Oahu: Explore Beyond Waikiki
This Oahu trip is a delightful blend of comfort and exploration. Enjoy all of the amenities that the Four Seasons has to offer, including an amazing breakfast buffet and poolside relaxation at the adults-only pool. The Pink Pillbox hike offers stunning views, while the North Shore's beaches and food trucks add adventure and local charm. A visit to Pearl Harbor offers a historical element and pairs with just a touch of the hustle and bustle of downtown Honolulu and Waikiki.
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Where to stay
Four Seasons Resort Oahu at Ko Olina
Oahu’s most luxurious beach resort, with postcard-perfect Pacific Ocean views, a playground of pools, lagoons and ocean watersports, and a prized kids’ club.
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Day 1: Hotel Check-in — Four Seasons Oahu at Ko Olina
After a long flight, especially if you are coming from the east coast, you'll arrive at Honolulu International Airport. Collect your luggage and make your way to the car rental center, where you can pick up your pre-booked rental car. From there, head straight to your hotel, the Four Seasons Oahu at Ko Olina, located on the island's sunny western shore. The drive from the airport to the resort takes about 30-40 minutes, depending on traffic.
Once you've arrived and been greeted with a fresh floral lei, check in and settle into your room. Take it easy to start your relaxing vacation and adjust to the time zone change.
For dinner, keep things easy by staying on property and enjoy a delectable meal at Mina's Fish House. Enjoy fresh, locally sourced seafood and take in the beautiful sunset and surroundings.
Day 2: Beaches exploration
You will probably be up early with the time change so embrace it and start your day with a delicious breakfast buffet at the Four Seasons. Fuel up for an exciting day of exploring Oahu's North Shore.
After breakfast, pick up your rental car and hit the road towards Oahu's North Shore.
Your first stop is Leonard's Bakery Malasada Truck, where you can indulge in fresh, warm malasadas—delicious Portuguese doughnuts. Order a few to try out the flavors they have available that day. Next up, make a quick stop at Green World Coffee in Haleiwa for an extra caffeine boost needed for the day's adventures.
Continue your drive to Haleiwa, a charming North Shore town known for its art galleries, boutiques and food trucks. Spend some time walking around, shopping for souvenirs and enjoying the laid-back atmosphere.
From there, continue to explore some of the North Shore's iconic beaches. Stop at Banzai Pipeline to watch surfers riding the massive waves and then head to Laniakea Beach, also known as "Turtle Beach," where you can often spot Hawaiian green sea turtles basking in the sun.
For lunch, visit one of the North Shore's famous food trucks. Ry's Poke Shack, located a bit past Turtle Bay Resort, is an excellent choice for fresh and flavorful poke bowls. Garlic shrimp is also a super popular choice up here so if that's up your alley be sure to check out Giovanni's Shrimp Truck. Finish off your lunch with some fresh Hawaiian Shave Ice.
After refueling, continue your journey. Visit Lāʻie Point State Wayside, where you can take in breathtaking coastal views and see the iconic "Finger of God" rock formation.
Head to Kualoa Regional Park to admire the dramatic backdrop of the Koolau Mountains and the tranquil bay.
After this full-day adventure across the top of Oahu, begin your drive back to the Four Seasons, continuing to take in the scenic beauty along the way.
Arrive back at the resort, relax, and freshen up for the evening. Tonight's dinner is on property at the Four Seasons again, this time at Noe Italian Restaurant. Indulge in delectable Italian cuisine with a Hawaiian twist in an elegant setting.
Day 3: Honolulu and Waikiki
Begin your day with another amazing breakfast from the buffet at the Four Seasons. Before you leave for breakfast, make sure to grab iced coffees to go and then take a leisurely walk along the beautiful Ko Olina lagoons. Find a comfortable spot, whether it's on the beach or by the pool, to relax and soak up the Hawaiian sun. Take some time to unwind before your afternoon adventures.
Grab the rental car and start to head in the direction of Honolulu. As you drive, make a stop at a local 7-11 store to pick up some unique Hawaiian snacks that you can't find at other locations in the U.S. Be sure to try the spam musubi (go for the deluxe version!), li hing gummies and sample some local Slurpee flavors.
Arrive at Pearl Harbor, a significant historical site. Spend some time exploring the Pearl Harbor Visitor Center and the USS Arizona Memorial. Be sure to purchase tickets in advance to secure your entry.
After your visit to Pearl Harbor, continue your drive into Waikiki. Parking can be a bit crazy here, but you have restaurant reservations that include free valet parking (planning for the win!) Before you head to those reservations, take a walk around Waikiki Beach. Explore the vibrant shops, boutiques and street performers along Kalakaua Avenue.
As the evening approaches, head back to where you parked at Halekulani Hotel for your reservations at House Without a Key. This iconic spot offers a picturesque setting with live Hawaiian music during their nightly happy hour. Enjoy refreshing cocktails and appetizers as the sun sets over Waikiki Beach. Maybe you head to dinner at another location or maybe you stick around and continue to listen to the music here after the sun sets, there is definitely enough on the menu to make it into a full meal.
After you've finished your time in Waikiki, it's time to leave this bustling area behind and head back to the relaxing atmosphere of the Four Seasons. If you could use a sweet treat to end the evening, walk over to Black Sheep Cream Co. also located within the Ko Olina complex.
Day 4: Morning Ma'i'li hike, evening relaxation and Hawaiian night skies
Start your day with an early morning adventure by heading to the Ma'i'li Hike, also known as the Pink Pillbox Hike. This hike offers stunning views of the coastline and the surrounding area. At the top, here are several pillboxes (military bunkers from World War II) that you can check out, including one that has been painted in all pink! Since there is very little shade, it's essential to begin early to beat the heat. Don't forget to pack plenty of water and wear a hat for sun protection.
After completing the hike, return to the Four Seasons for a well-deserved breakfast buffet to refuel after your morning adventure.
Today is the day for total relaxation. Head to the adults-only pool area and choose a comfortable spot to unwind. Spend the afternoon at your leisure, whether it's lounging by the pool, reading a book, or taking a refreshing dip. Order drinks poolside from Dr. Mai Tai's and take in the breathtaking ocean views.
For your final dinner on Oahu, make your way to Monkeypod Kitchen. The restaurant is also located within the Ko Olina complex, which means you can reask for a house car from the Four Seasons to drive you over. Don't miss the famous honey-lilikoi foam on the Mai Tai cocktails and be sure to leave room for one of their cream pies for dessert.
After dinner, consider some stargazing on the resort's beach, taking advantage of the clear Hawaiian night skies.
Need to Know
Looking for more inspiration on adventures in Hawai'i? Find more guides about traveling to Hawai'i written by your favorite travel experts (aka Fora Advisors).
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This guide is part of our ongoing series on travel to Hawai'i.