The Perfect Day In Waikiki

How to get the most out of 24 hours in this beautiful beach area. Almost all visitors to the Hawaiian Islands will arrive via Honolulu. This short itinerary is designed for you to get the most out of a single day in Waikiki for the perfect layover, or as part of a larger vacation. You shouldn’t miss the natural beauty and great culture this city and island has to offer.

Departing from the West coast, you will arrive in Honolulu in the middle of the afternoon. This will leave you with enough time to get to your hotel and settle in for a relaxing evening, sunset, and some nightlife before retiring to bed.

The next morning will be an early one. The time difference between Minnesota and Hawaii is four to five hours depending on the time of year with daylight savings time. That means, if your body is used to waking up at 8 AM in Minnesota, it will be 3 or 4 AM in Hawaii. Take advantage of this by staying up late the night before and sleeping in all you want. Eventually, your body will wake you up bright and early (or should I say dark and early). A beautiful sunrise on Diamond Head is waiting for you and so is a great walk through the heart of Waikiki.

I will detail this itinerary and offer you a few essential tips for traveling to Waikiki your first time.

Sunset Swim on Waikiki Beach

Welcome to Waikiki. You just arrived and you step outside to breathe the fresh air and dip your feet in the warm, salty ocean. The sun is already getting low in the sky and you only have a couple of hours of good light left. This is a great time to take advantage of the beach and enjoy a beautiful sunset swim.

There is a beach for everyone in Waikiki. The beaches run most of the way through the entire stretch of Waikiki but are broken up into a couple of different sections. On the furthest point to the northwest is Kahanamoku Beach by the Hilton Hawaiian Village. This particular beach continues to the Fort Derussy Beach Park. Continuing southeast past the Sheraton is Waikiki Beach. Both of these beaches are wide open to the ocean and provide the perfect place to rent a surfboard as the waves gently break over the long shallow bay.

Next down, is Kuhio Beach which has a man-made structure to break the waves. This is a wonderful place for those who are trying to avoid any waves or have small children. These three southwestern facing beaches are spectacular places to sit and watch the sunset over the ocean.

During my own visit, I made a point to get into the water. Some guests rented surfboards and stand up paddle boards and others just sat on the beach. All of us took in the vibrant colors, fresh ocean water, and the beautiful sounds of the waves breaking onto the sandy beaches. Immediately after the sunset, I returned to my hotel for a shower and cleaned up for some nightlife.

Fine Dining, Shopping, and Evening Street Performances

Don’t forget to stay up late and enjoy the evening in Waikiki. Most activity runs parallel to the beach on Kalakaua and Kuhio Avenues. These two streets have no shortage of craziness. Be prepared for everything from karaoke bars and open-air markets to breakdancing in the streets. A few notable places to visit include the International Marketplace and Dukes Market.

International Marketplace is a very high-end shopping mall that integrates open-air spaces and indoor restaurants and shopping. Live performances at night fill these spaces with a fun, musical atmosphere.

Many street corners have professional performers. They are trolling for tips and will interact with you and love to get a crowd dancing. Don’t miss some of the hilarity of watching an average guy trying to spin on his head during a break dance or a magician wow a small crowd.

You can also find a small pop-up market that stays open late into the night. It is a great place to find a souvenir or inexpensive gift for kids at home.

Besides the shopping and entertainment, vacationers will find numerous restaurants spotted throughout the entire city. If you haven’t been to Hawaii before, you may be surprised by the quantity and influence of Japanese culture here. It is easy to seek out excellent sushi and other traditional Japanese food and there are a genuine kindness and respect that flavors the culture here. It is truly a breath of fresh air.

This particular evening I ended up beach-side looking down Waikiki toward tomorrow’s challenge: Diamond Head. After an appetizer, it was time to sleep. It’s been a long day of travel topped off with some entertainment, food, and a sunset swim on the beach. There is more to get rested for tomorrow.

Sunrise Hike On Diamond Head

Diamond Head is a crater that beautifully caps the southeastern end of Waikiki. In the early 1900s, the US Military purchased the land and built the first Hawaiian base. This base, named Fort Ruger took advantage of the sweeping views of the ocean as a lookout to protect Honolulu. Today, the crater is a tourist attraction and state park that enjoys the same views but 100 years later is more of a vantage point for tourists to enjoy sunrises and rainbows than a military base.

Getting To Diamond Head

The park and hiking trail up Diamond Head is very easy to get to. I stayed at the Princess Kaiulani Hotel in the middle of Waikiki and simply walked the 2.8 miles to Diamond Head State Park in the middle of the crater. I recommend the route shown above which starts down Kalakaua in a southeastern direction before angling to the left on Monserrat Ave. This will take you to the north side of the Diamond Head. A small road will take you through a tunnel on the northeastern end of Diamond Head to get to the park itself in the middle. That is where the trail that leads to the rim of the crater begins.

