OAHU SAILING TOURS

Explore the Pacific Paradise from a Whole New Perspective

THE BEST OAHU SAILING TOURS

Set Sail on an Unparalleled Ocean Voyage!

Embark on a captivating Oahu sailing adventure starting with our Diamond Head Sail Tour, where you can admire the iconic volcanic crater while gliding across the crystal-clear waters. Immerse yourself in the Polynesian culture and traditions on the Huakai na Mokulua, a journey aboard a traditional sailing canoe that offers a glimpse into ancient navigation techniques. Witness the breathtaking beauty of a Hawaiian sunset on our enchanting Sunset Cruise, where you can sip champagne and soak in the vibrant colors painting the sky. For an exclusive experience, indulge in a Private Traditional Sailing Canoe charter, where you can customize your itinerary and enjoy a tailored sailing excursion. Don’t miss the chance to create lasting memories and explore the stunning coastline of Oahu on these remarkable sailing tours.

Best Oahu Sailing Tours

Experience the best Oahu sailing tours in this Pacific paradise. With crystal-clear waters and breathtaking beauty, our tours seamlessly blend adventure and relaxation. Discover hidden gems along the coastline aboard luxurious sailboats, guided by experienced captains. Capture the magic of the Hawaiian twilight with our unforgettable sunset sailing experience. Dive into an underwater wonderland with our exhilarating snorkeling adventures. For a personalized and exclusive experience, our private charters provide tailored itineraries and exceptional service. Book your Oahu sailing tour now and create cherished memories in this tropical heaven.

Traditional Polynesian Sailing Canoe

5/5

Enjoy a truly unique native Hawaiian sailing experience…

2 Hrs. Canoe Cruise From Kewalo Basin Harbor
shopping
Guide, Food, Drinks, And Entertainment Included
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$200

Sunset Cruise On A Traditional Sailing Canoe

5/5

Sunset Cruise On A Traditional Sailing Canoe

2.5 Hrs. Canoe Cruise From Kewalo Basin Harbor
guide
Guide, Food, Drinks, and Entertainment Included
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$250

Waikiki Sunset Sail And Pupu Tour

5/5

Relax aboard a 39 foot catamaran and enjoy the sunset from the…

Approximately 2 hours
Views of Waikiki and Diamond Head
from

$90

Diamond Head Sail And Snorkel

5/5
Enjoy Snorkeling And Take In The Picturesque Views Of Diamond…

2 Hrs. Afternoon Snorkel From Kewalo Basin Harbor

Guide And All Equipment Provided

from

$86

Private Experience On A Traditional Sailing Canoe

5/5
Experience this exclusive charter on a traditional sailing canoe….

2 Hrs. Sailing Cruise from Kewalo Basin Harbor

Guide, Food and Drinks Provided

from

$1000

Spirit Of Aloha Adventure Sail

5/5
Take a sail from the Waikiki port to a canyon full of turtles…

1 Hrs. Sunset Sailing From Hilton Pier

Snacks And Drinks Provided

from

$50

Ko Olina Morning Sail And Snorkel

5/5
Sail and snorkel the Oahu Coast on this unforgettable experience….

3 Hrs. Sailing Adventure from Ko Olina Marina

Guide, Food, Drinks and All Equipment Included

from

$179

Ko Olina Sunset Sail

5/5
Enjoy a Hawaiian sunset at sea as you sip on a refreshing…

3 Hrs. Sunset Sail From Ko Olina Marina

Guide, Snacks, Alcoholic Drinks

from

$119

Huaka’i Nā Mokulua (Sailing Canoe)

5/5
Experience sailing on a Hawaiian canoe off the Kailua Coast….

