Tradewind Charters
About
Tradewind Charters has been sailing these Honolulu waters for years, and they've got the trade winds figured out better than most. Based right here in Honolulu, they're the kind of local outfit that knows exactly when the wind shifts and where the fish are biting.
You've got nine different ways to get out on the water with them. Want to start your day right? Their sunrise mimosa cruise catches that perfect golden hour light bouncing off Diamond Head. Or maybe you're more of a night person – their fireworks cruises give you front-row seats to Waikiki's Friday night show, with the city lights creating this incredible backdrop.
The fishing here is something else. These guys know the productive spots where the reef fish hang out, and their snorkeling trips will show you coral gardens that most tourists never see. If you just want to sail and feel those trade winds doing what they've done for centuries, their daytime cruises let you disconnect completely. The sunset trips? Pure romance, especially if you spring for a private charter.
What really sets them apart is the crew. These aren't just boat drivers – they're storytellers who'll share the kind of local knowledge you can't find in guidebooks. They keep groups small, so you're not fighting for space or attention. Safety's obviously their priority, but they make it feel effortless.
Both locals and visitors keep coming back, and once you're out there with the wind in your face and Oahu's coastline stretching out before you, you'll understand why.
Activities (9)
Join a Group
Looking to join a group snorkeling adventure without the expense of a private charter? Tradewind Charters' shared afternoon cruise is perfect for ocean lovers wanting to explore Honolulu's underwater paradise with fellow travelers at a per-person rate. This 2.5-hour journey departs from 1125 Ala Moana Boulevard—just minutes from Waikiki—making it incredibly convenient for visitors staying in the heart of Honolulu. Aboard the well-appointed Aloha Kai, you'll cruise toward Diamond Head while taking in spectacular coastal views. The vessel comes equipped with comfortable seating, shade areas, a sundeck, and onboard restrooms. Quality snorkeling gear is provided, and handicap accessible boarding ensures everyone can participate. The experienced captain selects prime snorkel spots known for crystal-clear waters where Hawaiian green sea turtles glide alongside vibrant reef fish. Once anchored, the crew provides helpful instruction before you slip into the water. They stay close by to assist anyone who needs support, creating a welcoming environment for swimmers of all experience levels. For safety reasons, this trip is best suited for comfortable swimmers who can swim independently in open water to fully enjoy the snorkeling experience. The onboard bar offers drinks and snacks for purchase, though you're welcome to bring your own non-alcoholic beverages and light snacks. This adventure suits solo travelers, couples, friends, and small families eager to join a group of ocean enthusiasts. Participants must be at least 7 years old and comfortable swimming independently in open water. Don't forget swimwear, reef-safe sunscreen, and towels. Please note: If your group is larger than 5 guests, you'll get a better experience and better value by booking one of their private charters instead. With 4.7 stars from 141 Google reviews, it's an authentic way to experience Oahu's marine life. Full refunds are available with 72 hours advance cancellation notice, making it easy to join a group Honolulu snorkeling adventure.
Reef Fishing
Just 25 minutes from Honolulu harbor, Tradewind Charters offers some of the best reef fishing Honolulu has to offer. Their light spinning tackle approach works perfectly in these crystal-clear waters, where vibrant coral and lava rock reefs sit in just 15-25 feet of water. The calm, protected grounds make this ideal for families, while the exceptional underwater visibility means you'll see every fish before it hits your line. What sets this reef fishing experience apart is the incredible marine life you'll encounter. Hawaiian green sea turtles are frequent visitors to these shallow waters, and you might spot monk seals or eagle rays gliding beneath your boat. The smooth conditions keep everyone comfortable, from kids to grandparents, while the proximity to coral formations guarantees steady action on your spinning gear. Tradewind runs three vessels to fit any group size. Their intimate 43-foot sailing yacht accommodates up to 6 people, perfect for close-knit families. Mid-sized groups of up to 12 can book the 40-foot sailing catamaran, while their spacious 50-foot power catamaran handles up to 49 people for larger celebrations. Daily departures at 8AM, 11AM, and 2PM give you flexibility, with standard 3-hour charters plus extended 4, 6, and 8-hour options available every day. Whether you're planning a family reunion, corporate outing, or wedding party adventure, these reef fishing Honolulu charters can include catering, bar service, and transportation. Starting from $895 for up to 6 people, it's an accessible way to combine fishing with sightseeing and marine wildlife watching. The operator requires 72-hour cancellation notice for full refunds and provides complete refunds for weather-related cancellations.
