South Shore Open Sail from Kewalo Harbor Including Drinks

A Sail on the South Shore of Oahu: A Practical, Authentic Experience

If you’re looking to combine spectacular views of Waikiki, relaxed vibes, and a touch of adventure, the South Shore Open Sail from Kewalo Harbor might just be your perfect island escape. For just $47.50 per person, you’ll hop aboard the Na Hoku II, a charming, retired Waikiki Beach catamaran painted in cheerful yellows and reds, and cruise for about 90 minutes along Honolulu’s iconic coast.

What we love most about this trip is the intimate size—with a maximum of 49 guests, it feels more like a friendly gathering than a crowded tour. The setting, right in Kewalo Basin Harbor, offers a close-up perspective of Honolulu’s bustling waterfront, and the views of Diamond Head from the water are simply unforgettable. Plus, the complimentary drinks—including maitais—add a relaxing touch we all appreciate while soaking in the scenery.

A possible consideration is timing and weather. Since it’s a daytime sail, you’ll want good weather to truly enjoy the experience, and cancellations can occur if conditions turn unfavorable. Also, while alcohol is included, you need to be 21+ with ID to enjoy the drinks, so this isn’t a tour for kids or those avoiding alcohol.

This experience suits travelers who enjoy a laid-back outing with great photo opportunities, want to see Honolulu from a different angle, and appreciate value for money. It’s especially popular among those celebrating special occasions or simply wanting a memorable way to enjoy Hawaii’s ocean.

Key Points

• Stunning views of Waikiki and Diamond Head from the water
• Intimate group size provides a more personal experience
• Complimentary drinks, including maitais and a lively, relaxing vibe
• Flexible schedule with free cancellation up to 24 hours in advance
• Suitable for most travelers, including service animals and those with mobility needs
• A great way to spot wildlife, possibly whales, during the season

An In-Depth Look at the South Shore Open Sail Experience

The Location and Its Significance

Starting from Kewalo Basin Harbor, this tour offers a chance to see Honolulu’s waterfront from a fresh perspective. Located near downtown Honolulu, this harbor is a hub for local boats and charters, giving a more authentic feel than the tourist-heavy Waikiki beach area. The Na Hoku II, with its bright yellow and red exterior, is impossible to miss and immediately signals a fun, relaxed outing.

The Itinerary and What to Expect

The sailing route takes you from Kaka’ako to Waikiki, with the highlight being the stunning views of Diamond Head. As the sail progresses, you’ll pass the Kaka’ako waterfront, known for its trendy shops and murals, and the Ala Moana area, a favorite among locals for its large shopping center and park.

While the itinerary is simple, the magic lies in the experience of being on the water. The boat glides through Honolulu’s waves, giving you ample opportunities to take photos of the skyline, the coastline, and the majestic Diamond Head volcano looming in the background. The crew often keeps the vibe upbeat with music, making this a perfect setting for casual conversation or just soaking up the sun.

The Boat and Crew

The Na Hoku II is a classic catamaran, offering plenty of space to move around. Reviews praise the attentiveness of the crew—all three mentioned by name in reviews are noted for their professionalism and friendliness. The crew’s role is crucial in making sure everyone gets drinks, has a good view, and feels comfortable.

Drinks and Atmosphere

A standout feature is the complimentary drinks, which include a tasty maitai and other options (alcoholic and non-alcoholic). For those of age, the alcoholic beverages add to the relaxed, celebratory atmosphere—perfect for birthdays, honeymoons, or just unwinding. Reviewers repeatedly mention the flowing drinks and the great music, which helps create a laid-back, fun environment.

Wildlife and Scenic Highlights

While whales are not guaranteed, some travelers have seen them, adding a bit of magic. Even if wildlife spotting isn’t consistent, the views of Honolulu’s coastline and Diamond Head more than make up for it. The crisp ocean breeze and warm sun make this an ideal daytime escape.

Practical Details

• Duration: About 1 hour 30 minutes, enough to relax without feeling tiring
• Price: At $47.50, the value is clear—you’re paying for a memorable, scenic outing with drinks included
• Booking: Usually booked about two weeks in advance, which is reasonable for peak seasons
• Accessibility: Most travelers can participate, and service animals are allowed
• Cancellation: Fully refundable if canceled 24 hours ahead, a flexible option for unpredictable Hawaii weather

Why Travelers Keep Coming Back

Repeated reviews highlight how this small, intimate sail feels more like a friendly gathering than a tour, making it highly recommended for celebrating special occasions. For example, one traveler celebrated a birthday, describing it as a “perfect way to celebrate with friends.” Others mention great value, friendly crew, and beautiful scenery.

Who Should Consider This Tour?

If you:

• Want a relaxed day on the water with a friendly crowd
• Love stunning coastal views and photo ops
• Appreciate good value for a short, enjoyable experience
• Are okay with alcoholic beverages and warm weather
• Seek an authentic taste of Honolulu’s waterfront life

then this tour is a fantastic choice.

Final Thoughts

This South Shore Open Sail offers a refreshing way to enjoy Hawaii without the hefty price tag. The cheerful atmosphere, spectacular scenery, and personalized service make it a standout among Honolulu’s water activities. It’s especially well-suited for those who want a fun, laid-back experience that doesn’t overpower or over-schedule.

For travelers craving a memorable, scenic, and social outing, this sail combines beautiful views, delicious drinks, and friendly crew at a great price point. Whether you’re celebrating something special or just want a relaxing way to enjoy Honolulu’s coast, it’s a worthwhile addition to your Hawaii itinerary.

FAQ

Is this tour suitable for children?
The tour is primarily aimed at adults, especially since alcoholic drinks are offered for those 21 and over. However, most travelers of all ages can participate, and service animals are allowed.

How long does the sailing last?
The experience lasts approximately 90 minutes, giving plenty of time to relax and take photos without feeling rushed.

Are drinks included in the price?
Yes, complimentary drinks are included, including maitais and other beverages, with alcoholic options for those with valid ID.

What is the meeting point?
The tour starts at Na Hoku 2 Catamaran, 1025 Ala Moana Blvd, Honolulu.

Can I cancel if my plans change?
Yes, you can cancel free of charge up to 24 hours before the activity for a full refund.

Is the boat accessible for most travelers?
Most travelers can participate, and service animals are permitted. The boat offers ample space for movement.

What if the weather is poor?
If weather conditions are unfavorable, the tour may be canceled, and you’ll be offered a different date or a full refund.

Do I need to book far in advance?
Booking about two weeks ahead is recommended, especially during peak seasons, to secure your spot.

Will I see wildlife like whales?
Whale sightings are not guaranteed, but some travelers have been lucky enough to observe them during the season.

Is there a dress code?
Casual, comfortable clothing is perfect—think shorts, T-shirts, sunglasses, and sunscreen. Bring a hat if you’d like extra sun protection.

This sailing adventure offers a beautiful, relaxed way to enjoy Honolulu’s coast, making it a solid choice for those who value scenic beauty, good company, and a laid-back atmosphere. With a friendly crew, excellent views of Diamond Head, and drinks to toast the day, you’ll find it hard not to smile as you drift along Hawaii’s sunny waters.