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Your Private Hawaiian Catamaran Adventure Awaits
Experience Maui’s only floating tiki bar on an exclusive charter designed just for you. Hawaiian-owned, locally captained, and tailored to create unforgettable memories on the water.
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Featured Private Charter Tours
5 Hours – Up to XX guests – From $888
Snorkel Adventure at Turtle Town
Dive into crystal-clear waters at Maui’s premier snorkeling destination. Swim alongside Hawaiian green sea turtles and explore vibrant coral reefs teeming with tropical fish. Our experienced crew ensures a safe and unforgettable underwater adventure for guests of all skill levels.
5 Hours – Up to XX guests – From $888
Coral Gardens Snorkel + Whale Watching Tour
Discover two of Maui’s most spectacular marine environments in one exclusive charter. Snorkel through the pristine Coral Gardens before searching for majestic humpback whales (seasonal: December-April). Our spacious catamaran provides the perfect vantage point for wildlife viewing and underwater exploration.
5 Hours – Up to XX guests – From $888
Sunset Sailing on a Floating Tiki Bar Catamaran
Enjoy an unforgettable evening on a sunset cruise with seasonal whale watching (Dec–Apr) along Maui’s coast aboard Winona, our locally built catamaran known for comfort and warm hospitality. Relax at the floating tiki bar with Hawaiian pupus, local beers, tropical cocktails, and more—all in a casual, open-air setting.
5 Hours – Up to XX guests – From $888
Discover Maui's Most Spectacular Ocean Destinations
Set sail to Maui’s most treasured marine sanctuaries aboard our classic Hawaiian catamaran. From the turtle-rich waters of Coral Gardens to the volcanic beauty of La Perouse Bay, each destination offers unique charm. Our experienced Hawaiian captains guide you to pristine snorkeling spots where tropical fish and sea turtles glide by.
Whether you’re exploring beneath the waves or enjoying a handcrafted cocktail at our floating tiki bar, your private charter offers unforgettable experiences. With deep local knowledge and decades of experience, we ensure every journey is filled with moments most visitors never get to see.
Your Charter, Your Way
Completely Customizable Adventures Your vision becomes reality on the water. Whether celebrating a milestone birthday, hosting a corporate retreat, or planning the perfect proposal at sunset, we tailor every detail to your desires. Our experienced team works closely with you to craft an itinerary that exceeds expectations.
Unmatched Local Expertise As a Hawaiian-owned and operated company, we bring authentic island knowledge to every charter. Our local captains know the secret spots, optimal conditions, and share stories that connect you to the true spirit of Maui. This isn’t just a boat ride – it’s an immersion in Hawaiian maritime culture.
Why Choose Us?
Excellence at Every Turn
Superior Comfort
Our catamaran offers wide decks, shade, and a stable twin-hull—ideal for both small groups and large celebrations.
Award-Winning Service
Guests praise our attentive crew, pristine vessel, and unforgettable moments—making Sail Winona one of Maui’s most trusted charters.
Decades of Reliability
Locally owned for 35+ years, we deliver Hawaiian hospitality with strong community ties, proven safety, and true professional care.
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Guest Reviews
About us
With over 30 years of experience on the waters of Maui, our seasoned Hawaiian captains and crew bring unmatched local knowledge, professionalism, and passion to every tour. We know these waters like the back of our hand, allowing us to guide you safely and confidently through some of the most breathtaking ocean experiences Hawai‘i has to offer. Safety is always our top priority, and we take great pride in creating a welcoming, fun, and memorable atmosphere for all our guests—from first-time visitors to returning adventurers.
Frequently asked questions
Most frequent questions and answers
What is the temperature of the water in Hawaii?
The water temperature around Maui varies between 74°F and 82°F, depending on the season.
Where and when does the charter meet, and when will we be back?
We operate out of Ma‘alaea Harbor (233 Ma‘alaea Rd, Wailuku, HI 96793 is the closest address). You will meet us at the boat Winona on the North Dock, in front of the first condo complex just east of the Coast Guard Station. Please be sure to arrive 30 minutes before launch time.
Launch and return times are as follows:
• Morning Turtle Town Snorkel at Coral Gardens
9:00 AM – 12:00 PM
• Afternoon Turtle Town Snorkel at Coral Gardens
1:00 PM – 4:00 PM
• Sunset Sailing on a Floating Tiki Bar Catamaran
5:00 PM – 7:30 PM
Do you rent cameras or have photography packages available?
Not at the moment. We are currently developing new offerings for camera rentals and photo packages.
When are the busiest times of year on Maui?
The busiest times are during the summer months (June–August), as well as the Thanksgiving, Christmas–New Year’s, and Spring Break holidays.
What is your cancellation policy? What if I get sick?
Cancellations made at least 48 hours before your scheduled tour or charter will receive a full refund.
Trust Indicators
• Hawaiian-Owned & Operated for Over 35 Years
• Coast Guard Certified & Fully Insured
• TripAdvisor Travelers’ Choice Award Winner
• Consistently Top-Rated on Review Platforms