Sea Spa Cruise
Nothing beats floating across Oahu's turquoise waters while getting a professional massage—which is exactly what makes Tradewind Charters' sea spa cruise Honolulu experience so special. Choose between their 50-foot power catamaran Aloha Kai or 40-foot sailing catamaran Sea Scape, each offering a completely different way to unwind on the water. The Relaxation Package gives you 1.5 hours of pure bliss: a private cruise with 60-minute massages on actual massage tables, complete with bathrobes and linens. Step it up with the Luxury Package for a 2-hour cruise featuring 90-minute massages, complimentary pupus, and dedicated time to watch the sunset paint the sky. Adventure seekers will love the Adventure Package—either a 2-hour sunset sail or 3-hour daytime excursion where you'll get your massage right on the vessel's trampolines while enjoying swimming, snorkeling, stand-up paddleboarding, sea scootering, and whale watching. Every charter comes with complimentary Mai Tais and works perfectly for couples' getaways, family bonding time, or celebrating birthdays, anniversaries, showers, and bachelor or bachelorette parties. Both fully equipped catamarans feature shaded and open deck areas plus onboard restrooms. The Adventure Package includes boogie boards, snorkeling gear, and water toys, while Luxury and Adventure packages come with light appetizers. Here's what to expect: trampoline massages on Sea Scape require swimwear, while Aloha Kai's table massages provide bathrobes and linens for privacy. Licensed massage therapists and USCG licensed captains handle everything professionally. Starting from $1,050 for two guests, these private sea spa cruise Honolulu charters accommodate up to 6 guests on power catamaran packages or up to 12 on the Adventure Package. Just bring hats, swimwear, sunscreen, and towels. Full refunds available with 72 hours advance cancellation notice.
Sailing Instruction “Learn to Sail”
Master the art of sailing with hands-on sailing instruction "learn to sail" Honolulu experiences aboard luxury yachts in Oahu's pristine waters. Tradewind Charters delivers comprehensive sailing lessons led by USCG licensed Captains — your chance to develop real sailing skills while exploring Hawaii's stunning coastline. Two distinct sailing experiences await, each designed for hands-on learning. The monohull option puts you aboard a luxury equipped sloop rigged Jeanneau 43' sailing yacht. You'll take the helm, trim the sails, and practice essential maneuvers like tacking while mastering sailing vocabulary. Prefer something different? The catamaran instruction utilizes a 40' Scape Sailing Catamaran, delivering exciting speed and performance with easy sail trimming and thorough training techniques. Every 3-hour session is intentionally limited to just 4 guests, guaranteeing personalized attention and maximum hands-on opportunity with your USCG licensed Captain instructor. This intimate group size creates the perfect learning environment as you practice maneuvering techniques and build confidence handling a sailing vessel. You'll meet at Kewalo Harbor, which provides convenient access to Honolulu's prime sailing waters. Starting from $595 for the monohull experience or $995 for catamaran instruction, these sailing lessons deliver exceptional value for hands-on yacht training. Your experience includes all necessary sailing instruction and equipment use during the 3-hour session. Flexible cancellation policies offer full refunds with 72 hours notice, while instant confirmation secures your spot immediately upon booking. Whether you're a complete beginner or looking to refine existing skills, this professional sailing instruction "learn to sail" Honolulu program provides the foundation for a lifetime of sailing adventures in Hawaii's spectacular waters.
