South Shore Open Sail from Kewalo Harbor Including Drinks

If you’re visiting Honolulu and looking for a way to enjoy the ocean without the hassle of a crowded tourist boat, the South Shore Open Sail from Kewalo Harbor might just be what you need. Touted as a 90-minute daytime sailing experience aboard one of Honolulu’s most iconic catamarans, this tour offers a refreshing and laid-back way to soak in the views of Oahu’s southern coast. From the vibrant colors of the vessel to the gentle sway of the waves, this trip is designed for travelers who love scenic moments paired with a casual vibe.

What makes this tour particularly appealing? First, it’s the intimate feel — with a maximum of 49 passengers, it’s small enough to foster a friendly atmosphere without feeling crowded. Second, the complimentary drinks and stunning vistas give you good value for your modest price of $47.50 per person. However, a potential consideration is that since it’s a short, 90-minute voyage, it might not suit travelers after a full-day adventure or those seeking a longer cruise. It’s best suited for those who want a relaxed, scenic break in their busy Hawaii itinerary, especially if you enjoy sailing, wildlife spotting, or just relaxing on the water with a drink in hand.

Key Points

• Short and sweet: About 90 minutes, perfect for a quick scenic escape.
• Intimate setting: Small group size enhances comfort and camaraderie.
• Great views: Passes by Waikiki, Diamond Head, Kaka’ako, and Ala Moana.
• Value for money: Includes complimentary drinks, with alcohol available for adults 21+.
• Flexible options: Free cancellation up to 24 hours in advance.
• Ideal for casual outings: Suitable for almost all travelers, service animals included.

Setting the Scene: What to Expect on the Tour

This sail departs from Na Hoku 2 Catamaran at 1025 Ala Moana Blvd, a convenient location near public transportation and central Waikiki. The boat itself is a retired Waikiki Beach catamaran, now painted in cheerful yellow and red, adding a touch of fun and vibrancy. Though it’s a smaller vessel with a capacity of 49, it feels spacious enough for everyone to enjoy the ride comfortably.

The Itinerary: A Gentle Glide Along Oahu’s South Shore

The trip begins with a straightforward sail from Kaka’ako to Waikiki, offering ample opportunities to capture photos of Diamond Head — a Honolulu icon — from the water. The view of Diamond Head during the sail is consistently praised, with travelers noting that it’s a “beautiful” sight that makes the experience memorable.

As the catamaran glides through Honolulu’s crisp waves, you’ll enjoy coastal scenery that includes the bustling Kaka’ako waterfront, the upscale Ala Moana area, and the legendary Waikiki Beach. The sail provides an excellent vantage point for sightseeing, and many reviews highlighted how the views were stunning, making it an ideal way to relax and take in the city’s skyline and natural beauty from the water.

Wildlife and Atmosphere

While wildlife sightings—like whales or dolphins—are not guaranteed, the crew does their best to spot whales, especially during the winter months. Travelers have said they “saw whales,” which adds a special element to the trip, though it’s more of a bonus than a guarantee. The overall atmosphere is chill and friendly, with music playing and plenty of room to move around. The vibe is perfect for celebrating a special occasion, or just unwinding with friends and family.

Drinks and Refreshments

Included in the ticket price are complimentary drinks, offered throughout the sail. Adults 21+ can enjoy alcoholic beverages with valid ID, which means you can sip on a maitai or other tropical cocktails while soaking in the views. Reviewers consistently highlighted how “the drinks were flowing” and helped set a relaxed, fun tone for the trip. Non-alcoholic drinks are also available, ensuring everyone stays refreshed.

The Crew and Service

Multiple reviews mentioned the attentiveness and friendliness of the crew, with names like Allison, Dave, Caleb, and Captain Dan getting special praise. Travelers appreciated the crew’s willingness to help with photos, drinks, or simply making everyone feel welcome. This personal touch significantly enhances the experience, transforming it from a simple boat ride into a warm, friendly outing.

Pricing and Value

At $47.50 per person, this tour offers excellent value—especially considering the included drinks, the scenic views, and the intimate atmosphere. It’s more affordable than many larger, commercial excursions, and the small group size means you’re less likely to feel like just another face in the crowd. The duration of 1.5 hours is perfect for fitting into a busy day, and most travelers reported feeling it was a worthwhile, relaxing experience.

Practical Details and Logistics

The meeting point at Na Hoku 2 Catamaran is accessible via public transit and nearby parking options. Confirmations are automatic upon booking, and the tour runs rain or shine—though poor weather may lead to cancellations or rescheduling. You can cancel free of charge up to 24 hours in advance, giving plenty of flexibility if your plans change.

Most travelers can participate, and service animals are allowed, making it inclusive for different needs. The maximum group size of 49 ensures a more personal experience compared to larger tour boats, which can sometimes feel impersonal.

Is This Tour Right for You?

If you’re in Honolulu and craving a casual, scenic escape on the water, this is a solid choice. It’s especially well-suited for first-time visitors, small groups, or couples who want a taste of sailing without committing to a longer or more expensive cruise. It’s also a good option for celebrations or relaxing afternoons—say, celebrating a birthday or just enjoying a lazy day in paradise.

Travelers who prefer more adventurous or wildlife-focused tours might want to look elsewhere, but if your priority is stunning views, good company, and a relaxing vibe, this sail fits the bill.

For travelers seeking a budget-friendly, authentic ocean experience in Honolulu, this tour offers great value. The scenic views of Diamond Head and Waikiki, combined with the friendly crew, lively atmosphere, and included drinks, make it a memorable and enjoyable outing. The small group size enhances the experience, making it feel personal rather than crowded.

While it’s a short trip, it’s packed with enough visual delight and relaxed fun to leave a lasting impression. It’s particularly suited for those who want a laid-back day on the water without the fuss of larger, more commercial cruises.

If your Hawaii plans include a taste of sailing combined with stunning scenery and friendly vibes, this tour won’t disappoint.

How long is the tour?
The tour lasts approximately 90 minutes, making it a perfect short break from more intensive sightseeing.

Where does the tour depart from?
It departs from Na Hoku 2 Catamaran at 1025 Ala Moana Blvd, Honolulu, HI, close to public transportation.

Are drinks included?
Yes, complimentary drinks are provided, including alcoholic beverages for guests 21+ with valid ID.

Is the tour suitable for children or service animals?
Most travelers can participate, and service animals are allowed.

Can I cancel if my plans change?
Yes, you can cancel free of charge up to 24 hours before the scheduled start. Cancellations after that are non-refundable.

What if the weather turns bad?
The tour requires good weather; if canceled due to poor conditions, you’ll be offered a different date or a full refund.

To sum it up, the South Shore Open Sail from Kewalo Harbor offers a wonderful, accessible way to enjoy Honolulu’s coast from the water. Its blend of stunning views, relaxed atmosphere, and friendly service make it ideal for travelers who value authenticity and comfort. Whether celebrating, sightseeing, or simply relaxing, this sail provides a genuine taste of Hawaii’s oceanic charm—worth considering for your island itinerary.