What are the best kid-friendly options for Hawaii Sailing Trips Activities?

According to verified reviews on Cool Hawaii and TripAdvisor, the best kid-friendly Hawaii Sailing Trips are: Waikiki Sunset Cocktail Sail on the Moana Catamaran Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady Waikiki 2 hour Turtle Canyon Snorkeling Adventure Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB View all kid-friendly Activities →

Which Hawaii Sailing Trips have Instant Confirmation?

Hawaii Sailing Trips with Instant Confirmation include: Waikiki Sunset Cocktail Sail on the Moana Catamaran Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Waikiki Turtle Snorkel and Sail on Hawea Catamaran Waikiki 2 hour Turtle Canyon Snorkeling Adventure Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB View all Activities with Instant Confirmation →

Which Hawaii Sailing Trips have Free Cancellation?

Hawaii Sailing Trips with Free Cancellation (in most cases up to 24 hours in advance of your activity date, check the specific activity page) include: Waikiki Sunset Cocktail Sail on the Moana Catamaran Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Waikiki Turtle Snorkel and Sail on Hawea Catamaran Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady Waikiki 2 hour Turtle Canyon Snorkeling Adventure View all Activities with Free Cancellation →

I need a ride! Which Hawaii Sailing Trips have Hotel Pickup?

No problem. These Hawaii Sailing Trips include Hotel Pickup: Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup Waikiki Turtle Snorkeling Adventure(8am) Half Day Oahu Combo Adventure: Bike, Sail and Snorkel Private Cruise Swim with Dolphin View all Activities with Hotel Pickup →

Got any more Hawaii trip ideas?

We sure do. Check out our curated lists of hand-picked Hawaii Activities. Top 10 Hawaii 2026 Senior-friendly tours Hawaii The best tours and activities for culture lovers in Hawaii Top Day Trips from Hawaii Things to do in Hawaii this summer View all Hawaii Trip Ideas →

What are the most popular styles of Tours and Activities in Hawaii?

Based on our sales data over the past year, the most popular styles of tours and activities in Hawaii are: Hawaii Luxury & Special Occasions Hawaii Luxury Tours Hawaii Outdoor Activities Hawaii Cruises, Sailing & Water Tours Hawaii Tours & Sightseeing View all tour styles in Hawaii →

THE TOP 10 Hawaii Sailing Trips (w/Prices)

Glass Bottom Boat Fireworks and After Dark Reef Walker Cruise

Waikiki transforms into a vibrant spectacle on Friday nights, and the Friday Fireworks Cruise offers a unique vantage point to experience this magic. Departing from …More

Oahu, USA

5.0 (3)

Glass Bottom Boat Fireworks and After Dark Reef Walker Cruise

Waikiki transforms into a vibrant spectacle on Friday nights, and the Friday Fireworks Cruise offers a unique vantage point to experience this magic. Departing from...

1 hour 30 minutes Free Cancellation

5.0 (3)

from
$69

Glass Bottom Boat Morning Coffee Cruise in Waikiki

Wake up to the serene beauty of Waikiki on the Morning Coffee Cruise, where you can savor locally roasted Ali’i Coffee Co. and fresh pastries …More

Oahu, USA

5.0 (3)

Glass Bottom Boat Morning Coffee Cruise in Waikiki

Wake up to the serene beauty of Waikiki on the Morning Coffee Cruise, where you can savor locally roasted Ali’i Coffee Co. and fresh pastries...

1 hour 30 minutes Free Cancellation

5.0 (3)

from
$69

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

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 …More

Oahu, USA

5.0 (2)

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

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...

3 hours Free Cancellation

5.0 (2)

from
$1,595

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 …More

Oahu, USA

5.0 (2)

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6...

2 hours Free Cancellation

5.0 (2)

from
$1,200

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 …More

Maui, USA

5.0 (2)

Sound of the Ocean Whale Watch Sail

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...

