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: Waikiki Sunset Cruise from Oahu Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value South Shore Open Sail from Kewalo Harbor Including Drinks Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast View all kid-friendly Activities →

Which Hawaii Sailing Trips have Instant Confirmation?

Hawaii Sailing Trips with Instant Confirmation include: Waikiki Sunset Cruise from Oahu Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value South Shore Open Sail from Kewalo Harbor Including Drinks Sunset sail Aboard Manakai Catamaran Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed 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 Cruise from Oahu Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value South Shore Open Sail from Kewalo Harbor Including Drinks Sunset sail Aboard Manakai Catamaran Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed 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)

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

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

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

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing …More

Maui, USA

4.8 (213)

Maui Sunset Sail

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing...

2 hours Free Cancellation

4.8 (213)

from
$138

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

Kona Manta Ray Night Snorkel — 85–95% Sighting Rate

• 85–95% manta ray sighting rate at Manta Village, Kona • Return free within 7 days if no mantas seen — space available • Owner …More

Big Island of Hawaii, USA

4.8 (744)

Kona Manta Ray Night Snorkel — 85–95% Sighting Rate

• 85–95% manta ray sighting rate at Manta Village, Kona • Return free within 7 days if no mantas seen — space available • Owner...

1 hour 30 minutes Free Cancellation

4.8 (744)

from
$141

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

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

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 …More

Big Island of Hawaii, USA

4.9 (856)

Sunset and Manta Ray Snorkel Adventure

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...

2 hours 15 minutes Free Cancellation

4.9 (856)

from
$155

Waikoloa Signature Catamaran Sunset Sail

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers …More

Big Island of Hawaii, USA

4.8 (419)

Waikoloa Signature Catamaran Sunset Sail

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers...

90 to 120 minutes Free Cancellation

4.8 (419)

from
$159

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

Happy Hour Sunset Sail on Maui's Luxury Catamaran

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted …More

Maui, USA

4.9 (101)

Happy Hour Sunset Sail on Maui's Luxury Catamaran

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted...

2 hours Free Cancellation

4.9 (101)

from
$169

Hawaii Sailing Trips

Hawaii Activities

Attractions

Guides

Calendar

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

2-Hour Oahu Sunset Catamaran Sail

Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay

Kona Afternoon Snorkel to Captain Cook Monument

Maui Sunset Sail

BYOB Friday Night Fireworks Cruise

Kona Manta Ray Night Snorkel — 85–95% Sighting Rate

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

Moana’s Luxury semi-private Sunset Cruise on Nalu

Sunset and Manta Ray Snorkel Adventure

Waikoloa Signature Catamaran Sunset Sail

Sound of the Ocean Whale Watch Sail

Happy Hour Sunset Sail on Maui's Luxury Catamaran

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