Private Catamaran Sunset Sail in Waikiki

Imagine gliding over the sparkling waters of Waikiki aboard a sleek 48-foot catamaran named Hawaiian Style, just as the sun begins to dip toward the horizon. For around $900 per group (up to six people), this two-hour private sunset sail offers a perfect blend of relaxation, stunning scenery, and personalized service. Whether you’re celebrating a special occasion or simply craving an intimate escape on the ocean, this tour provides a flexible and memorable way to end your day in paradise.

What we love most about this experience are the generous lounging nets at the front of the boat, perfect for soaking in the sun and ocean breezes, and the crew’s attentiveness, making sure your preferences are always front and center. The option to swim in a designated anchorage with views of Diamond Head is another highlight—ideal for those who love a refreshing dip in crystal-clear waters. However, keep in mind that this is a private tour—so if you prefer to relax and sightsee without swimming, the crew is happy to adjust the itinerary.

One potential consideration is the price point—$900 might seem steep for some, but the private nature, personalized service, and exclusive sunset views make it a worthwhile splurge for those seeking a tailored experience. This tour suits travelers who enjoy intimate, flexible outings and want a scenic, relaxed evening with no crowds.

If you’re after a peaceful, scenic, and highly customizable way to enjoy Waikiki’s natural beauty—this private catamaran sail is an excellent choice. It’s especially great for small groups, couples, or families looking for an authentic, crowd-free experience that combines the thrill of sailing with the tranquility of a Hawaiian sunset.

Key Points

• Private and personalized: You decide whether to swim, relax, or sightsee.
• Beautiful views: Sail into the sunset with iconic Diamond Head in sight.
• Comfortable and spacious: Lots of room for lounging in sun or shade.
• Value for money: More than just a cruise—an exclusive, tailored experience.
• Family-friendly: Suitable for all ages, with safety gear provided.
• Flexible itinerary: Adaptable to your interests, whether swimming or sightseeing.

A Closer Look at the Experience

The Vessel and Its Amenities

The Hawaiian Style is a modern, low-profile catamaran designed for stability and comfort. Its sleek design ensures a smooth ride, even when the waters are a bit choppy, which we appreciate because no one likes feeling seasick during a sunset cruise. Its large lounging nets are perfect for stretching out and catching the last rays of sunlight, while the seating in shade provides a cool retreat if the Hawaiian sun gets too intense.

The boat is equipped with bluetooth surround sound, allowing you to play your favorite Hawaiian tunes or relax with a playlist of your choice. The two coolers filled with ice are ready to keep your drinks cold, but note that food and beverages are not included—you’re encouraged to bring your own, whether it’s pupus, cocktails, or just water.

The Itinerary and Flexibility

The tour begins at 5:30 pm from the Ala Wai Boat Harbor, offering prime sunset viewing. The crew is eager to cater to your preferences, whether you want to anchor at a favorite swimming spot or sail along the coast for sightseeing. The fishermen’s favorite anchorage offers great views of Diamond Head—a photographer’s dream and a wonderful backdrop for swimming, jumping, or snapping pictures.

If swimming is your priority, the crew will take you to their preferred anchorage for a refreshing dip. Amy, one reviewer, shared how her family enjoyed the “beautiful sunset” and appreciated the crew’s attentiveness and fun attitude, even when the weather wasn’t perfect. Dennis described the experience as “profound” and “surreal,” highlighting the peaceful ride and the delightful company of seals and whales—though the latter may depend on the season.

For those who prefer just to relax and take in the scenery, the crew can sail along the coastline, showcasing the beauty of Oahu’s shoreline and Diamond Head. This flexibility is what makes the tour stand out: it can be as active or as laid-back as you wish.

What’s Included and What To Bring

The experience includes life jackets for adults and children, a lilypad float for lounging, and coolers with ice. The bluetooth speaker is a nice touch, so you can customize your playlist. However, food and drinks are not included, which means you’re encouraged to bring your own snacks and beverages. Towel and sunscreen are also your responsibility, so don’t forget them—especially if you plan to swim.

