Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 104 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 4Coral Gardens Snorkel & Whale Watch
Sail through Maui’s renowned Au‘Au Channel, a world-class whale-watching destination famous for its calm waters and breathtaking scenery. During whale season, this prime playground offers unmatched opportunities to spot majest... More

Coral Gardens Snorkel & Whale Watch
-
Hawaii
-
Superb39 reviews4.8
Sail through Maui’s renowned Au‘Au Channel, a world-class whale-watching destination famous for ....
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
-
Hawaii
-
Superb4 reviews5
Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....
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
-
Hawaii
-
Superb12 reviews4.8
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel
Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above Honolulu to snorkeling off a catamaran off Waikiki. Explore lush rainforest and... More
Private Tour

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel
-
Hawaii
-
Superb67 reviews4.7
Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour....
Private Tour
Private Catamaran Charter in Waikiki (7-12 Guests)
(IMPORTANT: Make sure you have over 6 guests selected to see availability for this activity. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot catamaran has a sleek low-profile des... More
Private Tour

Private Catamaran Charter in Waikiki (7-12 Guests)
-
Hawaii
-
Superb67 reviews4.7
(IMPORTANT: Make sure you have over 6 guests selected to see availability for this activity. If you ....
Private Tour
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 g... More
Private Tour

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
-
Hawaii
-
Superb189 reviews4.9
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....
Private Tour
Hawaiian Canoe Sailing Experience in Maui
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More
Private Tour

Hawaiian Canoe Sailing Experience in Maui
-
Hawaii
-
Superb55 reviews4.8
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....
Private Tour
Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani
Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. This 1.5-hour journey from Honokohau Harbor offers a chance to bask in the sun and enjoy the ocean breeze while taking in the breath... More
Private Tour

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani
-
Hawaii
-
Superb35 reviews4.8
Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. Th....
Private Tour
Snorkel Sail Adventure off Ka'anapali Beach, Maui
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More
Private Tour

Snorkel Sail Adventure off Ka'anapali Beach, Maui
-
Hawaii
-
Superb9 reviews4.9
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....
Private Tour
Pau Hana Sunset Cocktail Cruise
Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed catamaran. This cruise includes unlimited soft drinks, tropical juices, beers, wines, cocktails and a variety of appetizers.. Great f... More
Private Tour

Pau Hana Sunset Cocktail Cruise
-
Hawaii
-
Superb48 reviews4.8
Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed cat....
Private Tour
Deluxe Turtle Snorkeling Escapade at Waikiki
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More
Private Tour

Deluxe Turtle Snorkeling Escapade at Waikiki
-
Hawaii
-
Superb4 reviews4.8
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
Private Tour
Waikiki Friday Firework Catamaran Tour
The Blue Ocean Waikiki luxury catamaran is the perfect place for guests to enjoy following a breathtaking fireworks just outside the Hilton Hawaiian Village. Every Friday at 6:45pm, you have the opportunity to watch a spectacular ... More
Private Tour

Waikiki Friday Firework Catamaran Tour
-
Hawaii
-
Superb27 reviews4.7
The Blue Ocean Waikiki luxury catamaran is the perfect place for guests to enjoy following a breatht....
Private Tour
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the flagship 420 Outrage a boat like no other. From the expansive bow with innovative seating galore, to the beautifully designed convert... More
Private Tour

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
-
Hawaii
-
Superb7 reviews4.9
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the fla....
Private Tour
Friday Night Catamaran Fireworks Sail with Open Bar
Who doesn't love fireworks, especially with all inclusive drinks? The famous weekly Hilton Hawaiian Village fireworks display seen from the water feels like you’re right under the action! There's no better way to kick off the we... More
Private Tour

Friday Night Catamaran Fireworks Sail with Open Bar
-
Hawaii
-
Superb53 reviews4.9
Who doesn't love fireworks, especially with all inclusive drinks? The famous weekly Hilton Hawaiian ....
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
-
Hawaii
-
Superb32 reviews4.7
Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Bea....
Private Tour
Oahu, Waikiki Sunset Catamaran Boat Tour
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

Oahu, Waikiki Sunset Catamaran Boat Tour
-
Hawaii
-
Superb14 reviews4.9
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē....
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
-
Hawaii
-
Superb15 reviews4.7
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....
Private Tour
4-Hour Koa Kai Molokini Adventure Snorkel
Join us on this 3-hour snorkel adventure at Maui's most iconic snorkeling location, Molokini Crater. You will be treated to exceptional service and premium equipment. Koa Kai is a multi-purpose raft that creates a unique close-u... More
Private Tour

4-Hour Koa Kai Molokini Adventure Snorkel
-
Hawaii
-
Superb10 reviews5
Join us on this 3-hour snorkel adventure at Maui's most iconic snorkeling location, Molokini Crater.....
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
-
Hawaii
-
Superb14 reviews5
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....
Private Tour
Waikiki Private Sunset Sail Romantic and Private
Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a spectacular Hawaiian sunset on your private yacht. Get a chance to see whales, dolphins and sea turtles. Immerse yourself in a bucke... More
Private Tour

Waikiki Private Sunset Sail Romantic and Private
-
Hawaii
-
Superb14 reviews5
Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a sp....
Private Tour