Honolulu: Waikiki Sunset Sail & Swimming with BYOB

Stepping aboard the Hokulani, you sail straight toward Diamond Head at golden hour

You board a three-hulled sailing trimaran and spend the evening moving past Diamond Head, Magic Island, and the Royal Hawaiian Hotel as the light changes. You get a swim off Waikiki during the golden hour, a full 1,000-square-foot deck to move around on, and the option to bring your own drinks (no glass). The smooth hull design keeps the ride stable even in rougher conditions, and you're back on shore by nightfall.

Step-by-step itinerary

Waikiki sunset sail and swim

• Sail past Diamond Head
• Sail past Royal Hawaiian Hotel
• Sail past Magic Island
• Swim at Waikiki during sunset

The Experience

The boat leaves the dock and you're moving almost immediately—the trimaran cuts through the water with a steadiness that surprises you. Hokulani is 41 feet long and built with three separate hulls instead of one, which means even when the ocean gets choppy, the ride stays smooth. The deck alone is almost 1,000 square feet, so there's room to spread out. You've got netted seating areas, bench seats scattered across the bow and stern, and a shaded lounge spot the crew calls "the nook"—the kind of place where you can actually relax instead of gripping the rail.

As you sail past Magic Island and the Royal Hawaiian Hotel, the light starts to shift. Diamond Head rises up on your left, and the angle is the kind of thing you can't get from shore. The open-air design means there's no glass between you and the view—just the wind and the sound of the water. You're moving the whole time, so the perspective keeps changing. Some people stay up on deck; others drift down to the nook when they want shade. The crew doesn't rush you through any of it.

When you reach the swimming spot off Waikiki, the sun is low enough that the water catches the color. You can jump in or stay aboard—it's your call. The water's warm, and the boat's right there. After you're done, you dry off and watch the actual sunset happen, which is when most people realize they should have brought a drink. That's where the BYOB part matters: you can bring beer, wine, whatever you want, just nothing in glass bottles. It's a small thing that changes the whole vibe from "tour" to "evening on the water with friends."

Arrive 20 minutes early at the meeting point. The whole sail runs through the golden hour and into dusk, and you're back before it gets fully dark. If you're coming by public transport, there are options nearby the dock.

What’s included

• Your evening includes sailing past Diamond Head, Magic Island, and the Royal Hawaiian Hotel, a swim off Waikiki during sunset, and access to multiple seating areas across the 1,000-square-foot deck.
• You can bring your own beverages (no glass bottles).
• The boat is a 41-foot trimaran with a three-hull design built for smooth, stable sailing in Hawaiian waters.

Good to know

Easy physical levelPublic transport nearbyNot for heart conditionsNot for back problems

Operated by Three Tiki Sailing

Is this one for you?Book this if you want a sunset on the water without the crowded beach scene—the boat moves you past the landmarks instead of anchoring, and you control what you drink and how long you stay in the water.

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Top questions

Can I bring alcohol on the boat?

Yes, BYOB is allowed. You can bring beer, wine, or other beverages, but glass bottles are not permitted.

Is swimming included?

Yes. There's a designated sunset swim off Waikiki as part of the experience. You can participate or stay on board.

How many people fit on the Hokulani?

The boat is 41 feet long with nearly 1,000 square feet of deck space. Exact passenger capacity isn't listed, but the size allows for comfortable seating with multiple areas—netted sections, bench seats, and a shaded lounge.

What if the weather is rough?

The trimaran's three-hull design is specifically built to provide a smooth, stable ride even in rougher conditions, which is one of its main features.

Do I need to arrive early?

Yes, arrive at the meeting point 20 minutes before the scheduled departure time.

Is there shade on the boat?

Yes. There's a shaded lounge area called "the nook" where you can sit out of the sun while still enjoying views.

How do I get to the dock?

Public transportation options are available near the meeting point in Waikiki.