the TV series, Lost. Just past Pupukea Road lies Waimea Bay, an excellent spot for spectacular surf watching. About half way around the bay on the left is the entrance to Waimea Valley. There’s a 45 ft waterfall about 3/4 of a mile past the entrance booth (this park requires pay to gain admission, but it’s definitely scenic if you have time.
The end of your journey to the North Shore is the town of Hale’iwa. It’s a small rustic beach town with lots of shops and restaurants. There’s often lots of art shows and local festivals in what I can best describe as an Old Western Hawaiian Cowboy Town. Stop by the M. Matsumoto Grocery Store for shave ice. Haleiwa Joe’s Seafood Grill and Jameson’s by the Sea both have really excellent fresh, locally caught fish for dinner. Have dinner and head back the way you came. This is definitely a full days excursion. In fact, if you do an ATV tour or Horesback riding, it’d probably be better to go back a second time. Just make sure you hit the Macadamia Farm, Kualoa Ranch and Hale’iwa town. If you choose to stay up on the North Shore the best place to stay is Turtle Bay Resort.
Valley of the Temples
One of the most beautiful spots on Oahu is gorgeous Japanese-style Buddhist Temple sitting inside The Valley of the Temples Memorial Park. (47-200 Kahekili Highway, Kaneohe, HI 96744)
Follow your GPS and drive to the back of this cemetery where you’ll find the most stunning Japanese Temple you’ve ever seen. In fact, though, you might remember already seeing this Temple in movies and TV shows as it appears regularly. If you’re a Lost fan you’ll remember this as the setting for Jin and Sun’s Wedding. For a small donation you can walk around and take photos of the temple. There’s a large bell that you are allowed to gong as you enter the site, many stocked koi ponds and plenty of swans to fill your photos with magical beauty.
Pearl Harbor
There is not much for me to add about Pearl Harbor. If you are interested in history, particularly WWII history, you really can’t miss Pearl Harbor. Get to the harbor early in the morning and consider purchasing your tickets ahead of time. If you just show up at like 10am, chances are good you won’t actually be able to get to some of the best exhibits like the USS Arizona Memorial which requires a boat to get to and can only handle a limited number of visitors. There’s plenty of things to do and see. You can walk aboard old submarines and ships and even sit behind the anti-aircraft guns used during the attack.
Be respectful, particularly when visiting the USS Arizona Memorial as there are still service members entombed inside the sunken ship. Your visit to that memorial should be a somber one. Also, don’t bring purses or backpacks. They are not allowed and you’ll have to keep your stuff in lockers at the cost of a few dollars.
Shark Cave Dive
One of the coolest experiences you can do in Hawaii is do a shark cage dive. I’ve done one of these here in Oahu as well as in Cape Town, South Africa. While the one in Cape Town was cool because you got to see Great White sharks, the one in Oahu was vastly superior. The water in Hawaii is crystal clear, allowing you to see the sharks much better than the murky conditions in South Africa. The water does not need to be chummed as the sharks respond to the sounds of the boats diesel engines which they’ve grown accustomed to being crabbing boats that provide them with some food. As curious creatures they will come up to your cage and circle it to check you out. Having these apex predators circle your cage and look at you like you are food is an experience you’ll never forget. Don;t get your hopes up, you most likely will not see a Great White, and if you do they’ll pull the cage back into the boat. But, we saw about six 8-12 foot long sharks on our trip. We used North Shore Shark Adventures and they were great!
Kayak to the Mokes
You can rent kayaks from Kailua Beach Adventures or if you’re a member of the military the marine base has plenty of cheap rental options. Take the kayaks out from Lanikai beach and kayak out to the two tiny islands, called the Mokes, that you saw from the Pill Boxes Hike. One of the islands has a nice beach. And, if you hike around the back side of the island there’s a pretty cool spot to do cliff jumping. Don’t mess with any of the bird nests. They are protected and you’ll get a hefty fine if you touch them.
Stairway to Heaven
During WWII the US Navy built a radio and satellite station on top of the tallest mountain on Oahu. To get there, they built a 3922 step staircase into the side of the mountain. These stairs became known as the Haiku Stairs or “Stairway to Heaven”. For years you could walk up this incredible hike and get to the old base at the top. After years of disrepair and parts of the staircase being washed away the hike has been closed. Info on how to do the hike and what the penalties are if you get caught change all the time. So, I can’t give you great info, as I last did it in 2011. Lookup up to date information, if it is open…go! If it’s not realize there might be security, hefty fines and it might be dangerous to hike certain parts of it.
