Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 108 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 4 
                  
                                    Waikiki Fireworks Cocktail Cruise
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                      Hawaii
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                                            Exellent6 reviews4.3
Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....
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
 
                  
                                    Hawaiian Canoe Sailing Experience in Maui
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                      Hawaii
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                                            Superb58 reviews4.8
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....
Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More
 Likely to Sell Out
                  
                  Likely to Sell Out                  Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran
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                      Hawaii
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                                            Superb82 reviews4.8
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....
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
 Likely to Sell Out
                  
                  Likely to Sell Out                  South Shore Open Sail from Kewalo Harbor Including Drinks
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                      Hawaii
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                                            Superb19 reviews5
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....
Moana’s Luxury semi-private Sunset Cruise on Nalu
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 additional cost. Dolphins, Sea turtle... More
 Likely to Sell Out
                  
                  Likely to Sell Out                  Moana’s Luxury semi-private Sunset Cruise on Nalu
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                      Hawaii
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                                            Superb9 reviews4.6
The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizabl....
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
 Likely to Sell Out
                  
                  Likely to Sell Out                  Sunset Sail Experience by Catamaran in Waikiki
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                      Hawaii
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                                            Superb6 reviews4.8
Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....
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
 Likely to Sell Out
                  
                  Likely to Sell Out                  Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
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                      Hawaii
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                                            Exellent22 reviews4.5
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....
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
 Likely to Sell Out
                  
                  Likely to Sell Out                  BYOB Friday Night Fireworks Cruise
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                      Hawaii
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                                            Exellent6 reviews4.3
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....
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
 Likely to Sell Out
                  
                  Likely to Sell Out                  Polynesian Canoe Day Sail
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                      Hawaii
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                                            Superb29 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
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
 Likely to Sell Out
                  
                  Likely to Sell Out                  Sunset sail Aboard Manakai Catamaran
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                      Hawaii
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                                            Superb6 reviews5
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....
Sunset Cruise with the Whales from Anaeho'omalu Bay
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise! Cruise along the Kohala... More
 Likely to Sell Out
                  
                  Likely to Sell Out                  Sunset Cruise with the Whales from Anaeho'omalu Bay
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                      Hawaii
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                                            Superb46 reviews4.8
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the b....
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
 Likely to Sell Out
                  
                  Likely to Sell Out                  Polynesian Canoe Sunset Sail
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                      Hawaii
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                                            Superb124 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Sunset Sail from Ma'alaea Harbor in Maui
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 ex... More
 Likely to Sell Out
                  
                  Likely to Sell Out                  Sunset Sail from Ma'alaea Harbor in Maui
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                      Hawaii
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                                            Superb214 reviews4.6
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....
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
 Likely to Sell Out
                  
                  Likely to Sell Out                  Waikiki Friday Night Fireworks Boat Cruise on O'ahu
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                      Hawaii
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                                            Exellent27 reviews4.5
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....
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
 Likely to Sell Out
                  
                  Likely to Sell Out                  Friday Night Catamaran Fireworks Sail with Open Bar
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                      Hawaii
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                                            Superb55 reviews4.8
Who doesn't love fireworks, especially with all inclusive drinks? The famous weekly Hilton Hawaiian ....
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
 Likely to Sell Out
                  
                  Likely to Sell Out                  2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People
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                      Hawaii
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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
Private Oahu Sunset Charter with Tasting and Drinks
This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people while enjoying the West Oahu Sunset on this 2.5-hour experience. There’s more than enoug... More
Private Tour
 Likely to Sell Out
                  
                  Likely to Sell Out                  Private Oahu Sunset Charter with Tasting and Drinks
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                      Hawaii
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                                            Superb46 reviews5
This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world....
Private Tour
Waikiki Sail and Snorkel Adventure Best of Hawaii 2023
Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with an array of tropical fish. The clear waters of Turtle Canyons reveal a kaleidoscope of colors, from dazzling schools of fish to vi... More
Private Tour
 Likely to Sell Out
                  
                  Likely to Sell Out                  Waikiki Sail and Snorkel Adventure Best of Hawaii 2023
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                      Hawaii
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                                            Very Good4 reviews4
Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with ....
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
 Likely to Sell Out
                  
                  Likely to Sell Out                  Waikiki Private Sunset Sail Romantic and Private
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                      Hawaii
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                                            Very Good4 reviews4
Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a sp....
Private Tour
Morning Whale Watch: Lahaina 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
Private Tour
 Likely to Sell Out
                  
                  Likely to Sell Out                  Morning Whale Watch: Lahaina Harbor
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                      Hawaii
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                                            Superb10 reviews5
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
Private Tour
