Menu

Top 10 Best Hawaii Sailing Trips

Found 114 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 3
 

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

(4.9 of 204 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Free Cancellation
Start From $79.00
 
Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

  • Hawaii
  • Superb204 reviews4.9

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Free Cancellation
    Start From $79.00
 
 

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

(4.7 of 17 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
Start From $70.00
 
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

  • Hawaii
  • Superb17 reviews4.7

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē....

    Free Cancellation
    Start From $70.00
 
 

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

(4.7 of 17 reviews)

Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and unforgettable views in one trip. We reach Turtle Canyon quickly, giving you more time in the water to s... More

Free Cancellation
Start From $130.00
 
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

  • Hawaii
  • Superb17 reviews4.7

Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining a....

    Free Cancellation
    Start From $130.00
 
 

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 316 reviews)

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More

Free Cancellation
Start From $99.00
 
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

  • Hawaii
  • Superb316 reviews4.8

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....

    Free Cancellation
    Start From $99.00
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 859 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
  • Superb859 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
 
 

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

(4.9 of 254 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

Free Cancellation
Start From $49.99
 
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

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

  • Hawaii
  • Superb254 reviews4.9

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

    Free Cancellation
    Start From $49.99
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 710 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
  • Superb710 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
 
 

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

Free Cancellation
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
  • Superb18 reviews4.8

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

    Free Cancellation
    Start From $279.00
 
 

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

(4.8 of 217 reviews)

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More

Free Cancellation
Start From $200.00
 
Molokini Snorkel and Performance Sail: Mā’alaea Harbor

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

  • Hawaii
  • Superb217 reviews4.8

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....

    Free Cancellation
    Start From $200.00
 
 

Luxury Diamond Head Sunset Sail

(5 of 3 reviews)

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private 50' luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from... More

Free Cancellation
Private Tour
Start From $1,398.00
 
Luxury Diamond Head Sunset Sail

Luxury Diamond Head Sunset Sail

  • Hawaii
  • Superb3 reviews5

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....

    Free Cancellation
    Private Tour
    Start From $1,398.00
 
 

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
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(4.8 of 24 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
Private Tour
Start From $47.50
 
South Shore Open Sail from Kewalo Harbor Including Drinks

South Shore Open Sail from Kewalo Harbor Including Drinks

  • Hawaii
  • Superb24 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $47.50
 
 

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

(5 of 36 reviews)

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based on weather, tides, and ocean conditions. • Explore Lana... More

Free Cancellation
Private Tour
Start From $216.22
 
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

  • Hawaii
  • Superb36 reviews5

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where ....

    Free Cancellation
    Private Tour
    Start From $216.22
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 250 reviews)

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adve... More

Free Cancellation
Private Tour
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument

Afternoon Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb250 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....

    Free Cancellation
    Private Tour
    Start From $136.19
 
 

Kona Tradewind Catamaran Day Sail

(4.8 of 44 reviews)

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails as you glide across the water, taking in panoramic views of volcanic cliffs, sparklin... More

Free Cancellation
Private Tour
Start From $89.00
 
Kona Tradewind Catamaran Day Sail

Kona Tradewind Catamaran Day Sail

  • Hawaii
  • Superb44 reviews4.8

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Waikiki: Afternoon Sail with Open Bar | Oahu - Best Value

(4.8 of 251 reviews)

This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoon in the sun. We'll be keeping a sharp eye out for dolphins, whales and other sea life while getting as close as possible so you c... More

Free Cancellation
Private Tour
Start From $53.36
 
Waikiki: Afternoon Sail with Open Bar | Oahu - Best Value

Waikiki: Afternoon Sail with Open Bar | Oahu - Best Value

  • Hawaii
  • Superb251 reviews4.8

This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoo....

    Free Cancellation
    Private Tour
    Start From $53.36
 
 

Friday Night Firework Cruise in Waikiki

(4.7 of 30 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

Free Cancellation
Private Tour
Start From $69.99
 
Friday Night Firework Cruise in Waikiki

Friday Night Firework Cruise in Waikiki

  • Hawaii
  • Superb30 reviews4.7

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

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Oahu: 3 Hours - Kane‘ohe Sandbar Splash and Snorkeling Adventure

(3 of 4 reviews)

Discover an unforgettable side of O‘ahu most visitors never experience! Our Kāneʻohe Sandbar Splash & Snorkeling Adventure takes you beyond Waikiki to the serene waters of Kāneʻohe Bay, framed by the dramatic Ko‘olau mount... More

Free Cancellation
Private Tour
Start From $155.93
 
Oahu: 3 Hours - Kane‘ohe Sandbar Splash and Snorkeling Adventure Likely to Sell Out

Oahu: 3 Hours - Kane‘ohe Sandbar Splash and Snorkeling Adventur....

  • Hawaii

Discover an unforgettable side of O‘ahu most visitors never experience! Our Kāneʻohe Sandbar Spl....

    Free Cancellation
    Private Tour
    Start From $155.93
 
 

Coral Gardens Coastal Snorkel & Sail

(4.8 of 39 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

Free Cancellation
Private Tour
Start From $122.40
 
Coral Gardens Coastal Snorkel & Sail Likely to Sell Out

Coral Gardens Coastal Snorkel & Sail

  • Hawaii
  • Superb39 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $122.40
 
 

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

Free Cancellation
Private Tour
Start From $196.63
 
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel Likely to Sell Out

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....

    Free Cancellation
    Private Tour
    Start From $196.63
 
1 2 3 4 5
Booking.com
Booking.com
Booking.com