Winona Sail Catamaran Private Charter

Host your celebration on a Hawaiian-built catamaran with crew, music, and snorkel gear included

4.8 stars• 1K reviews

From$3,300

Ideal For

Up to 45 people

Includes

Captain & crew, Music, Snorkel gear

Highlights

Celebrate aboard Winona, a Hawaiian-built sail catamaran. Enjoy a private charter with a professional crew, island-style music, and space for up to 45.

Check in 30 minutes early at Maalaea Harbor
Sign the waiver and board the catamaran
Enjoy beverage service while you sail
Use sanitized snorkel gear and flotation devices
Spot whales in season December to April
Return to Maalaea Harbor at the end of your charter

What's Included

Island-style music
Experienced captain and crew
Sanitized snorkel equipment and flotation devices
Seasonal whale watching (December–April)
Sailing experience

Things to know

Capacity up to 45 guests; check in 30 minutes before departure at Maalaea Harbor. This is a barefoot vessel; wear shoes easy to remove.

Cancellation policy

Full refunds require at least 24 hours' notice for groups of up to 4, 48 hours for groups of 5 or more, and 7 days for private charters. Weather or mechanical cancellations are honored at any time. The operator may cancel due to low customer count.

Review summary

4.8

Excellent

1K reviewsGoogle Maps

Captain Matt and his rotating crew members (Shelby, Lucia, and others) consistently earn praise for creating memorable snorkeling adventures. Guests rave about the friendly, knowledgeable approach that makes everyone feel safe and welcome, whether it's their first time snorkeling or a honeymoon highlight. The crew clearly knows the best spots and timing to maximize the experience while keeping groups small and comfortable. The actual snorkeling delivers what people hope for: close encounters with sea turtles at Turtle Town, colorful fish at Molokini Crater, and occasionally even dolphins. Reviewers appreciate the well-maintained boat and gear, plus thoughtful touches like fresh sandwiches. Several families mention bringing kids along successfully, noting the crew's patience and the manageable three-hour timeframe. The early departure times help beat crowds and catch calmer waters, which seems to pay off with better visibility and a more relaxed vibe overall.

What people are saying

Best trip ever!! This is Mom’s first visit to Hawaii and she’s always wanted to explore the ocean! This week that dream came true!! We had an incredible time, tons of fish, tons of turtles and an awesome crew and music!! The lunch was delicious after all the snorkeling! I highly recommend this charter to anyone looking for a memorable and amazing experience!!