Private Waikiki Sunset Sail to Diamond Head
Private 2-hour couples sail along Waikiki to Diamond Head with sunset views
From$332incl. taxes and fees
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Discover what we've curated for you
Private 2-hour couples sail along Waikiki to Diamond Head with sunset views
Discover what we've curated for you
2 Hours
Up to 2 people
USCG licensed Captain
Celebrate your love on a private sail designed for couples seeking a romantic way to explore Waikiki and enjoy sunset views. Set out from Ala Wai Boat harbor along the coastline past Diamond Head aboard the yacht The Universe.
Couples only; maximum 2 people.
Cancel or reschedule at least 24 hours before your tour. After that, no refunds or rescheduling. If the tour is canceled due to weather such as strong wind, high waves, or heavy rain, you will receive a full refund or may reschedule.
Ala Wai Boat harbor
Captain Tony clearly runs an outstanding operation here, with multiple reviewers praising his sailing expertise, storytelling abilities, and genuine hospitality. He's frequently mentioned by name, along with crew members like Abe, who shines as a snorkel guide with impressive knowledge of marine life. Guests consistently rave about swimming with turtles at Turtle Canyon, often spotting 8-10 during their outings, and appreciate the well-maintained 45-foot yacht that provides an intimate alternative to large group tours. The flexibility stands out too. When weather forces cancellations, Tony works to reschedule and even offers local sightseeing tips. Tours range from sunrise snorkel adventures to romantic sunset sails, with all necessary gear provided. The crew includes certified lifeguards, adding peace of mind for families. One guest did experience seasickness while snorkeling, though the captain handled it compassionately. If you're prone to motion sickness, come prepared. Overall, visitors describe their time on the water as a trip highlight, praising both the spectacular Diamond Head coastline views and the crew's ability to balance professionalism with laid-back island vibes.
We recently did a morning snorkel trip with Waikiki Sailing Company on their catamaran, and it was a really great experience. Check-in is right on the beach about 30 minutes before departure, and after that you walk over to the boat. You can leave your shoes in a bin or bring your own bag to keep them with you. Before we even left the beach, we were incredibly lucky — we saw a whale jumping in the distance! The captain headed that direction, and we got an even closer look at two whales. It was amazing. A little later we also spotted a pod of dolphins, and the captain made sure to follow them just enough so everyone could get great photos. After the wildlife show, we had about an hour of snorkeling at Turtle Canyon. They provided all the gear, which was clean and in good shape. There were two instructors in the water who guided everyone to the best spots to see turtles, which was super helpful. Overall, it was a really fun and memorable morning. We definitely recommend this tour if you’re looking for a snorkel trip in Waikiki!
Kate Full
December 4, 2025
We recently did a morning snorkel trip with Waikiki Sailing Company on their catamaran, and it was a really great experience. Check-in is right on the beach about 30 minutes before departure, and after that you walk over to the boat. You can leave your shoes in a bin or bring your own bag to keep them with you. Before we even left the beach, we were incredibly lucky — we saw a whale jumping in the distance! The captain headed that direction, and we got an even closer look at two whales. It was amazing. A little later we also spotted a pod of dolphins, and the captain made sure to follow them just enough so everyone could get great photos. After the wildlife show, we had about an hour of snorkeling at Turtle Canyon. They provided all the gear, which was clean and in good shape. There were two instructors in the water who guided everyone to the best spots to see turtles, which was super helpful. Overall, it was a really fun and memorable morning. We definitely recommend this tour if you’re looking for a snorkel trip in Waikiki!
Kate Full
December 4, 2025