South Shore Open Sail from Kewalo Harbor Including Drinks

If you’re looking for a breezy, laid-back way to see Oahu’s beautiful south shore, the South Shore Open Sail on the Na Hoku II might just be what you need. This 90-minute daytime cruise offers a chance to kick back on a bright yellow and red catamaran, sip on complimentary drinks, and enjoy some of the best water views Honolulu has to offer. It’s a popular choice, with many booking about two weeks in advance, and for good reason — it’s simple, fun, and offers a great mix of scenery and good vibes.

What really appeals about this experience is how intimate and relaxing it feels. The boat isn’t a giant cruise ship — with a maximum of 49 passengers, it feels cozy enough to really enjoy the scenery and the company. Plus, the price point of around $47.50 per person makes it an accessible way to add a memorable element to your trip without breaking the bank. On the flip side, it’s a short trip, so if you’re craving a full-day adventure or a more structured tour, this may not be your best fit. Still, if you’re after a chill, scenic sail with some good drinks and potential wildlife sightings, this tour works well.

This tour suits travelers who appreciate relaxed outings, love scenic views of Diamond Head, and enjoy the idea of sailing with a friendly crew. It’s also ideal for those wanting a quick escape from the busy city for a bit of ocean air—whether you’re celebrating a special occasion or just looking to unwind. It’s picnic-friendly, casual, and best suited for those comfortable on the water for about an hour and a half.

Key Points

• Relaxed, intimate vibe with a small group of up to 49 people
• Beautiful views of Honolulu, Waikiki, and Diamond Head during the cruise
• Complimentary drinks, including alcoholic options for guests 21+
• Potential wildlife sightings, including whales (not guaranteed)
• Great value for the price, with a laid-back, friendly crew
• Ideal for a short, relaxing activity that adds a splash of adventure to your day

What to Expect from the South Shore Open Sail

This tour is a straightforward, enjoyable water outing. From the moment you step aboard the Na Hoku II at Kewalo Basin Harbor, you’ll notice the inviting, vibrant yellow and red colors of the catamaran. It’s a retired Waikiki Beach boat, repurposed for these scenic day sails, and it’s clear that the crew takes pride in making sure everyone has a good time.

The Itinerary and the Experience

Your journey begins at Na Hoku 2 Catamaran at 1025 Ala Moana Blvd. The crew will welcome you aboard and set sail from Kewalo Basin Harbor, heading toward the Honolulu shoreline. The main highlight is sailing from Kaka’ako to Waikiki, with stunning views of Diamond Head visible throughout — a classic postcard scene that makes for fantastic photos.

The cruise lasts approximately 90 minutes — a perfect amount of time to enjoy the ocean without feeling rushed. During this period, you’ll be able to sit back, soak up the sun, and take in the scenery while vibing to some good music. The crew is attentive and friendly, making sure everyone is comfortable and has what they need.

Drinks and Atmosphere

A big plus of this tour is the complimentary drinks. Most guests rave about the flowing beverages, especially on sunny days when a cold mai tai or beer hits the spot. Adults 21+ will need valid ID to enjoy the alcoholic choices, but everyone can indulge in non-alcoholic options too.

The atmosphere onboard is described as super chill and fun. Many reviews mention the crew: “Allison, Dave, and Caleb are great,” one reviewer wrote, highlighting how welcoming and attentive they are. The vibe is laid-back, with plenty of space to move around, take photos, or just lounge and enjoy the views.

Wildlife Sightings and Weather Considerations

While whales are not guaranteed, some travelers have been lucky enough to see them splashing around during the season. Since the cruise takes place during the day and in good weather, clear skies and calm waters usually make for a comfortable ride.

Group Size and Personal Touch

Many reviews emphasize how the smaller size of the boat makes the experience feel more personal and less commercial. This is a big plus if you prefer sailing with fewer people and enjoying a more intimate, friendly environment.

The Pros and Cons of the Na Hoku II Sails

What Travelers Love

Stunning Views: The sight of Diamond Head, the Honolulu skyline, and the coastline is consistently praised. These views make for memorable photos and give a real sense of place. “It was so beautiful to take a sail across the ocean in front of Waikiki,” one reviewer notes.

Good Value for Money: At around $47.50, the experience offers a lot — a scenic cruise, drinks, music, and the chance to relax on a large, comfortable boat. Many mention it’s “well worth the price,” especially considering the friendliness of the crew and the gorgeous scenery.

Friendly Crew and Atmosphere: Multiple reviewers highlight the crew’s attentiveness and welcoming attitude. Whether it’s helping with photos or ensuring everyone has a drink, they make sure you feel cared for.

Potential Wildlife Encounters: Seeing whales, even if not guaranteed, is a bonus many travelers mention fondly. It adds a special thrill to the cruise.

