Waikiki: Sunset Swim & Sailing Experience

If you’re dreaming of watching the sun set over Waikiki with a cocktail in hand and the gentle sway of a sailboat beneath you, this tour might just be your kind of evening. We’ve looked into the Waikiki Sunset Swim & Sailing Experience, offered by Three Tiki Sailing, and it promises a blend of scenic beauty, relaxing vibes, and a bit of island adventure. Whether you’re celebrating a special occasion or simply want to unwind with friends or loved ones, this cruise offers a memorable way to experience Hawaii’s stunning coastline.

What we like most? First, the panoramic views of Waikiki and Diamond Head from the deck, and second, the chance to bring your own drinks—a nice touch that keeps the experience casual and personalized. One thing to consider: on Friday nights, the tour skips the swimming portion to stay out for the fireworks, so if swimming is your priority, you might want to pick another day. This tour suits those looking for a laid-back, scenic evening on the water with plenty of comfort.

Key Points

• Spectacular Views: Unobstructed sights of Waikiki, Diamond Head, and the sunset from a spacious trimaran.
• Flexible and Relaxed: Bring your own drinks, relax on a large deck with plenty of shade.
• Comfort and Convenience: Restrooms aboard, large cooler for beverages, and a smooth, modern vessel.
• Ideal for Various Occasions: Romantic evenings, friends’ gatherings, or peaceful solo escapes.
• Limited Swimming on Fridays: Expect no swimming on Friday nights due to fireworks.
• Affordable Value: At $86 for two hours, it offers a good balance of experience and price.

You can check availability for your dates here:

Setting the Scene: What Is This Tour?

This Sunset Swim & Sail Tour is designed for travelers who want more than just a sunset view—they want to feel Waikiki from the water, hear local island music, and enjoy a relaxed, friendly atmosphere. Aboard Hokulani, a sleek trimaran with a 1,000-square-foot deck, you’ll find plenty of space to stretch out, socialize, or simply soak in the scenery.

The boat’s open layout offers panoramic views of Waikiki’s shoreline and Diamond Head, making it a photographer’s dream. The Sunbrella bimini provides ample shade, ensuring comfort without sacrificing those unbeatable vistas. Whether you’re an early riser or prefer a late afternoon sail, the tour generally departs in the afternoon or evening, aligning well with sunset timing.

The Boat: Comfort Meets Style

Hokulani feels more like a cozy lounge than a boat. With ample seating, you can sit back and enjoy the gentle Hawaiian breeze. The large deck (over 300 square feet of shade and space) is perfect for lounging, dancing, or just relaxing with a drink. Two clean, sanitized bathrooms add a layer of convenience that makes the cruise comfortable for everyone.

The boat’s surround sound system fills the air with relaxing island tunes, setting a perfect mood. Whether you’re into reggae, soft ukulele melodies, or just background music, this feature is a subtle but appreciated detail.

What to Bring and Expect

Because the tour is BYOB, you’re encouraged to bring your favorite beverages in cans or bottles and keep them cool in the large onboard cooler. The operator also provides complimentary bottled water, a thoughtful gesture that helps you stay hydrated while enjoying the views. Remember to bring swimwear and a change of clothes if you plan to swim, as well as a camera to capture the sunset.

Important: Drones and glass objects are not allowed, mainly for safety. Also, on Friday nights, the tour skips swimming to stay out for the fireworks, so if swimming is your main goal, pick a different night.

The Itinerary: What Does a Typical Evening Look Like?

The tour begins at the Ala Wai Harbor, behind the Prince Hotel, where crew members dressed in navy blue greet you. After a quick check-in, you’ll board Hokulani and settle into your spot.

The first part of the cruise involves sailing along Waikiki’s coastline, with unobstructed views of Diamond Head and the skyline. You can relax, chat, or take photos as the boat glides smoothly through the water. The surround sound music creates a relaxing, island-inspired ambiance.

