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Top Maui Sailing Trips

Day's End Cocktail Sunset Sail
Likely to Sell Out
Likely to Sell Out

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (85)
from
$166.50

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in...

5 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
4.8 (816)
from
$223.41

Half-Day Deluxe Molokini Snorkel Excursion in Maui

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical...

5 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
5.0 (124)
from
$299

Turtles & Tacos Luxury Catamaran Snorkel
Likely to Sell Out
Likely to Sell Out

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 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.8 (138)
from
$206.50

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar
Likely to Sell Out
Likely to Sell Out

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.6 (61)
from
$149.48

Hawaiian Canoe Sailing Experience in Maui
Likely to Sell Out
Likely to Sell Out

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (59)
from
$186.50

Paragon Lahaina Sunset Sail
Likely to Sell Out
Likely to Sell Out

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (17)
from
$109.50

Midday Whale Watch: Mā’alaea Harbor
Likely to Sell Out
Likely to Sell Out

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (103)
from
$107.72

'Alihilani Lahaina Sunset Sail
Likely to Sell Out
Likely to Sell Out

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 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
5.0 (151)
from
$124.80

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve,...

5 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
4.9 (216)
from
$210

Maui Sunset Sail
4.8 (208)

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (208)
from
$145.32

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Likely to Sell Out
Likely to Sell Out

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (58)
from
$299

Morning Whale Watch: Lahaina Harbor
Likely to Sell Out
Likely to Sell Out

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (29)
from
$107.72

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

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.8 (18)
from
$289

Luxury Catamaran Whale Watch

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.9 (90)
from
$126.50

Maui Turtle Snorkel & Sail with Lunch & Open Bar
Likely to Sell Out
Likely to Sell Out

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 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (39)
from
$129.90

Snorkel Sail Adventure off Ka'anapali Beach, Maui

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky,...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
5.0 (41)
from
$199.67

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based...

5 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
5.0 (55)
from
$226.22

Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and...

5 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
5.0 (23)
from
$213.16

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers,...

5 hoursFree Cancellation
5 hoursFree Cancellation
5 hours • Free Cancellation
4.9 (103)
from
$170.70

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