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)

Moana’s Luxury semi-private Sunset Cruise on Nalu

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 …More

Oahu, USA

5.0 (21)

Moana’s Luxury semi-private Sunset Cruise on Nalu

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...

2 hours Free Cancellation

5.0 (21)

from
$150

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

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, …More

Maui, USA

4.8 (19)

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

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,...

2 hours Free Cancellation

4.8 (19)

from
$279

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 …More

Oahu, USA

5.0 (18)

Polynesian Canoe Morning Sail

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...

2 hours Free Cancellation

5.0 (18)

from
$180

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

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 …More

Oahu, USA

4.9 (18)

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

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...

2 hours Free Cancellation

4.9 (18)

from
$70

Waikiki private Day Tour and Sunset sail for couples

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples …More

Oahu, USA

5.0 (17)

Waikiki private Day Tour and Sunset sail for couples

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples...

2 hours Free Cancellation

5.0 (17)

from
$300

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 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

4.8 (14)

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 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...

2 hours Free Cancellation

4.8 (14)

from
$1,150

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

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 …More

Oahu, USA

5.0 (13)

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

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...

1 hour 30 minutes Free Cancellation

5.0 (13)

from
$53

Private Catamaran Sunset Sail in Waikiki

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 …More

Oahu, USA

5.0 (11)

Private Catamaran Sunset Sail in Waikiki

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...

2 hours Free Cancellation

5.0 (11)

from
$900

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, …More

Big Island of Hawaii, USA

5.0 (6)

Afternoon Ali'i Adventure

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,...

3 hours Free Cancellation

5.0 (6)

from
$276

Sunset Sail Experience by Catamaran in Waikiki

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 …More

Oahu, USA

4.8 (6)

Sunset Sail Experience by Catamaran in Waikiki

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...

2 hours Free Cancellation

4.8 (6)

from
$92

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 …More

Oahu, USA

5.0 (5)

BYOB Friday Night Fireworks Cruise

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...

2 hours 30 minutes Free Cancellation

5.0 (5)

from
$139

2hr 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 (4)

2hr 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...

2 hours Free Cancellation

5.0 (4)

from
$1,495

Waikiki Sunset Cruise and Iconic Views with Swimming

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide …More

Oahu, USA

5.0 (4)

Waikiki Sunset Cruise and Iconic Views with Swimming

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide...

2 hours Free Cancellation

5.0 (4)

from
$65

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

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 …More

Oahu, USA

5.0 (4)

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

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...

2 hours Free Cancellation

5.0 (4)

from
$450

2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

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 …More

Oahu, USA

5.0 (3)

2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

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...

2 hours Free Cancellation

5.0 (3)

from
$70

Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha

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. …More

Oahu, USA

5.0 (3)

Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha

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....

1 hour Free Cancellation

5.0 (3)

from
$60

Hawaii Sailing Trips

Hawaii Activities

Attractions

Guides

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Moana’s Luxury semi-private Sunset Cruise on Nalu

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

Polynesian Canoe Morning Sail

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Waikiki private Day Tour and Sunset sail for couples

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

Private Catamaran Sunset Sail in Waikiki

Afternoon Ali'i Adventure

Sunset Sail Experience by Catamaran in Waikiki

BYOB Friday Night Fireworks Cruise

2hr Luxury Private Sailing Catamaran for 7-12 People

Waikiki Sunset Cruise and Iconic Views with Swimming

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

2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha

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