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Top 10 Best Hawaii Sailing Trips

Found 104 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 4
 

Hawaiian Canoe Sailing Experience in Maui

(4.6 of 63 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
  • Superb63 reviews4.6

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

    Free Cancellation
    Start From $179.00
 
 
-10% Kona Coast Luxury Private Yacht Charter

Kona Coast Luxury Private Yacht Charter

(4.6 of 63 reviews)

Indulge in a personalized sailing experience aboard the luxurious 51-ft Lagoon catamaran, No Wiki. This private charter offers an unforgettable journey along the stunning Kona Coast, where you can snorkel vibrant reefs or simply r... More

Special Offer
Free Cancellation
Private Tour
Start From $1,075.50
(Saving 10% ) $1,195.00
 
-10% Kona Coast Luxury Private Yacht Charter

Kona Coast Luxury Private Yacht Charter

  • Hawaii
  • Superb63 reviews4.6

Indulge in a personalized sailing experience aboard the luxurious 51-ft Lagoon catamaran, No Wiki. T....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,075.50
    (Saving 10% ) $1,195.00
 
 
-inf% 2hr Luxury Private Sailing Catamaran for 7-12 People

2hr Luxury Private Sailing Catamaran for 7-12 People

(5 of 3 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

Special Offer
Free Cancellation
Private Tour
Start From $1,495.00
(Saving inf% ) $0.00
 
-inf% 2hr Luxury Private Sailing Catamaran for 7-12 People

2hr Luxury Private Sailing Catamaran for 7-12 People

  • Hawaii
  • Superb3 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,495.00
    (Saving inf% ) $0.00
 
 
-inf% Waikiki Turtle Snorkeling Adventure(8am)

Waikiki Turtle Snorkeling Adventure(8am)

(5 of 98 reviews)

Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our spacious and comfortable catamaran to Turtle Canyon, where you’ll have the opportunity to snorkel with Hawaiian green sea turtles ... More

Special Offer
Free Cancellation
Private Tour
Start From $100.00
(Saving inf% ) $0.00
 
-inf% Waikiki Turtle Snorkeling Adventure(8am)

Waikiki Turtle Snorkeling Adventure(8am)

  • Hawaii
  • Superb98 reviews5

Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our sp....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $100.00
    (Saving inf% ) $0.00
 
 
-inf% Private Catamaran Sunset Sail in Waikiki

Private Catamaran Sunset Sail in Waikiki

(5 of 11 reviews)

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large ... More

Special Offer
Free Cancellation
Private Tour
Start From $900.00
(Saving inf% ) $0.00
 
-inf% Private Catamaran Sunset Sail in Waikiki

Private Catamaran Sunset Sail in Waikiki

  • Hawaii
  • Superb11 reviews5

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $900.00
    (Saving inf% ) $0.00
 
 
-10% Waikiki Fireworks Cocktail Cruise

Waikiki Fireworks Cocktail Cruise

(4.5 of 8 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

Special Offer
Free Cancellation
Private Tour
Start From $76.58
(Saving 10% ) $85.09
 
-10% Waikiki Fireworks Cocktail Cruise

Waikiki Fireworks Cocktail Cruise

  • Hawaii
  • Exellent8 reviews4.5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $76.58
    (Saving 10% ) $85.09
 
 
-inf% Friday Night Firework Cruise in Waikiki

Friday Night Firework Cruise in Waikiki

(4.8 of 34 reviews)

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More

Special Offer
Free Cancellation
Private Tour
Start From $69.99
(Saving inf% ) $0.00
 
-inf% Friday Night Firework Cruise in Waikiki

Friday Night Firework Cruise in Waikiki

  • Hawaii
  • Superb34 reviews4.8

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $69.99
    (Saving inf% ) $0.00
 
 
-inf% Morning Whale Watch: Lahaina Harbor

Morning Whale Watch: Lahaina Harbor

(4.9 of 29 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

Special Offer
Free Cancellation
Private Tour
Start From $100.22
(Saving inf% ) $0.00
 
-inf% Morning Whale Watch: Lahaina Harbor

Morning Whale Watch: Lahaina Harbor

  • Hawaii
  • Superb29 reviews4.9

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $100.22
    (Saving inf% ) $0.00
 
 
-inf% Small Group Waikiki Sunset Sailing Tour

Small Group Waikiki Sunset Sailing Tour

(4.9 of 118 reviews)

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More

Special Offer
Free Cancellation
Private Tour
Start From $99.00
(Saving inf% ) $0.00
 
-inf% Small Group Waikiki Sunset Sailing Tour

Small Group Waikiki Sunset Sailing Tour

  • Hawaii
  • Superb118 reviews4.9

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $99.00
    (Saving inf% ) $0.00
 
