Tradewind Charters
Activities (9)
Direct Booking Guarantee: the tour operator takes your booking and runs your tour. We may earn a commission, never added to your price.
Join a Group
Tradewind Charters runs this shared snorkel cruise from Honolulu's south shore, just a short distance from Waikiki. Guests board the Aloha Kai, a fully equipped vessel with comfortable seating, shade and sundeck areas, and on-board restrooms. The boat travels along the coastline toward Diamond Head before mooring at a snorkel spot where guests can look for Hawaiian green sea turtles, reef fish, and other local marine life. The captain and crew provide basic snorkeling instruction and stay nearby throughout the snorkeling portion. This cruise fits solo travelers, couples, friends, and small families who are comfortable swimming independently in open water. Snorkeling equipment is provided, and the boarding area is handicap accessible. Drinks and snacks are available for purchase on board. Guests should bring swimwear, reef-safe sunscreen, and towels. Light snacks and non-alcoholic beverages are also welcome to bring along. The experience is rated moderate in physical intensity, so guests who are not yet confident swimming in open water should consider that before booking. The tour is weather dependent, meaning conditions may affect departures.
Sailing Instruction “Learn to Sail”
The tour begins at Kewalo Harbor, where guests meet a USCG licensed captain for a safety briefing and sailing overview before heading out. Once underway, participants actively steer the vessel, trim the sails, practice tacking and maneuvering, and learn the vocabulary that goes with each skill. This is a private charter, so the captain shapes the lesson around each group's comfort level, whether that means a relaxed introduction to sailing or more focused technical instruction. The tour suits anyone with basic swimming ability who wants genuine hands-on experience rather than a passive cruise. Physical intensity is moderate, so reasonable fitness helps. Water and soft drinks are provided on board, though meals and gratuity are not included. A catamaran option is also available through the same operator for those who prefer that style of vessel.
Mimosa Sunrise Cruise
The Mimosa Sunrise Cruise is a private charter that departs from Kewalo Harbor in Honolulu before sunrise. Chilled champagne and orange juice are included, served as complimentary mimosas during the outing. The boat travels along the Waikiki coastline with Diamond Head crater coming into view as the sun rises. A USCG licensed captain is at the helm, and the vessel offers ample deck and cockpit seating along with restrooms below deck. This cruise suits romantic couples and anyone drawn to an early morning outing on the water. It also works well for vow renewals or wedding ceremonies at sea. Guests traveling from distant time zones may find the early hour a natural fit for their schedule. Bring sunscreen, a hat, and a camera. The trip is weather dependent, and the duration can be extended after purchase. There is no hotel pickup, so guests should arrange their own transportation to the harbor.
Sunset & Moonlight Cruise
The Sunset and Moonlight Cruise by Tradewind Charters departs from Kewalo Basin, a short distance from Waikiki, and takes small parties or larger groups out on a private sailing yacht or catamaran along the Oahu coastline. The route follows the shore past Diamond Head during golden hour, continues into twilight as Honolulu's city lights come on, and extends into a calm moonlit sail before returning to harbor. A USCG licensed captain and crew are aboard for the trip. Non-alcoholic beverages, stereo sound, and restrooms below deck are included. Alcohol is not part of the base package, though customized bar options can be arranged in advance. Catering carries separate terms. Dress comfortably for an evening on the water, and plan to go barefoot on the smaller vessels. Bringing a camera is recommended. The operator notes that the waters are sheltered and smooth, which can be helpful for anyone concerned about motion sickness. The operator will reach out after booking to coordinate timing around the sunset.
Whale Watching
Tradewind Charters runs this private whale watching charter out of Kewalo Harbor in Honolulu, departing along Oahu's south shore in search of humpback whales. The entire vessel is reserved for your group alone, so there is no sharing the deck with strangers. A sailing yacht or power catamaran can be selected depending on your group's size and preference, and each option comes with an experienced captain and crew on board. Humpback whales visit the Hawaiian Islands seasonally to calve in warm, sheltered waters. During the trip, the crew searches for breaches, tail slaps, and mother-and-calf interactions. Dolphins, sea turtles, and manta and eagle rays are also frequently spotted along the way. The crew shares information about whale behavior and the local marine environment throughout the outing. Water and soft drinks are included.
