Sailing Trips in Oahu
Top 10 Best Oahu Sailing Trips
Found 65 Sailing Trips activities in Oahu. Sort by Popularity. - Page 2Waikiki Sunset Boat Cruise
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More

Waikiki Sunset Boat Cruise
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Oahu
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Superb20 reviews5
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....
Sunset Sail Experience by Catamaran in Waikiki
Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu skyline from offshore Waikiki and feel the warmth of the setting Hawaiian sun and tropical ... More

Sunset Sail Experience by Catamaran in Waikiki
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Oahu
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Superb5 reviews5
Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....
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 b... More

Polynesian Canoe Sunset Sail
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Oahu
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Superb121 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
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 b... More
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Polynesian Canoe Day Sail
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Oahu
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Superb26 reviews4.8
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Free Cancellation
(Saving 10% )
Small Group Waikiki Sunset Sailing Tour
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More

Small Group Waikiki Sunset Sailing Tour
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Oahu
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Superb93 reviews4.9
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....
Private Catamaran Charter in Waikiki (7-12 Guests)
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot ca... More
Private Tour

Private Catamaran Charter in Waikiki (7-12 Guests)
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Oahu
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Superb93 reviews4.9
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....
Private Tour
Private Catamaran Sunset Sail in Waikiki
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large ... More
Private Tour

Private Catamaran Sunset Sail in Waikiki
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Oahu
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Superb7 reviews5
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....
Private Tour
Waikiki small group turtle snorkeling & sailing
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More
Private Tour

Waikiki small group turtle snorkeling & sailing
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Oahu
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Superb69 reviews5
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....
Private Tour
Oahu 3pm Tradewind Sail from Honolulu
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 getting as close as possible so you c... More
Private Tour

Oahu 3pm Tradewind Sail from Honolulu
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Oahu
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Superb234 reviews4.8
This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoo....
Private Tour

Waikiki Fireworks Cocktail Cruise
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Oahu
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Very Good3 reviews4
Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....
Private Tour
2-Hour Oahu Sunset Catamaran Sail
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for... More
Private Tour

2-Hour Oahu Sunset Catamaran Sail
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Oahu
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Superb103 reviews4.9
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....
Private Tour
BYOB Friday Night Fireworks Cruise
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More
Private Tour

BYOB Friday Night Fireworks Cruise
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Oahu
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Exellent5 reviews4.2
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....
Private Tour
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise lets you see whales (December through March), fish, even green s... More
Private Tour

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
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Oahu
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Superb12 reviews4.6
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....
Private Tour
Waikiki Sunset Cruise and Iconic Views with Swimming
Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide along the iconic Gold Coast as the sun sets, painting the sky with vibrant co... More
Private Tour

Waikiki Sunset Cruise and Iconic Views with Swimming
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Oahu
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Superb1 review5
Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in....
Private Tour
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More
Private Tour

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People
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Oahu
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Superb14 reviews4.8
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu
Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback Whale watching at no... More
Private Tour

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu
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Oahu
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Superb27 reviews4.9
Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, ....
Private Tour
South Shore Open Sail from Kewalo Harbor Including Drinks
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! We are a 49-passenger beautiful yellow and red retired Waikiki Beach catamaran now operating from Kewalo... More
Private Tour

South Shore Open Sail from Kewalo Harbor Including Drinks
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Oahu
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Superb15 reviews5
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....
Private Tour
Waikiki Panorama Sail: Search for Hawaiian Sea Turtles
Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Beach and out towards Diamond Head crater. The cruise departs from Kewalo Basin by Ala Moana Beach Park, and includes snacks, non-alc... More
Private Tour

Waikiki Panorama Sail: Search for Hawaiian Sea Turtles
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Oahu
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Superb32 reviews4.7
Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Bea....
Private Tour
Honolulu BYOB Fireworks Boat Cruise
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More
Private Tour

Honolulu BYOB Fireworks Boat Cruise
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Oahu
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Exellent25 reviews4.5
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....
Private Tour
Diamond Head Sunset Sail
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from the... More
Private Tour

Diamond Head Sunset Sail
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Oahu
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Superb15 reviews4.7
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....
Private Tour