Considerations and Drawbacks

Short Duration: If you’re after a full-day adventure or a more competitive activity, this 90-minute sail might feel a bit brief. It’s perfect for a quick escape, but not for those wanting a full afternoon on the water.

Weather Dependent: Like all outdoor activities, this tour depends on good weather. If the day turns windy or rainy, there is a possibility of cancellation — but you’ll be offered a new date or a full refund if that happens.

Limited Time for Wildlife: While whale sightings are possible, they aren’t guaranteed. If spotting whales or other marine life is a priority, you might want to consider other tours focused on that.

Who is This Tour Best For?

This sail is ideal for travelers wanting a relaxed, scenic water experience without a large crowd. It’s great for those who appreciate good views, good drinks, and easy-going fun. It’s also perfect for a quick midday escape that fits easily into a busy itinerary. Families with older children or couples looking for a romantic, casual outing will find this cruise hits the right notes.

Deep Dive into the Details

The Itinerary Breakdown

Your departure point at Na Hoku 2 is conveniently located near public transportation, making it easy to access. The ship departs in the late morning or early afternoon, aligning with the typical weather patterns that bring sunshine and calm waters.

The cruise heads from Kewalo Basin, sailing past the Kaka’ako waterfront and toward the iconic Waikiki shoreline. The boat’s route offers uninterrupted views of Diamond Head, a volcanic tuff cone that’s instantly recognizable and a favorite backdrop for travelers.

The sail’s focus is on the scenery and the ambiance — with plenty of opportunities for photos along the way. The crew’s music playlist adds to the relaxed vibe, making it feel like a floating party.

Onboard Experience

The boat itself is spacious and comfortable, with ample room to sit or stand as you take in the sights. The colorful yellow and red hulls make it stand out against the ocean and city skyline. Many reviews mention how the crew is attentive, always available to help with photos or refills.

Drinks are part of the experience, with complimentary options kept flowing. The atmosphere is described as “super beautiful, very chill,” perfect for unwinding or celebrating a special occasion like a birthday.

Photos and Scenery

Expect plenty of photo opportunities, from the sail with Diamond Head in the background to candid shots of friends or family enjoying the ocean air. The crew is praised for being helpful with capturing moments, ensuring everyone leaves with great memories.

Group Size and Personal Touch

With a maximum of 49 travelers, the tour maintains an intimate feel. You won’t be lost in a crowd, and the crew can tailor some of the experience to your needs — whether that’s helping with photos or chatting about the local sights.

Cancellation and Weather Policy

Booking is flexible with free cancellation up to 24 hours in advance. If the weather looks poor on the day, you might find the cruise canceled, but you’ll be offered a different date or a full refund.

Who Should Book This?

People who enjoy laid-back experiences, beautiful scenery, and a bit of ocean air will find this cruise a perfect addition to their Hawaii trip. It’s especially good if you’re traveling with friends or a partner and want a relaxed, enjoyable outing without the fuss of a larger tour. This sail isn’t suited for those seeking a full-day activity or adventure sports, but it hits the sweet spot for a scenic, social cruise.

Final Thoughts

The South Shore Open Sail from Kewalo Harbor offers a straightforward, enjoyable way to see some of Oahu’s most iconic sights from the water. Its combination of stunning views, friendly crew, and complimentary drinks make it a hit among travelers. While it’s short and weather-dependent, many reviews highlight how worthwhile and fun the experience is.

If you’re after a gentle, scenic escape with a relaxed vibe and excellent value, this cruise could be a highlight of your trip. It’s perfect for those who want to take in the scenery without a lot of fuss, and who enjoy sharing good moments with others out on the water.

FAQ

• How long is the cruise? The cruise lasts approximately 1 hour and 30 minutes.
• What is the meeting point? It starts at Na Hoku 2 Catamaran, located at 1025 Ala Moana Blvd, Honolulu.
• Are drinks included? Yes, complimentary drinks are provided, including alcoholic beverages for guests 21+ with valid ID.
• Can I see whales on this cruise? Whale sightings are not guaranteed, but some travelers have been lucky.
• Is the tour suitable for children? The data doesn’t specify, but since most travelers enjoy a casual, family-friendly vibe, it’s likely suitable for older children comfortable on the water.
• What is the maximum group size? Up to 49 travelers.
• Is the tour weather dependent? Yes, it requires good weather. Cancellations due to poor weather are fully refunded or rescheduled.
• Can I cancel if I change my mind? Yes, you can cancel free of charge up to 24 hours before the departure.
• Is the tour accessible via public transportation? Yes, it’s near public transit, making it easy to access.
• What should I bring? It’s best to wear comfortable clothing, bring sunscreen, and perhaps a hat or sunglasses for sun protection.

Whether you’re celebrating something special or just want a relaxing day on the water, this sail offers a friendly, scenic, and affordable taste of Oahu’s coast. It’s a straightforward choice if you value good views, drinks, and a laid-back atmosphere without the fuss of larger boats.