Epic Waikiki Exploration Roars From Hawaii’s #1 Mountain to #1 Beach

Here are two of the most memorable Waikiki adventures that we never grow tired of. We aren’t alone in our take. TripAdvisor readers also rate these as among their top picks in Hawaii.

If you’re not keen on a surf lesson but still want an authentic Hawaii water adventure, we can recommend looking no further than a Waikiki outrigger canoe experience. These offer a guaranteed unique and exhilarating time that some have called the original Hawaii roller coaster ride. And you find these at none other than Hawaii’s iconic but disappearing Waikiki Beach.

Outrigger canoes are known for their safety.

Because of that, they are one of just a small number of ocean vessels the US Coast Guard exempts from requiring life jackets. Participants can be as young as 5 years old, and all skill levels are welcome. This is an ideal Hawaii family event as you enjoy a thrilling surf adventure on an outrigger canoe.

On your next Hawaii vacation, head down to Waikiki Beach for something we’re sure you’ll never forget. The companies provide reservations online, and you must generally have at least 3 people going out with you to book, although most will help you find others as needed. Do an online search, as there are multiple vendors, and prices vary, starting at under $50.

Outrigger canoes accommodate a number of passengers, typically along with two crew. Guests are provided seat assignments, and each is given something to do based on ability and size. Comprehensive instructions on boarding and disembarking the boat, as well as proper paddling techniques, are provided prior to getting started. Have no fear; you’ll be in good hands here.

As you experience an exhilarating paddle, the canoe will be optimally positioned by the crew to catch the waves heading back to shore. The duration of a canoe ride typically ranges from 20 to 40 minutes, depending on ocean conditions.

Be prepared to see lots of marine life on board, including fish, turtles, dolphins, and more.

Honestly, just writing about it makes us want to do this again. At the beginning, you receive paddling instructions from your guide. Then, the teamwork starts, and everyone participates. You’ll move the outrigger to shallow water and take turns climbing in. It’s not a graceful movement that adds to the fun.

As you paddle away from the Waikiki shore, you’ll eye Diamond Head as your next adventure destination. The waves suddenly take on a larger dimension close up as you become part of the ocean and its movement.

Did you know? Outrigger positioning. When on dry land, it’s traditional for the canoe’s nose to point towards the water. This is the Hawaiian way and shows respect for both the outrigger and its spirit.

The steersman (captain onboard) sits at the back of the outrigger to help position the canoe and wait for the best waves. When he calls, you’ll paddle with all of your ability as you catch the wave and experience the exhilaration. This is why it is analogized with board surfing. At that moment when the wave’s energy moves you, it lifts the outrigger towards the sky. Paddle on! Everyone onboard will share in the sheer adrenaline as you glide effortlessly across the ocean’s surface. Be prepared for fun and for the unexpected.

As you start to slow down, returning finally to the shore, you’ll again see Diamond Head, which could well be your next adventure, begging to be hiked. It’s just a short drive by car or via The Bus and is one of Honolulu’s other top-rated attractions.

The hike – Diamond head volcano will always be epic Honolulu.

If you’re up for navigating stairs, an uneven trail, and a moderately steep climb, we strongly recommend adding this activity to your next Honolulu itinerary. Just keep in mind that advance reservations are required.

This, too, promises to deliver an unforgettable experience. Plan for about 90 minutes, allowing time to admire the breathtaking views from the lookout points atop the 300,000-year-old crater. Check out the latest updates and our tips below to ensure you make the most of your visit.

Diamond Head is a significant feature of the Koolau Volcano and the home of the renowned trail to the summit. This round-trip adventure covers 1.6 miles, including a 560-foot elevation gain leading to the breathtaking lookout point at the summit. From this vantage, you’re promised unparalleled views of Waikiki Beach and Honolulu, the vast expanse of the Pacific Ocean, and sometimes during season, sightings of Hawaii’s humpback whales. The trail was originally constructed in 1908 as part of Oahu’s coastal defense system and is now a living testament to the natural wonder and its historical significance.

Make Diamond Head reservations starting 30 days in advance.

Entry fee (non-resident): $5 per person. Parking fee (non-resident): $10 per vehicle. Non-residents must purchase both advance entrance and parking unless arriving on foot (in which case there’s no parking fee, but the advance entrance fee requirement stands). Children 3 and under are free. Payment is by credit card only.

Parking and entry for Hawaii residents are free with proper ID.

When to Visit Diamond Head. Make reservations for early in the day or later in the afternoon when it isn’t as hot. If you hike without the sun directly on the largely exposed trail, you’ll be much happier. The monument is open from 6 a.m. to 6 p.m. daily, with the last entry at 4 p.m. Hours are strictly enforced. The monument is closed on Christmas and New Year’s days.

What to Wear. Bring sunscreen and a hat, and wear closed-toe shoes with your athletic wear. Leave flip-flops or high heels in your car.

Packing List. Obviously, your phone for capturing fantastic views. Bring water to keep hydrated or purchase at the visitor booth before you hike. Also, bring a change of shirt for when you return – you’ll surely be sweaty.

Fitness Level. The hike starts moderately on a deceiving paved trail before reaching gravel. It is within the reach of most fitness levels. Even should you decide to hike only partway, there will be views to enjoy and to photograph.

Trail Guide. After the tunnel you enter near the top, there are two options for reaching the summit. The easiest one is accessed by turning left along the outside trail. Those seeking more adventure should turn right to access the top via 99 steps leading to the bunker, followed by the 43-step spiral staircase, plus the crawl-out along a narrow opening near the top.

History of Diamond Head. Le`ahi is considered a sacred ground to Native Hawaiians. In the 1700s, Western explorers gave the crater the “Diamond Head” name. In the early 1900s, the U.S. government designed it for military use as Le’ahi and the heiau had gun emplacements within the slopes.

Do you remember the old Diamond Head Hike?

BOH editors have hiked Diamond Head for decades. Back in the day, the parking was free, albeit sometimes hard to find, and hawkers lined the path to the start of the trail. We still remember bringing a flashlight, which was once needed to navigate dark tunnels and bunkers. Now those tunnels are lit.