South Shore Open Sail from Kewalo Harbor Including Drinks

The best part of this South Shore open sail is the view: you leave Kewalo Harbor, cruise past Honolulu, and keep Diamond Head in sight as Waikiki opens ahead. With about 90 minutes on the water, it gives you a real taste of sailing without taking up half your day.

I like two things here. Drinks are included, from mai tais and other cocktails to cold beer, and the roomy catamaran gives you space to move around rather than trapping you in one seat. The crew also helps with photos and drink refills, which keeps the outing easy and social. The main consideration is that this is a shared sailing with as many as 49 people, so it is not a private or silent cruise.

Key points at a glance

• Diamond Head stays in view: The route from Kakaʻako toward Waikiki offers a clear visual thread, with Honolulu and the famous volcanic crater framing the ride.
• Included drinks add real value: Mai tais, other cocktails, and beer are part of the experience, not an extra purchase once you are aboard.
• A roomy Na Hoku II catamaran: You can move around the boat, change your view, and find a comfortable spot during the sail.
• A short 90-minute outing: The timing works well before dinner, after a morning on Oahu, or between other Honolulu plans.
• A social crew-led experience: Allison, Dave, Caleb, and Captain Dan have been named as crew members on different sailings, with help offered for photos and drink top-ups.
• Possible whale sightings: Whales have been seen during a sailing, but wildlife is never guaranteed.

Leaving Kewalo Harbor for the South Shore

Your meeting point is Na Hoku 2 Catamaran at 1025 Ala Moana Boulevard, Honolulu. This is at Kewalo Harbor, close to the Ala Moana and Kakaʻako area. The activity begins and ends at the same place, which makes planning simpler than a cruise that drops you somewhere else along the coast.

The route heads from Kakaʻako toward Waikiki. That direction matters because you get more than a generic ride offshore. The city remains part of the view, while Diamond Head provides a strong focal point as the catamaran works along the South Shore.

I like this kind of route for a first or final day in Honolulu. It gives you a fresh look at places you may already have seen from land. Waikiki appears differently from the water, with the beach district, hotels, and mountains arranged in one broad view.

The boat returns to the same harbor after roughly an hour and a half. You are not signing up for a full-day ocean trip, so the experience can fit around sightseeing, shopping, or an evening meal. At the same time, 90 minutes is long enough to settle into the rhythm of the boat instead of simply taking a quick harbor spin.

What the Na Hoku II offers on the water

The Na Hoku II is described as a large, roomy catamaran with plenty of space to move around. That is useful on a short open sail because the best view changes as the boat moves. You might want one side for Diamond Head, another for the city, and a different spot when the boat is under sail.

A catamaran also gives the outing a more relaxed feel than a narrow single-hull boat. You can shift position without feeling as if you are in the way. The boat is still shared, though, and the maximum group size is 49 people. If you want a quiet private sunset or a personal sailing lesson, this is the wrong format. If you want a friendly boat ride with room to circulate, the size works well.

Music and the general mood are part of the appeal. The experience is built around an easygoing social atmosphere rather than formal narration or a detailed lesson about sailing. You should expect time to look around, take pictures, talk with the crew, and enjoy a drink while the boat moves along the coast.

That balance suits people who want to be on the ocean without needing a packed schedule. You are not being rushed from one activity to the next. The boat ride itself is the point.

Included mai tais, cocktails, and cold beer

The drink package is one of the clearest reasons this sailing offers good value at $47.50 per person. Included options feature mai tais, other cocktails, and beer. The crew handles drink top-ups during the trip, so you can spend less time thinking about a bar tab and more time watching the coast.

I would still keep expectations in proportion. This is a 90-minute sailing, not an unlimited all-day party cruise. The value comes from combining the boat ride, the views, and included drinks at a moderate price. If you already planned to buy one or two drinks during an afternoon out, this package can make financial sense.

The drinks also shape the tone. This is more suited to adults looking for a relaxed social outing than to someone seeking a quiet nature cruise. The boat welcomes a mix of people, and the crew appears to focus on making everyone comfortable. You can enjoy a mai tai, choose beer instead, or simply concentrate on the scenery.

Alcohol is not the only reason to book, though. If the drinks disappeared, the Diamond Head views and roomy boat would still give the trip a purpose. Treat the included beverages as a useful extra rather than the whole attraction.

Diamond Head, Waikiki, and the changing views

The route’s main visual reward is the sight of Diamond Head from the ocean. From shore, the crater can feel like a backdrop. From the water, it helps you understand how Waikiki sits along the coast and how the volcanic terrain shapes Honolulu’s setting.

The sail from Kakaʻako toward Waikiki keeps the city in view. You can take photographs with Honolulu behind you, then turn toward Diamond Head as the boat changes position. The crew can help with photos, a small but worthwhile service when you are traveling with friends or celebrating a birthday.

Weather will affect the quality of the views. On a clear day, you can expect the strongest contrast between the blue water, city shoreline, and mountain profile. Cloud cover or rough conditions can change the mood and visibility. The operator requires good weather and may cancel if conditions are poor, offering a new date or a full refund.

Wildlife sightings are possible but not promised. Whales have been seen during a sailing, which is a wonderful bonus during the right season, but you should book this for the catamaran ride and coastal views, not as a dedicated whale-watching trip.

A crew that keeps the ride easy

The crew’s role is practical. They serve drinks, help with photographs, and keep an eye on what people need. Allison, Dave, Caleb, and Captain Dan have been named in connection with different sailings, but crew assignments can change.

That personal attention makes a difference on a short boat ride. You do not need a long safety briefing followed by an hour of figuring everything out alone. The crew helps create the relaxed mood, answers basic questions, and keeps the service moving.

The experience does not appear to depend on a formal guide giving a long historical talk. If you want a detailed account of Hawaiian geology, local history, or navigation, you may need a separate tour. Here, the crew’s strength is hospitality and keeping the boat ride comfortable.

I especially like the photo help. A shared boat outing often leaves one person out of every group picture. Having the crew take a photo lets you capture the whole group with Diamond Head or Honolulu behind you.

Is $47.50 a fair price?

At $47.50 per person, this is a solid midrange price for a 90-minute Honolulu boat experience with drinks included. The cost is easier to justify if you plan to have cocktails or beer anyway. You are paying for the boat, crew, coastal views, and beverages in one simple price.

The value is less convincing for someone who does not drink and mainly wants a quiet sail. In that case, you are still getting the catamaran and scenery, but part of the package has little use. You should also remember that the activity is shared, so the price does not buy privacy.

The maximum capacity is 49 people, yet the boat is roomy enough to move around. That combination is worth noting. You may have a lively onboard atmosphere, but you are not necessarily stuck shoulder to shoulder in one fixed position.

A current 5 out of 5 rating from 21 reviews, with all recommending the experience, supports the idea that the basic formula is working well. Still, I would judge the purchase by your priorities: included drinks, an easy social mood, and a strong Honolulu view.

Who will enjoy this open sail most?

This is a good fit for couples, friends, birthday groups, and solo visitors who like meeting people during a casual outing. One sailing included a birthday celebration, and the crew helped make it feel special without turning the trip into a formal event.

It also works well for someone who wants a taste of sailing but does not want to spend several hours offshore. The 90-minute length keeps the commitment manageable. You can enjoy the coast, have a drink, and return to Kewalo Harbor with most of your day intact.

The outing is also practical for people staying near Waikiki, Ala Moana, or Kakaʻako, since the meeting point is on Ala Moana Boulevard and close to public transportation. You still need to allow time to reach the harbor, but the activity does not require a separate one-way transfer afterward.

Most people can participate, and service animals are allowed. The available information does not describe specific accessibility features aboard the catamaran, so anyone needing detailed mobility accommodations should confirm those arrangements before booking.

What to know before you book

The experience is offered in English and includes a mobile ticket. Confirmation arrives at booking, which makes it easy to keep the details on your phone.

Bring your attention to the weather forecast. The sailing depends on suitable conditions, and poor weather can lead to a new date or a full refund. The same options apply if the minimum number of people is not reached.

For a full refund, cancel at least 24 hours before the start time. Changes or cancellations inside that 24-hour window are not accepted for a refund. Cutoff times follow local Honolulu time, so check the exact start time before making changes.

The boat returns to the starting point, which is helpful if you have dinner or another activity planned afterward. I would avoid scheduling something too tightly, however. Boat operations and harbor timing can vary, and a little breathing room makes the day more pleasant.

Should you book the Na Hoku II?

Book this South Shore open sail if you want Diamond Head views, included drinks, and an easy 90-minute outing without committing to a full-day cruise. The roomy catamaran, helpful crew, photo assistance, and return to Kewalo Harbor make it a practical choice for a relaxed Honolulu afternoon.

Think twice if you want privacy, a quiet sailing lesson, or a detailed guided tour. This is a shared, social experience with up to 49 people, and its strength is the simple pleasure of being on the water with a drink in hand and Waikiki ahead.

For most people who like a friendly boat ride, $47.50 is a fair price. I would book it for the combination of views and convenience, not just for the cocktails. The drinks make the deal better, but Diamond Head from the ocean is the part you will remember.

FAQ

How long is the South Shore open sail?

The sailing lasts approximately 1 hour and 30 minutes.

Where does the boat depart?

The boat departs from Na Hoku 2 Catamaran at 1025 Ala Moana Boulevard, Honolulu, Hawaii 96814.

Where does the activity end?

The activity ends back at the same meeting point at Kewalo Harbor.

What route does the catamaran take?

The boat sails from Kakaʻako toward Waikiki, with views of Honolulu and Diamond Head along the way.

Are drinks included?

Yes. Included drinks feature mai tais, other cocktails, and beer.

How many people can join the sailing?

The experience accepts a maximum of 49 travelers.

Is the tour offered in English?

Yes. The activity is offered in English.

Are service animals allowed?

Yes. Service animals are allowed.

Can I cancel for a full refund?

Yes. You can cancel at least 24 hours before the experience start time for a full refund.

What happens if bad weather cancels the sailing?

If poor weather causes a cancellation, you will be offered a different date or a full refund. The same type of option applies if the minimum number of participants is not met.