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Note that because of the convenient location and not needing to drive to a harbor, they do beach loading. That means you’ll be wading into the water up to your knees in order to board. A local and experienced crew hosts each tour, which usually lasts anywhere from 2-3 hours. Cruises depart from many popular West Maui and South Maui locations, such as Ka'anapali or Ma'alaea, and include options for a full dinner or appetizers and cocktails only. Maalaea Harbor serves as the point of departure for this two-hour trip around the Pacific, where guests are treated to a number of sensory pleasures. Enjoy your choice of delectable rosemary garlic roasted prime rib or locally caught island fish as you watch the sun slip behind the horizon.
Teralani (Ka'anapali Beach) $119.00
Once aboard, you’ll be served a complimentary drink as you relax to island-style music before the dinner service starts. Last but not least on our list is a one-of-a-kind Sunset Luau Dinner Cruise hosted by the top-rated Pride of Maui aboard their 65-foot, double-deck power catamaran. Explore all three decks, and take your time to find just the right spot in sun or shade. The front of the boat is the most open to sun and wind, so wear a secure hat and, as one of our lighthearted guests advised, “consider leaving your fake eyelashes on shore”! After you’ve settled in, pick up a fizzy soda, tropical juice or island themed adult beverage.
Sunset Dinner Cruises in Maui
Price includes more space with limited capacity at 60%, freshly prepared food & open bar.Taxes and fuel surcharge are added to the price. While you won’t find as much food on this sail as you will on the others, you’ll enjoy champagne and chocolate. We loved this sunset cruise experience and we were able to go out for a great night in Wailea after it ended.
FROM MA'ALAEA HARBOR: MAUI SUNSET DINNER CRUISE ABOARD THE CALYPSO
Learn more about their standard Ka’anapali sunset cocktail cruise. Sunset dinner cruises are a great option for families, friends, and couples alike. The atmosphere is relaxing, with fresh food, music, and cocktails to help slow things down after an adventurous day on the island. For those traveling with their significant other, there are even romantic cruise options for adults only. Are you looking for a unique and immersive experience in Maui? Luau Dinner Cruises offer an intriguing blend of a traditional Hawaiian luau with the magic of a sunset dinner cruise.
Sunset Cocktail Cruises
Nick and his crew made the experience so much more than we expected. The cocktails we supreme and they ensured our glasses were never empty. Register and enjoy smoother booking, as well as being able to save your wish list and recently viewed activities. The island’s coral reefs, teeming with life, are a testament to the richness of Maui’s marine ecosystem. The vibrant underwater world, with its myriad of colors and shapes, is a paradise for divers and snorkelers. Many of our guests bring a backpack or soft bag to keep their personal items in.
We took the Sunset Sail on the Trilogy I from Maalaea Harbor. We all felt very welcome & the crew couldn't have been more sweet. If you're ever in Maui, make sure you take this sunset cruise.
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They give you a 4 hour parking validation for Whalers Village. Once aboard, you’ll have an open bar and a buffet dinner to enjoy. There’s something for nearly everyone when it comes to the food selection. If you’re looking for a smaller group, this is the sunset sail for you.
Enjoy a premium dinner menu and a full open bar as you enjoy the sunset with that special someone. This cruise conveniently includes pick-up from many West and South Maui hotels. Set sail on Teralani Sailing’s original sunset sail in Maui. Cruise board a modern catamaran while relishing in stunning coastal views. As the day winds down, sip refreshing drinks and savor appetizers prepared by a skilled chef.

The Wailea sunset is not just a visual feast; it’s an experience that touches every sense. The gentle lapping of the waves, the salty breeze, and the kaleidoscope of colors in the sky create a symphony of sensations, making every sunset cruise a journey to remember. At sunset, we pour their sparkling wine for a sunset toast. Most sunset sails on Maui are two hours, though you will find some that run a bit longer, at 2.5 hours. But they are quick tours that will usually get you back in time for any dinner plans you have that evening.
Relax while the boat drifts along Maui’s coastline with Ma'alaea Harbor as your backdrop as the sun dips below the horizon. Maui sunsets are as exceptional as the rumors suggest, ranging in colors from whisper pink to fiery red and reminding all who witness them that nature’s shows are the best. Savoring them from the island’s shores is a highlight for kamaʻaina and visitors alike, but watching them from the stern of a boat? What sets the Wailea sunset cruise apart is not just the stunning views but also the exceptional service and attention to detail. The crew is dedicated to making every journey special, providing insights about the island’s history, flora, and fauna, and ensuring every guest’s comfort and enjoyment. Aboard the Pride of Maui Sunset Dinner Cruise, you will enjoy Hawaiian entertainment, an open bar, and freshly prepared Hawaiian-style cuisine.
Glide out onto the water, cocktail in hand, and relax while taking in a beautiful Maui sunset. Let the live music soothe your soul as you consider if life can get any better than this moment. That’s when it happens, a whale breaches the water on the horizon as the sun goes down. Let the beautiful Maui Sunset, our unique amenities, expert crew, and relaxed atmosphere make memories that last a lifetime.
It is a specifically designed buffet-style menu just for you. Find out more about the inclusions of the Premium Sunset Cruise here. Sail on a luxurious catamaran, feel the thrill of the trade winds, and dine on a gourmet meal by Chef Paris Nabavi while the sun sets over Maui’s coast. Enjoy the open bar, breathtaking ocean views, and a relaxing Maui evening. Sitting down to a beautiful sunset on the beach with a fresh drink is a moment we forever chase. Add a boat and some live music to the equation, and we are really talking!
Vegetarian options are available and they can accommodate most food allergies. Add an open bar, complete with local beer and Maitais, and you’re in for a night you won’t soon forget. As the cruise returns to shore, the fading light of the day sets a serene backdrop for reflection and relaxation. It’s a moment to take in the beauty of the islands, the warmth of the people, and the joy of life’s simple pleasures. A sunset cruise in Maui is more than just an activity; it’s a highlight of any Hawaiian vacation, a story to be told, and an experience that will be remembered forever.
Despite being a newbie in the field, we are not new to sailing in Hawaii. Many of our crew started working on boats on Waikiki Beach. Good Ol’ Fashioned – Redemption Bourbon, agave syrup, splash of water, Watkins bitters. Please pay via the digital parking kiosks (QR Code) for parking prior to checking in.
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