Sail the North Shore with a naturalist and seasonal whale listening
4 hrs
Up to 6 people
Private sail, naturalist
Explore Oahu's North Shore from the water on a private sail for friends and family. Set the experience around your group's preferences, with wildlife viewing opportunities along the way.
Private charters require 7 days' notice for a refund. A 20% fee applies to any canceled private charter. Full refund if the operator cancels due to weather or other unforeseen circumstances.
Haleiwa Harbor, Pier 300, slip 322, 66-105 Haleiwa Rd, 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.
We could not have asked for a better sunset selling experience! Thank you Captain Porter and Ashley! We would come back out with you again and again and again.
Sam Mikelic
July 1, 2026
We could not have asked for a better sunset selling experience! Thank you Captain Porter and Ashley! We would come back out with you again and again and again.
Sam Mikelic
July 1, 2026
Sail Oahu's North Shore at sunset on a private 3-hour charter for up to six.
Private sailing charter on Oahu’s North Shore for up to 6 people
Private North Shore sail to spot dolphins and see Waimea Bay
Private 6-hour sail to Waimea Bay for up to 6 people
Cage dive with sharks off Oahu’s North Shore—no scuba experience needed
Private half-day or full-day fishing out of Haleiwa Harbor