Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 104 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 3Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adve... More
Afternoon Sail & Snorkel to the Captain Cook Monument
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Hawaii
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Superb254 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....
Kona Tradewind Catamaran Day Sail
Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails as you glide across the water, taking in panoramic views of volcanic cliffs, sparklin... More
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Kona Tradewind Catamaran Day Sail
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Hawaii
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Superb50 reviews4.8
Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....
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Midday Whale Watch: Mā’alaea Harbor
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More
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Midday Whale Watch: Mā’alaea Harbor
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Hawaii
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Superb104 reviews4.9
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
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Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More
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Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch
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Hawaii
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Superb222 reviews4.8
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
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Deluxe Sail & Snorkel to the Captain Cook Monument
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters... More
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Deluxe Sail & Snorkel to the Captain Cook Monument
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Hawaii
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Superb480 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....
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Luxury Catamaran Whale Watch
From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More
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Luxury Catamaran Whale Watch
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Hawaii
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Superb89 reviews4.9
From December through April, the waters off Maui come alive with the sights and sounds of the majest....
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2 Hour 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
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Likely to Sell Out 2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
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Hawaii
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Superb2 reviews5
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....
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Waikiki Friday Night Fireworks 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
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Likely to Sell Out Waikiki Friday Night Fireworks Cruise
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Hawaii
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Superb32 reviews4.6
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....
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Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu
Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, you’ll glide along the coastline and experience an exclusive o... More
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Likely to Sell Out Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu
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Hawaii
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Superb59 reviews4.8
Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village di....
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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
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Likely to Sell Out Private Catamaran Charter in Waikiki (1-6 Guests)
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Hawaii
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Superb25 reviews5
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....
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Waikoloa Catamaran Snorkel Sail Including Lunch
Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy a smooth, comfortable ride to one of the region’s best sno... More
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Likely to Sell Out Waikoloa Catamaran Snorkel Sail Including Lunch
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Hawaii
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Superb110 reviews4.6
Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautif....
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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
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Likely to Sell Out 2-Hour Oahu Sunset Catamaran Sail
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Hawaii
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Superb135 reviews4.8
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran fr....
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Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More
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Likely to Sell Out Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....
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Hawaii
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Superb970 reviews4.7
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....
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Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More
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Likely to Sell Out Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu
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Hawaii
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Superb1,335 reviews4.6
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....
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Sunset and Manta Ray Snorkel Adventure
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays! Upon arriving, receive an in... More
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Likely to Sell Out Sunset and Manta Ray Snorkel Adventure
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Hawaii
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Superb870 reviews4.9
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....
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North Shore Catamaran Charters
Perfect for families, couples, and ocean lovers seeking an unforgettable Hawaiian experience. Witness the majestic whales and stunning sunsets on the North Shore of Oahu. Explore the crystal-clear waters aboard your Summer snorkel... More
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Likely to Sell Out North Shore Catamaran Charters
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Hawaii
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Superb1 review5
Perfect for families, couples, and ocean lovers seeking an unforgettable Hawaiian experience. Witnes....
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Polynesian Canoe Sunset Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and bec... More
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Likely to Sell Out Polynesian Canoe Sunset Sail
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Hawaii
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Superb128 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) off....
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Maui Sunset Sail
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing catamaran, Ocean Spirit. It’s the perfect way to expe... More
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Likely to Sell Out Maui Sunset Sail
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Hawaii
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Superb221 reviews4.6
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....
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Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets. Snorkel calm waters and lush coral gardens u... More
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Likely to Sell Out Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
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Hawaii
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Superb718 reviews5
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....
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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
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Likely to Sell Out 3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
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Hawaii
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Superb1 review5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
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