Sunset & Moonlight Cruise
There's something magical about watching the sun dip into the Pacific while Honolulu's lights begin to twinkle across the shoreline. Tradewind Charters delivers this experience with intimate 2-hour private charters starting from $595, taking you out on sheltered waters where seasickness isn't a concern. Your sunset & moonlight cruise Honolulu adventure begins as you sail past Oahu's dramatic coastline with panoramic views stretching in every direction. Keep your eyes peeled for dolphins and sea turtles – during whale season, you might even spot humpbacks breaching in the distance. As darkness settles in, the real show begins: Honolulu transforms into a sparkling jewel against the black ocean, followed by fireworks displays that look absolutely spectacular from your unique vantage point on the water. Tradewind offers three vessels to match your group size. The sailing yacht handles up to 6 passengers ($595), the sailing catamaran accommodates up to 12 ($995), and their power catamaran takes 7-49 passengers ($750 per hour). All departures are from Kewalo Basin – just minutes from Waikiki – with timing perfectly coordinated for optimal sunset viewing. Every charter includes a USCG licensed captain, non-alcoholic beverages, and a quality sound system. The yachts feature comfortable seating areas plus restrooms below deck. Plan to go barefoot on the smaller vessels, and definitely bring your camera – these views are Instagram gold. Want to make it extra special? They offer optional limousine service for worry-free transportation, plus customized bar service with advance notice. Groups of 20 or more can arrange catering too. This sunset & moonlight cruise Honolulu experience combines the best of tropical sunsets, city lights, and ocean magic into one unforgettable evening on the water.
Daytime Sailing Charter
Experience authentic blue-water sailing in Hawaiian waters with Tradewind Charters' daytime sailing charter Honolulu adventure. These luxury yachts host private parties exclusively—no crowded tour boats here. It's perfect for visitors wanting genuine sailing in an intimate setting, and yes, you can take the helm during your ocean adventure. You'll have three vessel options: a sailing yacht for up to 6 passengers, a sailing catamaran accommodating 6 guests, or a power catamaran that hosts up to 49 passengers. Each 3-hour charter departs from Honolulu, with extensions available for longer adventures. Daily departures at 8AM, 11AM, and 2PM give you flexible scheduling for morning or afternoon sailing. Honolulu's waters offer exceptional marine life viewing year-round. Dolphins, sea turtles, manta rays, and eagle rays are frequent companions during your charter. Between December and May, humpback whales visit Hawaiian waters—these magnificent 35-50 foot mammals weighing up to 50 tons return annually to give birth in Hawaii's warm, sheltered waters. An exclusive anchorage provides delightful snorkeling opportunities away from the crowds. Fishing enthusiasts will love the reef fishing charters using light spinning tackle in 15-25 feet of crystal-clear water over coral and lava rock reefs. A fish catch guarantee is included. For hands-on learning, USCG licensed Captain/Instructors provide sailing instruction to international standards and issue certificates upon completion. This daytime sailing charter Honolulu experience starts from $750 per hour for the power catamaran option. Full refunds are provided with 72 hours advance cancellation notice or when operators cancel due to weather conditions.
Mimosa Sunrise Cruise
There's something magical about watching the sun rise over Diamond Head while sipping mimosas on the open ocean. This intimate sunrise cruise aboard My Sunshine and Aloha Kai—rated 4.7 stars with 141 Google reviews—is a perfect antidote to jet lag or simply the most memorable way to start any Hawaiian morning. Your USCG licensed captain will reach out to coordinate the ideal departure time, ensuring you're perfectly positioned when dawn breaks over the iconic crater. As the sky erupts in brilliant colors, you'll toast the new day with complimentary mimosas made from chilled champagne and orange juice. The 2-hour private charter accommodates up to 12 passengers, featuring excellent stereo systems, plenty of deck seating, and convenient below-deck restrooms. This mimosa sunrise cruise Honolulu experience creates an unforgettable setting for vows—whether you're getting married or renewing promises with Diamond Head as your witness. The private charter format means no crowds, just you and the Pacific's morning serenity. Available daily, you can extend your time on the water beyond the standard 2 hours if you're not ready to return to shore. Pricing starts from $495 for up to 6 passengers, with options for groups of up to 9 passengers ($795) or up to 12 passengers ($995). Your charter includes the private 2-hour cruise, USCG licensed captain, chilled champagne and orange juice, and use of all onboard amenities. Pack a hat, swimsuit with cover-up, towel, sunscreen, binoculars, and camera to capture those golden moments. With full refunds available with 72 hours notice or for weather cancellations, this mimosa sunrise cruise Honolulu offers a risk-free way to create lasting Hawaiian memories.
