You can get a downloadable map of this itinerary here.
**Ally is a Kentucky native and lived on Oahu for three years after graduating from The University of Alabama. A lifelong ocean enthusiast, Ally is an avid surfer, diver, and SUPer. Living on Oahu was a dream with the most diverse sea life and best waves in the world. In her next home (Phoenix), she will be on the lookout for good poké and weekend trips to find waves in California.
BEST TIME TO TRAVEL: September-November because of fewer tourists. A lot of people visit in the Summer, Christmas time, and for Spring Break. Anytime year-round is a good time to visit with good, warm weather. Oahu has cloudier and rainier days in January and February, but one of the great things about Oahu is: if it is raining where you are, just drive to another part of the island!
WHERE TO STAY: If you are looking for a relaxed/resort-style vacation, you might consider the Marriott Beach Club in Ko’Olina, or Turtle Bay on the North Shore. Hawaii legislators recently outlawed Airbnb so staying in someone’s cozy rental home on the east side is no longer an option. If you are looking to experience the action or nightlife of Honolulu, my favorite “town” hotels are: The Laylow, Surfjack Hotel and Swim Club, The Modern Honolulu, and my favorite cheaper option: The Paniolo at the Equus.
You want to plan your days based on different sections of the island! The North Shore has a CLASSIC “beach bum” feel and is the surf capital of the world. Oahu’s East Side is STUNNING and feels more remote. The southern part of Oahu, Honolulu or “town” is busy, high end, but still beachy. Oahu’s far west side is beautiful as well and full of history, but best to travel with a local. You don’t want to stand out or look lost in Waianae. Before you get that far west, there are different resorts at Ko’Olina, if kicking back and relaxing in paradise is the main goal of your trip.
day 1-2: the north shore.
Start traveling up north: if you are driving up the section past Haleiwa and toward the famous Bonzai Pipeline, you are traveling “up the pipe.” Kamehameha highway at this point is just a two-lane road with the ocean on your left and mountains on your right. You might see a world-famous surfer crossing the street headed to their favorite break. Wahiawa and Waialua are more rural areas, Haleiwa (hah-lay-EE-va) has a beach town vibe, and up the pipe toward Kahuku is pretty rustic with food trucks galore on both sides of the road.
BEST FOOD: The best acai bowls are at Banzai Bowls or Haleiwa Bowls. If you’re looking for something a little heartier, Haleiwa Cafe has amazing breakfast burritos, as well as Konosin Haleiwa. If you’re craving pancakes on this part of the island, you might stop by the KOA pancake house in Wahiawa for a very authentic Hawaiian breakfast. You may be surprised to find rice on the menu at a pancake house. Banzai Sushi, Giovanni’s Shrimp Truck, The Beet Box, andMaya’s Tapas are all great lunch options.
ACTIVITIES: My favorite place to rent paddle boards is Tropic Rush, they’ll load the board in the water for you off of their own ramp. “Turtle River” is a great place to paddle since it’s protected from waves, and keep your eyes peeled for any turtles swimming under your board.
If you’re looking to shop and not be active today, there are incredible stores all down the main Haleiwa strip and in the Northshore Marketplace. My favorites are:
The Brazilian Showroom is where you can get some high quality bikinis, and Red Dirt Shirts give a 20% military discount (Most stores give a military discount, don’t hesitate to ask!)
A really cool experience if you like handmade bath products is to take a tour of the North Shore Soap Factory in the Waialua Sugar Mill. You can even stamp an image of your choice onto your soap!
In my opinion, Haleiwa has it all. Good food, shops, beaches, and water sports. Haleiwa has the “hawaiian feel” that I imagined all of Oahu having before I visited and discovered how BEAUTIFUL and DIVERSE this place is.
day 3-4: the east side.
The East Side of Oahu has the BRIGHTEST blue water, white sandy beaches, and in some spots, is a little more remote. Good luck keeping your eyes on the road if you’re driving on Highway 3, I guarantee it’s the most scenic and jaw dropping drive you’ll ever take.
Makap’uu Lighthouse Trail (easy). This hike has a paved path and INCREDIBLE views. Halfway up on a clear day, you can see the islands of Moloka’i, Lanai, and Maui on the horizon. At the top, you can look at the entire stunning eastern side of Oahu. Look down and you can spot the lighthouse itself!
Lanikai Pillbox Hike(moderate). This hike’s entrance is tucked into a neighborhood, so you’ll need to park somewhere on the street and walk to the entrance. This hike doesn’t take long and has an incredible view of the “Mokes” islands. If you rented a paddle board during this week, I suggest making your way out to these islands!
