Oahu Sailing
Set sail on the sparkling waters of Oahu and experience the island from a whole new perspective. Oahu sailing tours offer a perfect mix of relaxation and adventure, taking you along the stunning coastline with views of Diamond Head, Waikiki Beach, and beyond. Choose from a variety of options, including daytime sightseeing cruises, romantic sunset sails, or exhilarating snorkeling adventures. Many tours feature comfortable catamarans, friendly crews, and complimentary refreshments, making your journey as enjoyable as the destination itself. Feel the ocean breeze and soak in the beauty of Hawaii's tropical paradise as you glide across the water.
Oahu sailing experiences are perfect for couples, families, or solo travelers looking for a memorable adventure. Some tours even include whale watching during the winter months or live music and dining for an extra special touch. Whether you're chasing a vibrant sunset or simply relaxing under the Hawaiian sun, sailing in Oahu offers an unforgettable way to connect with the magic of the islands and create memories that will last a lifetime.
Featured Oahu Sailing Tours
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll get splashed if you decide to give it a...
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oahu’s iconic Coast, you’ll find...
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will bring a calmness and serenity like no...
Polynesian Canoe Sunset Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and become immersed in the stories and...
Sunset Boat Cruise: Swim and Cruise Waikiki
There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the ocean, with the iconic Waikiki coastline as your backdrop. As the sun begins to set, you'll be surrounded by the...
Waikiki 3pm Tradewind Sail - Open Bar Included
Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoon in the sun. We'll be keeping a sharp eye out for dolphins, whales and other sea life while...
Waikiki Beach Sunset Sail
Join us on Ke Kai for a 90-minute popular sunset sail departing directly off of Waikiki Beach! Enjoy a stunning Hawaiian sunset on a yellow and purple 49-passenger catamaran with complimentary drinks! Set sail on the high seas and enjoy tasty beverages, great views of...
Waikiki Sunset Cocktail Sail with Open Bar
This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruise! Strangers become fast friends on this one regardless if your cruising solo or with a crew! We provide juice, soda, bottled water, wine, champagne, and a variety of...
More Oahu Sailing Tours to Inspire Your Trip
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)
Polynesian Canoe Day Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and become immersed in the stories and...
Polynesian Canoe Morning Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and become immersed in the stories and...
Waikiki Signature Sunset Catamaran Sail
Experience a Hawaiian sunset like no other on a cocktail cruise along Oahu's coast. Departing from Waikiki and heading toward Diamond Head, this catamaran journey offers breathtaking views as the sun sets over the horizon. Enjoy complimentary local beer, signature...
West Oahu Sunset Cocktail Cruise with Appetizers
Nothing beats a Hawaiian sunset at sea. Enjoy a scenic cruise of the West Oahu coast, catching the moment the sun slips below the horizon – you may even see the green flash. Array of “pupus.”
Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that she was designed with three separate...
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views of Diamond Head, and rolling waves!...
Friday Fireworks Cruise in Oahu, Hawaii
Discover the beauty and serenity of Waikiki and Honolulu on the water with Pacific Luxury Yacht Charters. Perfect for family and friends looking to elevate their visit to Oahu, celebrate a special occasion, entertain guests, or simply escape the hustle and bustle, we...
Private Luxury Sunset Cruise in Waikiki
Experience the ultimate luxury and exclusivity with a private yacht cruise in Waikiki, where you can bask in the breathtaking beauty of the Hawaiian sunset against the backdrop of the iconic Waikiki skyline coming to life with shimmering lights. With a maximum of six...
1-Hour Diamond Head Sail of Waikiki Beach
Join us for a 1-hour fun-filled sail departing directly off of Waikiki Beach! Enjoy a breezy midday diamond head sail with complimentary drinks on a big yellow and purple catamaran! Set sail on the high seas and enjoy complimentary beverages of all kinds, great views of...
Frequently Asked Questions
What types of sailing tours are available on Oahu?
Options include daytime sailing, sunset cruises, snorkeling sails, whale watching sails (in season), and private charters.
Where do sailing tours usually depart from?
Most tours depart from Waikiki, Kewalo Basin Harbor, or Ko Olina on the west side of the island.
Do I need sailing experience to join a tour?
No experience is needed. All tours are crewed and include safety briefings and full guidance.
What should I bring on a sailing tour?
Bring sunglasses, sunscreen, a light jacket, and a camera. If the tour includes swimming or snorkeling, bring swimwear and a towel.
Are food and drinks provided on board?
Many sailing tours include snacks, beverages, or even full meals, especially on sunset or dinner cruises. Check the tour description for details.