Fireworks Cruise
There's something truly magical about watching fireworks explode over Waikiki from the deck of your own private vessel. This fireworks cruise Honolulu experience launches from Kewalo Basin, just minutes from the heart of Waikiki, setting you up for an unforgettable evening on the water. Your 2-hour private charter positions you perfectly for the Hilton Hawaiian Village Fireworks Show, which lights up Friday nights with spectacular color and drama. But the fireworks are just the grand finale – your evening begins with a leisurely sail along Oahu's gorgeous coastline, where dolphins often play in the wake and Hawaiian green sea turtles surface nearby. During whale season, you might even spot humpbacks breaching in the distance. As golden hour approaches, there's nothing quite like watching the sun melt into the Pacific while Honolulu's skyline begins to twinkle. The city transforms before your eyes, creating the perfect backdrop for what's to come. When those first fireworks burst overhead, you'll have the best seats in the house – no crowds, no traffic, just you and your group enjoying an unobstructed view from the water. Tradewind Charters offers three different vessels to match your group size. Their sailing yacht fits up to 6 passengers, perfect for intimate celebrations, while the sailing catamaran accommodates up to 12. Need more space? The power catamaran handles groups of 7-49 passengers with ease. Throughout your cruise, they'll keep you refreshed with complimentary non-alcoholic beverages, and catering is available for groups of 20 or more. Starting from $595, this private fireworks cruise Honolulu adventure requires 72-hour cancellation notice for full refunds. Weather concerns? No problem – they'll refund you completely if conditions force them to cancel, giving you confidence when booking this spectacular way to experience Honolulu's weekly fireworks show.
Whale Watching
Skip the crowded tour boats and discover whale watching Honolulu the way it should be experienced – aboard your own private yacht with Tradewind Charters. These luxury sailing adventures depart from Kewalo Harbor, giving you exclusive access to witness Hawaii's magnificent humpback whales without fighting for a spot at the rail. Every December through May, these incredible 35-50 foot giants make their annual pilgrimage to Hawaii's warm waters. Weighing up to 50 tons, these intelligent mammals return here to give birth and nurture their newborns – a spectacular natural cycle that's been playing out for generations of this endangered species. Your 2-hour private charter isn't just about whale watching. You'll experience real sailing (even take the helm if you're feeling adventurous), plus frequent encounters with dolphins, sea turtles, manta rays, and eagle rays. The captain will anchor at an exclusive spot perfect for snorkeling, turning your whale watching Honolulu adventure into a complete marine experience. With departures at 6AM, 8AM, 10AM, 2PM, and 4PM, you can easily find a time that works. Want to stay out longer? Extensions beyond the standard 2-hour duration are available. Three vessel options accommodate different group sizes: sailing yacht from $595 for up to 6 passengers, sailing catamaran from $995 for up to 12 passengers, or power catamaran from $1,495 for up to 49 passengers. All charters leave from Honolulu's Kewalo Harbor. The beauty of going private means no rushing, no crowds, and no sharing your whale encounters with strangers. Plus, you'll get full refunds for cancellations made 72 hours ahead or weather-related operator cancellations. This is how locals would choose to experience Hawaii's marine life – intimately and on your own terms.