Crouching Lion Hike–this one is for intermediate hikers or people in relatively good shape (hard). The trail head is hard to find, search “crouching lion” on google maps, and drive until you spot cars parked alongside the road. Park somewhere safely, then you will have to cross the street and walk until you see the signs “Area Closed–do not go beyond this sign” and “Hazardous Cliff!” Despite the threatening signs, this hike is very safe and open to the public. The hike is short, steep, and sweet. Don’t be afraid to use the ropes along the way and don’t look back at the view until you’ve made it to the first platform (it’s a flat section of ground with a small memorial site). After this first flat portion, hike any other peaks at your own risk (the views are just as good as the first peak)! I would say the stunning scenery of this hike is worth the effort!
BEST BEACHES: The East Side of Oahu is known for the most STUNNING beaches on island. The best in my opinion are Bellows Beach Park/Waimanalo Beach Park and Lanikai Beach Park. Parking is limited (especially in Lanikai) so get to the beach early! For lunch across from Lanikai, try Buzz’s! If you dare, order the “famous” maitai–just pure rum in a glass.
ACTIVITIES: Try the Kualoa Ranch ATV tour if you want to see the site where Jurassic Park and so many other films were made.
day 5-6: honolulu, “town”.
I ADORE Honolulu because it has everything you could want out of a vacation. A picturesque beach, upscale shopping, familiar chain restaurants, local eats, great hikes, board rentals, etcetera.
BEST BEACHES: Waikiki Beach is fun to walk along the coastline. If you’re staying in town but are looking to get away from the hustle and bustle, I suggest Kaimana or Sandy Beach.
ACTIVITIES: Skip the Honolulu Zoo and the Waikiki Aquarium! Save your money and time–there are less animals/fish to see here than literally any other zoo. If you want to see incredible reef fish up close, rent snorkel gear at Hanauma Bay Nature Preserve.
If you’re itching to try surfing, take lessons in Waikiki right in front of the Moana Surfrider hotel (Dive Oahu & Surf) in the summer/fall. In the fall/winter/spring, you might see Uncle Bryan’s Surf School trucks/tents at Pua’ena Point or Chun’s Reef (North Shore). Check surfline.com to look at the size of waves on different parts of the island! The following sizes are suitable for beginners: 1-2ft, 2-3 ft, and 3-4ft overhead. I wouldn’t recommend paddling out in 5ft+ overhead for a beginner. Surfline will also tell you if conditions are “fair/ good” meaning the wind and currents are in your favor, vs “poor” conditions where the water will be choppy and the wind working against you.
Anytime I go on the Maitai Catamaran cruise, I HAVE THE TIME OF MY LIFE. You can find a groupon for the “tradewinds sail” 2 people for $40. After you purchase, call the catamaran company themselves and tell them you ordered a groupon. You can schedule your discounted cruise with this office anywhere between 11am-3pm. The catamaran “office” is right behind the Sheraton Waikiki on the beach side. Check in at the counter 30 minutes prior to your sail, then 10 minutes before the sail you will need to show ID then will pose for a photo. I suggest putting on sunscreen while you’re waiting around. Some people wear only swimsuits for the cruise, some wear street clothes, up to you! On the catamaran, beers are $3, champagne is $5, and mai tais are $5 cash. This is a steal considering cocktails in waikiki will run you $15 each. Have your cash ready, drink up, and enjoy the stunning landscape of waikiki and Diamond Head Crater.
day 7-8: “west side” ko’olina/waianae
Ko’Olina is a very well-manicured section of the island featuring a row of luxury resorts, each with its own man-made lagoon. Past Ko’Olina is Waianae, a part of the island filled with local residents, largely untouched by development. So many of my friends who have lived on Oahu for awhile tell me this is their favorite part of the island, and if you make it all the way out to Yokohama Bay, you’ll see why.
BEST FOOD: Monkeypod Kitchen (owned by Disney) for locally sourced food with unique flavors. I recommend the lobster deviled eggs, pumpkin patch ravioli, any of the pizzas, or Macadamia Nut Crusted Mahi Mahi. The Beach House by 604 is right on the water farther into Waianae and is located on a military camp site. You don’t need military ID to go to the restaurant, just tell the gate guard you are there to eat. The Beach House has INCREDIBLE blended drinks and hawaiian-style plate lunches.
BEST HIKE: Pink Pillbox Hike (moderate). Park somewhere along the road near the trailhead (google maps is your friend) and make your way up the mountainside. I LOVE this hike because the deep blue panoramic views contrast nicely with the pink pillboxes at the top.
BEST BEACH: Yokohama Bay is basically the farthest point west on Oahu, so far west you can practically touch the North Shore. Trust me–you don’t want to skip this beach.
I could write a whole book on how magical the island of Oahu is, but in summary, take the trip! There is something for everyone to enjoy on Oahu. I will never forget my first visit–I was blown away at the vivid flora, lush landscape, and teal water. A part of Hawaiian culture is taking care of the ʻāina (land)–please make sure to enter each place on island with respect and aloha. Hawaii will always hold a special place in my heart and I know if you visit you will feel the same.
1 comment
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January 25, 2020 at 1:59 am
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