3 Hrs. Traditional Sailing from Kailua

Guide and All Equipment Included

from

$149

Best Oahu Sailing Tours Sites

Explore the best Oahu sailing tour destinations and embark on unforgettable adventures in this stunning Pacific paradise. With our curated selection of destinations, you can immerse yourself in a world of extraordinary experiences tailored to your preferences. Sail across the crystal-clear waters, effortlessly discovering hidden coves, pristine beaches, and breathtaking coastal landscapes. Marvel at the magic of the Hawaiian sunset as it paints vibrant colors across the horizon, or dive into a mesmerizing underwater world, snorkeling amidst vibrant marine life and vibrant coral reefs. With the guidance of our expert guides, you’ll gain exclusive access to insider knowledge and discover the most captivating spots along Oahu’s picturesque coastline.

*The majestic sunset you might catch while joining our sailing tours.

Oahu Sailing Tour FAQs
What Should I Bring On This Tour?

The most important thing is to be comfortable on this tour. Remember to bring your swimwear and a towel, as well as any of the following items:

  • Cover-up clothing
  • Reef-safe sunscreen
  • Hat
  • Sunglasses
  • Camera

You will be sailing on a shoeless boat, so it is also best to wear sandals or slippers that can easily be removed.

Will I Get Seasick?
We generally have very smooth sailing and few issues with seasickness. However, as a precautionary measure, motion sickness medicine taken the night before the adventure solves all worries.
What Are The Chances That The Trip Will Be Canceled Due To Poor Weather Or Sea Conditions?
If the captain feels the weather will affect the safety of our guests, then they will cancel the cruise and guests receive a full refund. Also, staff will do their very best to have you rescheduled on another cruise before you return home. Tropical weather is known for quickly passing rain showers and changing weather conditions. Because of this, our captains address weather concerns on the day of the cruise.
Is Your Crew Trained In First Aid And Emergency Response?
Yes, our captains and crew take Coast Guard-certified first aid and emergency response courses.
Do I Need To Know How To Swim To Participate In This Tour?
It is not necessary that you know how to swim for this tour, however, we require all guests to wear lifejackets.
Similar Tours to Sailing Tours on Oahu

Discover extraordinary adventures with our similar tours to Oahu sailing tours. Indulge in luxury excursions crafted with meticulous attention to detail for unparalleled comfort and elegance. Dive into vibrant underwater worlds with our snorkeling tours, exploring captivating coral reefs and mesmerizing marine life. Embark on ocean tours revealing hidden treasures and stunning coastal landscapes. For a truly magical experience, join us for enchanting dinner cruises, savoring gourmet cuisine while sailing along the picturesque coastline. Whether seeking relaxation or adventure, our tours offer unparalleled opportunities to immerse yourself in the wonders of the ocean. Choose from our selection and create lasting memories.

Jurassic Valley Adventure Tour

5/5
See everything from Jurassic World movie sites and other popular…

2.5 Hrs. Jurassic Tour at Kualoa Ranch

Ride and Explore Popular Cinema Sites

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$140

Jurassic Valley UTV Ride

5/5
This UTV tour will take you deep into Jurassic Valley, a stunning…

2-Hour Tours with Multiple Daily Departures

Drive Your Own Ultra Terrain Vehicle

from

$145

Paradise Cove Luau

5/5
An evening at Paradise Cove gives you a glimpse into the Hawaiian…

3 hrs. Luau Celebration At Paradise Cove

Award Winning Entertainment & Food

from

$150

Waikiki Submarine Dive

5/5
Go down over 100ʻ below the waves on a submarine off the coast…

2 Hour Under Sea Submarine Tour

View Marine Life from Our Submarine

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$148

Hollywood Movie Sites Tour

5/5
Enjoy a 90-minute open-air bus tour around “Hollywoodʻs Hawaii…

1.5 Hrs. Movie Sites Tour At Kualoa Ranch

Guide Provided

from

$52

North Shore Shark Adventure

5/5
Enjoy a once-in-a-lifetime experience that brings you…

2 Hrs. From Haleiwa Harbor

Swim In A Cage With Sharks

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$120

Hawaii Tours delivers experiences. Book Hawaii better by going with locals who treat you like ohana.

Free Cancellations & Easy Refunds

Full cash or credit refunds on every experience.

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