Each Hawaiian island has its own magic. But Oahu holds a special place in my heart for more reasons than I called it home for four years. Oahu has everything. Want a chill beach vibe and watch surfers on insane waves? Oahu’s got that. Want to go on hikes with waterfalls that make you feel like you’re in Avatar? Yep, got those. Amazing beaches, food, shopping and the ability to go out at night. Oahu gives you the best of all the worlds when you know where to go.
First off, rent a car. I know it’ll cost you extra at most hotels but being able to get out and explore is a must on Oahu.
I recommend people staying in Waikiki and venturing out. Staying in Waikiki gives you walking distance to restaurants, grocery stores, shopping, and nightlife. If Waikiki isn’t your vibe I’d then recommend somewhere near Diamond Head. In my opinion, it’s easier to stay where the restaurants and bars are and venture to the Westside or North Shore for day trips.
Below are my recommendations, favorites, and must-dos. They’re sectioned off by area of the island. If you do any or go to any place on your vacation I’d love a tagged Instagram story or photo. Hawaii will forever hold a special place in my heart and I love seeing others fall in love with it as I did.
Kono’s – An awesome spot for breakfast right in the town of Haleiwa. Some of the best breakfast burritos.
Uncle Bo’s Bar & Grill in Haleiwa – Try the Dynamite Shrimp and Boca Rota, where garlic cheese bread gets an upgrade with prime rib strips.
Banzai Sushi Bar in Haleiwa – You can sit outside atop zabutons (Japanese cushions) on the floor while watching a projector of surf videos. Sushi is fresh and the atmosphere is great. Doesn’t get much more North Shore.
Matsumoto Shave Ice – There will most likely be a long line and you’ll be tempted to go to the shave ice next door. Don’t give in! Wait it out and enjoy the best shave ice you’ll probably ever have. The Hawaiian flavors like coconut, mango, and pineapple are my favorite.
Crispy Grindz – For the longest time I didn’t know the name of this epic acai bowl spot. I simply told friends “the purple food truck right outside Pipeline beach” is the best acai bowls you’ll ever have. Since venturing back, I discovered it’s called Crispy Grindz and they now have two trucks on North Shore. One in the town of Haleiwa near all the shops and restaurants and one still on Pipeline. Surfers from Brazil opened it and are crushing the acai bowl game.
Foodland – A grocery store rather than a restaurant but a solid go to on the island. Get a poke bowl on rice and some drinks, take it to go, and go sit on Pipeline or Sunset beach and watch the surfers. My favorite picnic in the world. If you go for Foodland poke the California style and spicy poke with furikake are my jam. If you’re feeling like enjoying your day a bit more, grab a fresh coconut from the fruit stand on the way to Turtle Bay and add a splash of rum to it. You’re welcome.
Stuff to do
First off, North Shore waters are no joke. I personally know people who have been seriously injured from the power of North Shore and they walked away lucky to have their lives. Winter months typically bring big waves up north. The ocean is powerful and does not care if you’re on vacation. Know your limits and don’t test mother nature, especially in Hawaii.
Jump off the rock at Waimea- But only if you see people who look like you doing it. This is typically best in summer when waves are small and when the tide is in. Locals will jump off the rock in conditions that you might not be safe in. When in doubt politely ask someone if it’s safe.
Beach – Right after Foodland and before Pipeline, there’s a beach that’s one of my favorite spots. I’m cringing over telling people this because you can’t see the beach from the road, it’s typically not crowded, and I don’t want it to change. You can park along the side of the road, walk over to where there is the end of a small one-way road outside houses on the beach. Find any path through the trees to the beach and make your way west. The beach has beautiful sand and calm waters in the summer that is super clear and deep enough for solid swims.
Stand Up Paddle Board down the river – As you get to the end of Haleiwa you’ll pass over a bridge. Right after the bridge is a board rental spot where you can rent Stand-Up Paddle Boards and paddle up river. You won’t have to fight with the ocean current and will often get to see turtles and sometimes manta rays.
