Diamond Head views, cocktails, and 90 minutes of chill. On this South Shore open sail from Kewalo Harbor/Kaka’ako area aboard the Na Hoku II Catamaran, I like the combo of included mai tais and beers with the easy, social vibe that keeps things light and fun. The other big win is the route itself, you get coast-and-city scenery on a catamaran with room to move around, from photos to drink top ups.

One thing to keep in mind: this sail runs only when weather cooperates. If conditions are poor, your trip can be moved to a different date or refunded, so plan with a little flexibility.

Key points to know before you go

• Mai tais and beer included, with the crew keeping drinks moving.
• Diamond Head stays in view as you sail from Kaka’ako toward Waikiki.
• Roomy catamaran deck space for stretching out, photos, and passing the time.
• Small enough to feel personal, with a max of 49 people.
• A crew that actively helps, including photo moments and attentive service.
• Good chance of wildlife sightings, with at least one sail noting whales.

Na Hoku II Catamaran: roomy, city-sail energy

This is a city sail that still feels like a real ocean outing. You’re on the Na Hoku II, and the key is that it doesn’t feel cramped. From the moment you step aboard, you have space to shift around, grab a better angle for photos, and just live in vacation mode for the full 1 hour 30 minutes.

The group size matters here. With a maximum of 49 people, it’s large enough to have energy, but small enough that the crew can actually keep an eye on what everyone needs. That blend shows up in the reviews too, where people highlight how welcoming the captain and crew feel, not just how pretty the scenery is.

Also, since this is an open sail, you’ll want to dress like you’re spending time on the water, not like you’re commuting. Think sun protection, a light layer if you get chilled, and shoes you don’t mind getting a bit damp.

Included mai tais and beer: how the drinks feel onboard

The drinks are one of the main reasons to choose this sail. You get included cocktails, including mai tais, plus beers. In plain terms: you don’t have to keep asking what’s available or plan your budget around onboard drinks.

What I’d pay attention to is how the crew handles the flow. Multiple comments call out that the drinks were plentiful and that the crew stayed on top of topping you off. That means less time tracking cups, more time enjoying the ride. It also makes the sail feel like a guided experience rather than a “just board and fend for yourself” situation.

If you’re sensitive to sun, alcohol, or heat, you can still make this work. Pace yourself, drink water when you need it, and treat the mai tai as part of the fun, not the whole plan. The best sails feel easy, and this one is designed to stay that way.

From Kaka’ako toward Waikiki: Diamond Head all the way

The route is the headline. You sail from the Kaka’ako area toward Waikiki, with Diamond Head views running along the way. That matters because it’s not just one pretty moment at the start and then bland scenery for the rest.

Instead, you get a long stretch of coastal views: Honolulu and Waikiki from the water, the skyline feel, and the iconic shape of Diamond Head hanging in your field of view. Even if you’ve seen photos before, it lands differently when you’re actually moving across the ocean in front of the city.

The timing also helps. At about 90 minutes, it’s long enough to settle in, take photos, and enjoy the ride without feeling like a half-day event. If you’re trying to fit this into a busy Oahu plan, this is a solid length.

One extra note from experience reports: someone on a sail mentioned seeing whales. You can’t count on it, but it’s a nice reminder that this route can occasionally line up with wildlife.

Crew energy and photo ops: the human part of the sail

The catamaran experience isn’t only about views. It’s about how you feel standing on the deck, and the crew is a big reason this one gets a near-perfect rating.

Names show up in the feedback, including Allison, Dave, and Caleb. There’s also a mention of Captain Dan. What ties these comments together is the same theme: people felt welcomed and looked after, especially around drinks and photos.

So here’s how I’d use that information if you want the best experience. When you’re out there, take advantage of the crew’s attention. If you want a group photo, ask when you’re settled and the angle looks good. If you want a better shot of Diamond Head or the Waikiki side, don’t wait until everyone forgets. The crew is clearly used to helping people get the right moment.

