Let’s be real, Hawaii is on everyone’s buckle list. But the real question is, which island should you visit first? Hawaii has eight islands, but the four main islands are the Big Island, Maui, Oahu, and Kauai. This blog post features a 7-day Oahu Travel Itinerary. We thinks Oahu is a great place to start when tipping your toes into Hawaiian territory, and you’ll quickly see why.
Day 1: Fly to Honolulu
We flew with Delta Airlines out of Los Angeles (LAX) which was about a 6 hour flight to Honolulu (HNL)!
We HIGHLY recommend renting a car, more specifically a Jeep! Renting a Jeep was one of the best decisions we made for our Oahu Vacation. We absolutely loved taking the top off the Jeep while traveling to different regions of Oahu. Feeling the breeze and the sun shining down on you while taking in the beautiful Hawaiian surroundings was truly incredible.
First Stop on the Oahu itinerary: Pearl Harbor
Pearl Harbor is a must-see on your Oahu itinerary. Since it’s so close to the airport, we decided to make it our first-stop on the way to our resort. Reservations and tickets are not required to enter the Pearl Harbor Visitor Center, Pearl Harbor National Memorial, walk the grounds, or visit the museums. However, if you want to participate in the Pacific Historic Parks Pearl Harbor Audio Tour and Virtual Reality experience ($20) or the USS Arizona Memorial Program (FREE), this can be reserved in advance on recreation.gov.
Check-in at the Kahala Resort
We stayed at the Kahala Hotel & Resort, which is known as THE luxury 5-star resort in Oahu. It has been given the name “Ka-hollywood” due to all of the presidents, celebrities, and royals that choose to stay here.
We highly recommend making Kahala your home while visiting Oahu, especially if you prefer a secluded, hide-away vibe over the hustle and bustle of Waikiki. Kahala is located on a private beach in one of Oahu’s most upscale residential neighborhoods, but it’s still just a 10 minute drive to downtown Waikiki so you’re still close to everything!
Dinner with a View at Michel’s at the Colony Surf
Michel’s at the foot of Diamond Head Crater is the perfect place for sunset dinner after a long day of traveling. We chose the tasting menu which included ahi tartare, lobster bisque (flamed in cognac right in front of our eyes 🔥), Caesar salad prepared tableside, filet mignon rossini, and a Belgium chocolate decadence cake. I mean, could it get much better than that?
The views really were breathtaking, and we loved watching the waitress create dishes in front of us! We highly recommend adding this restaurant to your Oahu itinerary for a unique, romantic dining experience.
Day 2: Venture to North Oahu & Take a Sunset Cruise
Swim with Sea Turtles at Laniakea Beach
One of the highlights on our Oahu itinerary was a 50 minute drive from Honolulu to Northern Oahu: Laniakea Beach, AKA Turtle Beach. It’s home to a population of Hawaiian green turtles. Volunteers are on the beach to make sure the turtles stay safe, but you can still get up close to the beautiful creatures while they bask on the sand and swim through the waves. We recommend coming here in the morning when there’s less crowds and the turtles are more active. The beach is also BEAUTIFUL so make sure to take a nice long walk on the beach to help burn off some of those Piña Coladas.
Grab Lunch at Haleʻiwa Beach House
While visiting Oahu’s North Shore, we recommend grabbing lunch at the Haleʻiwa Beach House. It has the best views in Haleiwa and serves yummy surf ‘n’ turf, pu pu platters (Hawaiian food consisting of an assortment of small meat and seafood appetizers), and colorful cocktails.
Try the World-Famous Dole Soft Serve
Next up the Oahu Itinerary is a MUST for all pineapple lovers, the Dole Pineapple Plantation 🍍. If you’re obsessed about pineapples like we are, this is truly paradise on Earth. They have everything pineapple, including pineapple gummy bears, chocolate, and don’t forget the world-famous Dole Soft Serve! If you want to enjoy other activities the plantation has to offer, they also have a Pineapple Express Train Tour, Plantation Garden Tour, and Pineapple Garden Maze.
Enjoy Cocktails on a Sunset Cruise
After freshening up at the hotel after a long day, we recommend enjoying a romantic Sunset Cocktail Cruise out of Waikiki. Or if you spend too much time at the Dole Pineapple Plantation like us, you may need to drive directly there. We highly recommend booking the Waikiki Sunset Cocktail Cruise by Hawaii Nautical on Trip Advisor. It’s about $215 per couple and so worth it! You will get the most amazing Hawaiian sunset views from the deck of a luxury catamaran during a 1.5 hour cruise from Waikiki. Two cocktails per person and appetizers are included.
Day 3: Explore Waikiki & Go to a Luau
Start Your Morning with Kona Coffee
If you’re a coffee connoisseur, make sure Kona Coffee Purveyors is on your Oahu itinerary – voted ‘Best Coffee in Hawaii’ by Food & Wine. Stop by for a Kona coffee tasting prior to starting your hiking adventures!
Hike Diamond Head Crater
Due to its proximity to town, rich history, and stunning shoreline view, Diamond Head Crater hike is one of the most popular hikes in the entire state of Hawaii. We recommend getting an early start to avoid the heat and crowds. The hike is about 1.8 miles out-and-back and is generally considered an easy route – taking an average of 1 hour to complete. At the summit, you will see beautiful views of the Diamond Head Crater, the picture-perfect shoreline, bunkers, and a lighthouse. The crater was formed ~300,000 years ago during a single eruption. As the ash and material settled, they cemented together and formed Diamond Head Crater.