Places to Eat
Waikiki
– Siam Square
– Excellent and reasonably priced Thai food, seriously some of the best I’ve ever had. Located at 408 Lewers St within walking distance of all the main shops and restaurants
– Roy’s
– American/Hawaiian/Asian Fusion Restaurant. Right across from the street from the Hale Koa. Just walk out to the right and you’ll walk right past it. A nicer, slightly upscale, but casual place with nice outside bar. Located at 226 Lewers Street
– Duke’s Waikiki
– The food is meh, but the drinks are outstanding and it usually has a great atmosphere being on the beach and there’s usually live music. Definitely a fun place for after dinner drinks. 2335 Kalakaua Ave
– Alan Wongs
– Consensus best restaurant in Honolulu. Really upscale, really expensive, but excellent if you’re looking for fine dining.
– Sushi Sasabune
– Best Sushi in town. Located at 1417 S King St in Honolulu.
– Other than that, you can’t go wrong with Seafood/Sushi, Japanese, Thai, Korean…stuff like that. Stay away from chains like Jimmy Buffets, Yards House, cheesecake factory, ect.
– Rum Fire is a cool upscale place to get cocktails on the beach in a swanky lounge
Kailua
Kalapawai Cafe & Deli
– Excellent, small cafe with really good gourmet food, reasonably priced. Just don’t get outdoor seating they sit you on a busy road near the dumpster. Indoor is much preferred. Located at 750 Kailua Rd.
The Kailua Town Pub
– Great place to watch football on Sundays and drink. They actually have a great seared Ahi Tuna. You’ll most likely run into my old friend Torre sitting at the end of the bar. He’s the cranky bald guy in an Eagles jersey.
Kaneohe
Marine Base Officer’s Club – If you have a military connection and can get on base, head to The Officer’s Club on the Marine base in Kaneohe for an incredible Sunday brunch
Haleiwa Joe’s Haiku Gardens – The food is decent, nothing overly fancy. But, the atmosphere is exactly what you’d want from a traditional Hawaiian restaurant.
North Shore
Bonzai Sushi – Best sushi on the North Shore. Really cool atmosphere with pillow seating on the floors and giant Japanese lanterns lighting the outdoor seating.
M. Matsumoto Grocery – The best spot for shaved ice on Oahu.
Waialua Bakery – A bakery on the beach where every one of their delicious treats are made in house. Stop in for a delicious treat.
Kahuku Farms – Farm to table Hawaiian style. All ingredients are from their own farm 10 feet away.
Sprout Sandwich Shop – Unique sandwiches made from incredibly fresh ingredients.
Haleiwa Bowls – Your #1 spot for delicious granola and Acai berry breakfast bowls.
Other Top Restaurants
Koko Head Cafe – Elevated breakfast food with an Asian flare, brought to you by a chef that used to work at the French Laundry and starred on Top Chef. Their breakfast Congee is to die for.
Goofy Cafe & Dine – Low key surfer vibe with some excellent fresh dishes.
Mei Sum – The best dim sum restaurant in Hawaii
The Pig & The Lady – The best Vietnamese food on Oahu
Finally, on the first Friday of every month all the art galleries and shops in China Town/Downtown Honolulu open their doors, have wine and appetizers and all the bars and restaurants have incredible deals as people spill onto the streets and enjoy great food, drinks and live music.
Held annually on Memorial Day, The Oahu Lantern Festival is worth your time if you’re on Oahu over Memorial Day.
One last piece of advice…If you are not native Hawaiian stay out of the west side of the Island. It’s not closed off, you are technically allowed to go out there, but there is a decent amount of racism and aggression directed toward white people out there. If you’re a tourist it’s best to just stay in Honolulu, Waikiki, Kailua, Lanikai, Kaneohe and the North Shore. There’s really nothing for you outside of those areas. Hawaii is extremely safe…but, be aware that a small percentage of native Hawaiians really don’t like the fact that white people and tourists have spent the last 50 years moving into their island. Hawaiians are big people, you don’t want to mess with them and you should respect their island and way of life. If you do that you’ll be fine.