Oahu has a perfect combination of adventure, relaxation and amazing food. This guide will take you around the island for nine days of hiking, exploring, sailing, lounging, and lots of eating.
Another great location hotel but a more luxury option. This hotel is absolutely beautiful with expansive gardens, giving that escape feel while still being in the heart of Waikiki
Our favorite restaurant in Waikiki. Can't go wrong with anything on the menu. Be sure to stop at the bake case on the way out to grab some treats for later.
Stop in here for a great açaí bowl and coffee. They also have an awesome loco moco
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Day One
Travel day
Generally, travel to Hawaii is going to take the majority of your day. For that first day, you'll want to keep activity fairly simple- hotel checkin and a delicious meal. Taxi, Uber or Lyft are all available for transportation from the airport, and Waikiki hotels are a short distance away.
Day Two
Start your first full day with an easy hike and end with a sunset cruise. With the change in time zone, you will likely wake up early and ready to start exploring. By the end of the day while your energy is starting to fade, hop on a catamaran for a beautiful sunset.
This is an easy to moderate hike, great for sunrise or sunset, with beautiful views of the city and surrounding areas. During mid-day, this area can get quite hot, so early or late is best. It is close to the city center, you can either drive or take an Uber. You will need to make a reservation on the Diamond Head website to reserve a spot.
Another option for an easy to moderate hike. This one can get quite muddy, so it's not advised to go during the rainy season. Driving is recommended as it is a bit further out.
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Sunset Cruise Option
Moana’s Sunset Cocktail Sail along Oahu's Waikiki Coast
This is truly a trip highlight. From visiting coffee and macadamia nut farms, to secret beaches, to kayaking with sea turtles, all while enjoying delicious food along the way.
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Day Four
After a full day of venturing, day four can be spent enjoying the famous Waikiki beach. Lots of shops and restaurants are nearby when you need a break from the sun.
This is a beautiful beach with views of Diamond Head in the background. While crowded, there is so much to do. Options for beach rental include paddle boards and snorkeling equipment.
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Day Five
Transition day- check out of your Waikiki hotel and head over to a quieter side of the island for some resort time in Ko Olina. I also recommend sneaking in a morning hike before leaving Waikiki.
This is a great option for a sunrise hike. One of the easiest hikes on the island with incredible views. Keep an eye out for humpback whales swimming below.
This resort offers something for everyone in your party. With pools, slides and a lazy river, you can spend all of your days enjoying the water. Rooms are spacious and comfortable.
Everything is good here, but they are best known for their delicious mai tais and cream pies.
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Day 6
Resort Day. This is when the true relaxing begins. You've hiked and explored, now it's time to chill and enjoy all of the amenities of a Ko Olina resort.
Get a massage and relax in the tranquility of their hydrotherapy garden. A bit pricey but worth every penny
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Day 8
Book a rental car to take a day out to explore either the North Shore or the Windward side of Oahu. If staying at Aulani, you can book an Alamo rental car along with your hotel reservation and pick up directly from the resort.
Hello, I'm Emily - hit hard by the Wanderlust bug, I devote all that I can to experiencing new adventures. In between trips, I spend my time researching and cultivating the perfect itineraries in order to optimize my vacation time. I want everyone to have the best trip possible so please feel free to check out my itineraries for inspiration and guidance. Happy traveling!
