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Top 10 Best Hawaii Sailing Trips

Found 108 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 4
 

Waikiki Fireworks Cocktail Cruise

(4.3 of 6 reviews)

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to remember. ... More

Free Cancellation
Start From $85.09
 
Waikiki Fireworks Cocktail Cruise

Waikiki Fireworks Cocktail Cruise

  • Hawaii
  • Exellent6 reviews4.3

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....

    Free Cancellation
    Start From $85.09
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.8 of 58 reviews)

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

Free Cancellation
Start From $179.00
 
Hawaiian Canoe Sailing Experience in Maui

Hawaiian Canoe Sailing Experience in Maui

  • Hawaii
  • Superb58 reviews4.8

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....

    Free Cancellation
    Start From $179.00
 
 

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

(4.8 of 82 reviews)

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

Free Cancellation
Start From $119.00
 
Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran Likely to Sell Out

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

  • Hawaii
  • Superb82 reviews4.8

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....

    Free Cancellation
    Start From $119.00
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(5 of 19 reviews)

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

Free Cancellation
Start From $47.50
 
South Shore Open Sail from Kewalo Harbor Including Drinks Likely to Sell Out

South Shore Open Sail from Kewalo Harbor Including Drinks

  • Hawaii
  • Superb19 reviews5

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....

    Free Cancellation
    Start From $47.50
 
 

Moana’s Luxury semi-private Sunset Cruise on Nalu

(4.6 of 9 reviews)

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

Free Cancellation
Start From $149.99
 
Moana’s Luxury semi-private Sunset Cruise on Nalu Likely to Sell Out

Moana’s Luxury semi-private Sunset Cruise on Nalu

  • Hawaii
  • Superb9 reviews4.6

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizabl....

    Free Cancellation
    Start From $149.99
 
 

Sunset Sail Experience by Catamaran in Waikiki

(4.8 of 6 reviews)

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

Free Cancellation
Start From $92.31
 
Sunset Sail Experience by Catamaran in Waikiki Likely to Sell Out

Sunset Sail Experience by Catamaran in Waikiki

  • Hawaii
  • 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....

    Free Cancellation
    Start From $92.31
 
 

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.5 of 22 reviews)

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

Free Cancellation
Start From $156.79
 
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch Likely to Sell Out

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

  • Hawaii
  • Exellent22 reviews4.5

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....

    Free Cancellation
    Start From $156.79
 
 

BYOB Friday Night Fireworks Cruise

(4.3 of 6 reviews)

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

Free Cancellation
Start From $138.95
 
BYOB Friday Night Fireworks Cruise Likely to Sell Out

BYOB Friday Night Fireworks Cruise

  • Hawaii
  • Exellent6 reviews4.3

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....

    Free Cancellation
    Start From $138.95
 
 

Polynesian Canoe Day Sail

(4.9 of 29 reviews)

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

Free Cancellation
Start From $200.00
 
Polynesian Canoe Day Sail Likely to Sell Out

Polynesian Canoe Day Sail

  • Hawaii
  • Superb29 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Free Cancellation
    Start From $200.00
 
 

Sunset sail Aboard Manakai Catamaran

(5 of 6 reviews)

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

Free Cancellation
Start From $49.82
 
Sunset sail Aboard Manakai Catamaran Likely to Sell Out

Sunset sail Aboard Manakai Catamaran

  • Hawaii
  • Superb6 reviews5

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....

    Free Cancellation
    Start From $49.82
 
 

Sunset Cruise with the Whales from Anaeho'omalu Bay

(4.8 of 46 reviews)

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

Free Cancellation
Start From $165.00
 
Sunset Cruise with the Whales from Anaeho'omalu Bay Likely to Sell Out

Sunset Cruise with the Whales from Anaeho'omalu Bay

  • Hawaii
  • Superb46 reviews4.8

Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the b....

    Free Cancellation
    Start From $165.00
 
 

Polynesian Canoe Sunset Sail

(4.9 of 124 reviews)

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

Free Cancellation
Start From $250.00
 
Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • Hawaii
  • Superb124 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Free Cancellation
    Start From $250.00
 
 

Sunset Sail from Ma'alaea Harbor in Maui

(4.6 of 214 reviews)

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

Free Cancellation
Start From $125.10
 
Sunset Sail from Ma'alaea Harbor in Maui Likely to Sell Out

Sunset Sail from Ma'alaea Harbor in Maui

  • Hawaii
  • Superb214 reviews4.6

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....

    Free Cancellation
    Start From $125.10
 
 

Waikiki Friday Night Fireworks Boat Cruise on O'ahu

(4.5 of 27 reviews)

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

Free Cancellation
Start From $75.00
 
Waikiki Friday Night Fireworks Boat Cruise on O'ahu Likely to Sell Out

Waikiki Friday Night Fireworks Boat Cruise on O'ahu

  • Hawaii
  • Exellent27 reviews4.5

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....

    Free Cancellation
    Start From $75.00
 
 

Friday Night Catamaran Fireworks Sail with Open Bar

(4.8 of 55 reviews)

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

Free Cancellation
Start From $90.01
 
Friday Night Catamaran Fireworks Sail with Open Bar Likely to Sell Out

Friday Night Catamaran Fireworks Sail with Open Bar

  • Hawaii
  • Superb55 reviews4.8

Who doesn't love fireworks, especially with all inclusive drinks? The famous weekly Hilton Hawaiian ....

    Free Cancellation
    Start From $90.01
 
 

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

(4.8 of 14 reviews)

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

Free Cancellation
Private Tour
Start From $1,150.00
 
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People Likely to Sell Out

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

  • Hawaii
  • Superb14 reviews4.8

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Free Cancellation
    Private Tour
    Start From $1,150.00
 
 

Private Oahu Sunset Charter with Tasting and Drinks

(5 of 46 reviews)

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

Free Cancellation
Private Tour
Start From $1,413.61
 
Private Oahu Sunset Charter with Tasting and Drinks Likely to Sell Out

Private Oahu Sunset Charter with Tasting and Drinks

  • Hawaii
  • Superb46 reviews5

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world....

    Free Cancellation
    Private Tour
    Start From $1,413.61
 
 

Waikiki Sail and Snorkel Adventure Best of Hawaii 2023

(4 of 4 reviews)

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

Free Cancellation
Private Tour
Start From $695.00
 
Waikiki Sail and Snorkel Adventure Best of Hawaii 2023 Likely to Sell Out

Waikiki Sail and Snorkel Adventure Best of Hawaii 2023

  • Hawaii
  • Very Good4 reviews4

Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with ....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Waikiki Private Sunset Sail Romantic and Private

(4 of 4 reviews)

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

Free Cancellation
Private Tour
Start From $799.00
 
Waikiki Private Sunset Sail Romantic and Private Likely to Sell Out

Waikiki Private Sunset Sail Romantic and Private

  • Hawaii
  • Very Good4 reviews4

Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a sp....

    Free Cancellation
    Private Tour
    Start From $799.00
 
 

Morning Whale Watch: Lahaina Harbor

(5 of 10 reviews)

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

Free Cancellation
Private Tour
Start From $91.89
 
Morning Whale Watch: Lahaina Harbor Likely to Sell Out

Morning Whale Watch: Lahaina Harbor

  • Hawaii
  • Superb10 reviews5

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....

    Free Cancellation
    Private Tour
    Start From $91.89
 
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