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Top 10 Best Hawaii Sailing Trips

Found 104 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 5
 

Moana’s Luxury semi-private Sunset Cruise on Nalu

(4.8 of 19 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

Moana’s Luxury semi-private Sunset Cruise on Nalu

  • Hawaii
  • Superb19 reviews4.8

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

    Free Cancellation
    Start From $149.99
 
 

Honolua Snorkel Sail from Lahaina

(4.9 of 61 reviews)

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Marine Life Conservation District. Along the way, watch for wild dolphins, then snorkel among Hawaiian green sea turtles in this vib... More

Free Cancellation
Start From $180.92
 
Honolua Snorkel Sail from Lahaina

Honolua Snorkel Sail from Lahaina

  • Hawaii
  • Superb61 reviews4.9

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Ma....

    Free Cancellation
    Start From $180.92
 
 
-10% 2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

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

(4.8 of 18 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

Special Offer
Free Cancellation
Start From $251.10
(Saving 10% ) $279.00
 
-10% 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
  • Superb18 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $251.10
    (Saving 10% ) $279.00
 
 
-inf% Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

(4.7 of 68 reviews)

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

Special Offer
Free Cancellation
Start From $196.63
(Saving inf% ) $0.00
 
-inf% Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

  • Hawaii
  • Superb68 reviews4.7

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour....

    Special Offer
    Free Cancellation
    Start From $196.63
    (Saving inf% ) $0.00
 
 
-inf% Private Oahu Sunset Charter with Tasting and Drinks

Private Oahu Sunset Charter with Tasting and Drinks

(5 of 54 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

Special Offer
Free Cancellation
Private Tour
Start From $1,413.61
(Saving inf% ) $0.00
 
-inf% Private Oahu Sunset Charter with Tasting and Drinks

Private Oahu Sunset Charter with Tasting and Drinks

  • Hawaii
  • Superb54 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,413.61
    (Saving inf% ) $0.00
 
 
-inf% BYOB Friday Night Fireworks Cruise

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

Special Offer
Free Cancellation
Private Tour
Start From $138.95
(Saving inf% ) $0.00
 
-inf% BYOB Friday Night Fireworks Cruise

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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $138.95
    (Saving inf% ) $0.00
 
 
-inf% Sunset sail Aboard Manakai Catamaran

Sunset sail Aboard Manakai Catamaran

(5 of 24 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

Special Offer
Free Cancellation
Private Tour
Start From $49.82
(Saving inf% ) $0.00
 
-inf% Sunset sail Aboard Manakai Catamaran

Sunset sail Aboard Manakai Catamaran

  • Hawaii
  • Superb24 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $49.82
    (Saving inf% ) $0.00
 
 
-inf% Polynesian Canoe Morning Sail

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

Special Offer
Free Cancellation
Private Tour
Start From $200.00
(Saving inf% ) $0.00
 
-inf% 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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $200.00
    (Saving inf% ) $0.00
 
 
-inf% Sunset Sail Experience by Catamaran in Waikiki

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

Special Offer
Free Cancellation
Private Tour
Start From $92.31
(Saving inf% ) $0.00
 
-inf% Sunset Sail Experience by Catamaran in Waikiki

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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $92.31
    (Saving inf% ) $0.00
 
 
-inf% 2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

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

Special Offer
Free Cancellation
Private Tour
Start From $70.00
(Saving inf% ) $0.00
 
-inf% 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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $70.00
    (Saving inf% ) $0.00
 
 
-15% Waikiki Heritage and Diamond Head Wildlife Sail

Waikiki Heritage and Diamond Head Wildlife Sail

(4.7 of 32 reviews)

Set sail along the iconic Waikiki coastline for a laid-back 1.5-hour afternoon on the water. This experience emphasizes relaxation, scenic views of Oʻahu’s south shore, and casual wildlife watching—keep an eye out for dolphin... More

Special Offer
Free Cancellation
Private Tour
Start From $101.15
(Saving 15% ) $119.00
 
-15% Waikiki Heritage and Diamond Head Wildlife Sail

Waikiki Heritage and Diamond Head Wildlife Sail

  • Hawaii
  • Superb32 reviews4.7

Set sail along the iconic Waikiki coastline for a laid-back 1.5-hour afternoon on the water. This ex....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $101.15
    (Saving 15% ) $119.00
 
