What are the best options for Hawaii Sailing Trips?

According to verified reviews on Cool Hawaii and TripAdvisor, the best Hawaii Sailing Trips are: Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea Small Group Waikiki Sunset Sailing Tour Waikiki small group turtle snorkeling & sailing Maui Sunset Sail

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: #1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson The Nāpali Coast Snorkel Excursion Afternoon Ali'i Adventure Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion Nāpali Sunset Dinner Sail View all kid-friendly Activities →

Which Hawaii Sailing Trips have Instant Confirmation?

Hawaii Sailing Trips with Instant Confirmation include: Private Cruise Swim with Dolphin 3 Hour Luxury Private Sailing Catamaran for 7-12 People 3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People 2hr Luxury Private Sailing Catamaran for 7-12 People 2 Hour Private Catamaran Charter in Waikiki (7-12 Guests) 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: 3 Hour Luxury Private Sailing Catamaran for 7-12 People 3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People Private Catamaran Charter for Exclusive Celebrations 2hr Luxury Private Sailing Catamaran for 7-12 People Private Oahu Sunset Charter with Tasting and Drinks 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: Private Cruise Swim with Dolphin Half Day Oahu Combo Adventure: Bike, Sail and Snorkel Waikiki Turtle Snorkeling Adventure(8am) Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup 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)

Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay

Depart Keauhou Bay at 2:00 PM aboard the Hoku Nui — Sea Paradise’s 50-foot luxury sailing catamaran — and sail to the World Famous Captain …More

Big Island of Hawaii, USA

4.9 (737)

Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay

Depart Keauhou Bay at 2:00 PM aboard the Hoku Nui — Sea Paradise’s 50-foot luxury sailing catamaran — and sail to the World Famous Captain...

3 hours Free Cancellation

4.9 (737)

from
$136

Kona Afternoon Snorkel to Captain Cook Monument

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Spinner …More

Big Island of Hawaii, USA

4.9 (253)

Kona Afternoon Snorkel to Captain Cook Monument

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Spinner...

3 hours Free Cancellation

4.9 (253)

from
$136

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. …More

Oahu, USA

4.8 (142)

2-Hour Oahu Sunset Catamaran Sail

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu....

2 hours Free Cancellation

4.8 (142)

from
$130

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for …More

Maui, USA

5.0 (225)

Lahaina Maui Sunset Sail on 'Alihilani

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for...

2 hours 30 minutes Free Cancellation

5.0 (225)

from
$127

Maui Romantic Sunset Sail for Couples with Open Bar & Appetizers

Experience a romantic Maui sunset together aboard Akialoa, a luxury 55-foot sailing catamaran. This two-hour evening sail takes you into the picturesque ʻAuʻau Channel, where …More

Maui, USA

5.0 (53)

Maui Romantic Sunset Sail for Couples with Open Bar & Appetizers

Experience a romantic Maui sunset together aboard Akialoa, a luxury 55-foot sailing catamaran. This two-hour evening sail takes you into the picturesque ʻAuʻau Channel, where...

2 hours Free Cancellation

5.0 (53)

from
$127

Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing

Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing catamaran. Settle in together and experience the peace and serenity of sailing …More

Maui, USA

5.0 (46)

Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing

Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing catamaran. Settle in together and experience the peace and serenity of sailing...

2 hours Free Cancellation

5.0 (46)

from
$127

Maui Turtle Snorkel & Sail with Lunch & Open Bar out of Maalaea

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 …More

Maui, USA

4.8 (42)

Maui Turtle Snorkel & Sail with Lunch & Open Bar out of Maalaea

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...

2 hours 30 minutes Free Cancellation

4.8 (42)

from
$127

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the …More

Oahu, USA

4.5 (44)

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the...

1 hour 30 minutes Free Cancellation

4.5 (44)

from
$120

Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way …More

Maui, USA

4.9 (90)

Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way...

2 hours Free Cancellation

4.9 (90)

from
$119

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and …More

Maui, USA

4.8 (85)

Maui: Whalewatch Sail from Lahaina

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and...

2 hours Free Cancellation

4.8 (85)

from
$112

Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary

Experience Maui’s magnificent humpback whales on a 2-hour whale watch aboard a sailing catamaran in the ʻAuʻau Channel, home to one of Hawaii’s greatest concentrations …More

Maui, USA

4.9 (29)

Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary

Experience Maui’s magnificent humpback whales on a 2-hour whale watch aboard a sailing catamaran in the ʻAuʻau Channel, home to one of Hawaii’s greatest concentrations...

2 hours Free Cancellation

4.9 (29)

from
$110

Lahaina Maui Midmorning Whale Watch in the 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

4.5 (2)

Lahaina Maui Midmorning Whale Watch in the 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

4.5 (2)

from
$110

Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea

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

4.9 (103)

Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea

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

4.9 (103)

from
$110

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise …More

Oahu, USA

4.5 (50)

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise...

2 hours 30 minutes Free Cancellation

4.5 (50)

from
$110

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean …More

Big Island of Hawaii, USA

4.8 (382)

Kona Signature Catamaran Sunset Sail

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean...

1 hour 30 minutes Free Cancellation

4.8 (382)

from
$109

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

Hawaii Sailing Trips

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Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay

Kona Afternoon Snorkel to Captain Cook Monument

2-Hour Oahu Sunset Catamaran Sail

Lahaina Maui Sunset Sail on 'Alihilani

Maui Romantic Sunset Sail for Couples with Open Bar & Appetizers

Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing

Maui Turtle Snorkel & Sail with Lunch & Open Bar out of Maalaea

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

Maui: Whalewatch Sail from Lahaina

Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary

Lahaina Maui Midmorning Whale Watch in the Humpback Sanctuary

Maui Midday Whale Watch in the Humpback Sanctuary out of Maalaea

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Kona Signature Catamaran Sunset Sail

Lahaina Maui Afternoon Whale Watch Sail in Humpback Sanctuary

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