Sailing

Luxury Sailing in Maui , Hawaii


Luxury Maui Attractions
Maui

Road to Hana (Hana Highway)

Hana Highway, Kula

★★★★☆4.8 (19,533)
Maui

Molokini Crater

★★★★☆4.8 (17,294)
Maui

Waiʻanapanapa State Park

Hana

★★★★☆4.8 (16,943)

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

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 on weather, tides, and ocean conditions. • Explor…

🕐 5 hours ★★★★★5.0 (38)
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Free Cancellation
Maui

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 the warmth of paradise. From the experienced snorkele…

🕐 5 hours ★★★★☆4.7 (831)
Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar Free Cancellation
Maui

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 an open bar. This is our award-winning snorkel…

🕐 5 hours ★★★★☆4.8 (21)
Molokini Snorkel and Performance Sail: Mā’alaea Harbor Free Cancellation
Maui

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, and is home to over 250 species …

🕐 5 hours ★★★★☆4.8 (217)
Turtles & Tacos Luxury Catamaran Snorkel Free Cancellation
Maui

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 snorkel alongside Hawaiian green sea turtles and colorful tropical …

🕐 3 hours ★★★★☆4.8 (130)
Honolua Snorkel Sail from Lahaina Free Cancellation
Maui

Honolua Snorkel Sail from Lahaina

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Marine Life Conservation District. Along the way, watch for wild dolphins, then snorkel among Hawaiian green sea turtles i…

🕐 5 hours ★★★★☆4.9 (60)
Snorkel Sail Adventure off Ka'anapali Beach, Maui Free Cancellation
Lahaina

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, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot bu…

🕐 4 hours ★★★★☆4.9 (39)
Hawaiian Canoe Sailing Experience in Maui Free Cancellation
Maui

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 Hawaiian history and culture. Cold water and snorke…

🕐 2 hours ★★★★☆4.7 (60)
Sound of the Ocean Whale Watch Sail Free Cancellation
Maui

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 too. With a partnership with the award-winning immersive experience …

🕐 2 hours ★★★★★5.0 (1)
Day's End Cocktail Sunset Sail Free Cancellation
Maui

Day's End Cocktail Sunset Sail

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 happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drinks…

🕐 2 hours ★★★★☆4.7 (84)
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar Save 5% Free Cancellation
Maui

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, and ocean lovers, this Lahaina adventure …

🕐 5 hours ★★★★☆4.9 (94)
Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar Free Cancellation
Maui

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

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 offers breathtaking views of the sunset complemented b…

🕐 2 hours ★★★★☆4.5 (42)
Maui Sunset Sail Free Cancellation
Maui

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 catamaran, Ocean Spirit. It’s the perfect way…

🕐 2 hours ★★★★☆4.6 (218)
Maui Snorkel and Sunset Sail Lahaina Free Cancellation
Maui

Maui Snorkel and Sunset Sail Lahaina

Embark on a once-in-a-lifetime family adventure, where sun, sea, and stunning sunsets come together for the perfect day on the water! Whether you’re snorkeling or simply soaking in the views, there’s something for everyo…

🕐 4 hours
Coral Gardens Afternoon Turtle Snorkel Sail w/ Lunch & Open Bar Free Cancellation
Maui

Coral Gardens Afternoon Turtle Snorkel Sail w/ Lunch & Open Bar

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 waters teeming with vibrant coral…

🕐 2 hours and a half ★★★★☆4.8 (39)
Luxury Catamaran Whale Watch Free Cancellation
Maui

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 to witness the wonder than from the deck of our 65’ catamaran. This two-h…

🕐 2 hours ★★★★☆4.9 (89)
'Alihilani Lahaina Sunset Sail Free Cancellation
Maui

'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 a luxurious experience, allowing for incredible views of Maui and the inter island…

🕐 2 hours and a half ★★★★☆4.9 (116)
Akialoa Mā’alaea Sunset Sail Free Cancellation
Maui

Akialoa Mā’alaea Sunset Sail

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 inter-island channel, showcasing the beauty of Maui, Lāna‘i, …

🕐 2 hours ★★★★☆4.7 (13)
Paragon Lahaina Sunset Sail Free Cancellation
Maui

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 glassy, miraculous ‘au’au Channel is like floating inside an inf…

🕐 2 hours ★★★★☆4.6 (9)
Afternoon Sail With the Whales from Lahaina Harbor Free Cancellation
Maui

Afternoon Sail With the Whales from Lahaina 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, the ‘Au ‘au channel off the coast of Maui boasts the greatest nu…

🕐 2 hours ★★★★★5.0 (1)
Morning Whale Watch: Lahaina Harbor Free Cancellation
Maui

Morning Whale Watch: Lahaina 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, the ‘Au ‘au channel off the coast of Maui boasts the greatest nu…

🕐 2 hours ★★★★☆4.9 (28)
Midday Whale Watch: Mā’alaea Harbor Free Cancellation
Maui

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, the ‘Au ‘au channel off the coast of Maui boasts the greatest nu…

🕐 2 hours ★★★★☆4.9 (104)
Midmorning Whale Watch from Lahaina Harbor Free Cancellation
Maui

Midmorning Whale Watch from Lahaina 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, the ‘Au ‘au channel off the coast of Maui boasts the greatest nu…

🕐 2 hours ★★★☆☆3.3 (3)
Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor Free Cancellation
Maui

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

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

🕐 2 hours ★★★★☆4.6 (19)