 
-inf% Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

(4.7 of 19 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $70.00
(Saving inf% ) $0.00
 
-inf% Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

  • Hawaii
  • Superb19 reviews4.7

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (LÄ“â€....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $70.00
    (Saving inf% ) $0.00
 
 
-inf% South Shore Open Sail from Kewalo Harbor Including Drinks

South Shore Open Sail from Kewalo Harbor Including Drinks

(4.7 of 27 reviews)

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have complimentary drinks (alcoholic beverages available for adults 21+ with valid ID o... More

Special Offer
Free Cancellation
Private Tour
Start From $47.50
(Saving inf% ) $0.00
 
-inf% South Shore Open Sail from Kewalo Harbor Including Drinks

South Shore Open Sail from Kewalo Harbor Including Drinks

  • Hawaii
  • Superb27 reviews4.7

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $47.50
    (Saving inf% ) $0.00
 
 
-inf% Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

(4.6 of 250 reviews)

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty of interesting whale information Convenient location walking... More

Special Offer
Free Cancellation
Private Tour
Start From $79.00
(Saving inf% ) $0.00
 
-inf% Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

  • Hawaii
  • Superb250 reviews4.6

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well a....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $79.00
    (Saving inf% ) $0.00
 
 
-inf% Maui Turtle Snorkel & Sail with Lunch & Open Bar

Maui Turtle Snorkel & Sail with Lunch & Open Bar

(4.8 of 41 reviews)

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear waters teeming with vibrant coral reefs a... More

Special Offer
Free Cancellation
Private Tour
Start From $122.40
(Saving inf% ) $0.00
 
-inf% Maui Turtle Snorkel & Sail with Lunch & Open Bar

Maui Turtle Snorkel & Sail with Lunch & Open Bar

  • Hawaii
  • Superb41 reviews4.8

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine lan....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $122.40
    (Saving inf% ) $0.00
 
 
-inf% Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

(4.9 of 259 reviews)

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

Special Offer
Free Cancellation
Private Tour
Start From $49.99
(Saving inf% ) $0.00
 
-inf% Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

  • Hawaii
  • Superb259 reviews4.9

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $49.99
    (Saving inf% ) $0.00
 
 
-inf% Waikiki small group turtle snorkeling & sailing

Waikiki small group turtle snorkeling & sailing

(5 of 105 reviews)

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More

Special Offer
Free Cancellation
Private Tour
Start From $99.00
(Saving inf% ) $0.00
 
-inf% Waikiki small group turtle snorkeling & sailing

Waikiki small group turtle snorkeling & sailing

  • Hawaii
  • Superb105 reviews5

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $99.00
    (Saving inf% ) $0.00
 
 
-inf% Polynesian Canoe Day Sail

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

Special Offer
Free Cancellation
Private Tour
Start From $200.00
(Saving inf% ) $0.00
 
-inf% Polynesian Canoe Day Sail

Polynesian Canoe Day Sail

  • Hawaii
  • Superb29 reviews4.9

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $200.00
    (Saving inf% ) $0.00
 
 
-inf% Waikiki Sunset Cruise and Iconic Views with Swimming

Waikiki Sunset Cruise and Iconic Views with Swimming

(5 of 4 reviews)

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide along the iconic Gold Coast as the sun sets, painting the sky with vibrant co... More

Special Offer
Free Cancellation
Private Tour
Start From $65.00
(Saving inf% ) $0.00
 
-inf% Waikiki Sunset Cruise and Iconic Views with Swimming

Waikiki Sunset Cruise and Iconic Views with Swimming

  • Hawaii
  • Superb4 reviews5

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $65.00
    (Saving inf% ) $0.00
 
 
-inf% Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

(4.8 of 257 reviews)

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle, no bus, no wasted time -Sail toward Diamond Head on the famous Waikiki ... More

Special Offer
Free Cancellation
Private Tour
Start From $53.36
(Saving inf% ) $0.00
 
-inf% Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

  • Hawaii
  • Superb257 reviews4.8

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sai....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $53.36
    (Saving inf% ) $0.00
 
 
-inf% Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

(5 of 13 reviews)

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while searching for dolphins and sea turtles in their natural habitat.... More

Special Offer
Free Cancellation
Private Tour
Start From $53.36
(Saving inf% ) $0.00
 
-inf% Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

  • Hawaii
  • Superb13 reviews5

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $53.36
    (Saving inf% ) $0.00
 
 
-inf% 2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

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

Special Offer
Free Cancellation
Private Tour
Start From $1,150.00
(Saving inf% ) $0.00
 
-inf% 2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,150.00
    (Saving inf% ) $0.00
 
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