Maui Sailing Trips

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 (40)
from
$122.40
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
$119
'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 (179)
from
$117.30
Akialoa Mā’alaea Sunset Sail
Likely to Sell Out
Likely to Sell Out

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (21)
from
$108.11
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 (25)
from
$102
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
$100.22
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
$100.22
Afternoon Sail With the Whales from 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
5.0 (1)
from
$100.22
Midmorning Whale Watch from 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
4.5 (2)
from
$100.22
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...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
3.5 (4)
from
$59.95

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