Private sailing charter on Oahu’s North Shore for up to 6 people
1.5 - 6 Hours
Up to 6 people
Private sailing charter, Crew
Explore Oahu’s North Shore on a private sailing charter with options from 1.5 to 6 hours. Sail along the coast for sightseeing, with opportunities for sunset views, swimming, and snorkeling depending on your charter.
The captain may cancel or shift the booking time/day due to inclement weather.
Full refund with 72 hours notice of cancellation. Full refund if the operator cancels due to weather or other unforeseen circumstances. No-shows and late arrivals are charged full price. Private charters require 7 days notice for refund; 20% fee for any canceled private charters.
Meet at Haleiwa Harbor (Pier 300, slip 322). Arrive 10 minutes before your sail time for a meet-and-greet and safety briefing before heading out.
Park anywhere in the parking lot and walk to Pier 300. Walk to the very end of Pier 300 to the T-bone; the boat ("Keet") will be on your right.
Yes. The captain may cancel or shift your booking time/day due to inclement weather.
Pier 300, Haleiwa Boat Harbor, Haleiwa, HI 96712
Captain Porter and his crew, particularly Chad and Will, have built something really special here. Families consistently rave about the intimate, private experience - these aren't crowded cattle boats, with just one family or small groups of up to six guests at a time. The captains bring genuine enthusiasm and deep knowledge of sailing and marine life, expertly navigating to spots where guests regularly encounter dolphins, sea turtles, and during whale season, humpback whales. Multiple reviewers call their trip the highlight of their entire Oahu vacation. The operation runs smoothly from start to finish. Communication is excellent, with quick responses to questions and clear instructions. The crew is described as laid-back yet professional, creating a relaxed vibe without any pressure or time constraints. They provide thoughtful touches like homemade lunches, cold drinks, and even raincoats when weather shifts. The trimaran offers plenty of deck space for snorkeling, swimming, and dolphin watching, though there's minimal shade coverage, so bring sun protection. Whether you're booking a snorkeling adventure, sunset sail, or even a proposal, the consensus is clear: this experience delivers unforgettable memories and genuine value.
Porter is the most chill captain I've ever met. He was very flexible, friendly, and knowledgeable. We were a group of 4 and it was perfect. He was able to find us some whales which was amazing!!
John Shupe
April 29, 2026
Porter is the most chill captain I've ever met. He was very flexible, friendly, and knowledgeable. We were a group of 4 and it was perfect. He was able to find us some whales which was amazing!!
John Shupe
April 29, 2026