2 hours Free Cancellation

5.0 (2)

from
$164

Maui: Catamaran Sunset Whale Watch with Cocktails

Experience the best of whale season at sunset! Watch humpbacks breach and play from the deck of a 65' luxury catamaran as the sun sets …More

Maui, USA

5.0 (2)

Maui: Catamaran Sunset Whale Watch with Cocktails

Experience the best of whale season at sunset! Watch humpbacks breach and play from the deck of a 65' luxury catamaran as the sun sets...

2 hours Free Cancellation

5.0 (2)

from
$189

3 Hour Luxury Private Sailing Catamaran for 7-12 People

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 …More

Oahu, USA

5.0 (1)

3 Hour Luxury Private Sailing Catamaran for 7-12 People

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...

3 hours Free Cancellation

5.0 (1)

from
$1,995

Glass Bottom Boat Sunset and After Dark Reef Walker Cruise

Enjoy a stunning sunset cruise along the Waikiki coastline, where the heat softens and Diamond Head transforms into a silhouette against the vibrant sky. Departing …More

Oahu, USA

5.0 (1)

Glass Bottom Boat Sunset and After Dark Reef Walker Cruise

Enjoy a stunning sunset cruise along the Waikiki coastline, where the heat softens and Diamond Head transforms into a silhouette against the vibrant sky. Departing...

1 hour 30 minutes Free Cancellation

5.0 (1)

from
$69

Lahaina Maui Afternoon Whale Watch Sail in Humpback Sanctuary

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, …More

Maui, USA

5.0 (1)

Lahaina Maui Afternoon Whale Watch Sail in Humpback Sanctuary

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,...

2 hours Free Cancellation

5.0 (1)

from
$102

Private Catamaran Charter for Exclusive Celebrations

Enjoy the luxury of having your own 35-passenger catamaran for a private charter on the Pacific. Perfect for exclusive celebrations or a fun day with …More

Oahu, USA

5.0 (1)

Private Catamaran Charter for Exclusive Celebrations

Enjoy the luxury of having your own 35-passenger catamaran for a private charter on the Pacific. Perfect for exclusive celebrations or a fun day with...

2 hours Free Cancellation

5.0 (1)

from
$1,500

Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and …More

Oahu, USA

4.7 (2,102)

Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and...

2 to 3 hours Free Cancellation

4.7 (2,102)

from
$170

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never …More

Oahu, USA

4.7 (1,265)

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never...

2 hours Free Cancellation

4.7 (1,265)

from
$53

Waikiki Best Whale Watching in Honolulu: Whales Guaranteed

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 …More

Honolulu, USA

4.7 (242)

Waikiki Best Whale Watching in Honolulu: Whales Guaranteed

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...

2 hours Free Cancellation

4.7 (242)

from
$79

Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience …More

Maui, USA

4.7 (89)

Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience...

2 hours Free Cancellation

4.7 (89)

from
$148

Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden …More

Oahu, USA

4.6 (87)

Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden...

2 hours Free Cancellation

4.6 (87)

from
$68

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above …More

Honolulu, USA

4.7 (67)

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above...

5 hours 30 minutes Hotel pickup offered Free Cancellation

4.7 (67)

from
$197

Hawaii Sailing Trips

Hawaii Activities

Attractions

Guides

Calendar

Glass Bottom Boat Fireworks and After Dark Reef Walker Cruise

Glass Bottom Boat Morning Coffee Cruise in Waikiki

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

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

Sound of the Ocean Whale Watch Sail

Maui: Catamaran Sunset Whale Watch with Cocktails

3 Hour Luxury Private Sailing Catamaran for 7-12 People

Glass Bottom Boat Sunset and After Dark Reef Walker Cruise

Lahaina Maui Afternoon Whale Watch Sail in Humpback Sanctuary

Private Catamaran Charter for Exclusive Celebrations

Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

Waikiki Best Whale Watching in Honolulu: Whales Guaranteed

Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

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