What is unsaid in this description is how early visitors to the island wake up their first morning. We left well before sunrise and enjoyed Waikiki at first light. Then as we continued our walk, took in a majestic sunrise walking along Monserrat Avenue. The day I made this walk, the sun snuck over the ocean as we were just on the north side of Diamond Head crater and the sunrise ended by the time we reached the trailhead.

If that is more walking than you like to do it is easy to find a ride on buses or trollies and start hiking from the park inside the crater.

Diamond Head State Monument

Before hiking the trail there are a few things you need to know. Pedestrians are charged $1 each or $5 for a car full of people to hike. The hike itself is 1.8 miles out and back and gains 452 feet. Plan on spending about an hour and a half to go to the observation deck on top of the crater and back. Also, there are no services on the trail, all bathrooms and drinking fountains are at the trailhead, so plan ahead. If you go later in the day, the last time people are allowed to start hiking is 4:30 PM for a 6:00 PM park close. The trail itself is mostly paved and heavily trafficked. However, parts are uneven and there are some steep ascents up stairs.

Once you start the hike the real adventure begins. The first half mile is very easy and flat. Then the trial suddenly begins a series of switchbacks up the side of the cliffs. A lookout is available to recover from these switchbacks before the first set of 74 steep ascent stairs.

These stairs bring visitors to a 200-foot tunnel that is about six feet tall and about two people wide. Afterward is the second set of 99 stairs that leads hikers closer to the observation. Finally, the path to the tip top splits and visitors can choose more tunnels and stairs into the bunker to the right, or a slightly longer outdoor path to the left.

At the top, try to catch your breath while you enjoy the breathtaking views of Honolulu, Waikiki, and southern side of the island of Oahu.

As you return to the trailhead, there are vendors selling juice, fruit baskets made out of a pineapple bowl, smoothies, and other refreshing foods to help you recover from your hike.

The fresh coconuts were excellent as well as the fresh pineapple juice.

Walking Back From Diamond Head

Before returning back to Waikiki, if you are up for the mileage, hike back out of Diamond Head and continue to the right (southeast) on Diamond Head Road to finish a loop around the whole crater.

During this walk, there are a few notable sites. Along the southern side of Diamond Head, there is a turnout that looks over the Kuilei Cliffs to Diamond Head Beach Park. Inland is a marker for Amelia Earhart in remembrance of her being the first person to fly solo from Hawaii to the mainland in California in 1935. Oceanside visitors can look out at the blue waters of the Diamond Head Beach Park and the many people surfing this popular destination.

Just a bit further west, is the Diamond Head Lighthouse. The lighthouse is gated and not open to visitors, but is easily viewed from the street.

It is hard to get the real atmosphere of this area across in writing. Waikiki is a place of real beauty that has to be experienced to understand. This is the kind of place where people decorate trees by the road and hang leighs on statutes. Part of the experience of Waikiki has to come from simply exploring on foot, and that is exactly what you will get with this walk home.

On the way back toward downtown Waikiki, try to cut through the Leahi Park neighborhood below the summit of Diamond Head. Here you will see a very cute historic neighborhood. The road will eventually merge back into Kalakaua Ave and leads to the heart of Waikiki. From the park inside the Diamond Head Crater around this route, the walk is an additional 4.4 miles back to the hotel. In all, the total walked distance was 9 miles. That’s quite a hike! Consider renting a bike or scooter to make this trip a little faster and easier.

Breakfast In The Park

Before the hike was over though, I refilled my body with a bite to eat at Barefoot Beach Cafe at Queen’s Surf Beach. This restaurant is open air, serving fresh fruit, juice, and breakfast items. It was the perfect way to end this walking adventure.

It is almost time to get ready to head out and end our day in Waikiki. But before we go, there is one last easy stop top make.

Kings Village Shopping Center

Directly across the street from the Princess Kaiulani, is Kings Village Shopping Center. It is a mostly open-air marketplace similar to a farmers market. It is the perfect way to use up the last hour or so before your shuttle to the airport picks you up.

Useful Tips

Waikiki is a very high-end area. Below are a few tips that can help make your stay both affordable and help get you the most out of your time here.

Looking for something other than fancy restaurants and touristy shops? The Food Pantry is a grocery store located on Kuhio Ave and Walina Street. This is definitely the place to go for some reasonably priced food and basic items.

ABC stores are scattered throughout Waikiki. They have a lot of souvenir items, Hawaiian shirts, local coffee, and my wife’s favorite, chocolate covered macadamia nuts. This is a great place to pick up some Kona Coffee or other foods to bring home.

Other Must-Come-Back-For Attractions

The biggest challenge to writing this article is having to pick between the many world-famous activities within Waikiki and O’ahu. I listed a few of these below into two categories. The first is a list of attractions and things to do near Waikiki. The second are things you could do in a day trip by getting on a tour or renting a car.

Vacation Trip Reviews

A Perfect Day in Waikiki

The Perfect Day In Waikiki

Sunset Swim on Waikiki Beach

Fine Dining, Shopping, and Evening Street Performances