Reef Fishing
Reef Fishing with Tradewind Charters departs from Ala Moana Boulevard in Honolulu and heads out to coral and lava rock reefs sitting in clear, shallow water. Sea turtles frequent the area, and monk seals and eagle rays occasionally appear at the surface. The water at the reef location tends to be calm, which makes the outing comfortable for people who are not seasoned sailors. This charter suits families who want to mix light fishing with time on the ocean, and it also works well for family reunions, corporate groups, and pre- or post-wedding gatherings. Several vessel options are available depending on group size, ranging from a sailing yacht to a power catamaran that accommodates larger parties. Longer charter lengths are available beyond the short option, giving groups flexibility. Cancellation details and exact pricing appear on the booking page.
Sea Spa Cruise
The Sea Spa Cruise is a private catamaran charter that combines on-water massage treatments with ocean cruising along the Honolulu coastline, departing from Kewalo Harbor. Tradewind Charters offers several packages to suit different preferences. The Adventure Package boards a sailing catamaran and includes trampoline massages in swimwear, plus time for swimming, snorkeling, standup paddleboarding, and sea scootering. Complimentary mai tais are included across all packages, and light appetizers come with the Luxury and Adventure options. Boogie boards and snorkel gear are provided for the Adventure Package. These are fully private charters suited to couples, families, and groups marking occasions such as birthdays, anniversaries, showers, and bachelor or bachelorette parties. Basic swimming ability is required. Guests arrange their own transportation to the meeting point on Ala Moana Boulevard. Gratuity is not included. Bring sunscreen, a hat, towels, and a camera. Swimwear is recommended for trampoline massages, while table massage guests receive robes.
Fireworks Cruise
The Fireworks Cruise by Tradewind Charters departs from Kewalo Basin, a short distance from Waikiki, on Friday nights. The private charter takes guests out along the Oahu coastline by catamaran, passing Honolulu city lights and Diamond Head before positioning offshore to watch the Hilton Hawaiian Village fireworks show from the water. Non-alcoholic beverages and snacks are included. The route follows the Waikiki coastline during sunset, so guests catch the shifting light over the city before the fireworks begin. The trip ends with a return to Kewalo Harbor. This charter suits anyone who wants to watch the Friday night fireworks away from shore crowds, on a private boat with their own group. Guests should check in at Kewalo Harbor before the vessel departs. Catering beyond the included snacks and non-alcoholic drinks is available as an add-on for larger groups.
Daytime Sailing Charter
The charter is reserved for your group alone, so no other passengers share the boat. Guests can take the helm if they wish, and the vessel anchors at a snorkeling spot during the trip. Manta rays, dolphins, sea turtles, and humpback whales are frequently sighted on the water. The tour suits travelers looking for a low-intensity outing on the ocean. Basic swimming ability is needed since snorkeling is part of the experience. Water and soft drinks are provided on board, though meals and gratuity are not included. Hotel pickup is not available, so plan to make your own way to the meeting point on Ala Moana Blvd. before departure. The charter runs daily and can be extended beyond the standard length if your group prefers a longer time on the water.
About
Tradewind Charters runs private and group sailing experiences from a meeting point on Ala Moana Boulevard in Honolulu. For travelers who prefer not to book a private boat, a group snorkel cruise heads along the south shore coastline to a reef mooring spot where passengers can get in the water. Reef fishing charters are available for families, wedding groups, and corporate parties, with catering and bar options that can be arranged. Hands-on sailing instruction from a licensed captain is another option, covering both monohull and catamaran sailing. Private charters can carry small groups or larger parties depending on the vessel chosen, and the meeting point is the same for all listings.
Tradewind Charters is based in Honolulu, Oahu. Do Oahu lists 9 activities from Tradewind Charters.
Categories: Boat Tours & Cruises, Sunset Cruises and Entertainment.
Listings include Reef Fishing; Join a Group; Sea Spa Cruise; Sailing Instruction “Learn to Sail”; Mimosa Sunrise Cruise; Sunset & Moonlight Cruise; and 3 more.
Open a listing to see its price and duration, then use Check availability to see dates and book with the company directly.