Refuel with a Pineapple Smoothie
Imagine this, you are tired and sweaty after an hour long hike around the infamous and beautiful Diamond Head Crater Trail. You are thirsty and looking for something refreshing when you see Honolulu Pineapple Company food truck. You buy a delicious and refreshing pineapple smoothie, served from a pineapple itself, and sit in the shade while sipping on pure deliciousness.
Go Shopping in Waikiki
After breaking a sweat on the infamous Diamond Head Crater Hike, it’s time to reward yourself and unwind with some shopping in Waikiki. For upscale and authentic Hawaiian shopping, we recommend going to the Waikiki Shopping Plaza located on Kalakaua Avenue. It features internationally known brands such a Chanel, Gucci, Huge Boss, Tiffany & Co., and Yves Saint Laurent. It also features small local boutiques with authentic Hawaiian apparel and souvenirs.
Sip on a Famous Mai Tai at the Royal Hawaiian
Visit the famous ‘Pink Palace’ AKA The Royal Hawaiian, a Luxury Collection Resort. While you’re there, you have to try their famous Mai Tai cocktail while overlooking Waikiki Beach.
A Must-do on Any Oahu itinerary: Experience an Authentic Luau
Did you really visit Hawaii if you didn’t go to a luau?
For your Oahu itinerary, we HIGHLY recommend experiencing an authentic, intimate luau rather than one of the huge, cinematic luaus. We used Oahu’s #1 Luau with Experience Nutridge and couldn’t be happier with our decision! The luau was located on a large, historical estate with beautiful views of downtown Honolulu and the Waianae mountain range. It was such a unique and intimate backyard style luau with a small group of people, so we all became friends quickly! The amazing staff taught us about Hawaiian history and culture through performances and hands-on excursions over a 4-hour time period. The tour included a Kukui Nut Lei (we’re wearing ours in the photo above!), farm to table dinner, and 2 complimentary alcoholic beverages.
Day 4: Go Hiking & Snorkeling in Southeast Oahu
Climb the Koko Crater Railway “Stairs”
The Koko Crater Railway Trailhead is a short drive from Waikiki, about 20 minutes away from the Kahala Resort.
Even though it’s a short hike of 1.6 miles, it can be a challenge for the fittest due to the extreme incline of 885 feet. Let’s just call it the “Stair master on Steroids”. If you’re up for the challenge, the grueling hike will be worth it once you see the beautiful views at the top of the summit.
Go Snorkeling in Hanauma Bay
If you enjoy snorkeling, we recommend adding Hanauma Bay State Park to your Oahu itinerary as it’s a short drive from Koko Crater Railway Trail. Hanauma Bay has a unique marine ecosystem with diverse wildlife. The bay is formed within a volcanic cone and is protected by vertical crater walls and a peripheral reef, making the water calm and tranquil. The entrance fee to Hanauma Bay is $25 and snorkeling equipment costs $20 per standard set.
Have a Romantic Dinner at La Mer
For a fancy, romantic dinner out, we recommend dining at La Mer at the Halekulani. It’s named Hawaii’s only AAA Five Diamond and Forbes 5 Star restaurant and is one of the most upscale, prestigious fine dining restaurants in Oahu. The restaurant has open air dining with spectacular ocean views of the Pacific. When it comes to the food, you will not be disappointed with their high-end fixed menu featuring local and tropical ingredients in dishes inspired by flavors from the south of France.
Day 5: Discover the Beauty of Kailua and Kaneohe
Trek the Lanikai Pillbox Hike
Our favorite hike in Oahu was the Lanikai Pillbox Hike which is about 40 minutes away from the resort. It was picturesque and pleasant with some of the best views and instagrammable spots. It’s 1.7 miles in duration and ranked as intermediate (but seemed easy in comparison to the Koko Crater Railway Trailhead)
Wind Down on Lanikai Beach
Just a short stroll from the Lanikai Pillbox Hike Trailhead is Lanikai Beach, described as the “most beautiful” Oahu beach. It’s even ranked as one of the best beaches in the world! Our unfiltered picture doesn’t do it justice. The white powdery sand, crystal clear blue waters, and picturesque mountains makes Lanikai beach a true paradise.
Explore Kailua
We loved exploring the quaint town of Kailua after an eventful morning hiking and basking in the sun. First, we stopped by Nalu Health Bar and Cafe to try the purest açai bowl. It was pure deliciousness! Then we walked around town and stopped by Lanikai Brewing Company to try a flight of authentic Hawaiian craft beer and snack on some pizza before heading to our next adventure.
Visit the Enchanting Ho’omaluhia Botanical Garden
The Ho’omaluhia Botanical Garden is located on Oahu’s windward side in Kaneohe. We recommend driving through this enchanting park after visiting Kailua. The entry fee is free, but an important note is that it closes at 4PM. Spanning 400 acres, the lush tropical gardens are surrounding by the jagged and dramatic Koolau Mountain Range. The mountains appear Jurassic Park-like and are truly mesmerizing!
The Last Dinner at Haleiwa Joe’s Haiku Garden
Make your last dinner in Hawaii an unforgettable one at Haleiwa Joe’s Haiku Garden. While waiting for your table in this open-air restaurant, you can explore the tropical garden, koi pond, and beautiful views of the Koolau Mountain Range.
Day 6-7: Relax at the Resort & Travel Home
On our last day in Oahu, we spent the morning relaxing at our resort and packed up our things to travel home. It took us two days to get home because our flight was overnight, but this will vary for everyone.
We hope you enjoyed this itinerary and are inspired to visit Oahu!
