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Diamond Head Sunset Sail.Diamond Head Sunset SailDiamond Head Sunset SailDiamond Head Sunset Sail

Diamond Head Sunset Sail

5.0(20 reviews)
486 bookings
Estimated price
USD $195 / hour (2 hours minimum)


Super Owner

Highlight of Hawaii! Immerse yourself in a Hawaiian sunset and see dolphins, sea turtles, and whales in season. Enjoy a 2 hour Idyllic sail aboard a private 43' luxury yacht.  Escape the crowds and enjoy spectacular views of iconic Diamond Head and Waikiki. Honolulu’s city lights provide an enchanting backdrop for your return to port. An experience you don’t want to miss! Departures daily at 5:30pm near Waikiki for sunset cruises. We offer Sunset Sails, Sail & Snorkel Adventures,Whale Watching, Dolphin Quests, Sea Turtle Swims. There is an extra charge of $79 per person for groups over 6.* Large Swim Step with easy water access Accommodates parties up to 12* Bluetooth Speakers Large Shaded Cockpit Warm Freshwater Shower * Groups over 6 are required to complete a Bareboat Agreement and may designate a qualified captain prior to departure. A list of qualified captains will be provided for your convenience. Max Capacity is 12 per USCG regulations. *Additional guests over 6 added after booking are $100.00 per person. If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer.

Captain is included.
A captain is provided by the listing owner to host and operate the trip.
12 guests
Cruising Monohull

Check Availability


5.0 (20 reviews)
  • Listing Accuracy

  • Departure & Return

  • Vessel & Equipment

  • Communication

  • Value

  • Itinerary & Experience

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20 photos have been added by reviewers who booked this listing.
  1. Mia

    Will book again when we come back! Thank you!

  2. Tracie

    Perry was an amazing captain for us. Super friendly and laid back. We had a great time. We would recommend him to anyone.

  3. GA

    The sailing experience was great. I would definitely recommend it to others. Keep it up!!

  4. Bg

    This trip was amazing. Our captain was so friendly. Everything about the night was perfect! So glad we got to sail on the last night of our trip!

  5. VV

    Captain Perry and his main man Tai were great! Highly recommend, the whole experience is great and their knowledge of the vessel and maneuvering the yacht is apparent. Thank you to you both! Even prior to arriving, their operator was great in providing assistance and directions. If you’re looking for a great time, book this experience!



Super Owner

Explore the Wild Side of Hawaii and get ready for a new adventure! We offer private sailing cruises, sunset sails, snorkeling tours, whale watching, proposals, unique weddings, memorial services, and much more. Our carefully selected USCG Licensed Captains and crews with years of boating experience and a wealth of local knowledge will ensure you have the best time on the water. From showing you the best snorkeling spots or choosing the best anchorage for the perfect sunset our crews are here to create a lasting memory! Come sail with us and see the other side of Waikiki you’ve been missing…

Features & Details

  • Bluetooth
  • Life jackets/required safety gear
  • Watersports Equipment
  • Bimini
  • Head
  • Cabin

Approximate Location

You’ll get directions to the departure location when you make a booking.

The boat's approximate location on a map

Cancellation Policy

Full refund up to 7 days prior.

Additional Terms & Information

No refunds are available once a sailing adventure has commenced. Cancelling a booking can result in cancellation fees being applied. The general cancellation policy is as follows: If you cancel at least 7 days in advance of the scheduled departure of your sailing adventure, there is no cancellation fee. When cancelling within 7 days of the scheduled departure, there is a 100% cancellation fee. In case of overnight charters or special requests, an exceptional cancellation policy of 60 days applies. When cancelling any booking you will be notified via email or telephone of the total cancellation fees. 

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