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Quick Details

Sunset Sail

Beautiful Sunset Sailing and Whale Watching on a Charming Small Hawaiian Catamaran!


Treat yourself and your loved ones to experience a beautiful Sunset Sailing cruise and Whale Watching (Nov – May) on our Small Charming 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.

As the sun sets & we sail back, you’ll know that you have been treated to a truly magical experience to a perfect way to end your perfect day in paradise.

Your Itinerary:


  • Check-in is 30 minutes before your start time at Maalaea Harbor, North Dock address: 233 Maalaea Rd. Wailuku, HI 96796 vessel name Winona – Makena Coast Charters.
  • All guests sign in and complete our digital liability waiver.
  • Walk to the dock and board the vessel.

What’s included:

  • Appetizers
  • Soft Drinks, juice, water
  • Island-Style Music
  • Experienced Captain and Crew
  • Whale watching (December – April)
  • Sailing experience from and to locations
  • Two restrooms on board
  • Big iced-cooler for your BYOB

What’s excluded

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

What to bring with you:

  • A light jacket or shawl


  • 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.