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Top 10 Best Hawaii Sailing Trips

Found 107 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 4
 

Kona Afternoon Snorkel to Captain Cook Monument

(4.9 of 255 reviews)

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Spinner dolphins, eagle rays and dense tropical reef fish • Trade wi... More

Free Cancellation
Start From $135.64
 
Kona Afternoon Snorkel to Captain Cook Monument

Kona Afternoon Snorkel to Captain Cook Monument

  • Hawaii
  • Superb255 reviews4.9

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 â....

    Free Cancellation
    Start From $135.64
 
 

Maui: Whalewatch Sail from Lahaina

(4.8 of 86 reviews)

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and fun two-hour whalewatch is led by a team of... More

Free Cancellation
Start From $111.98
 
Maui: Whalewatch Sail from Lahaina

Maui: Whalewatch Sail from Lahaina

  • Hawaii
  • Superb86 reviews4.8

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catam....

    Free Cancellation
    Start From $111.98
 
 

Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha

(5 of 2 reviews)

This cruise is exceptionally family-friendly, with no snorkeling or in-water activities, making it ideal for guests who want to experience the ocean without getting wet. Unlike many Waikiki beach catamarans, the Spirit of Aloha o... More

Free Cancellation
Start From $59.95
 
Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha

Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha

  • Hawaii
  • Superb2 reviews5

This cruise is exceptionally family-friendly, with no snorkeling or in-water activities, making it i....

    Free Cancellation
    Start From $59.95
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(4.7 of 28 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

Free Cancellation
Start From $47.50
 
South Shore Open Sail from Kewalo Harbor Including Drinks

South Shore Open Sail from Kewalo Harbor Including Drinks

  • Hawaii
  • Superb28 reviews4.7

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
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 872 reviews)

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

Free Cancellation
Start From $154.51
 
Sunset and Manta Ray Snorkel Adventure

Sunset and Manta Ray Snorkel Adventure

  • Hawaii
  • Superb872 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Free Cancellation
    Start From $154.51
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 721 reviews)

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

Free Cancellation
Start From $189.00
 
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

  • Hawaii
  • Superb721 reviews5

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....

    Free Cancellation
    Start From $189.00
 
 

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
 
 

Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea

(4.9 of 104 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
Start From $110.27
 
Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea

Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea

  • Hawaii
  • Superb104 reviews4.9

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

    Free Cancellation
    Start From $110.27
 
 

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

(5 of 15 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

Free Cancellation
Start From $53.36
 
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

  • Hawaii
  • Superb15 reviews5

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

    Free Cancellation
    Start From $53.36
 
 

Lahaina Maui Midmorning Whale Watch in the Humpback Sanctuary

(3.3 of 3 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
Start From $110.28
 
Lahaina Maui Midmorning Whale Watch in the Humpback Sanctuary

Lahaina Maui Midmorning Whale Watch in the Humpback Sanctuary

  • Hawaii
  • Good3 reviews3.3

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

    Free Cancellation
    Start From $110.28
 
 

2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

(5 of 3 reviews)

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). Our snorkel, swim and sail is the perfect combination of warm sun, refreshing salty water, and b... More

Free Cancellation
Start From $70.00
 
2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

  • Hawaii
  • Superb3 reviews5

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolph....

    Free Cancellation
    Start From $70.00
 
 

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

(5 of 1 review)

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 $1,595.00
 
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

  • Hawaii
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $1,595.00
 
 

Polynesian Canoe Morning Sail

(5 of 18 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
Private Tour
Start From $200.00
 
Polynesian Canoe Morning Sail

Polynesian Canoe Morning Sail

  • Hawaii
  • Superb18 reviews5

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

    Free Cancellation
    Private Tour
    Start From $200.00
 
 

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

Free Cancellation
Private Tour
Start From $99.00
 
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....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

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

Free Cancellation
Private Tour
Start From $70.00
 
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 (Lēâ€....

    Free Cancellation
    Private Tour
    Start From $70.00
 
 

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

Free Cancellation
Private Tour
Start From $99.00
 
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....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

(4.9 of 20 reviews)

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea, this intimate evening cruise offers stunning views of the coast... More

Free Cancellation
Private Tour
Start From $279.00
 
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

  • Hawaii
  • Superb20 reviews4.9

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experien....

    Free Cancellation
    Private Tour
    Start From $279.00
 
 

Polynesian Canoe Sunset Sail

(4.9 of 129 reviews)

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

Free Cancellation
Private Tour
Start From $250.00
 
Polynesian Canoe Sunset Sail

Polynesian Canoe Sunset Sail

  • Hawaii
  • Superb129 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) off....

    Free Cancellation
    Private Tour
    Start From $250.00
 
 

Private Catamaran Charter in Waikiki (1-6 Guests)

(5 of 25 reviews)

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

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Charter in Waikiki (1-6 Guests)

Private Catamaran Charter in Waikiki (1-6 Guests)

  • Hawaii
  • Superb25 reviews5

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

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

Free Cancellation
Private Tour
Start From $900.00
 
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....

    Free Cancellation
    Private Tour
    Start From $900.00
 
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