5-Day Hawaiian Vacation Itinerary

Hawaii is a tropical paradise that many travelers never want to leave. By you probably already knew that. It’s why you chose it for your vacation! However, you might be unsure of how to do Hawaii right. There are six unique islands to visit and so many possibilities. But it is impossible to do every Hawaiian island justice in just five days.

Fortunately, this itinerary will let you have a taste of everything that Hawaii has to offer without wasting precious time hopping islands. Through this itinerary, you will be able to experience both adventure and relaxation without leaving the beautiful island of Oahu. The fondly named “Gathering Place” is beloved by both locals and tourists for its diversity, beauty and history. Preview our idea of the perfect five days in Oahu below.

Day 1: Waikiki

When you arrive your first day in Oahu, you will find yourself in Hawaii’s capital city, Honolulu. Nearby Waikiki has the largest array of hotels and resorts to choose from in all of Oahu. Even if you are not into tourist-filled beaches, starting out your stay in Waikiki might be just what you need after a long flight from the U.S. mainland.

After checking in to your hotel or resort, we recommend starting your tropical vacation right and heading to the beach. Most hotels in Waikiki are walking distance from the water and even with the plethora of tourists, the waters are crystal clear and breathtaking. You can even rent stand-up paddle boards if you’re too excited to relax on the sand.

Waikiki and its surrounding areas are filled with bars, restaurants and nightlife just like any big city on the mainland. Thus, after soaking in the sun, you can head over to Kalakaua Avenue which also known as the Waikiki strip. There, you can end your day exploring this lively street and dining on the water as you watch the sunset.

Day 2: Honolulu

On day two, you’re probably ready to dive headfirst into your Hawaiian adventure. It’s best to start your day early in the morning, before the suns starts to beat down.

Your first activity of the day is a hike up the Diamond Head crater. This is a landmark of Hawaii so you can’t miss it. The hike is about 0.8 miles one way and includes numerous scenic stops along the way.

After your hike, you can head to the downtown areas of Honolulu and learn about its history and past. There, you’ll be able to visit the Iolani Palace which was originally used by Hawaiian royalty. At the palace, you will be able to see the various rooms that the monarchs utilized such as the Blue Room, Throne Room and Imprisonment Room. You can also view one of the regularly scheduled performances.

Finally, end your day in Hawaii’s very own Chinatown. There, you can browse through the markets and try cuisine from many Asian cultures including Filipino, Korean, Thai and Chinese. Additionally, you can sign up for a walking tour on which you will learn about the history of this neighborhood and visit historical buildings and art exhibitions.

Day 3: Windward Coast

On day three, it’s time to leave the busy city of Honolulu and head east to the Windward Coast. We advise you to rent a car at this point to make traveling the island easier. Moreover, you will be able to spend as much time as you want at each location that you visit.

The Windward Coast is a short drive out of Honolulu, but it feels like a whole different world. The lifestyle on this side of the island is calmer and there are no skyscrapers blocking your view of the lush scenery and pristine waters.

Your first stop is the Lanikai Pillbox Hike. This isn’t a hike for beginners. The trails can be very steep at some points. However, the views the entire way up are totally worth the exertion.

To cool down afterward, head to Lanikai Beach. This is considered one of the most beautiful and pristine beaches on Oahu. It invites travelers from all over the world.

If you’re looking for something more adventurous, head further north to Kualoa Ranch. There, you will be able to tour the numerous filming locations on the ranch as well as have the chance to go zip lining, riding on an ATV or Jeep, horseback riding or all of the above!

Day 4: North Shore

On your fourth day on Oahu, you will be visiting the quiet countryside of the North Shore. This area of the island is more rugged and less developed. Thus, it is the perfect place to truly relax and get into the aloha spirit. The towns are small and primarily populated with locals and retirees. It’s also the best place to be for surfing.

Your first stop is the Polynesian Cultural Center. Here, you can learn everything about Polynesian cultures by visiting different “villages”. Each village offers daily presentations and activities for guests to take part in.

A go-to in the North Shore is the town of Haleiwa. It’s a historic surfing town where you can truly feel like a local. Here, you can eat all the shrimp your heart desires, try shaved ice and hit the beautiful Waimea Bay beach. If you’re visiting in the summer, you can safely swim, snorkel and fish in these waters.

Day 5: Central Oahu

Day five on Oahu will take place in the central part of the island as you make your way back to Honolulu. Your first stop after you leave the North Shore will be Dole Plantain. There, you can explore the world’s largest maze and learn about Hawaii’s pineapple history. You will be able see pineapples at different stages of growth and visit the numerous gardens that are filled with various tropical fruits and plants.

Next up in Central Oahu is the Pearl Harbor National Memorial. There, you can view the sunken USS Arizona underneath the memorial. Tours and boats are available throughout the day and are free. At the Pearl Harbor Memorial you can learn details about the attack as well as how war affected Hawaii. Oher attractions include the Pacific Aviation Museum and Battleship Missouri Memorial.