What are the best options for Hawaii Sailing Trips?

According to verified reviews on Cool Hawaii and TripAdvisor, the best Hawaii Sailing Trips are: Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full Open Bar Hawaiian Canoe Sailing Experience in Maui Kona Tradewind Catamaran Day 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)

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

Hawaiian Canoe Sailing Experience in Maui

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 …More

Maui, USA

4.9 (59)

Hawaiian Canoe Sailing Experience in Maui

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...

2 hours Free Cancellation

4.9 (59)

from
$179

Kona Morning Snorkel to Captain Cook Monument at Kealakekua Bay

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

Big Island of Hawaii, USA

4.9 (590)

Kona Morning Snorkel to Captain Cook Monument at Kealakekua Bay

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

4 hours 30 minutes Free Cancellation

4.9 (590)

from
$179

Kona Morning Snorkel to Captain Cook Monument

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along …More

Big Island of Hawaii, USA

4.9 (480)

Kona Morning Snorkel to Captain Cook Monument

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along...

4 hours 30 minutes Free Cancellation

4.9 (480)

from
$179

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 (28)

Polynesian Canoe Day 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 (28)

from
$170

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

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

Turtles & Tacos Luxury Catamaran Snorkel

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and …More

Maui, USA

4.8 (173)

Turtles & Tacos Luxury Catamaran Snorkel

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and...

3 hours Free Cancellation

4.8 (173)

from
$169

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

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

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

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

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

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

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

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

Hawaii Sailing Trips

Hawaii Activities

Attractions

Guides

Calendar

Polynesian Canoe Morning Sail

Hawaiian Canoe Sailing Experience in Maui

Kona Morning Snorkel to Captain Cook Monument at Kealakekua Bay

Kona Morning Snorkel to Captain Cook Monument

Polynesian Canoe Day Sail

Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed

Happy Hour Sunset Sail on Maui's Luxury Catamaran

Turtles & Tacos Luxury Catamaran Snorkel

Sound of the Ocean Whale Watch Sail

Waikoloa Signature Catamaran Sunset Sail

Sunset and Manta Ray Snorkel Adventure

Moana’s Luxury semi-private Sunset Cruise on Nalu

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

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

BYOB Friday Night Fireworks Cruise

Maui Sunset Sail

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