Maui Sailing Tours
Set sail on the sparkling Pacific with Maui sailing tours that showcase the island's stunning coastlines and marine life. From snorkeling adventures to relaxing sunset cruises, sailing in Maui combines luxury, adventure, and breathtaking scenery.
Popular choices include half-day catamaran trips to Molokini Crater and Turtle Town, where you'll snorkel with colorful fish and sea turtles. Evening sails feature cocktails, live entertainment, and panoramic views as the sun sets over the ocean. Private charters are also available for those who want a personalized experience, perfect for honeymoons, family gatherings, or special occasions.
Whether you're looking for a day of snorkeling, a romantic evening on the water, or a customized island adventure, Maui sailing tours provide the perfect way to experience the beauty of Hawaii from the sea.
Explore Maui Sailing
Original Sunset Cruise with Open Bar from Ka’anapali Beach
Part of the reason Maui has been so popular year after year is due to the breathtaking sunsets. Sure you could just watch from the beach or your hotel lanai, but a front row seat out on the water, sipping some cocktails, enjoying some awesome pupus (appetizers) and...
Sunset Sail from Ma'alaea Harbor in Maui
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 to experience the essence of ho’okipa...
Coast of Ka'anapali Beach Sunset Dinner Sail
Embark on an unforgettable two-hour Sunset Sail, promising a serene and memorable experience. Relax as our crew sets sail for two hours of smooth and exciting trade wind sailing with phenomenal views of the West Maui mountains, Molokai and Lanai. Sip a mai tai or a maui...
Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our captain and crew on a heartfelt journey...
'Alihilani 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 islands while watching the sunset out at sea. With a...
2 Hours Holo Holo 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 by delightful chef-inspired appetizers and a...
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the flagship 420 Outrage a boat like no other. From the expansive bow with innovative seating galore, to the beautifully designed convertible helm and cockpit areas, to the...
Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks
Set sail on a midday escape where cocktails meet culture aboard Maui’s most luxurious sailing catamaran. Explore the island through authentic storytelling, coastal beauty, and handcrafted island specialties, both sippable and savory. As we cruise the coastline, your...
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, vibrant music, and a...
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 snorkel gear are provided. Our adventure starts on Polo...