The Meeting Point and Timing

You’ll meet at Sail Hawaiian Style Catamaran slip 492 at the Ala Wai Boat Harbor. Parking nearby is usually available, and the location is accessible via public transportation, which adds to the convenience. The tour ends back at the same spot, making logistics simple.

Value and Booking Considerations

While $900 might seem high for just two hours, remember this is a private experience. The cost covers exclusive access for your group, personalized service, and the chance to enjoy Waikiki’s sunset in a peaceful, intimate setting. Compared to crowded group tours, the privacy and flexibility here can be well worth the extra expense.

Booking in advance—usually about 58 days ahead—ensures you secure a spot, especially during peak seasons. The cancellation policy is flexible, with free cancellation available if you cancel at least 24 hours in advance.

Authentic Trip Insights from Reviews

Amy appreciated the “wonderful time” on the boat, noting that the crew, Captain Tom and Savannah, “were very attentive and fun to be around.” Despite less-than-perfect weather, she mentions that her family “made the most of it and had the experience of a lifetime,” emphasizing that even imperfect conditions can yield memorable moments.

Lisa called it “top 5 best experiences,” highlighting the safety and stability of the boat, which is crucial when sailing in open waters. Dennis’s review was poetic: he described the ride as “profound” and “surreal,” with the added joy of seals apparently joining in their songs, illustrating the peaceful, almost magical atmosphere of the cruise.

April summed it up as “the absolute best splurge,” praising the crew’s kindness and the feeling of being “at home,” reinforcing that this tour isn’t just about the scenery but also about the personal touch and relaxed environment.

Who Would Enjoy This Tour Most?

This private sunset sail is perfect for small groups seeking a personalized and relaxed experience. Couples celebrating a special occasion will find it particularly romantic, and families will appreciate the flexible itinerary and safety features. It’s also ideal for travelers who want to avoid crowded tours and prefer an intimate, tailored outing with the option to swim or simply enjoy the scenery.

If you’re someone who values authentic, high-quality service and memorable vistas over basic sightseeing, this cruise offers a genuine taste of Hawaiian hospitality and natural beauty.

The Sum Up: Why Choose This Private Catamaran Sunset Sail?

For those seeking a peaceful, scenic, and personalized way to admire Waikiki’s iconic coastline, this private catamaran cruise stands out. The comfortable vessel, equipped with plenty of lounging space and modern amenities, ensures a smooth, enjoyable ride. The ability to customize your experience—whether that means swimming, sightseeing, or just soaking up the sunset—makes this an excellent choice for small groups, couples, or families.

While the price might seem steep, the intimacy and flexibility provided are rare in guided tours. If you want a peaceful evening on the water, away from crowds and with the chance to create your own memories, this sail could very well be the highlight of your trip to Oahu.

FAQ

Is this tour suitable for children? Yes, children of all ages are welcome, and life jackets are provided for both adults and children, making it a family-friendly outing.

What should I bring? Bring your own food and drinks, as they’re not included. Sunscreen and towels are also recommended if you plan to swim or spend time on the nets.

Can I swim during the tour? Absolutely, if you choose to. The crew will take you to their favorite swimming anchorage with views of Diamond Head, or you can opt to sail along the coast instead.

What’s included in the price? The tour includes the use of life jackets, a lilypad float, coolers filled with ice, and Bluetooth surround sound capability. Food, beverages, tips, and towels are not included.

How long in advance should I book? On average, travelers book about 58 days in advance, especially during peak seasons, to secure their private slot.

What is the cancellation policy? You can cancel up to 24 hours before the scheduled start for a full refund. Cancellations within 24 hours are not refunded.

Is transportation provided? The meeting point is at the Ala Wai Boat Harbor, which is accessible by public transportation and has parking nearby. No transportation is provided directly.

This private catamaran sunset sail offers an intimate, customizable way to experience Waikiki’s stunning coastline. Whether you’re celebrating, looking for a tranquil escape, or just want a memorable evening on the water, this tour promises a peaceful, scenic, and very Hawaiian end to your day.