Waikiki Day & Sunset Sail For Couples

Departing from Ala Wai Boat Harbor, this couples sail travels along the Waikiki coastline past Diamond Head Crater. A USCG licensed captain handles the boat for the duration of the trip. Because hotel pickup is not provided, arranging transportation to the harbor meeting point ahead of time is a good idea. The private format means the itinerary can be adjusted to suit personal preferences, and the operator notes that the experience can be extended or modified based on what a couple wants from their time on the water. Bringing a camera, a light jacket, and sunscreen is recommended for comfort on the water. Weather conditions such as strong winds, high waves, or heavy rain may lead the operator to cancel a trip. In that situation, guests receive a full refund or the option to reschedule. Outside of weather-related cancellations initiated by the operator, any change or cancellation request must be submitted before the cutoff window stated on the booking page.

Sunrise Turtle Snorkel

Sunrise Turtle Snorkel departs from Alawa'i Boat Harbor on a sailing vessel, heading along the Waikiki coast toward Diamond Head to reach the Turtle Canyon snorkeling site. The spot is known for sea turtles that float above the reef while fish swim around them and clean their shells. A snorkeling guide accompanies the group, and all snorkeling gear, water, soda, and juice are provided. This tour suits early risers, couples, and families. On the return trip to the harbor, spinner dolphins are often seen playing around the boat during these early morning hours. Bring swimwear, a towel, reef-safe sunscreen, and a camera. The tour is weather dependent, and the operator may contact guests to reschedule or cancel if conditions are unsafe.

Diamond Head Sail & Swim

Diamond Head Sail and Swim departs from Ala Wai Boat Harbor and heads along the Waikiki coastline, continuing past Diamond Head Crater before returning to drop anchor near Waikiki Beach for a swim and snorkel session in the Pacific Ocean. The tour runs on a yacht with a USCG licensed captain aboard. Snorkel gear is provided, so there is no need to bring equipment. Basic swimming ability is required to participate in the water portion. The tour suits couples, families, and small groups looking for a relaxed time on the water. Private tours can be extended or customized based on the group's preferences. There is no hotel pickup, so plan to meet at Ala Wai Boat Harbor. Bring swimwear, a towel, reef-safe sunscreen, and a camera. The operator may cancel due to weather conditions such as strong winds, high waves, or heavy rain, and will offer a full refund or the option to reschedule in those cases.

Special Events

Waikiki Sailing Tours offers private sailing charters aboard a vessel called The Universe, designed for groups marking a meaningful occasion. A USCG licensed captain handles the sailing so the group can focus on the event itself. The charter can be tailored to fit many types of gatherings, including weddings, anniversary celebrations, birthday parties, proposals, bachelor and bachelorette parties, corporate events, and memorials including committal of ashes. The operator can extend, customize, or modify the experience based on what the group needs. Because physical demands are minimal, the trip suits people who want a relaxed sailing experience rather than an active outing. Groups planning a specific event will want to communicate their needs in advance so the experience can be shaped accordingly before departure.