SAILING CHARTERS

Oahu - Sailing Charters

For those seeking a serene and adventurous experience on the waters surrounding Oahu, sailing charters offer an excellent opportunity to catch the gentle breeze and explore the island's stunning coastline. Here's a closer look at what Oahu sailing charters have See more...

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Waikiki Sailing Tours

Waikiki Sailing Tours in Hawaiʻi

Waikiki Sailing Tours offers unforgettable experiences on the crystal-clear waters off Waikiki Beach. Their tours feature scenic cruises, sunset sails, and snorkeling adventures, providing guests with spectacular views of Diamond Head and the chance to spot local marine life. Aboard comfortable and well-equipped sailboats, these tours epitomize relaxing and picturesque sailing.

Waikiki Turtle Snorkel Adventure with Manakai Catamaran
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Waikiki small group turtle snorkeling & sailing
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Mana Cruises

Mana Cruises in Hawaiʻi

Mana Cruises offers personalized sailing adventures off the coast of Oahu. Guests can enjoy luxurious catamaran experiences, including snorkeling, whale watching, and sunset sails. Each trip is designed to provide a unique and intimate view of Hawaii’s natural beauty, perfect for couples, families, and small groups seeking a memorable ocean journey.

Private Oahu Sunset Charter with Tasting and Drinks
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Three Tiki’s Sailing

Three Tiki’s Sailing in Hawaiʻi

Three Tiki's Sailing provides memorable sailing experiences off the beautiful coast of Oahu. Their catamaran cruises offer guests the chance to enjoy the island's stunning seascapes, snorkel in crystal-clear waters, and relax under the sun. With a friendly crew and tranquil settings, it's a perfect way to experience Hawaiian sailing.

Diamond Head Sailing and Turtle Snorkeling tour in Waikiki
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Sail Hawaiian Style Catamaran

Sail Hawaiian Style Catamaran in Hawaiʻi

Sail Hawaiian Style Catamaran offers a luxurious and relaxing sailing experience on the beautiful waters of Oahu. Guests can enjoy cruising along the scenic coastline, soaking in stunning views, and experiencing the island's marine life. The catamaran provides spacious and comfortable accommodations, with options for snorkeling, sunset cruises, and private charters. Perfect for families, couples, and groups, Sail Hawaiian Style Catamaran ensures an unforgettable and enjoyable adventure on the ocean.

Private Catamaran Charter in Waikiki
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Sail Blue Hawaii

Sail Blue Hawaii in Hawaiʻi

Sail Blue Hawaii on Oahu provides an unparalleled sailing experience, offering guests the chance to explore the island's breathtaking coastlines and clear blue waters. Whether it's a romantic sunset cruise, a private snorkeling adventure, or a relaxing day sail, their knowledgeable captain ensures a personalized and memorable journey across Oahu’s stunning seascape.

Pau Hana Yacht Charters

Pau Hana Yacht Charters in Hawaiʻi

Pau Hana Yacht Charters on Oahu offers luxurious sailing experiences, perfect for sunset cruises, snorkeling adventures, or private celebrations. Their fleet of elegant yachts, combined with exceptional service and stunning ocean views, provides guests an exclusive and memorable way to explore the waters around Oahu.

Luxury Private Sailing Catamaran in Waikiki
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Catamaran Kepoikai

Catamaran Kepoikai in Hawaiʻi

Catamaran Kepoikai in Waikiki offers thrilling sailing experiences along the beautiful Oahu coastline. Their catamaran cruises provide stunning views of Diamond Head and the chance to spot marine wildlife. With sunset sails and snorkeling trips, they cater to both relaxation seekers and adventure enthusiasts looking for a memorable sea adventure.

Oahu Catamaran

Oahu Catamaran in Hawaiʻi

Oahu Catamaran offers a variety of sailing adventures along the beautiful coast of Waikiki. Guests can enjoy activities such as snorkeling, turtle watching, and sunset cruises. These excursions provide a relaxing and scenic way to experience Oahu’s stunning marine life and vibrant sunsets, making them ideal for couples, families, and small groups seeking memorable ocean adventures.

OAHU CATAMARANS Sunset Tour on a 40 Foot Catamaran FOOD & BYOB!!!
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Moana Sailing Co.

Moana Sailing Co. in Hawaiʻi

Moana Sailing Co. offers unique sailing experiences around the picturesque waters of Oahu. Their tours provide an opportunity to enjoy the serene beauty of the ocean, spot local marine life, and witness breathtaking sunsets. Ideal for both romance and adventure, Moana Sailing Co. ensures a memorable sea voyage.

