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Top Maui Sailing Trips

26 Results
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

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, …More

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 hours Free Cancellation
4.8 (19)
from
$279
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 …More

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
Maui: Catamaran Sunset Whale Watch with Cocktails

Experience the best of whale season at sunset! Watch humpbacks breach and play from the deck of a 65' luxury catamaran as the sun sets …More

Experience the best of whale season at sunset! Watch humpbacks breach and play from the deck of a 65' luxury catamaran as the sun sets...

2 hours Free Cancellation
5.0 (2)
from
$189
Lahaina Maui Afternoon Whale Watch Sail in Humpback Sanctuary

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

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
5.0 (1)
from
$102
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
4.7 (89)
from
$148
Lahaina Maui Midmorning Whale Watch in the Humpback Sanctuary

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
4.5 (2)
from
$110

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