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Top 10 Best Hawaii Sailing Trips

Found 101 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 4
 

Midday Sail with the Whales Ma'alaea

(4.9 of 99 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 $91.89
 
Midday Sail with the Whales Ma'alaea Likely to Sell Out

Midday Sail with the Whales Ma'alaea

  • Hawaii
  • Superb99 reviews4.9

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

    Free Cancellation
    Start From $91.89
 
 

Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles

(5 of 1 review)

This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailboat including swimming or snorkeling with turtles. You can pick and choose the stops on the island tour and go at your own pace. ... More

Free Cancellation
Private Tour
Start From $1,100.00
 
Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles Likely to Sell Out

Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles

  • Hawaii
  • Superb1 review5

This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailb....

    Free Cancellation
    Private Tour
    Start From $1,100.00
 
 

Pau Hana Sunset Cruise with the Whales

(4.8 of 41 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
Private Tour
Start From $165.00
 
Pau Hana Sunset Cruise with the Whales Likely to Sell Out

Pau Hana Sunset Cruise with the Whales

  • Hawaii
  • Superb41 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.8 of 53 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
Private Tour
Start From $179.00
 
Hawaiian Canoe Sailing Experience in Maui Likely to Sell Out

Hawaiian Canoe Sailing Experience in Maui

  • Hawaii
  • Superb53 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $179.00
 
 

Morning Snorkel Sail from Lahaina Harbor

(4.4 of 36 reviews)

The Scotch Mist is a fun and fast sailing yacht, built in 1982 for racing by famed builder Bill Lee in Santa Cruz, California. In fact, she is the fastest production line sailboat of her size in the world, having won “first in c... More

Free Cancellation
Private Tour
Start From $143.60
 
Morning Snorkel Sail from Lahaina Harbor Likely to Sell Out

Morning Snorkel Sail from Lahaina Harbor

  • Hawaii
  • Exellent36 reviews4.4

The Scotch Mist is a fun and fast sailing yacht, built in 1982 for racing by famed builder Bill Lee ....

    Free Cancellation
    Private Tour
    Start From $143.60
 
 

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

(4.7 of 67 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
  • Superb67 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
 
 

Polynesian Canoe Day Sail

(4.8 of 24 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 Day Sail Likely to Sell Out

Polynesian Canoe Day Sail

  • Hawaii
  • Superb24 reviews4.8

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 Friday Firework Catamaran Tour

(4.7 of 27 reviews)

The Blue Ocean Waikiki luxury catamaran is the perfect place for guests to enjoy following a breathtaking fireworks just outside the Hilton Hawaiian Village. Every Friday at 6:45pm, you have the opportunity to watch a spectacular ... More

Free Cancellation
Private Tour
Start From $69.99
 
Waikiki Friday Firework Catamaran Tour Likely to Sell Out

Waikiki Friday Firework Catamaran Tour

  • Hawaii
  • Superb27 reviews4.7

The Blue Ocean Waikiki luxury catamaran is the perfect place for guests to enjoy following a breatht....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

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

(4.8 of 6 reviews)

Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the flagship 420 Outrage a boat like no other. From the expansive bow with innovative seating galore, to the beautifully designed convert... More

Free Cancellation
Private Tour
Start From $284.09
 
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests Likely to Sell Out

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

  • Hawaii
  • Superb6 reviews4.8

Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the fla....

    Free Cancellation
    Private Tour
    Start From $284.09
 
 

Private Catamaran Charter in Waikiki

(5 of 12 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 Likely to Sell Out

Private Catamaran Charter in Waikiki

  • Hawaii
  • Superb12 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
 
 

Waikiki Panorama Sail: Search for Hawaiian Sea Turtles

(4.7 of 32 reviews)

Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Beach and out towards Diamond Head crater. The cruise departs from Kewalo Basin by Ala Moana Beach Park, and includes snacks, non-alc... More

Free Cancellation
Private Tour
Start From $82.96
 
Waikiki Panorama Sail: Search for Hawaiian Sea Turtles Likely to Sell Out

Waikiki Panorama Sail: Search for Hawaiian Sea Turtles

  • Hawaii
  • Superb32 reviews4.7

Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Bea....

    Free Cancellation
    Private Tour
    Start From $82.96
 
 

Waikiki Sunset Cruise: Music and BYOB

(4.9 of 13 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 $83.40
 
Waikiki Sunset Cruise: Music and BYOB Likely to Sell Out

Waikiki Sunset Cruise: Music and BYOB

  • Hawaii
  • Superb13 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $83.40
 
 

Diamond Head Sunset Sail

(4.7 of 14 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 luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from the... More

Free Cancellation
Private Tour
Start From $695.00
 
Diamond Head Sunset Sail Likely to Sell Out

Diamond Head Sunset Sail

  • Hawaii
  • Superb14 reviews4.7

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 $695.00
 
 

4-Hour Koa Kai Molokini Adventure Snorkel

(5 of 10 reviews)

Join us on this 3-hour snorkel adventure at Maui's most iconic snorkeling location, Molokini Crater. You will be treated to exceptional service and premium equipment. Koa Kai is a multi-purpose raft that creates a unique close-u... More

Free Cancellation
Private Tour
Start From $169.00
 
4-Hour Koa Kai Molokini Adventure Snorkel Likely to Sell Out

4-Hour Koa Kai Molokini Adventure Snorkel

  • Hawaii
  • Superb10 reviews5

Join us on this 3-hour snorkel adventure at Maui's most iconic snorkeling location, Molokini Crater.....

    Free Cancellation
    Private Tour
    Start From $169.00
 
 

Luxury Private Sailing Catamaran in Waikiki

(4.7 of 10 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 $1,050.00
 
Luxury Private Sailing Catamaran in Waikiki Likely to Sell Out

Luxury Private Sailing Catamaran in Waikiki

  • Hawaii
  • Superb10 reviews4.7

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

    Free Cancellation
    Private Tour
    Start From $1,050.00
 
 

Private Catamaran Sunset Sail in Waikiki

(5 of 6 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 Likely to Sell Out

Private Catamaran Sunset Sail in Waikiki

  • Hawaii
  • Superb6 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
 
 

Sunset Sail Experience by Catamaran in Waikiki

(5 of 4 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
Private Tour
Start From $92.31
 
Sunset Sail Experience by Catamaran in Waikiki Likely to Sell Out

Sunset Sail Experience by Catamaran in Waikiki

  • Hawaii
  • Superb4 reviews5

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....

    Free Cancellation
    Private Tour
    Start From $92.31
 
 

Waikiki Private Sunset Sail Romantic and Private

(5 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
  • Superb4 reviews5

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
 
 

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
 
 

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure

(4.5 of 4 reviews)

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience is amazing for you to relax and have fun. ... More

Free Cancellation
Private Tour
Start From $1,199.00
 
Explore Turtle Canyons Waikiki Snorkel and Sail Adventure Likely to Sell Out

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure

  • Hawaii
  • Exellent4 reviews4.5

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience ....

    Free Cancellation
    Private Tour
    Start From $1,199.00
 
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