Moana’s Guided Turtle Snorkel & Sailing Adventure at Waikiki
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Whale Watching Experience in Waikiki
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Waikiki Coast Sunrise Sailing Experience
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Ko Olina Ocean Adventures

Ko Olina Ocean Adventures in Hawaiʻi

Ko Olina Ocean Adventures offers exciting marine excursions from Oahu's picturesque Ko Olina coast. Guests can enjoy snorkeling, dolphin and whale watching, and sailing on pristine waters. With professional guides and top-notch equipment, these tours provide unforgettable experiences with the abundant sea life and beautiful coral reefs of Hawaii.

Ko Olina Catamaran Sail and Snorkel
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2-Hour Oahu Sunset Catamaran Sail
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Holokai Catamaran

Holokai Catamaran in Hawaiʻi

Holokai Catamaran offers exceptional sailing experiences off the coast of Waikiki. Guests can enjoy stunning ocean views, snorkeling adventures, and vibrant sunset cruises aboard their spacious and comfortable catamaran. With a friendly crew and a relaxing atmosphere, Holokai Catamaran provides an unforgettable way to explore Hawaii's beautiful waters.

Oahu 3pm Tradewind Sail from Honolulu
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Waikiki Sailing Company

Waikiki Sailing Company in Hawaiʻi

Waikiki Sailing Company offers unforgettable sailing experiences along the beautiful Waikiki coastline. Guests can enjoy scenic sunset cruises, private charters, and snorkeling adventures aboard their comfortable and well-equipped catamarans. With stunning ocean views and professional crew, Waikiki Sailing Company provides a perfect way to explore Hawaii's waters and marine life.

Waikiki Turtle Snorkel Adventure with Manakai Catamaran
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Marine Life Sail Or Trade Wind Sail with the Manakai Catamaran
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Waikiki small group turtle snorkeling & sailing
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Hawaii Nautical

Hawaii Nautical in Hawaiʻi

Hawaii Nautical offers a variety of sailing experiences around Oahu, including scenic cruises, snorkeling adventures, and sunset sails. Guests can enjoy panoramic ocean views, spot marine life, and relax on comfortable catamarans. These tours provide a unique way to experience Hawaii's natural beauty, perfect for couples, families, and small groups seeking memorable ocean adventures.

Hilton Hawaiian Village Sunset Cocktail Cruise
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Waikiki Sunset Cocktail Cruise Including Drinks and Appetizers
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West Oahu Hawaiian Green Sea Turtle, Dolphin Snorkel Sail w lunch
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Hawaiian Sea Turtle Snorkel Sail from Waikiki with Lunch Included
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Afternoon "Honu" Hawaiian Green Sea and dolphin Snorkel and Sail
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Pink Sails Hawaii

Pink Sails Hawaii in Hawaiʻi

Pink Sails Hawaii offers diverse sailing charters along the picturesque Waikiki coastline. Guests can enjoy a variety of experiences, including snorkeling excursions, dolphin watching, and sunset sails. The charters feature comfortable catamarans and provide an ideal way to explore Hawaii’s marine life and stunning views, perfect for couples, families, and small groups seeking a memorable adventure on the water.

Sunset Boat Cruise (Swim & Cruise)
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Na Hoko 2 Catamaran

Na Hoko 2 Catamaran in Hawaiʻi

The Na Hoko 2 Catamaran offers unforgettable sailing experiences around Oahu’s picturesque waters. Guests can enjoy snorkeling, dolphin watching, and sunset cruises aboard this spacious and stable vessel. With expert crew and hospitality, each voyage is a blend of relaxation and adventure, showcasing the best of Hawaii's oceanic beauty.

North Shore Sailing Adventures

North Shore Sailing Adventures in Hawaiʻi

North Shore Sailing Adventures offers a unique opportunity to explore Oahu's legendary North Shore from the sea. Their tours emphasize eco-friendly practices and close encounters with marine wildlife, including dolphins, turtles, and seasonal whales. Experienced captains guide small groups for a personalized and intimate sailing experience, showcasing the area's stunning landscapes and tranquil waters.

Honolulu Sailing Company

Honolulu Sailing Company in Hawaiʻi

The Waikiki Sail & Snorkel Adventure by the Honolulu Sailing Company emphasizes the serene experience of sailing, harnessing the power of the wind for a tranquil and eco-friendly journey along Waikiki's picturesque coastline. Guests enjoy the elegance of smooth sailing aboard a well-equipped sailboat, offering a unique perspective of Hawaii's natural beauty. This adventure combines the joy of sailing with the thrill of snorkeling, creating a memorable maritime experience.

Manu Kai Catamaran

Manu Kai Catamaran in Hawaiʻi

Manu Kai Catamaran offers exciting sailing adventures off the coast of Waikiki. Guests can enjoy activities such as snorkeling, turtle watching, and sunset cruises aboard a spacious catamaran. These experiences provide a relaxing and scenic way to explore Oahu’s marine life and beautiful sunsets, perfect for couples, families, and small groups seeking memorable ocean excursions.

