Insider tips: Planning a trip to Oahu

As one of Hawaii's most popular islands, Oahu is fittingly called "The Gathering Place." To help you make the most of your time to the Hawaiian paradise, we've enlisted the help of travel expert Jackson from Journey Era. Read below for tips on how to best experience the island.

What should I do on my first trip to Oahu? 

If it's your first time to Oahu there are a few top things you cannot miss. If you are a keen hiker there are lots of epic trails on the island but there's also a short trail everyone should do. Hiking to the top of Diamond Head Crater is just a few kilometers and gives you an incredible view of the entire Waikiki area and the beaches in the south. 

If you are into history, visiting the Pearl Harbor Museum and memorial site is a very important piece of American war history and makes for a good half-day trip. Renting a car or jumping on a guided tour to the North Shore of Oahu to check out the iconic surf town of Haleiwa is a great way to relax while on vacation

What are some hidden gems to see in Oahu?

The Atlantis Submarine tour is an epic adventure where you will climb aboard a 48-passenger submarine and adventure through the underwater passages of the famous Waikiki beach. Through its portal windows, see Hawaiian fish, coral, turtles, sunken ships and airplanes, and more! 

It’s truly an amazing experience to see sunken warships and planes and all of the marine life that is now calling it home. Another unique activity on Oahu is to hike to the top of Koko Crater, which is a demanding and steep hike. The unforgiving incline will have you gasping for breath by the time you reach the top.

How much time should I spend in Oahu?

Most people feel that 7-10 days is a good amount of time to spend on Oahu. This gives you time to book a few tours, rent a car and explore for a few days and unwind with no activities with a few relaxing beach days. 

The time will fly by so any less than a week will feel rushed. Basing in Waikiki or the south is fine and how most people structure their stay. You can drive to all parts of the island within an hour from Waikiki so there's no need to base in multiple locations.

What neighborhood should I stay in when I visit Oahu?

Waikiki is the hub of Oahu. Let’s start with Waikiki because it is the most popular place to stay in Oahu. The majority of the hotels are on this famous strip of beach. There are hundreds of restaurants, cafes, tour centers, transport options, and convenience stores. It has a great little surf break perfect for beginners. The water is warm, the cocktails are flowing and it is an all-around beach vibe.

For families: Waikiki is the number one choice for families. They are centrally located for all of the tours to different spots around the island. Kids have protected beaches to swim in without worrying about waves. There are several man-made reef breaks, which act as saltwater swimming pools. For mom and dad, there are plenty of nightspots and relaxed bars throughout Waikiki. It is a safe neighborhood and it is also a shopping heaven with lots of high-end retailers.

For couples: Honeymooners and couples have found the perfect getaway spot in Waikiki. Think of dining out and nice restaurants each night after a day of adventures each day. It is the perfect base to hit the beaches, adventure the island but still have the luxury of great accommodation, dining, and convenience on your doorstep.

For older travelers: The older adventurers among us love Waikiki for a few reasons. It’s simple. Everything is on your doorstep. The tours pick you up and drop you off at your hotel lobby. There are quality restaurants in all directions and the famous Waikiki Beach is within walking distance. You are never far from a refreshing dip in your hotel pool, the ocean, or an air-conditioner.

What is the best way to get around Oahu? 

If you are booking several tours you may not want to rent a car. However, if you like to explore yourself, it is best to hire a car, which costs about $60-100 per day. This way you can visit the east, north and west coast at your leisure. Within Waikiki, you can use the local bus service or Uber to get around as it is quite a small area. Within Waikiki, you can walk from most hotels to the beach so there is no real need for transport services if you are just enjoying beach days.

What are the best months to visit Oahu?

Oahu is a great place to visit all year round due to its tropical, temperate climate. However, in the winter the big surf in the north of the island can be a huge attraction and there are a number of big-wave surfing events. The summer months of May, June, and July are very popular due to the warm, consistent weather making it perfect for tanning on the beach and sipping cocktails

What are the best neighborhoods for shopping?

Waikiki is the luxury shopping center of the island. You can find lots of upmarket stores in the strip, which is fun to walk up and down at night. Rolex, Gucci, and other high-end stores can be found in this area but there are also lots of regular stores like H&M and souvenir stores to find some Hawaiian-style gifts for your family and friends.