Located in Honolulu, Hawaii, Catamaran Kepoikai II is Waikiki’s original and longest-running catamaran, sailing since 1977. Hand-built by Captain Don Lipton, this 42-foot Hawaiian-style catamaran carries a rich legacy of aloha and ʻohana, offering an authentic sailing experience along the iconic shores of Waikiki Beach. With over 50 years of combined crew experience, the vessel is USCG certified for up to 37 passengers and features dual hulls with splash nets, providing a unique and comfortable way to enjoy the ocean. Its signature blue and white sails are a familiar sight on Waikiki Beach, and the boat is regularly maintained to meet the highest safety standards. The catamaran offers a variety of sails including four daily one-hour day sails, a daily sunset sail, and private charters for groups up to 37 guests. Passengers can enjoy stunning views of Diamond Head, the Honolulu skyline, and seasonal marine life such as humpback whales, dolphins, and sea turtles. Drinks are available for purchase onboard, or guests may bring their own non-glass beverages. The experience is suitable for all ages and occasions, from romantic evenings and family outings to corporate events and celebrations, all guided by a friendly and knowledgeable crew dedicated to sharing the beauty and spirit of Waikiki.

Tradewind Charters is a premier private sailing and charter service based in Honolulu, Hawaii, offering over 25 years of experience under the leadership of Captain Ken Middleton. Specializing in luxury yacht charters, the company provides an intimate and crowd-free experience on the waters surrounding Oahu. Their fleet includes well-equipped sailing yachts and catamarans that depart from Kewalo Basin, just minutes from Waikiki, allowing guests to enjoy the natural beauty and marine life of Hawaii in comfort and style. Tradewind Charters is distinguished by its personalized service, knowledgeable captains, and a variety of tailored adventures that showcase the islands’ stunning coastline and vibrant ocean ecosystem. The company offers a diverse range of activities including private daytime sailing and snorkeling charters, whale watching, fishing excursions, sunset and moonlight cruises, and sailing lessons. These experiences cater to couples, families, groups, and corporate clients seeking memorable ocean adventures or special event celebrations such as weddings and parties. Guests can expect fully equipped vessels with amenities like onboard restrooms, snorkeling gear, and complimentary beverages, along with expert instruction and guidance from USCG licensed captains. Whether sailing at dawn to witness a Hawaiian sunrise or enjoying a peaceful evening cruise under the stars, Tradewind Charters delivers a personalized and immersive way to explore Hawaii’s clear blue waters and abundant marine life.

Located in Honolulu, Hawaii, this sailing company offers an authentic and adventurous experience on the waters of Oahu. Operating from Kewalo Basin Harbor, their vessel, the Honu, is a Corsair F-31R racing trimaran known as the fastest sailboat available for charter in Hawaii. With a maximum capacity of six guests, the trimaran provides an intimate setting that allows passengers to feel connected to the ocean and the natural surroundings. The owners and captains bring a deep passion for sailing, emphasizing a personalized and invigorating journey that highlights the beauty of the Waikiki coastline and the iconic Diamond Head. The company offers a variety of sailing adventures tailored to different interests and schedules. Guests can choose from a two-hour sail and swim tour that includes anchoring in calm waters for swimming and wildlife viewing, a 1.5-hour sunset sail showcasing the Honolulu cityscape and Hawaiian sunset, or private charters that allow for a customized ocean experience along Oahu’s south shore. The trips are designed to be exhilarating yet relaxing, providing opportunities to see sea turtles, seabirds, and tropical fish while enjoying the thrill of sailing on a high-performance trimaran. This service caters to travelers seeking both adventure and tranquility on the Pacific.

Located in the Ala Wai Boat Harbor in Waikiki, Hawaii, Pau Hana Sailing specializes in private catamaran charters that offer an intimate and luxurious way to explore the scenic coastline of Waikiki and beyond. With a focus on personalized experiences, the company caters to groups of up to 12 passengers, providing a smooth and comfortable sailing adventure aboard a well-equipped performance catamaran. The experienced crew, led by Captain Jason Rose, brings extensive knowledge of local marine life and sailing conditions, ensuring a safe and engaging journey. Unique features such as a large shaded cockpit, front lounging nets, and easy access to swimming and snorkeling areas set this charter apart from typical tours. Pau Hana Sailing offers a variety of customizable excursions including sunset cruises, swim and snorkel trips, morning wildlife viewing, and Friday night fireworks sails. Guests can enjoy snorkeling gear, a floating magic carpet, and warm freshwater showers, enhancing comfort and convenience on the water. The charters are ideal for families, couples, and special occasions such as proposals, vow renewals, and family celebrations. With options to bring personal food and beverages or select from a chef-curated menu featuring local ingredients, the experience is tailored to each group’s preferences. The attentive crew is dedicated to creating memorable moments while highlighting Hawaii’s natural beauty and marine wildlife.

The Hawaii Yacht Club, located in Honolulu, Hawaii, offers a distinguished sailing experience with a rich tradition in yachting. Established as a premier club, it provides members with access to well-maintained facilities and a vibrant community of sailing enthusiasts. The club is known for its commitment to fostering seamanship and competitive sailing, making it a unique destination for both novice and experienced sailors. Its prime location in Hawaii allows for exceptional access to some of the most scenic and challenging waters in the Pacific. The club offers a range of activities including organized regattas, social events, and sailing instruction tailored to various skill levels. Members can enjoy access to a fleet of boats and participate in family-friendly events that promote camaraderie and skill development. The experience at the Hawaii Yacht Club is both social and educational, appealing to individuals and families who appreciate the maritime lifestyle. With a focus on community and excellence, it provides a comprehensive yachting environment in a stunning island setting.

Honolulu Sailing Company, located in Honolulu, Hawaii, has been providing premier yacht chartering services for over 50 years. Specializing in private sailing cruises, snorkeling tours, whale watching, and sunset sails, the company offers a unique way to explore the scenic coastline of Oahu, including iconic landmarks such as Waikiki Beach and Diamond Head. Their fleet of luxury yachts, ranging from 43 to 50 feet, is maintained to the highest standards, ensuring a comfortable and safe experience. The crew, composed of USCG Licensed Captains and experienced staff, brings extensive local knowledge and a commitment to personalized service, making each voyage memorable. The company’s offerings cater to a wide range of customers, from families and friends seeking leisurely snorkeling adventures to avid anglers interested in offshore sport fishing. Popular excursions include the Waikiki Sail & Snorkel Adventure, Diamond Head Sunset Cruise, and private whale watching tours, all designed to showcase Hawaii’s vibrant marine life such as dolphins, sea turtles, and humpback whales. Additionally, Honolulu Sailing Company provides ASA Certified sailing instruction for all skill levels, as well as event planning services for special occasions like weddings and memorials at sea. Each trip emphasizes relaxation and discovery, with captains guiding guests to prime locations while handling all logistics.