As the sun begins to set, the boat turns slightly to maximize the view. You’ll witness that classic Hawaiian sunset—bright oranges, pinks, and purples filling the sky—the kind of scene that makes you want to pinch yourself. During this time, many guests simply sit back with their drinks, watching the horizon change colors.

On non-Friday nights, there’s the added excitement of swimming near Diamond Head, which many travelers say is a highlight—swimming in clear, warm waters with a view of the iconic volcanic crater overhead.

On Friday nights, however, the cruise remains on course for the fireworks display, which the crew points out is spectacular. This means no swimming on those evenings, but the fireworks show is a feast for the eyes and a perfect end to the evening.

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Authentic Moments and Reviews

Guests consistently praise the “stunning views” and the “relaxed atmosphere”. One reviewer called it “an experience you’ll cherish forever,” emphasizing the panoramic vistas and peaceful surroundings. Another said, “Really good! Definitely recommend,” highlighting the overall value and enjoyable vibe.

The music adds a local touch, and many mention that the crew is knowledgeable and friendly, making everyone feel at home. The large deck and shade mean you don’t have to worry about the harsh sun, especially if you’re sensitive or trying to avoid sunburn.

How Does It Compare in Terms of Value?

At $86 per person for 2 hours, this experience is quite reasonable considering the scenery and comfort offered. The large deck, complimentary water, and ability to BYOB add to its appeal. Compared to other water-based activities in Waikiki, it’s a relaxed, less commercial alternative that focuses on atmosphere rather than high-adventure thrills.

Who Should Book This Tour?

This cruise is ideal for romantic couples, small groups of friends, or solo travelers seeking a peaceful yet scenic evening. It’s perfect if you appreciate great views, local music, and a relaxed pace. However, if swimming is your main goal, plan accordingly—check whether it’s a Friday night or a different day for the full experience.

This Waikiki Sunset Swim & Sail tour offers a genuine chance to enjoy Hawaii’s natural beauty in a laid-back, comfortable setting. The modern trimaran ensures smooth sailing, and the panoramic views of Waikiki and Diamond Head are unforgettable. The fact that you can bring your own drinks and enjoy the local music makes it feel more like a private gathering than a tourist trap.

For those seeking a peaceful, visually stunning way to end the day, this cruise hits the mark. It’s especially suited for travelers who enjoy authentic, low-key experiences with a touch of luxury. The friendly crew, scenic backdrop, and the magic of Hawaii’s sunset make this a worthwhile addition to your Waikiki itinerary.

Is this tour suitable for children?
Yes, families can enjoy the cruise, especially if kids like boat rides and scenic views. Just be mindful of their swimming capabilities, especially since swimming isn’t available on Friday nights.

Do I need to bring my own drinks?
Yes, the tour is BYOB, so you can bring canned alcoholic or non-alcoholic drinks. There’s a large cooler onboard to keep them cold.

Are there bathrooms on the boat?
Yes, Hokulani is equipped with two clean, sanitized bathrooms for guests’ convenience.

What should I wear?
Swimwear is recommended if you plan to swim. Bring a change of clothes, and dress comfortably for the weather and boat environment.

Can I swim during the tour?
Yes, but only on non-Friday nights. On Fridays, the cruise stays out for fireworks, so swimming is not part of the schedule that evening.

How long is the tour?
The cruise lasts 2 hours, generally in the late afternoon or evening, perfect for catching the sunset.

Is there a guide or commentary?
The tour is conducted in English, and while there’s no extensive narration, the crew is friendly and knowledgeable about the area.

What’s the best time to book?
Booking in advance is recommended, especially during peak seasons. You can reserve now and pay later, giving you flexibility.

Are the views comfortable for photos?
Absolutely. The open layout and unobstructed views make it easy to take memorable photos of the sunset and coastline.

In sum, this Waikiki Sunset Swim & Sail experience offers a relaxed, authentic way to celebrate Hawaii’s natural beauty. It’s a fantastic option for travelers who want comfort, scenic views, and a touch of local flavor—all at a reasonable price.

You can check availability for your dates here: