It might seem odd to some that being Florida residents, our family’s beloved vacation spot is Hawaii. After all, we’ve lived where other people vacation and retire –  just two hours from the Gulf and Atlantic coastlines. Why would we fly thousands of miles just to gather at the beach again?

The allure of Hawaii lies in the fact that its waters are far bluer, its breeze much cooler, and its mountain backdrops far more dramatic than the flat, swampy marshlands of my humid home state.

Plus, the beach is just one part of it. Oahu, home to the state capital of Honolulu, and also the most developed, populated and visited of the Hawaiian islands, offers numerous things to do, from historic and cultural attractions, to relaxed activities or adventurous excursions, as well as modern, urban hot spots and experiences. Truly, Oahu, known as the “Gathering Place” of the Hawaiian Islands, has served as our family’s gathering place for decades – for honeymoons, anniversaries, Thanksgiving reunions and summer holidays. We’ve developed certain traditions, or activities in which we engage and sites we visit time and again. Here’s what we have found to be the best times, places and ways to gather to make lasting memories during family-friendly retreats in Oahu.

When & Where We Gather 

Some of our favorite activities are pursued at certain times of day. 

Hiking Diamond Head at Sunrise 

We wake up early to catch the sunrise from the island’s iconic Diamond Head crater, a dormant cone volcano formed from a single eruption that took place about 200,000 to 300,000 years ago. Its Hawaiian name, Lēʻahi, comes from its resemblance to the dorsal fin of a tuna, but its English name originates from British settlers mistaking calcite crystals on its adjacent beach for diamonds, according to the Hawaii Tourism Authority.

We typically get to the state park around 6 a.m. just as it opens. Driving from Waikiki to Diamond Head, I like to watch the slate-stained waters gradually take on brighter hues as the sun emerges. Upon arrival, the parking lot usually fills up with cyclists, trekkers, and joggers, who find this an ideal place to get in their morning exercise. It’s a 1.5-mile roundtrip up to the crater’s summit and back (feasible for children and older adults if you ask me), and the view from the top should not be missed.

Along the trail, the walls of the dormant crater glow as the sun rises and vaults shadows at different angles over the crater’s blonde ridges.

When you reach the “pillbox” at the top, you’ll get a sweeping view of the Waikiki coastline and the Diamond Head lighthouse. 

To help protect the marine life, visitors are required to watch a video on marine life conservation (reservations can be booked online in advance) before entering the park, which is also closed on Mondays and Tuesdays to allow the marine life two days a week of undisturbed rest. 

If you are unable to make it inside the park for snorkeling, you can still get a view of the bay from the top just before the park closes and as people are leaving for the day. 

Caveat: The couple of times that I actually went snorkeling in the bay, it was after I had lived in Guam for two years and had experienced snorkeling in Guam, Rota, and Fiji. In comparison, in Hanauma Bay, I noticed that much of the corals’ color had faded and had suffered bleaching over the years, but the swarms of marine life still make the park worth the visit. More recently, the shelter-in-place measures of 2020 due to the COVID-19 pandemic have allowed the coral’s condition to improve. 

Resorting Along Waikiki at Sunset

The hotels along Waikiki beach consistently offer great sunset views and are a fun spot to grab a beachside bite or cocktail. Our favorite spots along Waikiki are hotels with history: The Sheraton Princess Kauilani built on the royal estate of Hawaii’s last heir apparent, the Westin Moana, Waikiki’s oldest hotel and listed on the National Register of Historic Places, or the Royal Hawaiian, known as the “Pink Palace of the Pacific” for its rosy stucco design. Check out the Princess Kauilani about two hours before sunset, for the history, but head across the street an hour before sunset to the Royal Hawaiian or Moana for sunset views.  The Moana is where we typically spend a late afternoon at the Beach Bar, where we religiously order a basket of onion rings, mocktails, and listen to the lilting tunes of live music. From here, you have direct access to the beach, just feet away, or you can relax on one of the rocking chairs available on the verandas of the hotel. 

Another option is to take a sunset sail from Kewalo Basin Harbor, as my husband and I did one year with Hawaii Nautical. It was an overcast day when we sailed, but still, the scenes of swimmers, surfers and sailboats against the Waikiki coastline and Diamond Head backdrop made this picturesque. 

Shopping & Sipping Along Kalakaua Avenue at Night

Across from the Moana Surfrider is the International Market Place, what used to be a bargain-hunter’s paradise, but has now transformed into an upscale open-air shopping complex. The International Marketplace once consisted of a series of kiosks woven around a grove of banyans, where vendors would sell gift items like jewelry, clothing, wood carvings, hand-dipped candles, and more. The marketplace then changed form into the modern luxury complex along Kalakaua Avenue that it is today, with the kiosk vendors shifting to the side alley along the Prince Kuhio shopping plaza.

From there, you can keep the shopping and beach vibes going with an evening visit to the Tommy Bahama Rooftop Bar off of Kalakaua, where we’ve sipped on Mai Tais before heading to dinner on the grounds of the Hilton Hawaiian Village. 

The Hilton Hawaiian Village is one of the most famous resorts along the Waikiki strip, and you might even recognize its lobby and grounds from their appearance in several Hollywood movies. On some evenings, the resort hosts live cultural shows with Tahitian and Hawaiian dancers wielding knives and fire, or the tunes of local artists. On Friday nights throughout the year, you can view fireworks starting at 7:45 p.m.

Since this is where my family usually stays, we cook meals in our condo at the Lagoon Tower or Grand Waikikian, but when we do dine out, it’s takeout from Roundtable Pizza (if you’re health conscious – no sweat, their salads are filled with tons of veggies) dine-in at the fancier Fresco, or a casual oceanside dinner at Tropics Bar & Grill where we get nachos, or a salad and pasta. We finish off with something sweet at the local Lappert’s Ice Cream (which is also a good place to grab coffee in the morning). Most of these are located in the resort’s Rainbow Bazaar where you can shop for gifts before or after dinner as well. 

Taking a Scenic Drive 

We set apart roughly a full day for a scenic drive along the island’s southeastern beaches following Route 72 from Hanauma Bay and heading north. The first stop is the Halona Blowhole Lookout. The blowhole is created by a rock formation — old lava tunnels — through which sea water rapidly shoots out as high as 30 feet when waves crash against the rock and force water through the tunnels, resembling the plume from surfacing whales. Anticipating the next foamy sea spray to shoot up from the porous charcoal bed can be an exciting experience for little ones, as it was for me as a child.

From there, we head to Sandy Beach, where winds are ideal to fly a kite. Continue onward to Makapuu Point for a view of “Rabbit” Island.

With all the natural beauty ensconced in each crevice of the island, it can be easy to forget that the island is home to a thriving commercial hub.

To truly appreciate the metropolis that Honolulu is, you have to get to a good vantage point. Tantalus Point offer just that, with panoramic views of the city. While any time of day is worth the visit, it’s particularly scenic to catch this view as the sun sets and city’s nightlife sparks.

Meditating at the Byodo-In Temple

To get away from the city lights, head to the tranquil Valley of the Temples.  Tucked into the base of the Ko’olau Mountains, the temple grounds provide a calm respite from the city buzz and throngs of Waikiki. The serenity found here matches that of the shrines in Japan. In fact, this particular temple is a replica of one in Uji, Japan, and these temple grounds have been dedicated to the first Japanese immigrants to Hawaii. 

The Buddha enshrined within the temple is coated in gold leaf and represents infinite life. For us, visiting a Buddhist temple is like visiting one of our own temples, as some Hindus consider Buddha to be an incarnation of Vishnu, and Gautama Buddha, was born a Hindu. 

Taking Picnics at Kualoa Regional Park

Against the pleated ridges of the Ko’olau Mountain Range that resemble a sari on one side, and peaking tip of China Man’s Hat from the sea on the other, Kualoa Regional Park offers a picturesque place to picnic. We pack a taste of South India with tiffin favorites such as puliodhare, or tamarind rice, curd rice, pickle, and green beans thoran. Hawaiian accompaniments include Maui style potato chips and guava nectar, or crunchy macadamia nut snacks picked up from one of the farms along the way. 

Memorializing the Fallen

One should not miss a visit to Pearl Harbor & Arizona Memorial, the infamous site of the 1941 Japanese bombings of the U.S. naval base. However, it is better visited during a longer stay so you can pay it the respect it deserves. Everywhere else on the island, the sea breeze and sight of frothy sea waves is calming. But here at the naval base, this imagery conjures the memory of the 2,403 U.S. personnel killed during the surprise military attack by the Japanese Imperial Navy during World War II, and the submerged USS Arizona battleship that lies at the bottom of the bay with the remains of its crew onboard. 

The war exhibits, memorabilia, and tours available here are well worth the visit, but it can take a sizable portion of the day to do it full justice. 

Celebrating Pacific Island Cultures

Another full day can be spent at the Polynesian Cultural Center, a kind of a theme park located on Hawaii’s North Shore. For some, the center may feel a bit touristy, which is why I’ve listed it for longer visits, but our family has enjoyed experiencing the Pacific Island cultural showcase, not to mention, the center’s business model is interesting. Opened in the sixties as a way to provide the students of the neighboring Brigham Young University Hawaii a way to pay for their college tuition, it also provides a platform to support traditions of island cultures – from Aotearea to Samoa. Those employed at the PCC get Tuition Assistance to pay for their university studies and earn their degree. Students report the ability to graduate debt free thanks to the non-profit providing a means to support their education. 

Shopping Til We Drop

Avoiding Other Gatherings

Due to our personal preferences, there are still a few key activities I’ve never done in Oahu, but that I would suggest to others who may be interested or visiting for their first time: 

• Attending a Luau – This is a pit-fire pig roast, and for obvious reasons, our Hindu, vegetarian family has avoided these events, but they are a common around the island and part of the local culture.
• Taking Surf lessons – If there’s anywhere to learn to surf, it’s along Waikiki. The waves and winds are ideal. 
• Hiking the Haiku Stairs, also known as the “Stairway to Heaven.” I don’t know how people do this but I believe there is a roughly $1000 fine if you get caught by officials. Still, many people do it every year without getting caught. 

Taking Comfort in Tradition 

As I recently exchanged notes with friends about the top sights to see in Hawaii, I realized my family’s itinerary may be different than most. Thanks to Instagram and other social media platforms, remote areas of the island or obscure food spots have become mainstream must-see attractions. However, I don’t foresee our family changing the activities or restaurants visited too much on future trips because we take comfort in the familiarity and nostalgia that it brings. Sure, we occasionally may add a variation of an activity or try a slightly new experience, and at a personal level, I may try hiking more now that I have a partner to do that with on these trips. However, frankly, it’s a relief to not have to put too much emphasis on planning new things when we have grown accustomed to and have loved our routine activities.