Maui Sailing Trips

Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

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 …More

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 hours • Free Cancellation
5.0 (131)
from
$306
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 …More

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 hours • Free Cancellation
4.8 (830)
from
$213
'Alihilani Lahaina Sunset Sail

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

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 minutes • Free Cancellation
5.0 (195)
from
$117
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

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 (96)
from
$181
Paragon Lahaina Sunset Sail

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 …More

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 hours • Free Cancellation
5.0 (34)
from
$102
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

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 (159)
from
$199
Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

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 …More

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 minutes • Free Cancellation
4.8 (61)
from
$289
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

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 hours • Free Cancellation
4.6 (83)
from
$142
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

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 hours • Free Cancellation
4.9 (59)
from
$179
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 …More

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 hours • Free Cancellation
5.0 (79)
from
$216
Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take …More

Likely to Sell Out
Likely to Sell Out

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take...

2 hours • Free Cancellation
3.5 (4)
from
$60
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 …More

Likely to Sell Out
Likely to Sell Out
4.8 (211)

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 (211)
from
$138
Midday Whale Watch: Mā’alaea Harbor

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

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 hours • Free Cancellation
4.9 (103)
from
$100
Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch

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, …More

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 hours • Free Cancellation
4.9 (218)
from
$200
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, …More

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 hours • Free Cancellation
5.0 (130)
from
$163
Snorkel Sail Adventure off Ka'anapali Beach in 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, …More

Likely to Sell Out
Likely to Sell Out

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 hours • Free Cancellation
5.0 (49)
from
$193

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