Turtle Beach – When driving through North Shore you’ll come to a spot usually with tons of traffic, cars parked on the side of the road, and a bunch of tourists standing on the beach. This is Turtle Beach. You can almost always spot turtles either in the water or sunbathing on the sand.
Pipeline or Sunset Beach – Some of the most famous surf breaks in the world. Waves are powerful and huge in the winter months (Nov-Feb). Sit on the shore and watch famous surfers in their backyard on some of the craziest waves in the world.
Surf Lessons – Being able to say you’ve surfed North Shore feels pretty cool. No one needs to know you were taking lessons on a foamie. At Pua’ena Point there are numerous surf schools that will take you out. I’ve had a handful of lessons out there and my favorite hands down was with Mikey and Kalae O’Shaughnessy. Brothers from Hawaii, you can find them on Instagram @kalapanakalae & @mickey.redd or on Facebook at Number One Surf School.
Free Dive with Sharks through One Ocean Diving – Anyone remember the picture of the girl swimming next to a massive great white shark that went viral on social media a few months ago? Yea, well that chick is Ocean Ramsey and is the dive safety officer, head field researcher, and the founder of the Pelagic Shark Snorkel. While you won’t be around great whites, thanks no thanks, you’ll get to learn about shark behavior, biology, physiology, up to date research and how to safely interact with sharks.
Skydive – If you’re going to skydive, do it on North Shore. I had views of whales breaching out of the gorgeous blue ocean on one side and the lush green mountains on the other.
Windward Side (northeast)-
Haleiwa Joe’s at Haiku Gardens – Yes, they have a Haleiwa Joe’s in Haleiwa North Shore, but my favorite is their Haiku Gardens location. With gorgeous garden views in front of the mountains, it’s the perfect spot for date nights or wedding rehearsal dinners. Home to one of the best prime ribs I’ve ever had but it sells out early so reserve a slice when you first get there.
Stuff to do
Lanikai Beach – Often making the world’s top beaches lists, this is one of the most perfect white sand beaches you’ll ever see. No parking lot here so you may have to hunt for a spot along the neighborhood but it’s worth it. The sand feels like flour, the water is crystal blue and typically calm being perfect for laying on floaties. Great view of the Na Mokulua islets, better known as the Mokes.
Kayak to the Mokes – If you’re feeling active rent a kayak from Kailua Beach and make your way out to the island.
Lanikai Pillbox Hike – An epic hike for sunrise. Park in the Lanikai neighborhood around Mid Pac Country Club and walk up the street to the hike entrance. An incredible view, only about 25-40 minutes to hike, but sometimes it can be crowded.
Tom Tom Hike – Similar to Pillbox Hike but even better views and far less crowded. I’ve heard that it is now private property and cops now give out citations for trespassers. Yet people still hike it on lucky days when there are no cops. If that sounds intriguing to you, you can google Tom Tom Hike and get after it at your own discretion.
Makapu’u Tidepools – Getting to these can be a bit of an adventure but so worth it. To get to the pools you’ll hike up the Makapu’u Lighthouse to the third rest stop where you’ll see warning signs and a trail going down the mountain, take that of course. There are white arrows and dots to follow down. The lava rocks can be steep so I’d recommend shoes, but the pools are incredible and everyone says it’s worth it.
Kualoa Ranch – Home to movies like Jurassic Park, 50 First Dates, Pearl Harbor and numerous more, tour Kualoa on an ATV or horseback if possible.
East Side / Waikiki / Honolulu
Uncle Bo’s – Don’t make it up to North Shore? The original Uncle Bo’s is about 10 minutes from Waikiki if you want to get away from all the tourists.
Leonard’s Bakery – Famous for their malasadas, a Portuguese donut without the hole. With tons of flavors to choose from, I recommend the origional because you just can’t go wrong with the OG. People dream about these, they’re really that good.
