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A 360-degree view of the open sea with the seasonal appearance of whales and dolphins as live music plays in the background. Sea Maui’s famous sunset sail options are simply the best evening tours Ka’anapali has to offer. At Sea Maui, we know that Hawaii is a major destination for relaxation and fun times.
Soak In The Golden Hour On A Wailea Sunset Cruise
Each sunset sail in Maui is designed to offer a unique experience. You’ll be greeted with a traditional Hawaiian welcome, complete with lei and a smile from the friendly crew who will be your guides through this journey. While the sunset cruise is a highlight, Maui offers a plethora of other experiences that cater to different interests and preferences. If you’re not interested in live music, or you can’t go on Tuesday or Thursday, they offer a regular sunset cruise (sans live music) all other days of the week.
Maui Sunset Cruise
What we love about a sunset cruise is that you not only get to appreciate the sunset over the water, you get to see the island lit up in the glow of the setting sun. A standout feature here is that they offer private tables for two, which makes this a great option for a romantic evening on the sea. They serve plated appetizers and there is a premium open bar with beer, wine, and cocktails. The crew on the cruise were super fun and made sure to engage with everyone.
Lahaina, Ka’anapali, or Ma’alaea Sunset Sail
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Sunset Cruising On The Miss Avalon.
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Whether you’re seeking a romantic outing with your partner, a fun evening with friends, or a private family gathering, there’s a package that fits your needs. From private charters to intimate group settings, the emphasis is on creating moments that will be cherished for a lifetime. As you sail along Wailea’s coastline, keep your eyes peeled for playful dolphins, majestic humpback whales (during the winter months), and sea turtles gliding through the waters. The crew, knowledgeable about Maui’s marine life and culture, will share fascinating stories and facts, making this cruise not only enjoyable but also educational. Experience the breathtaking beauty of Maui’s coast with a Wailea sunset cruise, a must-do for any visitor to the island.
The crew were all so good and quick with a drink and a joke. Sail with our attentive crew and naturalists as we welcome Pacific humpback whales to their winter home. Our beach-loading location gets you on the water and in nature easily. The island’s farm-to-table dining experiences are a feast for the palate, showcasing the rich flavors of locally sourced ingredients prepared with culinary finesse. At 65 feet in length and a beam (width) over 30 feet, our very large (Maui’s largest), multi-hulled maxi-power catamaran offers unsurpassed stability and comfort. Very few of our guests become ill, even those prone to motion sickness.
Latest reviews of Sunset Cocktail Cruises
Make it more amazing by picking from multiple cruise times to fit your schedule. A sunset dinner cruise is a great way to take in a breathtaking Maui sunset while dining on a catamaran as you watch the sun go down over the Pacific Ocean. You’ll get a different view of Maui’s coastline, mountain ranges, and neighboring islands, Lanai and Molokai, as the day slowly turns into the evening. During the winter months, you’ll even have a chance to spot humpback whales breaching while you enjoy your dinner. This stable, comfortable, triple-deck catamaran leaves from centrally-located Ma’alaea Harbor. Seating on the Calypso sunset dinner cruise in Maui comfortably accommodates any size group, including couples, families, and even large corporate events.
Luxury Sunset Sail from Ma’alaea Harbor (10% off!)
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One of the Ka’anapali classics is Sea Maui’s Original Sunset Cocktail cruise where you can witness the picturesque and breathtaking view of Maui’s sea sunsets. You shall get the best view of the spectacular pastel sunset colors as they change and extend across the horizon and slowly dissolve into the waters of Hawaii. We will be loading from the beach, you can expect to get wet up to your knees when you board. Please watch the short Beach Loading video below, taken on a small surf day.
Even though the spacious Pride of Maui is Coast Guard Certified for 149 passengers, our trips operate at 60% capacity to ensure your experience is the absolute best. Our limited seating at 60% of our USCG capacity provides greater space and more comfort to safely roam throughout the vessel. Indulge in the extraordinary ‘Ike Maui Sunset Dinner Sail, set against the stunning backdrop of Ka’anapali & Lahaina. Join us for an unforgettable evening as we honor the rich heritage of Hawai’i and delve into its captivating culture through mele (music) and hula. Check-in time is 30 minutes prior to scheduled departure time. We serve a tasty spread of plated appetizers that are sure to satisfy even the most discriminating gourmet.

Hawaiian Island Cheat Sheets
If you are in doubt, there are products available over the counter at our local Longs Drug stores to ease your mind. Just ask the pharmacist for one of many preventative options. If you are susceptible to motion sickness, Pride of Maui is positively the right vessel for you!
This is a sailing experience, not just a sunset cruise on their Santa Cruz 50 sailing yacht. With a capacity of only 22 people, this is a fun small group experience. Can’t decide between going to a luau or enjoying a sunset cruise for an evening activity? While this isn’t a true full luau, you’ll still get to experience traditional music and dance with Maui’s gorgeous sunset as a backdrop. They depart from Ka’anapali beach (how convenient!) and if you’re not staying in Ka’anapali you’ll get a 4 hour Whalers Village parking validation.
Each adventure is thoughtfully designed to showcase Maui's marine wonders, from snorkeling to whale watching. The address to key into your GPS is 101 Maalaea Road, Maalaea, Maui, Hawaii. We are located in the central part of the island, off Highway 30.
Departing from Ka‘anapali Beach, this tour starts by boarding a luxury 65ft beach loading catamaran run by Sea Maui. Once aboard, you’ll be treated to an open bar and dinner of local foods followed by a champagne toast and cheers to mark the end of another magical Maui day. From the moment you step aboard, you’ll feel the magic of the Hawaiian islands.
As the sun dips below the horizon, the sky transforms into a canvas of fiery oranges, pinks, and purples mirrored by the crystal-clear waters of the Pacific. But a sunset cruise in Wailea is more than just a visual spectacle; it’s an immersive experience that combines relaxation, romance, and adventure into one unforgettable journey. Step aboard these cruises for a journey that combines the vibrant rhythms of a Hawaiian luau with the breathtaking beauty of a Pacific sunset. It’s a sensory delight where you can relish Hawaiian cuisine, enjoy cultural performances, and watch the sun dip below the horizon. Depart from Ma'alaea Harbor on this sunset cocktail cruise hosted by The Pacific Whale Foundation that offers drinks, appetizers, and dessert.
Guests aboard the Pride of Maui can move throughout the boat and mingle while enjoying a variety of freshly prepared, premium chef-inspired dishes. This is a beach loading boat, which means you’ll get a bit wet while getting on and off. The convenience of this beach loading cruise can’t be beat. Over the years, Sea Maui has worked out to become a staple in Ka’anapali Beach. We make sure our guests get the best time and the magical experience Hawaii has to offer to its tourists. In addition, all the crew members are experienced, certified, and skilled sailors, working together in harmony to give you the best possible experience.
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