Maui Sunset Sailing and Whale Watching

Avoid the over-crowded 40-50 and some with 100-passenger boats. Maui's sunset sail and boat trips are often overpriced and target tourists who don't know any better. We prioritize your comfort and take 30-40 passengers max. You'll enjoy personalized attention and plenty of space to move around. Don't miss capturing the moment when our colorful sails open – it's a sight you won't be able to resist capturing in photos and videos!
Winona is not just any sail catamaran; she's Hawaii's only Hawaiian-built, well-kept, and spacious vessel. Get ready to experience true Aloha hospitality, indulge in delicious Hawaiian snacks and drinks, and so much more. Join us for an unforgettable adventure!

Meeting Point

233 Maalaea Rd

233 Maalaea Rd, Wailuku, HI 96793, USA

Check-in is 45 minutes before the activity starts time. Google Maps 233 Maalaea Road, places you in front of the Coast Guard building. We are at the north dock to the left of the Coast Guard station in front of the condo building and gravel parking lot. Look for our Signs "Makena Coast Charters".

What's included:

• Two restrooms on board
• Appetizers
• Soft Drinks, juice, water
• Experienced Captain and Crew
• Island-Style Music

Not included:

• Gratuities
• Hotel Pick-Up and Drop-Off
• Parking Validation
• Bring your own drinks on board for more fun

What to expect:

233 Maalaea Rd

Treat yourself and your loved ones to experience a beautiful sunset sailing cruise and Whale Watching (Dec-Apr) on our Charming Small Hawaiian Catamaran "Winona". Hawaiian-built, well-kept & spacious catamaran where you’ll experience true Aloha hospitality, Hawaiian pupu, non-alcoholic beverages, refreshment drinks, and much more. Bring your own drinks on board for more fun. Lovely atmosphere and awesome photo opportunities! - The chance to see spinner dolphins, whales, and other sea life while we're out! End a day in Maui on a high note when you book this fun cruise from Maalaea.
Winona will sail you away until the sun starts to dip below the horizon. You’ll have the chance to enjoy the perfect view of West Maui's mountains, Molokai, and Lanai, while you lounge on our decks or main floor. Each year, from November through May, thousands of migrating humpback whales journey from chilly Alaska to the warm waters of Maui to breed and give birth. Our guests can get a close-up view of the majestic marine mammals on this tour. These whales play, breach, and interact in their natural environment, and our crew provides insights into their behavior and biology.