How long is the sail?

The cruise is 1.5 hours long and departs daily at 3 PM.

Where is the meeting point?

The meeting address is 2169 Kālia Rd, Honolulu, HI 96815; it’s walkable from many Waikiki hotels.

What is the cancellation policy?

There is a 24-hour no-refund, no-cancellation policy—plan accordingly.

Is this trip family-friendly?

Yes—families with older children typically enjoy the short duration and relaxed pace; confirm age requirements with the operator if concerned.

Do I need sailing experience?

No prior sailing experience is required; the crew manages navigation and sailing duties.

Is the trip wheelchair accessible?

Accessibility information is not provided in the listing; contact the operator directly to confirm accommodations.

Tradewind Sail Private Waikiki Afternoon Cruise Past Diamond Head | Private | Boat Tour

On Oahu’s southern shore, a 1.5-hour Tradewind Sail • Private launches from 2169 Kālia Rd in Honolulu, Hawaii, offering a breezy, low-commitment way to see Waikiki from the water. This afternoon cruise sails with the prevailing northeasterly trade winds, giving passengers a steady, comfortable ride and wide-open views of Diamond Head, the Waikiki Natatorium War Memorial, and the coastline that frames the city. The route hugs the shore past Black Point before sweeping toward Koko Head and the weathered slopes of Koko Crater, a volcanic tuff cone that rises above Hanauma Bay. From the deck you’ll scan for reef breaks and snorkeling bays, watch surfers catch inside waves, and — on very clear days — pick out the green profile of Molokai roughly forty miles across the channel. The trip’s short length makes it ideal for visitors who want an easy marine perspective without committing to a full-day charter. Operated as a private sail for up to 15 guests, this outing balances intimacy with room to move. The crew follows the trade winds, so expect a classic sailing rhythm: gentle heel, crisp salt air, and the soft music of rigging. Photographers get clean, oblique shots of Diamond Head Lighthouse and the Art Deco lines of the Waikiki Natatorium War Memorial; families appreciate the relaxed pace and frequent opportunities to point out marine life. Practical details matter: the sail is 1.5 hours long, departs daily at 3 PM, and carries a strict 24-hour no-refund, no-cancellation policy, so plan accordingly. The meeting address is 2169 Kālia Rd, Honolulu, HI 96815 — a convenient spot for hotel shuttles and walkers from Waikiki. Bring sun protection, a light windbreaker, and a camera with a polarizer to manage glare. Why book this rather than a crowded tour boat? The Tradewind Sail • Private is about perspective and timing: it’s intimate, short, and tuned to the steady local breeze that makes Hawaiian afternoons reliably picturesque. For travelers with limited time or those seeking a sunset-adjacent sail without an overnight commitment, it’s a smart, photogenic choice that connects you to Oahu’s coastal geology and ocean habits in under two hours. This sail is particularly good for first-time sailors, families with older children, couples looking for a romantic escape, and photographers chasing clean lines and coastal contrast. It doesn’t require prior sailing experience; crew members handle lines and navigation while you relax. Weather and wind determine the exact path, so the captain adapts to sea state for comfort. Note the strict 24-hour cancellation rule and plan accordingly if your schedule is tight. Booking in advance secures preferred departure; trips often fill during high season and holiday windows. For a compact, memorable taste of Oahu’s shore, this sail delivers.