Music and vibe also come up, with people describing great tunes and an overall chill feel. In practice, that means you can talk with friends without shouting, enjoy the wind, and still feel like something special is happening.

Where you meet: Na Hoku 2 at 1025 Ala Moana Blvd

The meeting point is Na Hoku 2 Catamaran, 1025 Ala Moana Blvd, Honolulu, HI 96814. The tour ends back at the meeting point.

Two practical tips here. First, arrive early enough to park your thoughts and find the boarding area without stress. Second, since it’s near public transportation, you don’t have to rely on a car if that’s not your plan for the day.

You’ll also use a mobile ticket. That’s usually the easiest way to handle entry, so have your phone charged and ready. If you’re with a group, make it simple by having one person manage the ticket on the spot.

Price and value at $47.50: what you’re really buying

At $47.50 per person, this isn’t a budget “just get on a boat” experience. You’re paying for three things at once: time on the water, the scenery package (Kaka’ako to Waikiki with Diamond Head), and the included drinks.

I think that combo is what makes the value feel fair. Ninety minutes of ocean views in front of Honolulu, plus cocktails like mai tais and beer, plus a crew that keeps things moving, is exactly the kind of experience where the onboard extras are the difference between okay and memorable.

It’s also a good price point for birthdays and friend hangouts, since the vibe is social and the deck space makes it easy to be together without being on top of each other. If you want a “Hawaii moment” that’s not complicated, this hits that sweet spot.

Who should book this South Shore open sail?

This sail is a great match if you want:

• A fun, chill time on the water rather than a formal tour with lots of narration.
• A day activity that includes drinks without you having to plan a whole schedule around them.
• Views that work for couples and groups, especially with Diamond Head in frame.

It’s also an easy pick for people who like a bit of comfort and space. Reviews specifically mention plenty of room to move around, and that’s the difference between enjoying the sail and spending the whole time stuck in one spot.

If you hate wind or sun, this might be a little less comfortable than a fully covered option. Since the sail depends on good weather, you should expect real outdoor conditions.

Booking smart: weather, small-group limits, and simple timing

The good news is it’s straightforward to plan. You’ll get confirmation when you book, it’s offered in English, and it typically sells with people booking about 21 days in advance on average.

One more planning reality: it requires good weather. If it gets canceled due to poor conditions, you’ll be offered a different date or a full refund. There’s also a minimum number of travelers, so if the group doesn’t meet that threshold, you may also get a change of plan.

If your schedule is set, pick a date where you have flexibility. If you’re staying in Honolulu for a few days, booking one of the earlier time slots can also help you avoid a weather domino effect later in the trip.

Should you book the South Shore Open Sail?

Yes, I’d book this if you want an easy, scenic catamaran cruise with real added value from included mai tais and beer. The route delivers with Diamond Head in view as you head toward Waikiki, and the overall tone from the crew sounds genuinely friendly and attentive, not stiff or rushed.

Skip it only if you strongly prefer fully covered sailing, or if you can’t handle outdoor sun and wind. Also, if you’re the type who hates uncertainty at sea, pick dates with backups, since the trip depends on good weather.

If you want a simple “Oahu, but make it fun” outing that’s good for photos, hanging out, and celebrating, this one is hard to beat.

FAQ

How long is the South Shore Open Sail?

It lasts about 1 hour 30 minutes.

What is the price per person?

The price is $47.50 per person.

What drinks are included?

Included drinks include cocktails such as mai tais, plus beers.

Where do I meet for the tour?

You meet at Na Hoku 2 Catamaran, 1025 Ala Moana Blvd, Honolulu, HI 96814.

Do I need a paper ticket?

No, it uses a mobile ticket.

Is the tour offered in English?

Yes, the tour is offered in English.

What happens if weather is poor?

This activity requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Is there a cancellation deadline?

Yes. You can cancel up to 24 hours in advance for a full refund. If you cancel less than 24 hours before the experience starts, you won’t get a refund.

How many people are on the boat?

The tour has a maximum of 49 travelers.