THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Set sail from Haleiwa on Oahu's North Shore for a private whale watching adventure where you can witness humpback whales breaching and playing in their natural habitat. Discover why this exclusive charter offers one of Hawaii’s most memorable wildlife experiences.
Set sail from Haleiwa on Oahu's North Shore for a private whale watching adventure where you can witness humpback whales breaching and playing in their natural habitat. Discover why this exclusive charter offers one of Hawaii’s most memorable wildlife experiences.
Verified experiences and guided adventures in the surrounding area.
Operated by North Shore Sailing Adventures · Haleiwa, Hawaii
easy.
3–4 hours.
No advanced fitness required; brief periods of standing and walking onboard are expected.
The best time is from November to April when humpback whales migrate to Hawaii's warm waters for breeding and calving.
The tour typically lasts about 3 to 4 hours, giving ample time to locate and observe whale behavior.
Yes, private charters accommodate up to six people, offering a personal experience great for families and small groups.
You may also spot spinner dolphins, sea turtles, and various seabirds during the trip.
While the boat is relatively accessible, guests with mobility issues should check in advance to ensure comfort and safety.
Typically, charters allow snacks and non-alcoholic beverages; check specific guidelines during booking.
The North Shore has been central to Hawaiian maritime culture for centuries and became a protected area to conserve marine life.
Operators follow strict guidelines to minimize disturbance to whales and protect the ocean environment under Hawaiian marine regulations.
North Shore Sailing Adventures is a private sailing operator based in Haleiwa, Hawaii, offering small-group charters along Oahu’s North Shore. The company provides a range of private trips—including the TBR Romance Cruise, Sunset Sailing Adventure, TBR Half-Day Private Charter, Full Day Private Charter: Waimea Bay, Sailing Adventure, Dolphin Watching Adventure, and Whale Watching Adventure—designed for up to six guests per vessel. Trips range from three-hour sunset and romance cruises to four-hour whale watching and half-day sails, plus a six-hour full-day charter to Waimea Bay for swimming, snorkeling, and anchoring in calm waters. Crews provide real sailing experiences and on some trips naturalist-style commentary and a hydrophone for listening to whales. Whale watching is available during Oahu’s humpback season (November through April). Guests are invited to bring their own food and beverages on many private charters for personalized celebrations such as honeymoons, engagements, and family outings. Safety and comfort are central: trips are private charters accommodating up to six passengers to maintain an intimate experience, and activities include snorkeling, wildlife viewing, and relaxation on the water. Bookings typically cover private time aboard a sailing vessel with options for sunset, wildlife-focused, and full-day itineraries. North Shore Sailing Adventures positions itself as a local operator focused on personalized, small-group sailing experiences that showcase the natural beauty of Oahu’s North Shore while providing informative and memorable outings for visitors and residents alike. Reservations are available online or by phone via The Adventure Collective listing; itineraries can be customized to match guest interests and schedules.
Book with North Shore Sailing Adventures