South Shore Open Sail from Kewalo Harbor Including Drinks

A boat ride might not be the first thing that comes to mind when thinking about Hawaii, but for those seeking a laid-back, scenic, and social experience, this South Shore Open Sail from Kewalo Harbor is hard to beat.

While I haven’t personally taken this specific tour, reviews and descriptions paint a picture of a memorable, value-packed adventure—especially for travelers looking to enjoy Honolulu from the water without breaking the bank.

What sets this sail apart? First, the stunning views of Diamond Head and Waikiki are simply unmatched, giving you a fresh perspective of the city’s iconic landscape. Second, the friendly crew and lively atmosphere make it feel more like a social gathering than a traditional tour. But, a word of caution—since it’s a shorter, 90-minute outing, it’s best suited for those wanting a quick, fun escape rather than a full-day excursion.

This experience is ideal for couples, small groups, or anyone craving a relaxed, scenic boat ride with plenty of chances to unwind.

Key Points

• Short and sweet: 90-minute sailing experience with great city and ocean views.
• Affordable: At $47.50 per person, it offers good value considering the scenery and drinks.
• Intimate atmosphere: Smaller group size (up to 49 passengers) enhances the social vibe.
• Complimentary drinks: Includes a maitai and other beverages, with alcohol for 21+.
• Stunning scenery: Sail from Kaka’ako to Waikiki, with Diamond Head as the backdrop.
• Highly rated: Consistently receives perfect or near-perfect reviews for fun, friendliness, and views.

What to Expect on This Sail

This tour offers a relaxed 90-minute voyage aboard the colorful Na Hoku II catamaran, a retired Waikiki Beach classic turned city-friendly cruising vessel. The boat’s vivid yellow and red colors make it a cheerful sight, and its capacity for 49 guests strikes a good balance between intimacy and social energy. The departure point is Na Hoku 2 Catamaran at 1025 Ala Moana Blvd, a convenient location close to public transport and central Honolulu.

The Itinerary in Detail

The sailing begins in Kaka’ako, a lively neighborhood known for its street art and local vibe. From here, you’ll glide across Honolulu’s shimmering waves toward Waikiki, with the iconic Diamond Head looming nearby—an unmistakable symbol of Hawaii.

While the trip is short, it’s packed with visual delights. The views of the Honolulu skyline, Kaka’ako waterfront, and Ala Moana are all on full display, making it an excellent opportunity for photos without the crowds or noise of a larger cruise. As you cruise, you’ll enjoy music and sunshine, with options to relax on deck and take in the scenery.

Wildlife & Nature

Wildlife sightings aren’t guaranteed, but some reviews mention whales—an exciting bonus if you’re lucky. The crew does their best to spot wildlife, adding an element of anticipation to the experience. Even if you don’t see whales, the crisp ocean air and gentle waves create a calming atmosphere.

The Drinks and Vibe

One of the highlights—complimentary drinks, including a maitai, are served throughout the sail. For those over 21, there are alcoholic beverages with valid ID. The crew is known for being friendly and attentive, making sure everyone has what they need, whether it’s a drink, a camera shot, or just a good laugh. The overall vibe is described as chill, fun, and lively, making it a perfect way to celebrate a birthday or just unwind after sightseeing.

The Crew and Customer Reviews

The reviews consistently praise the professional yet friendly crew. Passengers note how attentive and accommodating the team is, often mentioning that the crew made everyone feel comfortable and included. Multiple reviewers mention the great drinks and relaxed atmosphere, emphasizing how the experience feels more like a gathering with friends than a typical tour.

One guest described the trip as “incredible,” citing the beautiful scenery, great music, and crew’s attentiveness. Another highlighted the small size of the boat, which allows for a more intimate experience, leading to lively conversations and better views.

Pricing and Value

At $47.50 per person, this sail represents solid value—especially considering the scenic views, drinks, and friendly atmosphere. Since it’s booked on average 14 days in advance, it’s advisable to plan ahead to secure your spot. For many travelers, this price point offers a great introduction to Honolulu’s coast, without the hefty price tag of larger, more comprehensive tours.

While it’s a short experience, the cost includes all the basics—the boat, the drinks, and the scenic sailing—making it a convenient choice for a quick, memorable outing.

Practical Tips for Your Sail

• Arrive early at Na Hoku 2 Catamaran for a smooth start.
• Bring your camera or phone—the views of Diamond Head and Honolulu skyline are perfect for photos.
• Dress casually and comfortably, with sunscreen and sunglasses, as you’ll be outdoors.
• Bring ID if you plan to enjoy the alcoholic drinks.
• Book at least two weeks in advance to ensure availability, especially during peak seasons.
• Check the weather forecast—the tour requires good weather, and cancellations due to foul weather are fully refunded or rescheduled.

Who Should Consider This Experience?

This sail is best for travelers wanting a quick, scenic escape from the hustle of Honolulu. It’s perfect for couples, small groups, or solo travelers who want to enjoy the water and city views without a lengthy commitment. It also suits those who appreciate good value and a relaxed, social atmosphere. If you’re looking for a family-friendly outing, note that service animals are allowed, but children of all ages can enjoy the trip.

However, if you prefer a more active or longer adventure, this may not be the tour for you. It’s not an extensive sightseeing cruise, but rather a leisurely, social sail with a focus on enjoying the scenery, the company, and some drinks.

The Sum Up: Is It Worth It?

In short, this South Shore Open Sail offers a relaxed, scenic, and enjoyable way to see part of Honolulu’s coast from the water. The combination of stunning views, friendly crew, and good value makes it stand out among short boat tours. Its intimate size and lively atmosphere make it ideal for those looking to unwind, celebrate, or just experience a slice of island life on the water.

While it’s not a full-day adventure or an extensive wildlife tour, it excels in delivering a beautiful, laid-back experience that leaves a lasting impression. For travelers craving a light yet memorable activity during a visit to Honolulu, this sail hits the spot.

FAQ

How long is the tour?
The sailing experience lasts about 90 minutes, making it perfect for a quick break without taking up your whole day.

Where does the tour start and end?
It begins at Na Hoku 2 Catamaran, 1025 Ala Moana Blvd, and ends back at the same location.

Are drinks included?
Yes, the tour offers complimentary drinks, including a maitai. Alcoholic beverages are available for guests 21+ with valid ID.

Is the tour suitable for children?
Most travelers can participate, and service animals are allowed. It’s a relaxing outing suitable for families, but check with the provider if you have specific needs.

Can I cancel if the weather is bad?
Yes, cancellations due to poor weather are fully refundable or can be rescheduled. The policy offers free cancellation up to 24 hours before the tour.

How many people can join?
The boat accommodates up to 49 travelers, ensuring a more intimate experience compared to large cruise ships.

Is prior booking necessary?
Yes, it’s recommended, with bookings typically made 14 days in advance. This helps secure your spot and plan ahead.

What should I bring?
Bring sunscreen, sunglasses, a camera, and an ID if you plan to enjoy alcohol. Dress comfortably and be prepared for the weather.

Will I see wildlife?
Wildlife sightings, such as whales, are not guaranteed but happen occasionally, adding an extra element of surprise.

This scenic sail from Kewalo Harbor offers a simple yet delightful way to enjoy Honolulu’s coast, perfect for those looking to combine a quick ocean escape with great views and friendly company. Consider it an easy, enjoyable addition to your Hawaiian itinerary—whether for a celebration, a break from sightseeing, or just to indulge in some relaxing waves and sunshine.