Cruise Waikiki Beach for city views and sunsets

Last updated on September 16th, 2023

A Waikiki sunset cruise offers a chance to take a longer, more relaxing look at Honolulu’s iconic beach. Add sunset and a cocktail and you might not care that the fantasy of Waikiki bears little resemblance to reality.

What is it about Waikiki?

Hawaii’s Waikiki Beach is an icon. But it’s an icon that has long had a bad rap, as people come here expecting a type of tropical paradise that only existed in movies and on television. It’s a nice idea though. And, if you look, you can find a bit of that hoped-for magic.

(This is an older picture – there are more skyscrapers now, but you get the idea.)

Waikiki isn’t just one beach

When most tourists think of Waikiki, they probably picture the sandy strips behind the Royal Hawaiian and Moana Surfrider hotels. This is the busiest part of the beach, with the most activities and the most tourists.

But it’s just part of Waikiki Beach.

Waikiki Beach stretches from Fort DeRussy to the base of Diamond Head.

Depending on how you identify them, Waikiki Beach today includes seven or eight distinct beaches. Today these vary from broad flat strips of sand to rocky areas with little or no sand. Most areas also have fairly gentle surf, making it a popular place for visitors to play in the water, surf, or paddle board. However, different parts of the beach attract different types of visitors. And some very pleasant areas attract far fewer visitors than others.

If the Royal Hawaiian isn’t your scene, keep walking until you find a beach you like better!

Waikiki isn’t a natural sand beach

Waikiki’s sandy beaches came into being as the surrounding wetlands were drained and sea walls constructed. Additional sand was hauled in and regularly replenished to retain the sandy beaches along Waikiki.

Despite adding tons of sand to the beaches over the decades, aging sea walls and other infrastructure, higher than usual tides, and rising sea levels have taken their toll in recent years. The beach today is not nearly as “perfect” as it was in the 1950s.

The continual loss of sand isn’t a problem that will ever go away. Even if plans to rejuvenate the beach with fresh sand and build structures to better hold it in place are carried out, over time the sea will carry that sand away again.

But even if the beach isn’t as grand as it was a half century ago, it’s still a nice beach.

Under sail along Waikiki Beach

A variety of cruises offer visitors a chance to leave the shores of Waikiki Beach and get out on the water.

Whether you opt for a snorkeling excursion, a sunset cruise, or a sunset booze cruise, getting out on the water provides a different perspective on Waikiki.

You probably won’t come away thinking Waikiki is the most beautiful place you’ve ever been. (Although it does have a weird, slightly surreal beauty all its own.) But from the water you will get a good overview of what happens when a beautiful place draws millions of people to work and play along its shores. And later, while you relax on the beach, eat in a beachside restaurant, shop in a Waikiki boutique, or (if you are lucky) look out over the beach from your hotel room; you’ll better appreciate both the complexity and magic of Waikiki Beach.

Honolulu is a big city

From the water you can really see just how heavily developed Honolulu is. There are more than a half million people living in the city itself and that many again beyond the city boundary. And pretty much every one of those people would like a view of the sea from their living room. No wonder homes blanket the hillsides and towers rise up all along the shore!

Waikiki isn’t that much different from the rest of the city these days. Much of the beachfront – including the most popular parts of Waikiki Beach – is lined with massive hotels and residential towers.

(This photo shows Waikiki between the Royal Hawaiian Hotel and the edge of Kapiolani Regional Park.)

Looking closer, grand historic hotels like the Moana Surfrider and the famously pink Royal Hawaiian are tiny compared to the newer hotels (including the Royal Hawaiian’s own expansion) that have sprung up all around them.

But there are sections, like the beach at Kapiolani Park, where Waikiki looks a lot more like the tropical dream beach people expect to find at Waikiki!

There are a few more big condo developments as you move past Waikiki Beach toward Diamond Head. However, there is also something unexpected along this section of the shore: a small historic residential neighborhood that maintains a toehold along the beach.

(For a change of pace when you are back on land, take a walk through this tiny neighborhood where charming bungalows line the streets.)

From the water I love the way this break in the development creates a window with a view of the hills beyond. Imagine what Waikiki looked like before high rise towers blocked the view to the mountains!

Of course, Kapiolani Park isn’t the only spot in Honolulu that has escaped development.

Beyond Waikiki, Diamond Head rises up from an area that is only lightly developed.

Sunset

The cruise I am on is a sunset cruise, so all of this looking at Diamond Head and the development along the shore is really just a way to fill time before the main event.

And we aren’t the only ones out here. Lovers of watercraft can watch boats of various shapes and sizes as they maneuver back and forth while waiting for the sun to set.

Of course, as the sun drops closer to the horizon, everyone’s attention shifts to its agonizingly slow and yet surprisingly swift movement.

And then the sun sinks into low-lying clouds and vanishes for the day.

What to expect on a Waikiki sunset cruise

If, like me, you don’t have access to a private boat while visiting Waikiki, there are a number of companies that run daily cruises.

Most tour companies use catamarans of some type, and some leave right from Waikiki Beach. There are snorkeling and wildlife watching cruises, sunset cruises, and party cruises. A few larger enclosed boats offer evening dinner cruises. Just walk along Waikiki Beach to get an idea of what is available.

All sunset cruises start about an hour or more before sunset. They begin with a sail (more likely a motor sail) along Waikiki and out toward Diamond Head. These generally aren’t tours where someone will tell you about the places you are passing. (On the sunset cruise I took our captain answered questions and told stories about pretty much anything that caught our eye.) As it gets closer to the sunset, the boats all seem to move closer to their starting point (in our case, the center of Waikiki Beach) and sort of hang out there until the sun actually sets. Once the sun is down, most of the boats make a bee line back to shore to drop everyone off.

Prices for sunset cruises vary, from about $25 for the cruise I took to more than $50 for similar cruises on other boats. ($35 seems to be the price most often quoted.) All cruises seem to have alcohol available, a few offer snacks. A full dinner cruise costs much more, with most going for well over $100 per person.

Are you looking for a Waikiki sunset cruise or a booze cruise?

If you want to enjoy a drink while viewing the sunset from a boat, you could be headed for a booze cruise.

In Waikiki, sunset cruises have a (perhaps undeserved) reputation for being particularly drunken affairs.

While that might sound attractive to some people, an hour or two on the water with a bunch of drunks isn’t exactly what I’m looking for at any time of day. Sure, I’d like a drink or two while contemplating the scenery and waiting for the sun to set, but I’m not looking for a drunken party. If you aren’t that fussy, a number of boats pull up on the beach and take passengers as they come. You can just wander along the beach until you find one that offers you a good price. However, I had to do some research before I booked anything.

Choosing my cruise

In an attempt to find a boat that would provide a relaxing sunset cruise with a minimal amount of booze cruise partying, I ruled out all boats that offer an open bar. I also scratched those where a majority of online reviews feature the words “party” and “drinking.”

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In the end I went  with Kepoilaki II, a big catamaran designed specifically for various tours around Waikiki.

I choose Kepoilaki II because:

• Drinks were available for $2 each (cheap, but not free)
• It did NOT come up at the top under a search for “best Waikiki booze cruise”
• It had good reviews that generally didn’t include the word “party”
• The boat holds a maximum of 37 passengers (fewer than some others)
• At $25 per person it was among the least expensive options

My experience with the Kepoilaki II

Since the Kepoilaki II boards right behind the Royal Hawaiian Hotel on Waikiki Beach, it would have been easy to find even without a signature blue and white sail unfurled.

Limited seating

We weren’t sure how long it would take us to get there, so ended up being pretty early. That was a good thing, since most of the space for passengers is on the trampoline in front. As it was a windy evening and cooling off, I didn’t have any interest in sitting where we would get wet. That left a limited amount of seating in the cockpit. Because we were so early, we were able to snag one a spot on a bench in the cockpit. Most people ended up perched up on the top of the boat to avoid getting sprayed.

Passenger mix

The other passengers on our cruise were a bit of a mix. There were a couple other Gen X/Baby Boomers and one family with a couple of grade school kids, but most of the passengers were under the age of 30. Some were local college students and their friends. A couple of young women were obviously intoxicated when they boarded, but they seemed to be the only ones and they had friends keeping an eye on them.

Booze

As anticipated, there was a $2 charge for a beer or Mai Tai. At those prices the cruise isn’t really making any money from the drinks, so they weren’t pushing them at all. The drinks were there if you wanted them and at some point during the cruise they hoped you’d pay for them. It was exactly the right attitude and one that was very unlikely to encourage over-consumption.

However, it turned out that you also could bring whatever beverages you wanted on board with you. (It appears this is the practice on most boats.) While this was pretty much limited to a few beers and some half-consumed cocktails on our cruise, it seems like the sort of thing that could get out of control pretty easily.

General notes

The cruise itself was pleasant, if a bit crowded.

• We did the standard sail out toward Diamond Head and then come back and cruise around waiting for the sun to set.
• The captain seemed very competent. He was also really quiet, although he seemed perfectly happy to answer our questions.
• The crew was very outgoing and friendly.
• The Mai Tais were strong enough, but no one behaved too badly or got sick.
• There was music, but nothing really loud or obnoxious.
• We headed back to shore immediately after sunset.

All in all, it was almost a little boring.

I see why most of these operations open the bar and blast the music: Once you’ve made the loop toward Diamond Head and back, there just isn’t a lot going on until the sun actually sets.

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Tips for ensuring a relaxing sunset cruise

Who you sail with is the single most important factor determining whether you end up on a booze cruise or a quiet sunset sail. It’s mostly just a matter of luck. However, boats that describe their trip as a party and offer a free bar are more likely to attract people who a looking for a fun, cheap, place to drink.

But there are things you can do to increase your odds of having a pleasant experience:

• Read online reviews before you choose a boat because each captain and crew brings some of their own personality to the cruise.
• Look for a cruise that doesn’t offer an open bar.
• Look for pictures of the boat to get a sense of what the seating options are.
• Don’t worry about the length of the cruise, as all sunset cruises will have you on the water at sunset and an hour is plenty of time to admire Waikiki and Diamond Head.
• Know where to meet your boat AND (if you aren’t already on Waikiki) where to park your car because Honolulu traffic and parking is horrible and boats generally don’t wait for latecomers.
• Arrive early if you want a spot on the boat that is both comfortable and dry.
• Realize that boats leaving from the beach (rather than a dock) require passengers to wade out to the boat and climb a ladder that is bobbing in the surf.
• Go ahead and have a few drinks, but remember that you are on a moving boat where sure footing and not getting sick are both particularly important and harder to maintain.
• Bring a snack to eat on the cruise and go out for dinner afterward.
• If you have the option, bring a few friends because everything is better when shared with friends.

Most of all, remember that you are on vacation in paradise, so chill and try to ignore any bad behavior you might encounter!