Bogarts – I ate here probably 7 times in my last vacation to Oahu. You can walk or jog to it for brunch from Waikiki or take a 5-minute drive down the street. Everything I’ve had here has been great but the must is Mama’s Fried Rice. It is cash only but the Health Bar next door has an ATM.
da Cove Health Bar – Known as one of the best acai bowls on the island, Health Bar offers fresh bowls, smoothies, juices, salads, and sandwiches. Buy their honey! Trust me, it’s expensive and worth taking back home. It’s a game changer for home smoothies.
Tommy Bahama Restaurant – Yes you can get it elsewhere, but what you can’t get anywhere else is the vibe this one has. With rooftop seating, the food is good and the atmosphere is a great date spot.
Dukes- Go for a drink at dukes. It’s classic Hawaii but often filled with tourists in aloha shirts or families in matching Hawaiian print. They have a live band on Sunday’s from 4:30-7pm and is a great time for apps and drinks.
Ono Seafood – Known for some of the best poke bowls on the island.
Deck Waikiki – A rooftop restaurant at the Queen Kapiolani Hotel with happy hour from 4-6pm. I went for brunch, it was a buffet, not the best, not bad either. But the view of Diamond Head is epic. I’ve heard they do great pool parties if you want to follow their Instagram @deckwakiki or simply go for drinks.
Stuff to do
Hanauma Bay – Touristy yes, but the snorkeling there really is amazing. $23 in total for entrance, parking, and snorkel rentals, you can easily spend half a day here. And according to my good friend Natalie, bring a cooler with food and drink and simply hide alcoholic drinks in koozies. 😉
Scuba Dive! – I add the explanation because it is 100x better than snorkeling. This can even be great on a cloudy or rainy day because you’re under the water where it’s still beautiful. Chris and I both scuba dived for the first time with Living Ocean Scuba in Honolulu and cannot say enough great things about them. We opted for the Turtle Boat tour and swam with over 15 turtles. They have options for both first-timers and people with their scuba licenses. They’ll take photos of you swimming next to turtles and give you the option to purchase after.
China Walls – My all-time favorite for sunsets. End your day here before heading back to Waiks or town. Locals often bring small bbq pits, drinks and a speaker playing “Somewhere Over The Rainbow”. Have a seat, slow down and enjoy the sun slip away against the ocean and Diamond Head.
Waikiki beach – Get surf lessons, rent a stand-up paddleboard, buy a floatie to enjoy the calm waters, hop on a catamaran with bottomless matai’s. It is crowded but one of the most famous beaches with aqua blue water and beautiful views of Diamond Head.
Koko Head – While it’s a quick hike straight up, this hike feels more like mother nature’s Stairmaster. 1048 stairs are a quick 30 minutes to the top where the view makes your sweat all worth it.
Kuli’ou’ou Ridge Trail- A longer trail, about 5 miles total, but doable for the average hiker with breathtaking views. I’d recommend this hike in dry conditions to avoid mud. Walk through various types of forests that will have you thinking where am I??
Manoa Falls – With a waterfall at the end, this easy hike is a must do. Experience the Jurassic Park feel of Hawaii on this hike as part of it was filmed here.
Rum Fire – A chill bar with live music on the weekdays that turns into standing room only with a DJ on the weekends. They offer amazing drinks right on the beach of Waikiki. Long lines tend to form later in the night but if you’re staying at the Sheraton you get your own entrance with a short line, yay!
The Study – aka the Lobby Bar at the Modern Hotel. Open from 6-midnight Monday-Wednesday then until 2 am Thursday-Sunday, this is the spot for drinks. The bookshelf in the lobby of the Modern Hotel opens up and reveals a swanky bar and lounge with delicious cocktails.
Addiction – The only club I would recommend on Oahu. If you want a night out with dancing and a dope DJ, Addiction is your spot. Reserve a VIP table if you’re with a group for bottle service and your own private couches to dance on. Also, the big guy bouncer is an amazing dancer if you stay late enough and talk him into showing you his moves.
First Fridays – Happening, you guessed it, every first Friday of the month, First Fridays brings art and drinking together in a block party in Downtown Chinatown. Check out FirstFridaysHawaii.com for their upcoming calendars.