Private 90-Minute Sunset Sail Charter (Kewalo Harbor)
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Private Morning Ceremony Sailing Charter
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Private South Shore Sail Charter
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Tradewind Charters

Tradewind Charters in Hawaiʻi

Tradewind Charters on Oahu offers personalized sailing experiences along the island's stunning coastline. Guests can choose from private sails, snorkeling excursions, sunset cruises, and whale watching tours, all tailored to individual preferences. With experienced crews and well-equipped vessels, Tradewind Charters provides a luxurious and intimate way to explore Hawaii's marine beauty and tranquil waters

Bike Hawaii

Bike Hawaii in Hawaiʻi

Bike Hawaii, known for its bike tours, also offers an exciting adventure that includes biking, snorkeling, and sailing. This comprehensive tour allows participants to explore Oahu's scenic landscapes by bike, enjoy snorkeling in vibrant coral reefs, and experience a relaxing sail along the picturesque coastline, all in one incredible day.

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel
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Diamond Head Sail and Snorkel Adventure
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Waikiki Yacht Charters

Waikiki Yacht Charters in Hawaiʻi

Waikiki Yacht Charters provides luxurious sailing experiences off the coast of Oahu, offering guests the chance to explore Waikiki's iconic skyline and crystal-clear waters from the comfort of a private yacht. Their tailored services include sunset cruises, snorkeling adventures, and whale watching, all guided by skilled crews dedicated to ensuring a memorable and exclusive oceanic adventure.

Aloha Boats

Aloha Boats in Hawaiʻi

Aloha Boats on Oahu specializes in sailing adventures, offering guests the chance to explore the island's beautiful coastline. Their sailing experiences include scenic sunset sails, private charters, and snorkeling excursions. With professional crews and well-maintained yachts, Aloha Boats provides a memorable and relaxing way to enjoy Oahu's stunning ocean views.

1 Hour Diamond Head Sail (Waikiki Beach)
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Kamoauli

Kamoauli in Hawaiʻi

Kamoauli Polynesian Canoe offers a unique Day Sail experience, allowing guests to explore Oahu's waters aboard a traditional Polynesian canoe. This cultural adventure includes learning about ancient navigation techniques, Hawaiian history, and local marine life. The day sail provides an enriching and memorable way to connect with Hawaii's heritage and natural beauty.

Oahu Sailing Charters

For those seeking a serene and adventurous experience on the waters surrounding Oahu, sailing charters offer an excellent opportunity to catch the gentle breeze and explore the island's stunning coastline. Here's a closer look at what Oahu sailing charters have to offer:

Sailing Basics:

Oahu, surrounded by water and winds, is a prime location for sailing enthusiasts. Sailboats, designed to harness the wind and glide on the water, can be found on all coasts of the island. Whether you're looking for a leisurely sailing tour, sailing lessons, or a private charter, Oahu provides a variety of sailing experiences for you and your family.

Trade Winds:

Oahu, like other Hawaiian Islands, is blessed with prevailing trade winds for about 300 days a year. These winds typically blow from the northeast, ranging from 5 to 25 miles per hour. This creates ideal conditions for Oahu sailing charters. Mornings often offer calm or gentle winds suitable for light sailing, while afternoons see the trade winds strengthening, providing a consistent force for sailing vessels. Evenings and sunset times usually bring a return to a gentle breeze.

Departure Points:

Kewalo Basin, located in Honolulu just near Waikiki, is a central departure point for many Oahu sailing charters. Most charters offer pick-up services from Waikiki hotels, making it convenient for visitors. The oceans off Honolulu and Waikiki, while somewhat protected by mountains, still provide an excellent sailing experience, especially in the afternoons.

Oahu's North Shore, particularly Haleiwa, is another starting point for sailing charters. This coastline can offer stiffer winds due to its less protected positioning on the island, directly exposed to prevailing trades. However, winter months may bring giant surf, occasionally affecting or canceling sailing adventures.

Types of Sailing Boats:

Oahu sailing vessels come in various types and sizes, with catamarans being a popular choice. These catamarans range from 35' to 65' in length, accommodating varying passenger capacities from 20 to 80. Charter sailing yachts can provide an exclusive experience, hosting as few as six passengers with amenities comparable to a penthouse condo.

Considerations for Oahu Sailing Charters:

  • Weather Conditions: While Oahu enjoys favorable trade winds, it's essential to be mindful of weather conditions. Winter months, in particular, can bring significant surf, potentially impacting sailing plans.
  • Capacity and Amenities: Choose a sailing charter that suits your preferences regarding group size and onboard amenities. Whether you prefer an intimate experience or a lively group setting, Oahu offers options for every taste.

Embarking on an Oahu sailing charter promises a memorable adventure, allowing you to connect with the beauty of the island from the tranquil vantage point of the ocean.

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