Sailing Trips in Oahu
Top 10 Best Oahu Sailing Trips
Found 67 Sailing Trips activities in Oahu. Sort by Popularity. - Page 29am Turtle Canyon Snorkel Adventure
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

9am Turtle Canyon Snorkel Adventure
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Oahu
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Superb259 reviews4.9
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
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

BYOB Friday Night Fireworks Cruise
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Oahu
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Exellent6 reviews4.3
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....
Private Catamaran Charter in Waikiki (1-6 Guests)
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More
Private Tour

Private Catamaran Charter in Waikiki (1-6 Guests)
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Oahu
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Superb18 reviews5
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....
Private Tour
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
Private Tour

Small Group Waikiki Sunset Sailing Tour
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Oahu
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Superb100 reviews4.9
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....
Private Tour
Sunset sail Aboard Manakai Catamaran
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a smaller guest capacity and open-deck layout, it offers an intimate, lai... More
Private Tour

Sunset sail Aboard Manakai Catamaran
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Oahu
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Superb100 reviews4.9
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....
Private Tour
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More
Private Tour

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu
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Oahu
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Superb17 reviews4.7
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (LÄ“â€....
Private Tour
Friday Night Firework Cruise in Waikiki
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More
Private Tour

Friday Night Firework Cruise in Waikiki
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Oahu
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Superb23 reviews4.7
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....
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
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
Private Tour

Polynesian Canoe Day Sail
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Oahu
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Superb28 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Private Tour
12pm Turtle Canyon Snorkel Adventure
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More
Private Tour

12pm Turtle Canyon Snorkel Adventure
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Oahu
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Superb292 reviews4.8
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
Private Tour
#1 eFoil 2 hr group + 2 hr wing foil or windsurf or kayak lesson
You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed so you learn faster and safer. We will share with you the best locations to launch f... More
Private Tour

#1 eFoil 2 hr group + 2 hr wing foil or windsurf or kayak lesson
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Oahu
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Superb4 reviews5
You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets he....
Private Tour
Waikiki 3pm Tradewind Sail - Open Bar Included w/ General Ticket
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 dolphin... More
Private Tour

Waikiki 3pm Tradewind Sail - Open Bar Included w/ General Ticket
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Oahu
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Superb239 reviews4.8
Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise ....
Private Tour
Sunset Party Cruise–DJ, Trampoline, BYOB & Cocktails (18+)
This is not your average sunset cruise — it’s a party made exclusively for adults 18 and older. Our Disco Sunset Party Cruise blends the thrill of ocean adventure with vibrant party energy. You’ll kick off the evening with ... More
Private Tour

Sunset Party Cruise–DJ, Trampoline, BYOB & Cocktails (18+)
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Oahu
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Superb239 reviews4.8
This is not your average sunset cruise — it’s a party made exclusively for adults 18 and older. ....
Private Tour

Waikiki Fireworks Cocktail Cruise
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Oahu
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Very Good4 reviews4
Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....
Private Tour
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 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

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
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Oahu
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Superb1 review5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
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
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
Waikiki Friday Night Fireworks Boat Cruise on O'ahu
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

Waikiki Friday Night Fireworks Boat Cruise on O'ahu
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Oahu
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Exellent27 reviews4.5
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....
Private Tour
3 Hour Luxury Private Sailing Catamaran for 7-12 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

3 Hour Luxury Private Sailing Catamaran for 7-12 People
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Oahu
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Exellent27 reviews4.5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
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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Superb13 reviews4.6
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....
Private Tour