Sunset Sailing on a Floating Tiki Bar Catamaran

Quick Details

Capture Perfect Photos & Heartwarming Moments on an Enchanting Sunset Voyage 

Experience a truly memorable evening with an enchanting sunset cruise combined with whale watching (Dec-Apr) off the shores of Maui on our Hawaiin-built catamaran “Winona.” This vessel is a cherished part of our community, known for its spacious comfort and warm Pacific hospitality. As you drift across the sparkling waters, unwind at our floating tiki bar, where you can enjoy Hawaiian pupus, locally brewed beers, tropical cocktails, and a variety of beverages—all served in a relaxed, open-air setting.

Join us on Winona to honor the resilience and enduring spirit of Maui. Our vessel bravely survived the Lahaina fires and is now stationed at Ma’alaea Harbor. Our passionate crew and captain look forward to sharing inspiring stories of hope and strength as we sail through the clear waters of the Pacific. Keep your camera ready for breathtaking photo opportunities and chances to encounter playful spinner dolphins, majestic whales, and other fascinating marine life.

Booking this trip isn’t just about the memories you’ll make—it’s also about supporting a local small business. Your participation helps us keep the vessel active and contributes to the community’s recovery. Come aboard and be part of something special, ending your day on Maui with stories to tell and smiles all around.

Check-In info:

  • Arrive 30 minutes before your scheduled departure at Ma’alaea Harbor, North Dock, 233 Ma’alaea Rd., Wailuku, HI 96796.
  • Sign in digitally and complete our liability waiver.
  • Our boat encourages a casual, barefoot experience. We recommend comfortable footwear that’s easy to slip off, or simply go without shoes to fully enjoy the feeling of the sea beneath your feet.

What’s included:

  • Delicious Hawaiian-inspired appetizers
  • Drinks from our open bar—local beers, seltzers, cocktails
  • Soft drinks, juices, and bottled water
  • Island-style tunes to set the mood
  • A knowledgeable captain and crew
  • Whale watching (from December through April)
  • Sailing experience to and from your destinations
  • Access to two on-board restrooms

What to bring with you:

  • Gratuities for the crew (cash recommended)
  • Light jacket or shawl
  • A Coast Guard-approved life vest for infants 0 to 6 months

What’s excluded:

  •  Hotel transport to or from the harbor
  • Parking validation

Parking tips:

Ma’alaea Harbor is $1 per hour; we recommend paying for 3 hours total. This parking lot uses a QR code payment system. Arrive early to pay via the QR code (you must know your license plate number). Please be aware of where you are parking and follow the parking instructions on the parking signs. We are not responsible for cars that get towed. Give yourself 10-15 minutes for parking.

Adult age 13+

$119.56

Children age 6-12

$ 75.40

Children age 0-5

Free

Guest Experiences That Speak for Themselves

From unforgettable sunsets to laid-back snorkeling adventures, our guests share what made their Sail Winona experience so special.

Your Maui Adventure Starts Here

Escape the crowds and sail the island in true Hawaiian style where handcrafted cocktails, stunning views, and unforgettable moments await.
Scroll to Top