 
-inf% #1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson

#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson

(5 of 4 reviews)

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed so you learn faster and safer. We will share with you the best locations to launch f... More

Special Offer
Free Cancellation
Private Tour
Start From $450.00
(Saving inf% ) $0.00
 
-inf% #1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson

#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson

  • Hawaii
  • Superb4 reviews5

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets he....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $450.00
    (Saving inf% ) $0.00
 
 
-inf% 3 Hour Luxury Private Sailing Catamaran for 7-12 People

3 Hour Luxury Private Sailing Catamaran for 7-12 People

(5 of 4 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 $1,995.00
(Saving inf% ) $0.00
 
-inf% 3 Hour Luxury Private Sailing Catamaran for 7-12 People

3 Hour Luxury Private Sailing Catamaran for 7-12 People

  • Hawaii
  • Superb4 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 $1,995.00
    (Saving inf% ) $0.00
 
 
-inf% Afternoon Ali'i Adventure

Afternoon Ali'i Adventure

(5 of 6 reviews)

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More

Special Offer
Free Cancellation
Private Tour
Start From $276.00
(Saving inf% ) $0.00
 
-inf% Afternoon Ali'i Adventure

Afternoon Ali'i Adventure

  • Hawaii
  • Superb6 reviews5

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $276.00
    (Saving inf% ) $0.00
 
 
-inf% Honolulu Sailing and Snorkeling Activity

Honolulu Sailing and Snorkeling Activity

(5 of 6 reviews)

You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine creatures that call the Hawaiian islands home.... More

Special Offer
Free Cancellation
Private Tour
Start From $105.00
(Saving inf% ) $0.00
 
-inf% Honolulu Sailing and Snorkeling Activity

Honolulu Sailing and Snorkeling Activity

  • Hawaii
  • Superb6 reviews5

You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine c....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $105.00
    (Saving inf% ) $0.00
 
 
-inf% Private South Shore Sail Charter

Private South Shore Sail Charter

(5 of 2 reviews)

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and enjoy complimentary drinks while getting the ocean breeze, some Hawaiian sunshine, and even a splash or two! Experience the south ... More

Special Offer
Free Cancellation
Private Tour
Start From $1,000.00
(Saving inf% ) $0.00
 
-inf% Private South Shore Sail Charter

Private South Shore Sail Charter

  • Hawaii
  • Superb2 reviews5

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,000.00
    (Saving inf% ) $0.00
 
 
-inf% Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

(4.8 of 34 reviews)

Enjoy the Hawaiian Ocean, your way! 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... More

Special Offer
Free Cancellation
Private Tour
Start From $249.99
(Saving inf% ) $0.00
 
-inf% Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

  • Hawaii
  • Superb34 reviews4.8

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $249.99
    (Saving inf% ) $0.00
 
 
-inf% Afternoon Sail With the Whales from Lahaina Harbor

Afternoon Sail With the Whales from Lahaina Harbor

(5 of 1 review)

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% Afternoon Sail With the Whales from Lahaina Harbor

Afternoon Sail With the Whales from Lahaina Harbor

  • Hawaii
  • Superb1 review5

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% Midmorning Whale Watch from Lahaina Harbor

Midmorning Whale Watch from Lahaina Harbor

(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

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

Midmorning Whale Watch from Lahaina Harbor

  • Hawaii
  • Good3 reviews3.3

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% Sound of the Ocean Whale Watch Sail

Sound of the Ocean Whale Watch Sail

(5 of 1 review)

Step aboard a boat and experience whale watching like never before. On this special cruise, see humpback whales in their natural habitat and hear them too. With a partnership with the award-winning immersive experience “Sounds ... More

Special Offer
Free Cancellation
Private Tour
Start From $163.68
(Saving inf% ) $0.00
 
-inf% Sound of the Ocean Whale Watch Sail

Sound of the Ocean Whale Watch Sail

  • Hawaii
  • Superb1 review5

Step aboard a boat and experience whale watching like never before. On this special cruise, see hump....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $163.68
    (Saving inf% ) $0.00
 
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